5-MeO-DMT

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5-MeO-DMT
5-MeO-DMT.svg
5-MeO-DMT-3d-sticks.png
Clinical data
Routes of
administration 		Smoked, Insufflated, Oral (with a MAOI)
Legal status
Legal status
Identifiers
  • 2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.012.558 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C13H18N2O
Molar mass 218.300 g·mol−1
3D model (JSmol)
  • COc2ccc1[nH]cc(CCN(C)C)c1c2
  • InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3 Yes check.svgY
  • Key:ZSTKHSQDNIGFLM-UHFFFAOYSA-N Yes check.svgY
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Colorado River toad Bufo alvarius1.jpg
Colorado River toad

5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine) or O-methyl-bufotenin is a psychedelic 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 and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. [2] Slang terms include Five-methoxy, the power, bufo, and toad venom. [3]

Contents

Chemistry

5-MeO-DMT was first synthesized in 1936, and in 1959 it was isolated as one of the psychoactive ingredients of Anadenanthera peregrina seeds used in preparing Yopo 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 of 5-MeO-DMT, bufotenin. [4] [5] It is metabolized mainly by CYP2D6. [5]

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, panic, and ego death. [6] [ better source needed ]

Uses

It has anti-anxiety and anti-depressant effects. [7] [8]

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. From approximately 1971 to the late 1980s, 5-MeO-DMT was discreetly available to its members. [9] [10] Between 1970 and 1990, smoking of 5-MeO-DMT on parsley was probably one of the two most common forms of ingestion in the United States. [10] [ unreliable source? ]

Pharmacology

5-MeO-DMT is a methoxylated derivative of DMT. While most common psychedelics are believed to primarily elicit psychological effects through agonism of serotonin 5-HT2A receptors, 5-MeO-DMT shows 1000-fold greater affinity for 5-HT1A over 5-HT2A; [11] In line with its affinity for 5-HT1A receptors, 5-MeO-DMT is extremely potent at suppressing the firing of dorsal raphe 5-HT neurons. [12] Further, its activity in rats was attenuated with the 5-HT1A selective antagonist WAY-100635 while 5-HT2A selective antagonist volinanserin failed to demonstrate any change. [13] Additional mechanisms of action such as inhibition of monoamine reuptake may be involved. [14] A 2019 European study with 42 volunteers showed that a single inhalation produced sustained enhancement of satisfaction with life, and easing of anxiety, depression, and post-traumatic stress disorder (PTSD). [15] A 2018 study demonstrated that a single dose of 5-MeO-DMT induced neurogenesis in mice. [16]

Clinical development

5-MeO-DMT is being developed and evaluated for potential therapeutic effects in patients with Treatment-Resistant Depression (TRD). [17] Biopharmaceutical company GH Research has sponsored a completed phase 1 study in healthy volunteers [18] 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. [19] 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. [20]

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. [21] 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." [22]

Sources

In addition to naturally-occurring sources, 5-MeO-DMT can be produced synthetically. [23] [24]

Plant sources
FamilyPlants
Rutaceae Dictyoloma incanescens , [25] Limonia acidissima , [26] Melicope leptococca [27]
Fabaceae Anadenanthera peregrina , [28] Acacia auriculiformis , [28] Acacia victoriae , [28] Desmodium gangeticum , [28] Lespedeza bicolor , [27] [26] Mimosa pudica, [28] Mucuna pruriens , [26] [27] Phyllodium pulchellum [26] [27]
Poaceae Phalaris tuberosa [28]
Malpighiaceae Diplopterys cabrerana [29]
Cactaceae Echinocereus salm-dyckianus , [26] Echinocereus triglochidiatus [26]
Myristicaceae Horsfieldia superba , [26] Iryanthera macrophylla , [26] Osteophloeum platyspermum , [29] Virola theiodora , [26] V. calophylla , [29] V. multinervia , [29] V. peruviana , [29] V. rufula , [29] V. venosa [29]
Animal Sources
FamilyAnimals
Bufonidae Colorado River toad (Incilius alvarius) [30] [15] [27]

The Colorado River toad is a noted animal source of 5-MeO-DMT. First described in 1983 by Ken Nelson (writing under the pseudonym of Albert Most), smoking the parotoid secretions of the animal produces a powerful and short-lived psychedelic experience. [31] The smoking of I. alvarius secretions should not be confused with the urban legend of toad licking. [32] Since 1983, the animal has since became a popular source of 5-MeO-DMT for recreational or spiritual purposes. [33] Unfortunately, this increased demand and use of the toads as a source of 5-MeO-DMT has put strain on their populations. [34] Concerned with the ecological impacts of the growing use of I. alvarius secretions as a source of 5-MeO-DMT, Ken Nelson would later advocate for the use of synthetic 5-MeO-DMT and conservation of the Colorado River Toad. [35]

Fungal Sources
FamilyFungi
Amanitaceae Amanita citrina , [29] Amanita porphyria [29]

Australia

As a structural analog of N,N-dimethyltryptamine (DMT), 5-MeO-DMT is a Schedule 9 prohibited substance under the Poisons Standard. [36]

Canada

5-MeO-DMT is legal for personal use and possession in Canada, [37] though sale, distribution, and other activities involving the substance are illegal under Canadian federal law.

China

As of October 2015, 5-MeO-DMT is a controlled substance in China. [38]

Germany

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

Sweden

Sveriges Grodminister 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. [39]

Turkey

5-MeO-DMT has been controlled in Turkey since December 2013. [40]

United States

5-MeO-DMT was made a Schedule I controlled substance in January 2011. [41]

See also

Related Research Articles

<i>N</i>,<i>N</i>-Dimethyltryptamine Chemical compound

N,N-Dimethyltryptamine is a substituted tryptamine that occurs in many plants and animals, including humans, and which is both a derivative and a structural analog of tryptamine. DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.

<span class="mw-page-title-main">Dipropyltryptamine</span> Chemical compound

N,N-Dipropyltryptamine (DPT) is a psychedelic entheogen belonging to the tryptamine family. Use as a designer drug has been documented by law enforcement officials since as early as 1968. However, potential therapeutic use was not investigated until the 1970s. It is found either as a crystalline hydrochloride salt or as an oily or crystalline base. It has not been found to occur endogenously. It is a close structural homologue of dimethyltryptamine and diethyltryptamine.

<span class="mw-page-title-main">5-MeO-DiPT</span> Psychedelic tryptamine

5-Methoxy-N,N-diisopropyltryptamine is a psychedelic tryptamine and the methoxy derivative of diisopropyltryptamine (DiPT).

<span class="mw-page-title-main">Psilocin</span> Chemical compound

Psilocin is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. Acting on the 5-HT2A receptors, psilocin modulates the production and reuptake of serotonin. The mind-altering effects of psilocin are highly variable and subjective and resemble those of LSD and DMT.

<span class="mw-page-title-main">DiPT</span> Chemical compound

Diisopropyltryptamine is a psychedelic hallucinogenic drug of the tryptamine family that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily aural.

<span class="mw-page-title-main">Bufotenin</span> Psychedelic drug found in toads, mushrooms and plants

Bufotenin is a tryptamine derivative, more specifically, a DMT analog, related to the neurotransmitter serotonin. It is an alkaloid found in some species of mushrooms, plants and toads, especially the skin.

<span class="mw-page-title-main">5-MeO-MiPT</span> Chemical compound

5-MeO-MiPT is a psychedelic and hallucinogenic drug, used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT. It is commonly used as a "substitute" for 5-MeO-DiPT because of the very similar structure and effects.

<span class="mw-page-title-main">5-MeO-DALT</span> Chemical compound

5-MeO-DALT or N,N-diallyl-5-methoxytryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin.

<span class="mw-page-title-main">5-MeO-DET</span> Chemical compound

5-MeO-DET or 5-methoxy-N,N-diethyltryptamine is a hallucinogenic tryptamine.

<span class="mw-page-title-main">Colorado River toad</span> Species of amphibian

The Colorado River toad, also known as the Sonoran Desert toad, is a toad species found in northwestern Mexico and the southwestern United States. It is well known for its ability to exude toxins from glands within its skin that have psychoactive properties.

<span class="mw-page-title-main">4-HO-MiPT</span> Chemical compound

4-HO-MiPT is a synthetic substituted aromatic compound and a lesser-known psychedelic tryptamine. It is thought to be a serotonergic psychedelic, similar to magic mushrooms, LSD and mescaline. Its molecular structure and pharmacological effects somewhat resemble those of the tryptamine psilocin, which is the primary psychoactive chemical in magic mushrooms.

<span class="mw-page-title-main">5-MeO-DPT</span> Chemical compound

5-MeO-DPT, is a psychedelic and entheogenic designer drug.

<span class="mw-page-title-main">Indole alkaloid</span> Class of alkaloids

Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.

<i>O</i>-Acetylpsilocin Chemical compound

O-Acetylpsilocin is a semi-synthetic psychoactive drug that has been suggested by David Nichols to be a potentially useful alternative to psilocybin for pharmacological studies, as they are both believed to be prodrugs of psilocin. However, some users report that O-acetylpsilocin's subjective effects differ from those of psilocybin and psilocin. Additionally, some users prefer 4-AcO-DMT to natural psilocybin mushrooms due to feeling fewer adverse side effects such as nausea and heavy body load, which are more frequently reported in experiences involving natural mushrooms. It is the acetylated form of the psilocybin mushroom alkaloid psilocin and is a lower homolog of 4-AcO-MET, 4-AcO-DET, 4-AcO-MiPT and 4-AcO-DiPT.

<span class="mw-page-title-main">5-Fluoro-DMT</span> Chemical compound

5-Fluoro-N,N-dimethyltryptamine is a tryptamine derivative related to compounds such as 5-bromo-DMT and 5-MeO-DMT. Fluorination of psychedelic tryptamines either reduces or has little effect on 5-HT2A/C receptor affinity or intrinsic activity, although 6-fluoro-DET is inactive as a psychedelic despite acting as a 5-HT2A agonist, while 4-fluoro-5-methoxy-DMT is a much stronger agonist at 5-HT1A than 5-HT2A.

<span class="mw-page-title-main">Dimemebfe</span> Chemical compound

Dimemebfe (5-MeO-BFE) is a recreational drug and research chemical. It acts as an agonist for the 5-HT1A and 5-HT2 family of serotonin receptors. It is related in structure to the psychedelic tryptamine derivative 5-MeO-DMT, but with the indole nitrogen replaced by oxygen, making dimemebfe a benzofuran derivative. It is several times less potent as a serotonin agonist than 5-MeO-DMT and with relatively more activity at 5-HT1A, but still shows strongest effects at the 5-HT2 family of receptors.

<span class="mw-page-title-main">4-PrO-DMT</span> Chemical compound

4-Propionoxy-N,N-dimethyltryptamine is a synthetic psychedelic drug from the tryptamine family with psychedelic effects, and is believed to act as a prodrug for psilocin. It produces a head-twitch response in mice. It has been sold online as a designer drug since May 2019. It was first identified as a new psychoactive substance in Sweden, in July 2019. A number of related derivatives have been synthesised as prodrugs of psilocin for medical applications.

<span class="mw-page-title-main">5-MeO-MET</span> Chemical compound

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 studied to a limited extent, but was first identified on the illicit market in June 2012 in Sweden. It was made illegal in Norway in 2013, and is controlled under analogue provisions in numerous other jurisdictions.

<i>O</i>-Acetylbufotenine Chemical compound

O-Acetylbufotenine is a tryptamine derivative which produces psychedelic-appropriate responding in animal studies. It is an acylated derivative of bufotenine with higher lipophilicity that allows it to cross the blood–brain barrier; once inside the brain, it is metabolised to bufotenine. It also acts directly as an agonist at 5-HT1A and 5-HT1D receptors.

References

  1. ↑ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
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  3. ↑ "Ultimate Guide to 5-MeO-DMT - Experience, Benefits, & Side Effects". 29 June 2020.
  4. ↑ Ott J (July–September 2001). "Pharmañopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine". Journal of Psychoactive Drugs. 33 (3): 273–281. doi:10.1080/02791072.2001.10400574. PMID   11718320. S2CID   5877023.
  5. 1 2 Shen HW, Jiang XL, Winter JC, Yu AM (October 2010). "Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions". Current Drug Metabolism. 11 (8): 659–666. doi:10.2174/138920010794233495. PMC   3028383 . PMID   20942780.
  6. ↑ "5-MeO-DMT Effects by Erowid". Erowid.org. Retrieved 2021-07-30.
  7. ↑ Davis AK, So S, Lancelotta R, Barsuglia JP, Griffiths RR (March 2019). "5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) used in a naturalistic group setting is associated with unintended improvements in depression and anxiety". The American Journal of Drug and Alcohol Abuse. 45 (2): 161–169. doi:10.1080/00952990.2018.1545024. PMC   6430661 . PMID   30822141.
  8. ↑ Davis AK, Barsuglia JP, Lancelotta R, Grant RM, Renn E (July 2018). "The epidemiology of 5-methoxy- N, N-dimethyltryptamine (5-MeO-DMT) use: Benefits, consequences, patterns of use, subjective effects, and reasons for consumption". Journal of Psychopharmacology. 32 (7): 779–792. doi:10.1177/0269881118769063. PMC   6248886 . PMID   29708042.
  9. ↑ Mann J, Gottlieb A (2015) [First published 1970]. "back cover". The Book of Sacraments: Ritual Use of Magical Plants. Ronin Publishing. ISBN   978-1-57951-210-1.
  10. 1 2 "5-MeO-DMT Timeline". Erowid.
  11. ↑ Ray TS (February 2010). "Psychedelics and the human receptorome". PLOS ONE. 5 (2): e9019. Bibcode:2010PLoSO...5.9019R. doi: 10.1371/journal.pone.0009019 . PMC   2814854 . PMID   20126400.
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  14. ↑ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID   17223101.
  15. 1 2 Uthaug MV, Lancelotta R, van Oorsouw K, Kuypers KP, Mason N, Rak J, et al. (September 2019). "A single inhalation of vapor from dried toad secretion containing 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) in a naturalistic setting is related to sustained enhancement of satisfaction with life, mindfulness-related capacities, and a decrement of psychopathological symptoms". Psychopharmacology. 236 (9): 2653–2666. doi: 10.1007/s00213-019-05236-w . PMC   6695371 . PMID   30982127.
  16. ↑ Lima da Cruz RV, Moulin TC, Petiz LL, Leão RN (2018). "A Single Dose of 5-MeO-DMT Stimulates Cell Proliferation, Neuronal Survivability, Morphological and Functional Changes in Adult Mice Ventral Dentate Gyrus". Frontiers in Molecular Neuroscience. 11: 312. doi: 10.3389/fnmol.2018.00312 . PMC   6131656 . PMID   30233313.
  17. ↑ "Home | GH Research". GH Research Limited.
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  19. ↑ GH Research PLC (2021-12-06). "GH Research Announces Successful Outcome of the Phase 2 part of its Phase 1/2 Clinical Trial of GH001 in Treatment-Resistant Depression". GlobeNewswire News Room (Press release). Retrieved 2022-10-07.
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  29. 1 2 3 4 5 6 7 8 9 Khan JI, Kennedy TJ, Christian JR DR (2011). Basic Principles of Forensic Chemistry. Springer Science & Business Media. p. 195. ISBN   978-1-934115-06-0.
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  31. ↑ Nelson K. "Bufo alvarius: The Psychedelic Toad of the Sonoran Desert". Erowid . Illustrated by Gail Patterson. Retrieved October 20, 2023.
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  33. ↑ Romero S (2022-03-20). "Demand for This Toad's Psychedelic Toxin Is Booming. Some Warn That's Bad for the Toad". The New York Times. ISSN   0362-4331 . Retrieved 2023-10-20.
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  36. ↑ "Poisons Standard July 2016". Federal Register of Legislation. 24 June 2016.
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  38. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  39. ↑ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor" (PDF). Svensk författningssamling (in Swedish). 7 September 2004.
  40. ↑ "Turkish Law" (PDF). Resmi Gazete. 16 December 2013.
  41. ↑ Drug Enforcement Administration (DEA), Department of Justice (December 2010). "Schedules of controlled substances: placement of 5-methoxy-N,N-dimethyltryptamine into Schedule I of the Controlled Substances Act. Final rule" (PDF). Federal Register. 75 (243): 79296–79300. PMID   21171485.
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