5-methoxy-N,N-dimethyltryptamine
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5-MeO-DMT (5-methoxy-''N'',''N''-dimethyltryptamine) or O-methyl-bufotenin is a
psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science of ...
of the tryptamine class. It is found in a wide variety of plant species, and also is secreted by the glands of at least one toad species, the Colorado River toad. Like its close relatives
DMT ''N'',''N''-Dimethyltryptamine (DMT or ''N'',''N''-DMT, SPL026) is a substituted tryptamine that occurs in many plants and animals, including human beings, and which is both a derivative and a structural analog of tryptamine. It is used as a ...
and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include Five-methoxy, The power, and Toad venom.


Chemistry

5-MeO-DMT was first synthesized in 1936, and in 1959 it was isolated as one of the
psychoactive A psychoactive drug, psychopharmaceutical, psychoactive agent or psychotropic drug is a chemical substance, that changes functions of the nervous system, and results in alterations in perception, mood, consciousness, cognition or behavior. Th ...
ingredients of ''
Anadenanthera peregrina ''Anadenanthera peregrina'', also known as yopo, jopo, cohoba, parica or calcium tree, is a perennial tree of the genus ''Anadenanthera'' native to the Caribbean and South America. It grows up to tall, and has a horny bark. Its flowers grow ...
'' seeds used in preparing
Yopo ''Anadenanthera peregrina'', also known as yopo, jopo, cohoba, parica or calcium tree, is a perennial tree of the genus ''Anadenanthera'' native to the Caribbean and South America. It grows up to tall, and has a horny bark. Its flowers grow ...
snuff. It was once believed to be a major component of the psychoactive effects of the snuff, although this has recently been shown to be unlikely, due to the limited or sometimes even non-existent quantity contained within the seeds, which instead achieve their psychoactivity from the ''O''- demethylated
metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...
of 5-MeO-DMT, bufotenin. It is
metabolized Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...
mainly by CYP2D6.


Effects

Depending on whether smoked or insufflated, total duration of experience can last between 10 minutes for the former, or up to 2 hours for the latter. Effects vary and can range from radical perspective shifting and perception of new insights, euphoria, immersive experiences, dissociation and non-responsiveness, sensual/erotic enhancement, to dysphoria, fear, terror, and panic.


Uses

It has anti-anxiety and anti-depressant effects.


Religious use

The Church of the Tree of Life, founded in California in 1971 by John Mann but now defunct, declared the use of 5-MeO-DMT to be a
sacrament A sacrament is a Christianity, Christian Rite (Christianity), rite that is recognized as being particularly important and significant. There are various views on the existence and meaning of such rites. Many Christians consider the sacraments ...
. From approximately 1971 to the late 1980s, 5-MeO-DMT was discreetly available to its members. Between 1970 and 1990, smoking of 5-MeO-DMT on
parsley Parsley, or garden parsley (''Petroselinum crispum'') is a species of flowering plant in the family Apiaceae that is native to the central and eastern Mediterranean region (Sardinia, Lebanon, Israel, Cyprus, Turkey, southern Italy, Greece, Por ...
was probably one of the two most common forms of ingestion in the United States.


Pharmacology

5-MeO-DMT is a methoxylated derivative of
DMT ''N'',''N''-Dimethyltryptamine (DMT or ''N'',''N''-DMT, SPL026) is a substituted tryptamine that occurs in many plants and animals, including human beings, and which is both a derivative and a structural analog of tryptamine. It is used as a ...
. While most common psychedelics are believed to primarily elicit psychological effects through
agonism Agonism (from Greek ἀγών '' agon'', "struggle") is a political and social theory that emphasizes the potentially positive aspects of certain forms of conflict. It accepts a permanent place for such conflict in the political sphere, but seeks ...
of serotonin 5-HT2A receptors, 5-MeO-DMT shows 1000-fold greater
affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Partn ...
for 5-HT1A over 5-HT2A; further, its activity in rats was attenuated with the 5-HT1A selective antagonist WAY-100635 while 5-HT2A selective antagonist
volinanserin Volinanserin ( INN) (developmental code name MDL-100,907) is a highly selective 5-HT2A receptor antagonist that is frequently used in scientific research to investigate the function of the 5-HT2A receptor. It was also tested in clinical trials ...
failed to demonstrate any change. Additional mechanisms of action such as
inhibition Inhibitor or inhibition may refer to: In biology * Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity * Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotra ...
of monoamine reuptake may be involved. A 2019 European study with 42 volunteers showed that a single inhalation produced sustained enhancement of
satisfaction with life Life satisfaction is a measure of a person's Quality of life, well-being, assessed in terms of mood, relationship satisfaction, achieved goals, self-concepts, and self-perceived ability to cope with life. Life satisfaction involves a favorable Att ...
, and easing of anxiety, depression, and post-traumatic stress disorder (PTSD). In 2018, researchers also discovered that 5-MeO-DMT is a
psychoplastogen Psychoplastogens are a group of small molecule drugs that produce rapid and sustained effects on neuronal structure and function, intended to manifest therapeutic benefit after a single administration. Several existing psychoplastogens have been ...
, which refers to a compound capable of promoting rapid and sustained neural plasticity.


Research


Neurogenesis

A 2018 study demonstrated that a single dose of 5-MeO-DMT induced
neurogenesis Neurogenesis is the process by which nervous system cells, the neurons, are produced by neural stem cells (NSCs). It occurs in all species of animals except the porifera (sponges) and placozoans. Types of NSCs include neuroepithelial cells (NECs) ...
in mice.


Clinical Development

5-MeO-DMT is being developed and evaluated for potential therapeutic effects in patients with Treatment-Resistant Depression (TRD). Biopharmaceutical company GH Research has sponsored a completed phase 1 study in healthy volunteers and phase 1/2 study in TRD patients where 87.5% of patients with TRD were brought into remission on day 7 in the phase 2 part of the study. GH Research is currently planning a phase 2b study in TRD patients and have received approval for studies in patients with bipolar II disorder and a current depressive episode and patients with postpartum depression. Beckley Psytech in collaboration with King's College London research the safety and tolerability of intranasal 5-MeO-DMT in healthy subjects, in a phase 1 study. Beckley Psytech CEO Cosmo Feilding-Mellen sees a potential in the short-acting nature of 5-MeO-DMT compared to psilocybin: "Requiring one or two therapists to sit in a room with a single patient for the entire duration of an MDMA or psilocybin experience, which is essentially a whole working day, is probably going to be very resource-intensive and expensive. There is already a global shortage of psychotherapists, and this poses a potential bottleneck to patient access in the future."


Sources

5-MeO-DMT can be produced synthetically.


Legal status


China

As of October 2015, 5-MeO-DMT is a controlled substance in
China China, officially the People's Republic of China (PRC), is a country in East Asia. It is the world's most populous country, with a population exceeding 1.4 billion, slightly ahead of India. China spans the equivalent of five time zones and ...
.


Australia

As a structural analog of ''N'',''N''-dimethyltryptamine (DMT), 5-MeO-DMT is a Schedule 9 prohibited substance under the Poisons Standard.


Sweden

''Sveriges riksdags'' health ministry ''Statens folkhälsoinstitut'' classified 5-MeO-DMT, listed as 5-metoxi-N,N-dimetyltryptamin (5-MeO-DMT) in their regulation SFS 2004:696, as "health hazard" under the act ''Lagen om förbud mot vissa hälsofarliga varor'' (translated ''Act on the Prohibition of Certain Goods Dangerous to Health'') in October 2004, making it illegal to sell or possess.


Germany

As of 2001 5-MeO-DMT is listed as a controlled substance. Attachement I BtMG. BGBl. I 2001, 1180 - 1186;


Turkey

5-MeO-DMT has been controlled in Turkey since December 2013.


United States

5-MeO-DMT was made a Schedule I controlled substance in January 2011.


Possibility of Unknown Active Species

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamph ...
in his book TiHKAL experimented with different dosing regiments and forms of delivery for 5-MeO-DMT including: smoking, oral, and even IV injection. In his commentary on the bottom of the entry for 5-MeO-DMT he noted that the very potent effects attributed to this drug only seemed to exist when smoking it. Moreover, this curious feature was not found among most of the other related drugs including the parent compound DMT itself which can produce roughly equivalent experiences across all means of administration. The non-effect of Shulgin's oral dosing of 5-MeO-DMT can be dismissed as the result of monoamine oxidases degrading the drug in the digestive tract. This, however, does not explain why his IV dosing produced both much milder and rather different effects then his smoking regimen did. As a result, Shulgin speculates that there is a possibility that the active species actually responsible for the intense experience attributed to 5MeO-DMT may actually be an as-of-yet unknown compound that forms in the smoke of 5-MeO-DMT. A related possibility is that smoking 5MeO-DMT produces some unknown key enhancer compound whose co-administration with 5MeO-DMT mixed in the smoke is critical for the "traditional" 5MeO-DMT experience.


See also

*
4-MeO-DMT 4-MeO-DMT (4-methoxy-''N'',''N''-dimethyltryptamine) is a tryptamine derivative which has some central activity in animal tests similar to that of related psychedelic tryptamine drugs, although with significantly lower potency than either 5-MeO ...
* 5-MeO-AMT *
5-MeO-DIPT 5-Methoxy-''N'',''N''-diisopropyltryptamine (5-MeO-DiPT, sometimes called Foxy Methoxy or simply Foxy) is a psychedelic tryptamine and the methoxy derivative of diisopropyltryptamine (DiPT). Pharmacology The mechanism that produces the purport ...
*
5-EtO-DMT 5-Ethoxy-DMT (5-ethoxy-''N'',''N''-dimethyltryptamine, 5-EtO-DMT, ''O''-ethylbufotenine) is a tryptamine derivative which has been previously synthesized as a chemical intermediate, but has not been studied to determine its pharmacology. The wid ...
*
5-MeO-MET 5-MeO-MET (5-Methoxy-N-methyl-N-ethyltryptamine) is a relatively rare designer drug from the substituted tryptamine family, related to compounds such as N-methyl-N-ethyltryptamine and 5-MeO-DMT. It was first synthesised in the 1960s and was stud ...
* Dimemebfe *
EMDT 2-Ethyl-5-methoxy-''N'',''N''-dimethyltryptamine (EMDT) is a tryptamine derivative which is used in scientific research. It acts as a selective 5-HT6 receptor agonist, with a Ki of 16 nM, and was one of the first selective agonists developed ...
*
Hamilton's Pharmacopeia ''Hamilton's Pharmacopeia'' is an American docuseries, which premiered on Viceland on October 26, 2016. The show follows Hamilton Morris as he explores the history, chemistry and social impact of psychoactive substances. It chronicles Morris' ...
*
List of entheogens This page lists substances used in ritualistic context. Psychoactive use Entheogens This is a list of species and genera that are used as entheogens or are used in an entheogenic concoction (such as ayahuasca). For ritualistic use they may be cl ...
*
Psychoplastogen Psychoplastogens are a group of small molecule drugs that produce rapid and sustained effects on neuronal structure and function, intended to manifest therapeutic benefit after a single administration. Several existing psychoplastogens have been ...


References


External links


TiHKAL #38 on Erowid
an
Erowid's 5-MeO-DMT Vault

5-MeO-DMT Entry in TiHKAL • info

Free Harm Reduction Courses

5-MeO-DMT Harm Reduction Forums
{{DEFAULTSORT:MeO-DMT, 5- Ayahuasca Entheogens Psychedelic tryptamines Tryptamine alkaloids Indole ethers at the benzene ring Serotonin receptor agonists Psychedelic drugs Designer drugs Dimethylamino compounds