James Casey, a student at Colorado University Boulder, joins us on Psychedelics Today to share his experience with MDMA-assisted psychotherapy, forming the Psychedelic Club Boulder, and his interest in neuroscience. James had the unique opportunity to be a research participant in the MAPS phase-2 MDMA-assisted psychotherapy for PTSD trials and shares part of his experience with us. The MDMA-assisted psychotherapy has been a life saver for James, and now he advocates for the therapeutic use of MDMA for treatment of PTSD and other mental health issues.
I think it is criminal that we are really keeping this (MDMA-assisted psychotherapy) from people….. Veterans aren’t the only people suffering that need this (MDMA-assisted psychotherapy), people who have experienced childhood trauma, law enforcement, firefighters, people that are victims of rape, or gang violence. This really has the potential to heal so many people. To speak for the veteran community, I know so many people that I’ve deployed with or know that have been deployed, that I am afraid I am going to get a call tomorrow, next week, or next month because they killed themselves. To know that if they try to do the same treatment that I did outside of the MAPS study, that they risk getting thrown in a cage for years on end is criminal to me.
Show Notes
Researching the effects of LSA on cockroaches
Psychedelic Club Boulder
Tips on starting a psychedelic club/group
Drug testing on campus at CU Boulder
Results of testing – 88% of the MDMA samples tested positive for meth. About 40% of the LSD samples tested positive for a research chemical
Drug reform and war on drugs
Veterans, PTSD, and MDMA-assisted psychotherapy
Changing the psychedelic narrative among law enforcement
DMTx
About James Casey
U.S. Army veteran, participated in a study of MDMA-assisted psychotherapy for posttraumatic stress disorder (PTSD) in 2014. After three sessions of MDMA-assisted psychotherapy, James no longer qualifies for PTSD.
New York Times bestselling author, Don Lattin, joins us on Psychedelics Today to talk about his new book, Changing Our Minds: Psychedelic Sacraments and the New Psychotherapy. Lattin’s new book covers the current psychedelic renaissance by exploring the scientific and academic research examining these powerful substances for an array of mental health issues, spirituality, and more.
In this episode, we explored psychedelic history, Don’s new book, some personal experiences, and more.
Changing Our Minds is an essential read for those interested in the expanding field of psychedelic research for therapeutic and spiritual uses.
CHANGING OUR MINDS is an experiential tour through the social, spiritual and scientific revolution that is redefining our relationship with mind-expanding substances. It tells the inspiring and very human stories of pioneering neuroscientists, psychotherapists, shamans and ordinary people seeking to live more aware and compassionate lives by combining the miracles of modern chemistry, therapeutic techniques and the wise use of ancient plant medicines.
A new era of research into psychedelic-assisted therapy has begun. Party drugs like Ecstasy (MDMA) are used to help U.S. veterans struggling with the psychological aftermath of war. Psilocybin, the active ingredient in magic mushrooms, is employed as a medicine to help alcoholics get sober and cancer patients struggling with the existential distress of a life-threatening illness. Meanwhile, the use of the ayahuasca, a shamanic brew from the Amazon jungle, has grown into an international movement for those seeking greater spiritual and psychological insight.
Changing Our Minds is the essential primer for understanding and navigating this new consciousness-raising territory.
Don Lattin is an award-winning journalist and the author of six books.
His most recent work, CHANGING OUR MINDS – Psychedelic Sacraments and the New Psychotherapy, was published in the spring of 2017. It chronicles a quiet revolution underway in our understanding of how psychedelic drugs work and how they can be used to treat depression, addiction and other disease. The stories behind this cutting-edge medical research and religious exploration reveal the human side of a psychedelic renaissance.
Changing Our Minds is the latest installment in a trio of books about the recent history and future prospects for finding beneficial uses for drugs and plant medicines like LSD, psilocybin, MDMA, and ayahuasca.
Lattin’s journalistic work has appeared in dozens of U.S. magazines and newspapers, including the New York Times, Wall Street Journal and the San Francisco Chronicle, where Don worked as a staff writer for nearly two decades.
Don has taught as an adjunct faculty member at the Graduate School of Journalism at the University of California at Berkeley, where he holds a degree in sociology. He is a contributing writer for the Encyclopedia of Love in World Religions and the Encyclopedia of Religion in America.
This is the third article in a series on psychedelic chemistry, and the final article focusing on the tryptamine class. In the previous article we learned that though DMT and 5-MeO-DMT lack oral activity, chemistry wizards are able to change that. By making one of a variety of simple alterations to their structure they may be changed into analogs (“research chemicals”, or RCs), each possessing their own unique subset of characteristics including oral activity. That’s because the chemists changed the three-dimensional configuration of the molecules in such a way that the lone pair of electrons situated on the amine’s nitrogen (Figure 1) became shielded, thereby preventing their degradation by MAO. To recap, if one consumes monoamines (such as certain tryptamines) orally, MAO transforms them in the gut and by the time they enter the bloodstream they are no longer psychoactive – Figure 2.
Figure 1. Nitrogen has 7 electrons in total, and 5 valence electrons. It has one electron in each of the three 2p orbitals, which allows it to make three bonds (green), and two electrons in the 2s orbital which exists as a lone electron pair (blue).
Figure 2. After 5-MeO-DMT is consumed orally (1) it enters the gut (2) and is transformed by MAO-A (3). MAO-A uses oxygen to convert the amine into a carboxylic acid (4). This converts 5-MeO-DMT into the nonpsychoactive 5-MIAA (5-methoxyindole-3-acetic acid), the species which enters the circulatory system (5)
This article is going to unpack a study (Figure 3) that showed, by comparing the structures of the naturally-occurring molecules psilocin and bufotenin why the former is orally active while the latter is not. This is another pioneering study from the lab of Dr. David Nichols, who is, along with Albert Hoffman and Sasha Shulgin, in my estimation one of the three true giants of psychedelic chemistry. Its his work and excellent lectures from ESPD50, Psychedelic Science (2013 and 2017), and Breaking Convention that restoked my appreciation for chemistry and inspired me to not only deepened my knowledge, but also to start this series of articles. The outpourings from his majestic mind has fundamentally shaped the topics and content of these articles… Shout out Big D, whut-whut!
Figure 3
The structure and atomic composition of a chemical are obviously critical to our understanding, and the progression of, chemistry and pharmacology. The problem with that is that molecules are small – really small. Even with today’s stupefying repertoire of advanced scientific analytical instruments, there is still no practical way for us to observe their structure directly. So instead we have devised sophisticated methods in which to do so indirectly. One of these methods is called Nuclear Magnetic Resonance (NMR) Spectroscopy, which uses information about the spin of atomic nuclei to determine what a compound’s structure looks like.
In 1980 the team at Purdue University used NMR spectroscopy to investigate how the three-dimensional structures of bufotenin and psilocybin differ from one another. Even though these two compounds are constitutional isomers (Box 1; Figure 4), there is a critical difference in their activity – psilocin is orally active, whereas bufotenin is not. This tiny change, moving the hydroxyl group from position 5 to 4 made this critical difference in the way they are absorbed by a human body. Though 2D-representations of the respective molecules are too low resolution to allude to the reason for the disparity, the researchers (correctly) suspected that by looking at their 3D-structures they would be able to understand why one molecule could resist deamination by MAO, while the other could not.
Figure 4. Bufotenin and psilocin are constitutional isomers, the only difference in their structure is the position of the hydroxyl group (-OH).
NMR spectroscopy revealed that the ethyl sidechain of bufotenin is able to rotate freely, meaning it can spin around on its own axis (Figure 5). That is however not the case for psilocin, something locks it in place, preventing it from rotating freely. The ethyl sidechains of the molecules are identical, which means that whatever is preventing the free rotation of psilocin’s ethyl sidechain is related to the hydroxyl group being situated at position 4, and not 5. To find out exactly what that was, the researchers used specialized software called LAOCN3. Before we explore what they found it would be useful to our interpretation of the results if we brushed up on a couple of elementary concepts in chemistry.
Figure 5
There are two basic types of bonds that atoms can form with one another. The first, called an ionic bond, forms when atoms exchange electrons with one another. This happens if the encountering atoms possess large differences in their respective affinities for electrons (called electronegativity), one atom really wants to lose an electron, while the other really wants to gain it (Figure 6). So an electron (or electrons) are exchanged, and because it is negatively charged the transfer changes the charge of the each atom. The atom that gains the electron gains a negative charge and thus becomes negative, while the atom that loses the electron loses a negative charge and thus becomes positive. And as the old adage goes, opposites attract – the oppositely-charged atoms come together and form a stable bond with one another.
Figure 6. Ionic bonds.
The other type of bond that can unite atoms is a covalent bond. This happens when atoms with similar affinity for electrons encounter one another, neither really wants to lose/gain an electron so they reach a compromise – they share their electrons among each other. Both atoms pretend that the electron that it shares, as well as the electron shared by the other atom, belongs to it (Figure 7). It’s this overlap of shared electrons that connects the atoms together into a single molecule.
Figure 7. Covalent bond.
Because there are no electrons that are transferred in the covalent bond the atoms don’t assume a charge as was the case with ionic bonds. However, that’s only partially true… In certain cases, the atoms that take part in a covalent bond do have some difference in their affinity – not enough for them to exchange electrons and form an ionic bond, but enough so that when they form a covalent bond and share electrons those shared electrons are closer to one atom than the other. This is known as a polar covalent bond. The atom to which the shared electrons are in closer proximity has a higher electronegativity and thus becomes partially negative (δ-). Conversely, the atoms with lower electronegativity are further from the shared electrons and are partially positive (δ+). Because of this asymmetrical charge, polar molecules are able to form weak bonds with other polar molecules, or with compounds that have a net charge. Now that we’ve covered some basic concepts let’s get back to the results of the study and apply what we’ve learned by taking a closer look at psilocin (Figure 8).
Figure 8. In the red area is a hydroxyl group (Figure 9), and in the blue area is a tertiary amine (Figure 10).
Figure 9. The electronegativity of hydrogen (white) is 2.1, while that of the oxygen (red) is 3.5. This difference of 1.4 in their electronegativity is not enough to form an ionic bond, but does lead to partial charges – oxygen has a higher affinity for electrons meaning the electrons are closer to it and assumes a partially negative charge (δ-), while hydrogen assumes a partially positive charge (δ+).
Figure 10. The tertiary amine group consists of a nitrogen (blue) with an electronegativity of 3.0, connected to three carbons (grey) each with an electronegativity of 2.5. Nitrogen has a higher affinity for electrons and pulls the electrons closer to it, leading to a partial negative charge (δ-), while the carbons have partial positive charges (δ+).
Taken together: psilocin has hydroxyl group at position 4 with a partially negative oxygen and a partially positive hydrogen, and an amine with a nitrogen that is partially negative and carbons that are partially positive. Because of these partial charges something interesting happens – the partially positive hydrogen from the hydroxyl group and the partially negative nitrogen from the amine attract one another (Figure 11).
Figure 11
The hydrogen and nitrogen form a special type of bond with one another known as hydrogen bond (Box 2) which pulls the two atoms closer to one another, changing the shape of the molecule – Figures 12 and 13.
Figure 12. The partial positive charge on the hydrogen and partial positive charge on the nitrogen (left) are attracted to one another and form a hydrogen bond which pulls the atoms closer to each other, changing the molecule’s shape (right).
Figure 13. The hydrogen of the hydroxyl-group is bent backwards into a gauche conformation while the ethyl tail bends towards the indole ring to further shorten the distance between them.
It’s this hydrogen bond that locks the ethyl sidechain into place by forming a closed loop (Figure 14), preventing it from rotating freely. In bufotenin the ethyl sidechain can rotate freely because no such hydrogen bond exists. Because the hydroxyl-group is at position 5 and not 4, the partially charged molecules are too far away from one another to form the hydrogen bond, change the shape of the molecule, and lock the ethyl sidechain into place.
Figure 14
But what has any of this to do with the difference in oral activity between the two molecules? Turns out, everything. It’s this hydrogen bond and closed loop formation in psilocin which shields the lone pair of electrons situated on the nitrogen. Because MAO cannot access the electrons it cannot deaminate the molecule – this is why it can pass through the gastrointestinal system unchanged.
But there’s more. The hydrogen bond and resulting closed loop formation also lead to several other important changes in the property of the molecule which further accentuates its efficacy and potency as an orally-active psychedelic tryptamine. After generating 3D-models of the respective molecules, the researchers went on to compare their pKa (Box 3) and Log P (Box 4) values..
When they measured the pKa and the Log P for both psilocin and bufotenin they found the following:
The pKa for Bufotenin is 9.67, meaning that at that specific pH-value equal amounts of the molecule will be present in both the ionized (water soluble) and protonated forms (lipid soluble). When the molecule is in the blood, which has a pH of about 7.4, almost all of it (99.5%) is in the ionized form. In contrast, psilocin has a pKa of 8.47, closer to the pH of blood. So for psilocin, only about 52% is in the ionized form. That means that in the blood, 48% of psilocin will be in its unionized form versus only about 0.5% when it comes to bufotenin. As it is only the unionized form of the drug that can cross cell-membranes, this has profound implications for the potency of these two drugs – psilocin is not only able to better withstand degradation by MAO, but once it is in the blood there is also much more of it available in a form that can cross cellular membranes and thus can reach the target receptors and exert an effect.
The difference in pKa is also related to the shielding of the electron lone pair by the hydrogen bond. As we have learned, amines possess a nitrogen with a lone pair of electrons. These free electrons, which carry a negative charge, are all too happy to snap up positively-charged protons (H+) from a solution they are in. This is, according to the Bronsted-Lowry acid-base theory, the very definition of a base – something that accepts protons. When it comes to psilocin the lone pair of electrons are shielded and are thus much less likely to accept protons. As a consequence, psilocin is less basic that is bufotenin.
The researchers also detected a difference in the Log P values – 1.19 for bufotenin, and 1.45 for psilocin. In the Log P scale a negative value indicates a compound which is hydrophilic, whereas a positive value indicates one that is lipophilic. Both these compounds are thus lipophilic, and psilocin, with the higher value, is more lipophilic. For drugs, in general, it is preferable for them to be lipophilic so as to be able to cross cell membranes, but not too lipophilic because then they immediately migrate to, and are stored in, the body fat. Research indicates that a Log P value of about 3.0 is the “sweet spot”, so psilocin is closer to this number, again indicating that its properties are more favourable once it enters the body.
The researchers started with a simple question: how is it that two isomeric compounds with such a small difference have such widely different properties when they are consumed orally? With NMR Spectroscopy we learned that it all has to do with the fact that because the hydroxyl group of psilocin is a little bit closer to the amine it was able to form a hydrogen bond between the two groups. This hydrogen bond shields the electron lone pair from deamination by MAO, which means that, unlike bufotenin, psilocin is orally active. The hydrogen bond also decreases the molecule’s proton-accepting capacity thereby decreasing its pKa value which means that at blood pH there is more of psilocin in the non-ionized (lipid soluble) form which is able to cross cell membranes and thus enter the central nervous system (CNS). Finally, we saw that it also affected the Log P value, and that psilocin is a more lipophilic compound, closer to an ideal value for drugs to effectively enter and bind to the appropriate receptors in the CNS.
I hope you enjoyed this journey, in the next article we will start our exploration of the phenethylamine class.
Faan Rossouw was born and raised in Cape Town (South Africa) and currently resides in Montreal (Canada). He holds a MSc in Plant Science, and is the co-founder and Chief Strategy Officer of Indeeva Biomedical, a medical cannabis company that focuses on producing condition-specific cannabinoid therapeutics. Faan possesses theoretical expertise and practical experience in biological production systems, natural and pharmaceutical product development, phytochemistry, and psychopharmacology. Though his background is rooted in science he is most passionate about, and thrives in, the intersection of science, the humanities, and commerce. He is interested in how we can leverage the properties of the new global economy to develop superior and sustainable therapeutic solutions. In his free time he loves to practice Brazilian Jiu Jitsu, spend time in nature with his partner Robyn, or kick back in his lazy boy with a book, a cup of pu-erh tea and his cat Luna.
This is the second article in a series on psychedelic chemistry. In the previous article, I introduced the tryptamine class of psychedelics, and we discussed five well-known examples: DMT, 5-MeO-DMT, bufotenine, psilocybin, and psilocin. While the latter two, primary psychedelic constituents of Psilocybe mushrooms (Figure 1), are orally active, neither DMT, 5-MeO-DMT, nor bufotenine are. In this article we will explore two types of alterations that synthetic chemists can make to those molecules to bestow oral activity upon them. These alterations lead to the psychedelic tryptamine analogs (“research chemicals”): AMT (Indopan), MiPT, DiPT, 5-MeO-aMT (Alpha-O), 5-MeO-MiPT (Moxy), and 5-MeO-DiPT (Foxy Methoxy).
Figure 1
Monoamine Oxidase
L-monoamine oxidase (MAO) is a family of enzymes that catalyze the oxidation of monoamines. Monoamines contain a single amine connected to an aromatic ring via a 2-carbon chain, and include neurotransmitters such as serotonin and norepinephrine, as well tryptamines (Figure 2) such as DMT, 5-MeO-DMT, and bufotenin. The reason therefore that these compounds are not active after being consuming orally is because once they enter one’s gut they are inactivated by MAO.
Figure 2
If you want to experience the psychedelic effects of these compounds there are two basic strategies. The first is to use a route of administration that bypasses the gut. Smoking and vaporizing are by far the most common ways to achieve this, but are also the most intense (rapid onset) and shortest-lasting methods. Accordingly, some people favour other non-oral routes such as sublingual (under the tongue), insufflation (in the nasal passage), and rectal administration. Each of these administration routes has its own set of unique pharmacokinetic properties that may be favoured by certain people depending on the context and/or intention. Different strokes for different folks.
But that applies equally to oral delivery, which is unsurpassed in terms of its simplicity (swallow and then you’re done), ease (no thumbing around the butthole or snorting fiery salts up your schnoz), and duration. Except for transdermal delivery, which is technologically complex and has severe restrictions on what can be administered, oral delivery is the longest lasting. Hence its popularity for journeyers that wish to go in deep. So even with a number of non-oral administration routes available, there is still good reason to utilize the oral route.
How to do so if we all walk around with an enzyme in our belly that will deactivate the psychedelic? Simple – consume another compound, called a monoamine oxidase inhibitor (MAOI), that will deactivate that enzyme. Ayahuasca is a prime example of this, though there are a number idiosyncratic formulas of the brew, in essence, it is based on two core ingredients (Figure 3). One contains DMT, the most common being chacruna (Psychotria viridis), and the other contains the MAOI, which is always the ayahuasca vine (Banisteriopsis caapi).
Figure 3. A pot filled with chacruna leaves containing DMT, as well woody material from the ayahuasca vine containing harmine, tetrahydroharmine, and harmaline (MAOI’s). The former provides the visionary punch, the latter ensures that DMT is not broken down in the gut and is able to enter the blood plasma unchanged.
Synthetic chemists love to ask “what if” questions. Like “what if” I make this simple change to the molecular nature of the compound, how does that then affect its properties? These type of questions are explored not only in the name of scientific curiosity, but also because studying how simple changes affect the properties of compounds informs us about its structure-activity relationship, as well provide intimations of what the target receptor looks and behaves like. To the specific question of whether or not a simple alteration to DMT/5-MeO-DMT can actuate oral activity chemists have thus far provided two answers – α-methylation (Figure 4) and N-alkylation (Figure 6).
α-Methylation
Figure 4
As we covered previously, DMT is a tryptamine molecule with two methyls at the N-position. So what would happen if, instead of adding two methyls to the N-position of the tryptamine, we added a single methyl to the alpha-position? This yields AMT (alpha-methyltryptamine; Figure 5), a molecule originally developed in the ‘60s by a Michigan-based pharmaceutical company called Upjohn and which was prescribed in the USSR as an antidepressant. It is at once psychedelic, entactogenic (like MDA/MDMA), and a stimulant with an oral dose typically lasting upwards of 12 hours.
Figure 5
The same goes for 5-MeO-tryptamine (mexamine) – if instead of adding two methyls to the N-position to form 5-MeO-DMT we add a single methyl to the alpha-position, we get 5-MeO-AMT – 5-methoxy-alpha-methyltryptamine (Figure 5). This orally-active and potent psychedelic, commonly known as ‘Alpha-O’, is sometimes peddled as faux-LSD. This is problematic as, unlike LSD with no known lethal toxicity, 5-MeO-AMT has lead to deaths at fairly low doses. It’s not a War on Drugs, it’s a War on People.
With both AMT and 5-MeO-AMT there is a chiral centre at the alpha-position. Attaching a single methyl to the alpha position potentially yields either an S- or R-configuration. Both are psychoactive, both orally active, but work by Dr. David Nichols lab has found that the S-enantiomer is more potent.
N-Alkylation
Figure 6
With N-alkylation we manipulate DMT and 5-MeO-DMT as the departure point to realize oral activity. Both these molecules possess two methyls on the amine nitrogen. Work again by Dr. Nichols’ lab has found that if you replace one, or both, these methyls with isopropyl, the molecule becomes orally active (Figure 7).
Figure 7
In the case of DMT, if a single methyl is replaced by an isopropyl it results in MiPT (N-methyl-N-isopropyltryptamine), an obscure psychedelic with indistinct effects first introduced to the world in TiHKAL. In the case of 5-MeO-DMT, the same single substitution results in 5-MeO-MiPT (5-methoxy-N-methyl-N-isopropyltryptamine). Commonly known as “Moxy”, it is an extremely potent (4 to 6 mg p.o.) psychedelic with stimulating properties.
As my articles on chemistry are intended for the general reader, I just want to take a brief moment here to remind you that the reason I always write out the substitutive name of each compound is because it describes the actual molecule. If we know the substitutive name, we can draw the molecule, and vice-versa. Let’s briefly review this by using Moxy as an example (Figure 8), but please feel free to skip over to the next paragraph if this is old news for you by now. Starting from back we have tryptamine, so our “foundational” structure is an indole ring with an ethylchain at 3 which connects to an amine group (blue). Then we start from the front – at position 5 we have a methoxygroup (green), at N1 we have a methyl (fuschia), and then at N2 we have an isopropyl (red).
Figure 8
If both methyls are substituted by isopropyl, in the case of DMT the result is DiPT (N,N-diisopropyltryptamine), another bizarre creation of Sasha that primarily produces audial distortions. With 5-MeO-DMT the double substitution leads to 5-MeO-DiPT (5-methoxy-N,N-diisopropyltryptamine) which likely has the most endearing street name of any psychedelic – “foxy methoxy”. Note that in both cases, though making the additional isopropyl substitution retains oral activity, it decreases potency.
What’s Going On Here?
So why is it that in both the case of DMT and 5-MeO-DMT replacing a methyl with a slightly larger and more complex compound makes it impervious to deamination by MAO thereby giving it oral activity? To give us a clue we need to look at the nitrogen in the amine group – Figure 9. In order for MAO to deaminate a molecule, it needs to access the lone electron pair of electrons (blue) on the nitrogen. A change in the molecule, such as substituting functional groups, changes its 3D-conformation. In the case of substituting a methyl with an isopropyl group on the amine, it changes the molecule’s 3D shape in such a way that shields the lone pair of electrons from MAO, thus giving it oral activity.
Figure 9. Nitrogen has 7 electrons in total, and 5 valence electrons. It has one electron in each of the three 2p orbitals, which allow it to make three bonds (green), and two electrons in the 2s orbital which exists as a lone electron pair (blue).
How do we know this is the case that it’s the molecule’s 3D shape that protects the lone pair from attack by the MAO and thus allows it to retain oral activity? Earlier in this article, I said that MAO breaks down tryptamines. We then spoke about DMT and 5-MeO-DMT, but what about psilocybin and psilocin? They are naturally-occurring tryptamines, yet they are also orally active – how so? Pioneering work by Dr. David Nichols in the ‘80s using NMR spectroscopy showed that the fact that psilocin has a substitution at position 4 and not 5 (as with DMT/5-MeO-DMT) causes a critical change in the molecule’s 3D structure which ensures the compound is orally active. This study and all the profound implications for psychedelic chemistry gleamed from it will be the topic of our next article.
Afterword:
If it is your intention to consume DMT, and especially 5-MeO-DMT, orally by combining it with an MAOI please do your homework. And once you’ve done your calculations, double-check them. Terence McKenna used to quip that the only real danger with DMT is “death by astonishment”. Though that is the case for smoking it, overdoing orally-administered DMT/5-MeO-DMT can lead to serotonin shock, convulsions, and in some cases, death. The Psychedelic Ship is leaving the harbour, please don’t drop any cannonballs on the deck.
About the Author
Faan Rossouw was born and raised in Cape Town (South Africa) and currently resides in Montreal (Canada). He holds a MSc in Plant Science, and is the co-founder and Chief Strategy Officer of Indeeva Biomedical, a medical cannabis company that focuses on producing condition-specific cannabinoid therapeutics. Faan possesses theoretical expertise and practical experience in biological production systems, natural and pharmaceutical product development, phytochemistry, and psychopharmacology. Though his background is rooted in science he is most passionate about, and thrives in, the intersection of science, the humanities, and commerce. He is interested in how we can leverage the properties of the new global economy to develop superior and sustainable therapeutic solutions. In his free time he loves to practice Brazilian Jiu Jitsu, spend time in nature with his partner Robyn, or kick back in his lazy boy with a book, a cup of pu-erh tea and his cat Luna.
The ensuing series of articles are intended for the general reader that, like myself, have an appreciation for the beauty of chemistry, and/or desire to learn more about it. That being the case I am going to be pedantic throughout the articles, deconstructing technical terms and “dirty pictures”* with the assumption that you do not know what they mean. That way we can learn them as we go along. If you are already fluent in Chemistrian, it goes without saying that you are free to skip over these and peruse selectively. This first article is an introductory exploration of the tryptamine class, and will be followed by further forays into other interesting aspects related specifically to this class before I move on to the others. Enjoy.
The Three Main Classes of Psychedelics
There are three classes to which most psychedelic compounds belong – the tryptamines, phenethylamines, and ergolines (Figure 1). The tryptamines include most of the well-known naturally-occurring psychedelics, including compounds derived from entheogenic fungi (psilocybin and psilocin), DMT, 5-MeO-DMT, bufotenin, and ibogaine. Mescaline is the only common naturally-occurring phenylethylamine, yet the class includes numerous well-known synthetic compounds such as MDMA and the 2-C’s. Ergolines most notable representatives include the naturally-occurring LSA and the semi-synthetic compound that turned on a generation, LSD.
Figure 1. Notable psychedelic tryptamines include (from top right): 5-MeO-DMT and bufotenin (Bufo alvarius), psilocybin and psilocin (Psilocybe mushrooms), ibogaine (Tabernanthe iboga), DMT (Chacruna viridis), and various analogs including: 4-HO-MET (pictured), 5-MeO-DiPT, DPT, MET, and 4-AcO-DMT. Notable phenethylamines include (from top left): Mescaline (Peyote), the 2C’s (Inventor Sasha Shulgin pictured), MDMA (MAPS logo), and a wide range of analogs including: Bromo-DragonFLY (pictured), DOM, DOI, and NBOMe. Notable ergolines include (from top): LSD, LSA (Ipomoea sp), and various analogs including: AL-LAD (pictured), ALD-52, and 1-P-LSD.
Tryptamines
Psychedelics of this class are all derived from tryptamine (Figure 2), a ubiquitous endogenous ligand and agonist of the human trace amine-associated receptor 1 (TAAR1). The name tryptamine is derived from its structural similarity to l-tryptophan (Figure 3), an essential amino acid and the precursor to both serotonin and melatonin.
Figure 2. Tryptamine consists of an indole ring connected to an amine through an ethyl attached to position 3.
Figure 3. L-tryptophan
Substituted Tryptamines
Although the “template” for psychedelics tryptamines is the molecule with all the various positions presented in Figure 2, in actuality, there are limitations to how this manifests in psychedelic compounds. This is either because certain modifications are either difficult to impossible, or they lead to inactive compounds. An example of this is if something is attached to position 2 (Figure 2) the compound becomes a serotonin-2A receptor antagonist therefor losing its psychoactivity. Based on these restrictions we can simplify the template presented in Figure 2 to Figure 4, which is called the ‘substituted tryptamine’. The three main changes that synthetic chemists can make to derive psychedelic analogs is derived from this figure.
Figure 4
First, one can add side chains to either position 4 or 5, and those side chains have to contain an oxygen molecule. We can confirm this by looking at all the well-known psychedelic compounds that have side chains attached to the ring – bufotenine has a hydroxyl (OH) group at position 5, 5-MeO-DMT has a methoxy (O-CH3) at position 5, psilocin has a hydroxyl (OH) group at position 4, and psilocybin has a phosphoryloxy (OPO3H2) at position 4. All at position 4 or 5, all with an oxygen included.
The second major change that can be made is a substitution at the α-position. Chemists can methylate (add a methyl group) the alpha-position to change a non-orally active species into one with orally active. We will explore this in full detail in the next article.
The final feasible change is adding sidechains to positions N1 or N2. All five of the major naturally-occurring species we have discussed thus far possess methyls at both positions (hence “dimethyl” from which the DM in DMT is derived – more below). These methyls may be substituted with more complex alkyls, another way in which chemists can turn non-orally active tryptamines into orally active species.
Psychedelics Tryptamines
Now that we have an idea of the chemical “archetype” of tryptamine psychedelics and the possible changes chemists can make, let’s have a look at the five most well-known naturally-occurring examples: DMT, 5-MeO-DMT, bufotenin, psilocybin, and psilocin.
DMT
The substitutive name for DMT is N,N-dimethyltryptamine. One of the most magical parts of learning chemical language is that from it one can deduce what they actual molecule looks like, and vice-versa. Let’s explore that using DMT as an example. Starting from the back we have tryptamine (blue), so we know that is the foundation of our molecule – the indole ring with an ethyl in position 3 attaching to an amine. Then we have “dimethyl” (red), meaning two methyls. Okay so now we know it’s the tryptamine molecule that has two methyls added to it. And where are these two methyls? They’re both positioned on the nitrogen of the amine, hence ‘N,N’.
Figure 5
What’s interesting about N,N-dimethyltryptamine is that it forms the foundation for all four other compounds we are going to discuss. In other words, all four of them are N,N-DMT with a little something extra. We can see that because the term is contained within the substitutive name of all four other molecules. Let’s have a look.
5-MeO-DMT
The substitutive name for 5-MeO-DMT is 5-methoxy-N,N-dimethyltryptamine (Figure 6). We can see that it has the whole name of DMT in it, so when we draw it we know we can start with that molecule – a tryptamine with two methyls on the amine (red and blue). What’s left is ‘5-methoxy’, which means that at position 5 we have a methoxy (green). A methoxy is a combination of a methyl and an oxygen – hence the name.
Figure 6
Bufotenin
The substitutive name for bufotenin is 5-hydroxy-N,N-dimethyltryptamine (Figure 7). As was the case with 5-MeO-DMT, the molecule has DMT as a starting point (red and blue). But this time, instead of a methoxy at position five, we have a hydroxy, -OH (green).
Figure 7
Psilocin
The substitutive name for psilocin is 4-hydroxy-N,N-dimethyltryptamine (Figure 8). Same story, it starts with the structure of DMT (red and blue). If we compare them, we can see the psilocin is extremely similar to bufotenin, the only difference being where bufotenin had the hydroxy at position 5, here it’s at position 4 (green). In a future article we will learn why this small change is crucial to ensure that psilocin, unlike bufotenin, is an orally active species.
Figure 8
Psilocybin
The substitutive name for psilocybin is 4-phosphoryloxy-N,N-dimethyltryptamine (Figure 9). By now I’m sure you’ve grokked it – it’s a DMT molecule (red and blue) with a little something extra. As with it’s cousin psilocin, that something extra is at position 4, but here instead of a hydroxy, it’s a phosphoryloxy with the composition OPO3H2 (green).
Figure 9
All five molecules and their substitutions are reviewed in Figure 10 below.
Figure 10
In the next article, we will continue to explore psychedelic tryptamine chemistry by looking at the two changes synthetic chemists can make to DMT and 5-MeO-DMT to make them orally active.
* = Sasha Shulgin used to affectionately refer to organic molecule structures as “dirty pictures”.
About the Author
Faan Rossouw was born and raised in Cape Town (South Africa) and currently resides in Montreal (Canada). He holds a MSc in Plant Science, and is the co-founder and Chief Strategy Officer of Indeeva Biomedical, a medical cannabis company that focuses on producing condition-specific cannabinoid therapeutics. Faan possesses theoretical expertise and practical experience in biological production systems, natural and pharmaceutical product development, phytochemistry, and psychopharmacology. Though his background is rooted in science he is most passionate about, and thrives in, the intersection of science, the humanities, and commerce. He is interested in how we can leverage the properties of the new global economy to develop superior and sustainable therapeutic solutions. In his free time he loves to practice Brazilian Jiu Jitsu, spend time in nature with his partner Robyn, or kick back in his lazy boy with a book, a cup of pu-erh tea and his cat Luna.
Tim Cools joins us on Psychedelics Today to talk about his project, Psychedelic Experience, a web platform that allows individuals to post reviews about different psychedelic retreat centers and organizations. There is a psychedelic journal feature that is currently in beta-testing that allows users to write about their experiences, in hopes to further phenomenological and qualitative research in the future. As described on the site, this is a “one-stop-shop” for resources surrounding psychedelics.
About Psychedelic Experience
We aim to reduce harm and stigma associated with psychedelics by helping to best inform users, offer tools to help with integration of their experiences, and a space for communal support.
One-stop-shop web resource surrounding psychedelics
Online community by and for beginning and experienced psychonauts.
Promote safe use of psychedelics by providing scientific, responsible information.
Privacy is a top-priority. Users have full control over what is public and what isn’t.
Psychedelic experiences journal
Keep a private journal of your psychedelic experiences.
Share your experiences with your friends or the community. Reports are peer-reviewed by community to ensure quality.
Integrate your experiences by discussing them with fellow psychonauts and professional therapists.
Advanced search functionality by substance and keywords. Anonymous statistics can beused for scientific research.
Global organisations directory
A community managed global directory of organisations related to psychedelic experiences.
Connect people with honest organisations to stay updated on meetings, events and retreats.
Collect reviews by the community to create an unbiased image of the organisations.
Promote sustainable projects to help indigenous communities.
Issue warnings for organisations linked to abuse or dishonesty.
Tim lives in Belgium as a professional software developer/social entrepreneur. With his latest project, PsychedelicExperience.net, he aims to reduce harm and stigma associated with the use of psychedelics, and to support psychedelic research. Driven by some profound experiences, he hopes to make psychedelics more accessible in a safe way.
Nicholas Powers Ph.D. is a poet, journalist, and Associate Professor of English, SUNY Old Westbury. Nick joins us to talk about psychedelics, race, cultural diversity, and the future of psychedelics. Race and diversity within the psychedelic community has been a hot topic lately, and it is an important topic to continue discussing and examining. Unfortunately, the community is exclusive to people of privilege and power, which shows some concern when it comes to the future direction of this field, as it leaves out diverse ideas and beliefs from people from other cultural backgrounds and communities.
What are your thoughts on this topic? Leave us a comment below!
Show Topics
Diversity in research
Monica Williams – Diversity in the psychedelic research
The trust between diverse populations and institutional research
History of forced sterilizations and the Tuskegee syphilis study
The importance of storytelling and authentically listening to stories of people from other cultural backgrounds
Start your own psychedelic community
Psychedelics and intergenerational trauma
Including minority groups into the psychedelic community
Nicholas Powers is a poet, journalist and professor. His books, The Ground Below Zero and Theater of War, was published by Upset Press. He has written for The Indypendent, Alternet and The Village Voice. He has spoken and read all over the country. He teaches literature at SUNY Old Westbury and co-hosts the long running New York City College Poetry Slam at the Nuyorican Cafe. If you would like to work with Nick, please contact tara@upsetpress.org.
Dr. Scott Shannon joins Psychedelics Today to share his experience and insights about ketamine therapy used in conjunction with integrative psychiatry. Dr. Shannon has been working with ketamine for the past year within his psychiatry practice and has found tremendous benefit in using this medicine for particular disorders. Dr. Shannon is also part of the Fort Collins MAPS MDMA-assisted psychotherapy Phase 3 study, which is just starting up.
Show Topics/Notes
What is ketamine?
Mechanisms of action of ketamine.
What is the ketamine experience like?
Three types of administration methods – IV, IM, and oral
MDMA-assisted psychotherapy and the MAPS Phase 3 trials
Transpersonal experiences fostering change and transformation
Critiques of traditional psychiatry.
Patient with 40 years of depression became a new person no longer suffering from depression.
Electro Convulsive Therapy was almost an option, thankfully avoided.
The importance of music with ketamine therapy and other psychedelics
Scott Shannon: Cannabidiol in the Treatment of Anxiety
I decided to become a psychiatrist in high school after my first psychology class. The amazing capacity of the human mind simply astounded me. I wanted to help people by using this power of the mind. What intrigued me the most then (and now) is that our human potential remains only partially understood. I am still on that journey of discovery about our true potential. To this end, I resonate with the theme of empowerment: my greatest day is the day that you have the skills to thrive without my services.
I feel blessed with all that I have been given in my life. I have been married for almost thirty years to Suze with two wonderful children, Noah and Sarah. I love to travel the world teaching or just exploring. My nature is relentlessly creative and curious. I love to cycle, snowboard, golf, run, climb, backpack and listen to music. Seamus, my big black Lab, may accidentally show up to work with me occasionally just because he likes people so much. My spiritual life is very important to me and I have meditated for over thirty years. Helping people makes my heart sing.
As a child and adolescent psychiatrist, my current focus involves supporting young people to find wholeness and recover their full health in body, mind and spirit. Although I use prescription medication at times, I much prefer to employ natural methods like nutrition, supplements, mind-body skills, acupuncture and a shift in awareness to support the healing process. This approach represents the new field of Integrative Psychiatry. Most importantly, I employ a holistic philosophy to understand people and their struggles. The single most important thing that I have learned in my professional life is to listen well: deeply and intuitively. After this listening, much of my work involves teaching you what I have heard. I founded Wholeness Center to work in collaboration with a team of gifted healers to help you better understand your story.
College: University of Arizona
Medical School: University of Arizona
Internship: Columbia Program, Cooperstown, NY
Psychiatric Residency: Columbia Program, Cooperstown, NY
Child/Adolescent Psychiatry Fellowship: University of New Mexico
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Kyle and Joe report from the scene of the amazing Horizons: Perspectives on Psychedelics conference. We had the chance to interview attendees of Horizons NYC 2017 outside the venue on the closing day.
Horizons is a fantastic event at an amazing venue in the heart of Manhattan at the historic venue – “The Cooper Union.” The same podium on stage was shared by Abraham Lincoln, Susan B Anthony, and along with many other important historical figures.
It was an amazing event and we hope that this episode helps share some of the excitement. We talked to past guests, future guests, and also some new friends. You may recognize some of the voices 🙂 Let us know what you think of this episode and if you want to hear similar episodes to this in the future.
In the show, we speak about a lot of things from Horizons NYC including
The most interesting thing learned
The sense of community inside a conference like this
Some problems the movement has that we need to stay aware of
Issues with communicating the science of psychedelics with a wider audience
Volunteering for events for free tickets
Do you want to listen to Joe and Kyle recap their highlights of the conference and the Psymposia Microdosing event? Support us on Patreon to get exclusive access! Check out the video introduction to this episode – Here
Horizons: Perspectives on Psychedelics is an annual forum that examines the role of psychedelic drugs in science, medicine, culture, and spirituality.
In recent years, a growing community of scientists, doctors, artists, activists, seekers, and scholars have orchestrated a renaissance in psychedelic thought and practice.
Horizons brings together the brightest minds and the boldest voices of this movement to share their research, insights, and dreams for the future.
Horizons was founded in 2007 by Kevin Balktick, with Neal M. Goldsmith, Ph.D., joining as speaker curator and MC in 2008.
Horizons Media, Inc., a 501c(3) not-for-profit educational charity, is currently led by board members Kevin Balktick, Neal M. Goldsmith, Ph.D., James Vasile, Esq., and Ingmar Gorman, M.A.
Having outgrown Judson Memorial Church, its original location, Horizons is now hosted at The Cooper Union Great Hall, which has been a center for public dialogue since its founding in 1858, having hosted such illustrious speakers as Abraham Lincoln, Mark Twain, Frederick Douglass, Susan B. Anthony, and more recently, Barack Obama.
Horizons Media, Inc. conducts no other business besides the annual conference and is funded in solely by registration and concession sales. All profits go towards producing and improving the following year’s event. Its board members are not compensated.
Horizons Media, Inc. is not a political advocacy or scientific research organization, nor does it have any financial relationships with other organizations and businesses that participate as presenters or informational presences.
Sign up for our online course, “Navigating Psychedelics: Lessons on Self-Care & Integration”
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Animals are known to indulge in psychoactive compounds. Humans are not the only species who like to become intoxicated. From bees drinking to fermented nectars to reindeer of the Siberian tundra eating Amanita muscaria mushrooms, Aaron and Andras find a creative way to start a conversation about drug policy, harm reduction, and psychedelics. Aaron and Andras have started a company that produces tshirts depicting cute animals doing drugs. While this may seem like a way to promote drug use using cute animals, Aaron and Andras have a deeper meaning, which is about starting a conversation and trying to shift the cultural narrative about drug use.
If you want to get one of your own t-shirts, use the coupon code: PSYCHEDELICSTODAY25 to receive 25% off your purchase!
Cute Animals Doing Drugs was created by two friends to raise awareness around these issues, support drug policy reform, and encourage honest conversations about drugs in everyday life.
We believe individuals have the right to sovereignty over their own consciousness and that there is no reason to deny any adult the safe and beneficial use of psychoactive substances.
We believe social and political change can start from the bottom-up. Our apparel serves as a conversation-starter and a fun, unique way to show your support for an increasingly important social issue.
Cute Animals Doing Drugs is here to call attention to these issues, support psychedelic research, encourage drug policy reform, and promote cognitive liberty for all.
We also donate 10% of our pre-tax profits to MAPS, the Drug Policy Alliance, and other drug-related non-profit organizations.
Andras L is a cofounder of Cute Animals Doing Drugs Apparel, an initiative intended to help shift societal perceptions around drug use. Cute Animals builds on his previous work as a director on the board of Canadian Students for Sensible Drug Policy, where he advocated for the advancement of harm reduction and evidence-based drug policy reform. He is especially focused on reversing harmful policies and combating stigma. Andras graduated with an M.Sc. in Primary Care Research from McGill University and now researches infectious disease.
Aaron
Aaron co-founded Cute Animals Doing Drugs Apparel with Andras in the summer of 2017. He finished his BA at McGill University in 2014 and has since been traveling the world and working online. Aaron has a longstanding fascination with psychedelics, and is particularly interested in the subjective elements of psychedelics experience as well as the potential broad social impact of mainstreaming psychedelic use, especially in spiritual contexts. He writes about personal development, spirituality, and psychedelic experience at freedomandfulfilment.com.
Download Sara Gael joins us on this week’s episode. Sara is the Director of Harm Reduction at the Zendo Project. We get into some great stuff including some of Zendo’s biggest wins, how Zendo works, how to discuss harm reduction with festival organizers, and how to manage difficult experiences that arise in the Zendo. Something interesting that we learned during this talk was how law enforcement at Burning Man has really been interested in learning more about Zendo and their services, and requested Zendo to help train their staff.
Sara also shares her experience and insights working on the MAPS Phase 2 MDMA-assisted psychotherapy for PTSD trials and how she got involved in psychedelic research. We also explore how transpersonal psychology can serve as an important framework for working with psychedelic experiences.
We hope you enjoy this episode. Be sure to leave us a comment below and share this episode!
The Zendo Project
The Zendo Project is sponsored by the Multidisciplinary Association for Psychedelic Studies (MAPS). Zendo provides harm reduction services to the community and to festivals. Zendo strives to:
Reduce the number of psychiatric hospitalizations and arrests.
Create an environment where volunteers can work alongside one another to improve their harm reduction skills and receive training and feedback.
Demonstrates that safe, productive psychedelic experiences are possible without the need for law enforcement-based prohibitionist policies.
Sara Gael, M.A., Director of Harm Reduction, Zendo Project
Sara received her Master’s degree in Transpersonal Counseling Psychology at Naropa University. She began working with MAPS in 2012, coordinating psychedelic harm reduction services at festivals and events worldwide with the Zendo Project. Sara was an Intern Therapist for the recently completed MAPS Phase 2 clinical trial of MDMA-assisted psychotherapy for PTSD in Boulder, CO. She maintains a private practice as a psychotherapist specializing in trauma and non-ordinary states of consciousness. Sara believes that developing a comprehensive understanding of psychedelic medicines through research and education is essential for the health and well being of individuals, communities, and the planet.
Community is an important part of integration. One of the most difficult aspects of integration is returning to a society that doesn’t understand or support psychedelic exploration. In fact, re-entering society can feel like a stark contrast between the interconnected, transpersonal state of the psychedelic experience. Therefore, one of most important tools for successful integration is a supportive, understanding community. We encourage our Guests to connect with and build supportive communities around themselves when they return home from the event. We support them in seeking professional help if necessary.
In this episode, Kyle and Joe talk with Julie Megler from Entheogenic Research, Integration, and Education (ERIE) about psychedelics and integration. We learn about the work and mission of ERIE, and how Julie got involved/interested in psychedelics. Integration is a growing concern in the psychedelic world. We continue the conversation by having Julie on the show to learn more about her work. Leave us a comment below and let us know what you think!
ERIE is a 501(c)(3) organization dedicated to the sharing of entheogenic and transpersonal knowledge in a non-hierarchical, community based format, located in the San Francisco Bay Area.
We offer a platform for entheogenic research, integration and education. ERIE is not only a hub of integration information for entheogenic and transpersonal experiences, we also host peer integration circles to facilitate meaning-making and community building. We host monthly educational events including symposiums, forums, and conferences on varied topics surrounding entheogenic research and activism.
We are dedicated to supporting cognitive liberty by offering a learning environment to support grassroots education and outreach on the topics of integration and entheogenic potentials.
Mission
The Entheogenic Research, Integration, and Education (ERIE) mission:
1) Review and conduct research on the use of traditional plant medicines, and their modern analogs, for creativity, healing, personal growth, and spiritual exploration
2) Develop integration methods that combine new research with existing, tested practices to help people incorporate extraordinary experiences into their lives
3) Articulate a new educational paradigm that honors and draws upon the vast Indigenous knowledge of plant and fungi kingdoms, then envisions new applications of it within contemporary Western contexts
4) Create a forum for the responsible discussion of these topics.
*Psychiatric Nurse Practitioner * Trained in Somatic Experiencing * Shipibo/Vegetalista Dieta Experience*
Julie is a board certified nurse practitioner in psychiatry and family medicine. She received her Master’s of Science in Nursing from the University of Miami, Florida and post master’s certificate in psychiatry at the University of California-San Francisco. Julie maintains licenses in family medicine and psychiatry in an effort to close the gap between medical and psychiatric care, incorporating the mind/body connection for most effective treatment. She currently is in private practice in the San Francisco/Bay Area.
Her practice focuses on integrative mental health services for emotional and physical well being, as well as integration of non-ordinary states of consciousness. In addition to her clinical work, Julie is on the board of directors of ERIE (Entheogenic Research, Integration, and Education). She has presented on the topics of psychedelic risk reduction, integration, and therapeutic applications of ayahuasca at the Psychedelic Science Conference 2013 & 2017, The Women’s Visionary Congress, Detroit’s First Entheogenic Conference, and the Visionary Convergence 2015.
She has also co-authored chapters in the books Manifesting Minds and The Therapeutic Uses of Ayahuasca. As an experienced clinician, and activist for the psychedelic movement, Julie is dedicated to educating the community about safety and the therapeutic benefits of entheogens. Her particular emphasis on integration assists individuals to develop practices that bring insights from entheogenic work to daily life. You can learn more about Julie’s work at erievision.org & mindfulnp.com.
Julie has done many ayahuasca sessions and other plant work as well. This along with her medical provider practice as a nurse practitioner in the San Francisco Bay Area. She is able to speak about psychedelic integration from a unique perspective with her background. We think you will really enjoy this episode and please let us know what you think.
We discuss our recent trip to MAPS‘s Psychedelic Science 2017. It was incredibly fun and we loved being able to connect with so many with this shared interest. Many attendees are actively working to progress the case of psychedelic substances.
This was the largest psychedelic conference ever in recorded history attended by over 3000 people from 42 countries. There were discussions around ayahuasca, peyote, DMT, salvia, MDMA and many other substances. Some of the most interesting discussions were around ibogaine treating people with addiction. Turns out there are far more things that can be treated with ibogaine than simply opiate addiction.
I was very excited to discuss drug testing and harm reduction with the people from DanceSafe. We were also able to check out some really interesting technology – lights and music – that triggered some of the most intense visuals of my life. Illuminated SF put that demonstration together. It is highly recommend.
The experience of Psychedelic Science 17 was so incredible and encouraging that I cannot wait to go to the next one. Being around the movement was truly humbling and gratifying. Connecting with people from as far as Brussels, Poland and Hong Kong gave extra context to how far and wide this movement is spreading and that there is real depth in the movement.
We hope you enjoy the episode. If you want to connect with us please feel free to reach out using the contact page. If you want to stay in touch with us please join our mailing list and we will send some interesting links to you on a semi regular basis.
Links
https://www.solarwolfenergy.com/
https://maps.org
MAPS made available a tremendous amount of the talks for free on youtube. You should spend some time digging through the talks for things you may find very interesting.
Download Kevin is a science writer, graduate student researcher and aspiring clinician, harm reduction educator and substance use recovery advocate. Kyle and Joe talk to him about loads of topics including early Iboga therapies, an early Boston Ibogaine Conference, his approach to journalism and his future aspirations to do future clinical work and research.
Kevin graduated from Northeastern University in 2013 with a degree in neuroscience. As an undergraduate he completed an internship as a research assistant at Harvard Medical School working on the Phase 2 dose-response study investigating the therapeutic potential of MDMA-assisted psychotherapy for treatment of cancer related anxiety. Kevin was also one of the founders of the Northeastern chapter of Students for Sensible Drug Policy, and in 2009 the group hosted and co-sponsored the Boston Ibogaine Forum. He now lives in New York City where he is enrolled in a clinical psychology graduate program at The New School for Social Research and is pursuing a doctoral degree. Kevin has worked part-time for the Drug Policy Alliance, and also works as a writer covering topics related to psychedelic therapy, addiction, and mental health advocacy. His recent contributions include: New Scientist, Reason.com, Reset.me, Reality Sandwich, and VICE.com.
“Through my lens, so many problems in this world are driven by people acting from a reactionary place of fear and pain instead of from a place of compassion or love.” – Natalie Ginsberg
Joe and Kyle spoke with Natalie Ginsberg, Policy and Advocacy Manager at Multidisciplinary Association for Psychedelic Studies (MAPS). Natalie provides us with a summary on facets of the current state of global drug policy. She also discusses the role of racism and privilege in the psychedelic community in America. The following is an excerpt from our interview.
Edited by: Alyssa Gursky
Natalie: This past year, the UN General Assembly met for the first time in 20 years to revisit international drug treaties. A special session was called on the world drug problem. There were a series of different meetings. Vienna hosts something called the, Commission on Narcotic Drugs, every year. First, there is a big gathering in Vienna where reformers, non-reformers, and people working both from civil society on drug policy come to meet with delegates from around the world and educate them.
They tried to move drug policy from a criminalization approach to a more public health and harm reduction kind of approach.That was also pretty inspiring, and it was definitely a bit frustrating in terms of progress.We would’ve liked the outcome document to reflect much more progressive drug policy stances, but they’re very influenced by countries like Russia and China, who are really not open to the harm reduction approaches at all.
Being there, you meet so many global representatives. For example, the so-called drug czar, but he doesn’t like that name. The National Drug Coordinator of Czech Republic, for example, is really supportive of psychedelic advocacy and was able to host a lot of more innovative, progressive events. The Colombian health minister gave a really powerful speech on the floor of the United Nations (UN), basically saying the drug war… using that Einstein quote, “The definition of insanity is doing the same thing and expecting different results.” It was really epic for the minister from Columbia to be saying that to the whole UN.
Overall, for me, what was so, so valuable was really this coming together of the international reform community. Now, I work super-closely with advocates from Afghanistan, Mexico, and Nigeria. We’re much more in the same loop of what’s going on and learning about how we’re doing work in different countries is important because the UN is a really slow body that is quite reactionary, and it’s really driven forward by individual countries’ progress. The more we can support individual countries moving forward, the better chance we have for them to kind of influence the UN later.
Joe: Are there any star countries that you noticed that are really doing stuff that might not be on the radar yet?
Natalie: Bolivia actually legalized coca leaves and has done some really important work around protecting cultural indigenous plant medicines, like promoting the traditional use of these substances.
As I mentioned, the Czech Republic is really, I’d say, the leader on all things psychedelic that are not traditional, indigenous use. I would also say that even though Portugal gets a lot of attention for decriminalizing drugs, they actually weren’t the first place to do that. The Czech Republic has been decriminalizing drugs longer than Portugal, as has Spain. Portugal received a great deal of attention because they did it in response to a big opiate crisis. There’s some incredible results to show how dramatically things have shifted, but other countries have kind of taken that stance for a while, so there isn’t as much of a shift. But, they do have really promising results from not having a crazy drug war.
Spain is also really cool because of their cannabis social clubs. I was lucky to spend a few weeks in Barcelona this fall. They have these incredible spaces that basically was like a mix between coffee shop, co-worker space, maybe a little bar worked in there — just like a community space where you can go and become a club member.
Also, keep an eye on Colombia. When Ismail and I, my colleague from the policy team, were at the UN, we spoke to the Colombian health minister about MDMA therapy. He said, “Yeah, that sounds really promising.” I’m optimistic about that. They’re kind of still in the process of reforming their drug policies, and though they haven’t made as dramatic of strides as the other countries, a lot of the ministers and people doing work in Colombia are a lot more conscious. They see all of the horrible impacts of the drug war on their country and want to improve it. I think they will continue to do this work and lead some reform in South America.
Then also of course Canada is leading the way in so many ways on the drug policy front. From legalizing cannabis to really strongly supporting harm-reduction measures in response to opiate crises. I think Canada is going to be the leader on drug policy reform, and probably on a lot of other policies as well.
Joe: What else is going on in your world? Are you projected a couple years out to be working on some other interesting projects, or what do you see happening?
Natalie: I can speak about something that’s really near to my heart. In context of MDMA-assisted psychotherapy for PTSD, we are working to develop a study that would be focused on racial trauma, or PTSD from racism. We are working on another focusing on PTSD in trans communities as well. I’m really interested in talking about how social injustice can manifest in an individual as PTSD. I think that’s going to be a really important conversation.
Anti-racist work within the psychedelic community is really important. A lot of people I know are these peace-loving, hippie types who have really beautiful ideals, but don’t necessarily know the details or the reality of certain situations. I’ve heard from so many amazing, well-intentioned people in this community, “I don’t see race. All people are the same.” I think the concept is beautiful and well-intentioned, but that’s also really ignoring the experience of people of color in this country.
Unfortunately, police officers do see race. Breaking that conversation open I think is immensely important. If we’re a community that really talks about healing and working in solidarity with other social justice movements, I think that is really essential. I have seen more and more progress on that front, but I just want to definitely flag that because I think we have a lot of room to improve in that space.
Joe: What does that look like to you? How could we heal a bit? I know the research itself is very white, really kind of bland, but in terms of diversity, how do we heal that? What do you see?
Natalie: Yes, the research is quite white, unfortunately. This study focusing on racial trauma, we’re working with Dr. Monica Williams in process, but she’s a leading researcher on PTSD from racism. Working with experts and therapists of color to do outreach to their own communities. We have to work with communities and not just go in and be like, “Why don’t you come into our space?” We have to be willing to meet people where they are and really listen, and hear what different communities need from us and how we can best work with them. I think really the best way, when you ask how can we heal, it’s really we as white, psychedelic enthusiasts need to do our own work We need to do our own reading and need to start asking questions. And not questions just of people of color, and asking them to do this emotional labor for us, but maybe other white people who are doing this work who might be able to help support this process.
It’s a really long, difficult process that requires a lot of self-reflection, which is why I think there’s so much potential in our psychedelic community.We’re a community so focused on being conscious and self-reflection. All of these things that are essential to understanding racial consciousness, and the impact of racism on white people. There’s a lot of hugely harmful impacts of racism in white people, the way that sexism deeply harms men in patriarchy. I think it’s really important that we are doing some of our own work. That is a difficult process but a healing one, The more conscious we are of things, I believe that is really a way to move towards healing.
Returning war veterans are incredibly traumatized and don’t have adequate support, but yet compared to someone living in a poor, black neighborhood in Atlanta … There was a study that returning war veterans had way lower rates of PTSD than people living in this community. These people are also underdiagnosed, and don’t have the resources that even… It’s just interesting context because certainly, we dramatically need to improve our support for veterans as well, but even just stepping back and seeing that there’s so many people suffering from PTSD who have no access, or no even language to understand what they’re going through.
Kyle: Do you have any last-minute advice for students or anyone that is interested in getting involved with policy work? Because now, maybe, with this fear of the new administration taking over, we don’t really know what the climate is going to look like.
Natalie: In this political climate, it’s more important than ever to do work also outside of the so-called direct political system. Advocacy even means talking to your family or friends, creating a cultural space to support this political work is the most important thing we can do. This ties back into the conversation about the whiteness and privilege of the psychedelic space. I totally understand that there are such a span of people who are able to speak openly about this in certain contexts. You can be at risk for losing your job, your children, and certainly people of color are far higher risk for being arrested for drugs or things like that. I think that’s a really powerful part of recognizing being conscious of your privilege in this community — if you feel safe enough to speak in certain communities and speak out, that it’s super-important to do that and use that privilege to move the conversation forward. There’s so many ways for people to get involved. MAPS alone has a million volunteer opportunities, or we’ll help you host a global psychedelic dinner if you want help inviting people in your community, and having things to talk about. I encourage people also to just think of whatever they’re most passionate about and do that, and see how psychedelics can intersect with that, and how they can speak in their space.
Check out the full audio interview with Natalie Ginsberg here.
Transcribed by: Rev.com
About Natalie Ginsberg
Natalie earned her Master’s in Social Work from Columbia University in 2014, and her Bachelor’s in History from Yale University in 2011. At Columbia, Natalie served as a Policy Fellow at the Drug Policy Alliance, where she helped legalize medical marijuana in her home state of New York, and worked to end New York’s racist marijuana arrests. Natalie has also worked as a court-mandated therapist for individuals arrested for prostitution and drug-related offenses, and as a middle school guidance counselor at an NYC public school. Natalie’s clinical work with trauma survivors spurred her interest in psychedelic-assisted therapy, which she believes can ease a wide variety of both mental and physical ailments by addressing the root cause of individuals’ difficulties, rather than their symptoms. Through her work at MAPS, Natalie advocates for research to provide evidence-based alternatives to both the war on drugs and the current mental health paradigm.
The future of psychedelic research is endless. There seems to be thousands of ways to get involved, and thousands of ways to approach the topic. In this talk, Kyle and Joe talk with Thomas Roberts Ph.D. — author of the book, The Psychedelic Future of the Mind: How Entheogens Are Enhancing Cognition, Boosting Intelligence, and Raising Values. Tom shares his story with us about how he got involved in the field of psychedelic research and education. Starting in 1981, Dr. Roberts taught one of the world’s first university-cataloged psychedelic course, “Foundations of Psychedelics Studies.”
We get into a great conversation with Tom about his early days at Esalen to talking about mindapps, mindbody states, and different ways to approach psychedelic research.
Topics of Discussion:
Esalen Institute — Stanislav Grof, Holotropic Breathwork, and Maslow
Psychedelics in humanities and religion
Joseph Campbell
How the, The Hero with a Thousand Faces relates to the new archetype of the conscious explorer
The Good Friday Experiment
Huston Smith
Tips and advice about starting a psychedelic course/independent study
Thomas B. Roberts promotes the legal adaptation of psychedelics for multidisciplinary cultural uses, primarily their academic and spiritual implications. He formulated Multistate Theory (2013) coined Singlestate Fallacy, mindapps, neurosingularity, metaintelligence, and ideagen, and he named and characterized the Entheogen Reformation (2016). He is a founding member of the Multidisciplinary Association for Psychedelic Studies, a cofounder of the Council on Spiritual Practices and the International Transpersonal Association, originated the Rising Researcher conference sessions, and launched the celebration of Bicycle Day to commemorate the day that Albert Hofmann first intentionally took LSD.
AB Hamilton College, MA University of Connecticut, PhD Stanford, Roberts is an emeritus professor of educational psychology at Northern Illinois University, where he taught Foundations of Psychedelic Studies as an Honors Program Seminar. Started in 1981 and taught through 2013, it is the world’s first university-cataloged psychedelic course.
In the fall of 2006, he was a Visiting Scientist at the Johns Hopkins Medical Schools’ Behavioral Pharmacology Research Unit (Griffiths psilocybin team). His website is: www.niu.academia.edu/ThomasRoberts
It is the start of a New Year. People are saying 2016 has been pretty horrible, but 2016 has been pretty decent in regards to psychedelic science and research. We are hoping that 2017 will be a fruitful year as well.
Download Joe and Kyle talk to Shannon Clare Petitt about the current state of MDMA research and what MAPS needs to do in the next number of months with the FDA as the phase three trials become approved. A few days after the interview the New York Times reported that the phase three research was approved. Shannon’s story is great and optimistic. If you are interested in how to get a job in the psychedelic field, this is certainly an episode you’ll want to listen to. We also discuss some possible tweaks to the studies that could be done that may yield interesting results, and also why MAPS is taking the approach that they are (its the most straightforward way to push the research through the FDA). Continue reading “Shannon Clare Petitt – MAPS, Zendo and an update on MDMA’s status”
Download Kyle recently had the great opportunity to attend one module of the MAPS MDMA Therapy sessions. In this episode we talk about the experience at the workshop and about some other valuable topics as well. Let us know what you think, and please leave a review on iTunes! Continue reading “Kyle and Joe – MAPS MDMA training in New York”
In this episode Kyle and Joe speak about the recent interview they recorded with Dimitri Muganis. There were some relatively important points in the interview that needed further discussion and expansion and in this podcast we unravel some of the material. There is plenty more to unpack there.
Some of what is discussed in this episode includes.
Race
Class
Research and Treatment
When should one take priority
Democratization of the medicines
Privilege
Paying for people to participate in research
The white upper middle class bias in the research
The bias in research towards veterans
Overall there are loads of things that we discussed, and in short the real message here is that we all need to keep moving forward. There is plenty of room for growth in the field for all of us to move our agendas forward.
With endless amounts of research left to be run, we can still treat people. I’m not sure we are going to see Psychedelic medicines be used in the next 1-2 years in major hospitals outside of research, but we are going to see it in the next decade for sure.
Neal M. Goldsmith, Ph.D. is a psychotherapist specializing in psychospiritual development. He is a popular speaker on drug policy reform, spiritual maturation, and the emergence of an integral society (a six-minute clip of his talk on the “Fusion of Spirit and Science” may be found at: http://vimeo.com/7517009) and an author, most recently of Psychedelic Healing: The Promise of Entheogens for Psychotherapy and Spiritual Development.
Dr. Goldsmith has curated dozens of successful conferences and cross-disciplinary “meetings of minds” for corporations as well as the psychedelic community, including the Horizons and MAPS Psychedelic Science conferences. He is a founder of several discussion salons on integral philosophy, governance, media, postmodern science, healing, and the future of society.
Bio via Psymposia – Katherine MacLean is an academically trained research scientist and meditation practitioner with a long-standing interest in the brain, consciousness and the science of well-being. As a graduate student at the University of California, Davis, Katherine was supported by a prestigious National Science Foundation research fellowship to study the effects of intensive meditation training on concentration, emotional well-being and brain function.
As a postdoctoral fellow and faculty member at the Johns Hopkins University School of Medicine, she was one of the only scientists in the world studying psilocybin — a psychedelic chemical found naturally in certain types of mushrooms. Her groundbreaking research on psilocybin and personality change suggests that psychedelic medicines may be the key to enhancing mental health and promoting openness and creativity throughout the lifespan.
Ingmar Gorman, M.A. is a currently unlicensed doctoral student in Clinical Psychology at the New School for Social Research. His clinical work is supervised by licensed clinical psychologists at his training sites. After receiving his B.A. in Psychology from the New College of Florida. Ingmar completed a pre-doctoral externship at Bellevue’s Chemical Dependency Outpatient Program and Dual Diagnosis Inpatient Unit, where he obtained specialized training in treating people living with substance use disorders. He has also gained extensive experience treating severe mental illness at South Beach Psychiatric Hospital’s Heights Hill Outpatient Clinic. Ingmar has trained in individual and group psychotherapy at Beth Israel Medical Center’s Psychiatric Inpatient Services, as well as the Brief Psychotherapy Research Program. Ingmar uses an integrative approach to treatment utilizing Cognitive Behavioral Therapy (CBT) and Psychodynamic principles. When treating substance misuse, Ingmar draws on his extensive training with Dr. Andrew Tatarsky and Dr. Jen Talley, in Harm Reduction Psychotherapy and Mindfulness based approaches.
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Lex, Kyle and Joe discuss MAPS, Psymposia, Ibogaine, Mushrooms, Ketamine, LSD, Cannabis, and loads more. Lex is working on a book related to the supremely complex neurochemistry of cannabis.
Figure 3
Figure 14
When they measured the pKa and the Log P for both psilocin and bufotenin they found the following:
She received her Master’s of Science in Nursing from the University of Miami, Florida and post master’s certificate in psychiatry at the University of California-San Francisco. Julie maintains licenses in family medicine and psychiatry in an effort to close the gap between medical and psychiatric care, incorporating the mind/body connection for most effective treatment. She currently is in private practice in the San Francisco/Bay Area.
Kevin graduated from Northeastern University in 2013 with a degree in neuroscience. As an undergraduate he completed an internship as a research assistant at Harvard Medical School working on the Phase 2 dose-response study investigating the therapeutic potential of MDMA-assisted psychotherapy for treatment of cancer related anxiety. Kevin was also one of the founders of the Northeastern chapter of Students for Sensible Drug Policy, and in 2009 the group hosted and co-sponsored the Boston Ibogaine Forum. He now lives in New York City where he is enrolled in a clinical psychology graduate program at The New School for Social Research and is pursuing a doctoral degree. Kevin has worked part-time for the Drug Policy Alliance, and also works as a writer covering topics related to psychedelic therapy, addiction, and mental health advocacy. His recent contributions include: New Scientist, Reason.com, Reset.me, Reality Sandwich, and VICE.com.
talie earned her Master’s in Social Work from Columbia University in 2014, and her Bachelor’s in History from Yale University in 2011. At Columbia, Natalie served as a Policy Fellow at the Drug Policy Alliance, where she helped legalize medical marijuana in her home state of New York, and worked to end New York’s racist marijuana arrests. Natalie has also worked as a court-mandated therapist for individuals arrested for prostitution and drug-related offenses, and as a middle school guidance counselor at an NYC public school. Natalie’s clinical work with trauma survivors spurred her interest in psychedelic-assisted therapy, which she believes can ease a wide variety of both mental and physical ailments by addressing the root cause of individuals’ difficulties, rather than their symptoms. Through her work at MAPS, Natalie advocates for research to provide evidence-based alternatives to both the war on drugs and the current mental health paradigm.
Thomas B. Roberts promotes the legal adaptation of psychedelics for multidisciplinary cultural uses, primarily their academic and spiritual implications. He formulated Multistate Theory (2013) coined Singlestate Fallacy, mindapps, neurosingularity, metaintelligence, and ideagen, and he named and characterized the Entheogen Reformation (2016). He is a founding member of the 
