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Routes of administration | Smoked, Insufflated, Oral (with a MAOI) |
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ECHA InfoCard | 100.012.558 |
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Formula | C13H18N2O |
Molar mass | 218.300 g·mol−1 |
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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]
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]
When smoked, the duration of effects can be as little as ten minutes; when insufflated, up to two hours. 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 ]
It has anti-anxiety and anti-depressant effects. [7] [8]
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? ]
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]
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]
In addition to naturally-occurring sources, 5-MeO-DMT can be produced synthetically. [23] [24]
Family | Animals |
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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]
Family | Fungi |
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Amanitaceae | Amanita citrina , [29] Amanita porphyria [29] |
As a structural analog of N,N-dimethyltryptamine (DMT), 5-MeO-DMT is a Schedule 9 prohibited substance under the Poisons Standard. [36]
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.
As of October 2015, 5-MeO-DMT is a controlled substance in China. [38]
As of 2001 5-MeO-DMT is listed as a controlled substance. Attachement I BtMG. BGBl. I 2001, 1180 - 1186;
The Swedish government 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]
5-MeO-DMT has been controlled in Turkey since December 2013. [40]
5-MeO-DMT was made a Schedule I controlled substance in January 2011. [41]
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.
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.
5-Methoxy-N,N-diisopropyltryptamine is a psychedelic tryptamine and the methoxy derivative of diisopropyltryptamine (DiPT).
Psilocin, also known as 4-hydroxy-N,N-dimethyltryptamine (4-OH-DMT), is a substituted tryptamine alkaloid and a serotonergic psychedelic. 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 serotonin 5-HT2A receptors, psilocin's psychedelic effects are directly correlated with the drug's occupancy at these receptor sites. The subjective mind-altering effects of psilocin are highly variable and are said to resemble those of lysergic acid diethylamide (LSD) and N,N-dimethyltryptamine (DMT).
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.
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.
Bufotoxins are a family of toxic steroid lactones or substituted tryptamines of which some are toxic. They occur in the parotoid glands, skin, and poison of many toads and other amphibians, and in some plants and mushrooms. The exact composition varies greatly with the specific source of the toxin.
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.
5-MeO-DALT or N,N-diallyl-5-methoxytryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin.
5-MeO-DET or 5-methoxy-N,N-diethyltryptamine is a hallucinogenic tryptamine.
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.
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.
5-MeO-DPT, is a psychedelic and entheogenic designer drug.
Psilacetin, also known as O-acetylpsilocin or as 4-acetoxy-N,N-dimethyltryptamine, is a semi-synthetic serotonergic psychedelic 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.
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.
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.
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 synthesized as prodrugs of psilocin for medical applications.
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.
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.