Methylethyltryptamine
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| Other names | MET; N-Methyl-N-ethyltryptamine; N,N-MET |
| Routes of administration | Oral; Vaporized/inhaled[1][2][3] |
| Drug class | Serotonergic psychedelic; Hallucinogen; Serotonin 5-HT2A and 5-HT2C receptor agonist; Serotonin releasing agent |
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| Pharmacokinetic data | |
| Onset of action | Unknown[1] |
| Duration of action | Unknown[1] |
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| Chemical and physical data | |
| Formula | C13H18N2 |
| Molar mass | 202.301 g·mol−1 |
| 3D model (JSmol) | |
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Methylethyltryptamine (MET), also known as N-methyl-N-ethyltryptamine (N,N-MET), is a psychedelic drug of the tryptamine family.[1][4] It is taken orally or via inhalation.[1][3]
The drug acts as an agonist of the serotonin 5-HT2 receptors and to a lesser extent as a serotonin releasing agent.[5] It is closely related to dimethyltryptamine (DMT) and to diethyltryptamine (DET).[6][7]
MET appears to have been first described in the literature in 1981.[8] It was only briefly mentioned in Alexander Shulgin's 1997 book TiHKAL (Tryptamines I Have Known and Loved).[1] The drug was encountered as a novel designer drug in Europe in 2014.[9]
Use and effects
[edit]MET was briefly mentioned in Alexander Shulgin's TiHKAL (Tryptamines I Have Known and Loved) and other publications, where he has stated it to be orally active as a psychedelic at doses of 80 to 100 mg.[1][4][2] Its duration, onset, and peak were not provided.[1] The free base of MET has been reported to be active as a psychedelic via vaporization at a dose of 15 mg per informal anecdotal reports.[2][3] Very little information is available on the effects of MET.[2] However, its effects have been reported to include hallucinations, euphoria, tactile enhancement, cognitive effects, pupil dilation, muscle cramps, teeth grinding, and increased heart rate and blood pressure.[2]
Interactions
[edit]Pharmacology
[edit]Pharmacodynamics
[edit]MET is a serotonin 5-HT2A and 5-HT2C receptor partial agonist.[5] It shows very weak activity as an agonist of the serotonin 5-HT1A and 5-HT2B receptors.[5] In addition to acting at the serotonin 5-HT2 receptors, MET is a serotonin releasing agent with lower potency.[5] It produces the head-twitch response, a behavioral proxy of psychedelic effects, in animals.[7][5]
Chemistry
[edit]MET, also known as N-methyl-N-ethyltryptamine, is a substituted tryptamine derivative.[1][4][5] It is closely related to N,N-dimethyltryptamine (DMT) and to other N,N-dialkylated tryptamines.[1][4][5]
Analogues
[edit]Analogues of MET besides DMT include DET, DPT, DiPT, DBT, MiPT, MBT, EPT, EiPT, and PiPT, among others.[1][4] Derivatives of MET include 4-HO-MET, 5-MeO-MET, bretisilocin (5-fluoro-MET; GM-2505), and 7-F-5-MeO-MET, among others.[1][4]
History
[edit]MET appears to have first been described in the literature by 1981.[8] It was specifically mentioned in Michael Valentine Smith's Psychedelic Chemistry.[8] Subsequently, MET was briefly described in Alexander Shulgin's TiHKAL (Tryptamines I Have Known and Loved) in 1997.[1] MET was encountered as a novel designer drug in Europe in 2014.[9]
See also
[edit]- Substituted tryptamine
- Bretisilocin (5-fluoro-MET; GM-2505)
References
[edit]- ^ a b c d e f g h i j k l m Shulgin AT, Shulgin A (1997). TiHKAL: The Continuation (1st ed.). Berkeley, CA: Transform Press. ISBN 978-0-9630096-9-2. OCLC 38503252. Retrieved 30 January 2025.
MET; positive, psychedelic; 80–100 mg [...] Lying midway between DMT and DIPT is the ethyl compound, N-ethyl-N-methyltryptamine, or MET. It can be made by adding ethyl acetate to a reaction mixture where the formamide of tryptamine (see under NMT) has been reduced to NMT but there is still a goodly excess of hydride still remaining. The free base, as an oil, shows oral activity in the eighty to one hundred milligram range, so going from a methyl to an ethyl does indeed protect the compound from total enzymatic annihilation when taken orally.
- ^ a b c d e Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA (December 2020). "Toxicology and Analysis of Psychoactive Tryptamines". Int J Mol Sci. 21 (23): 9279. doi:10.3390/ijms21239279. PMC 7730282. PMID 33291798.
N-methyl-N-ethyltryptamine (MET): MET is structurally related to DMT but little scientific information is available on its pharmacology or toxicity in humans. Inhalation of 15 mg freebase MET or 80–100 mg oral freebase MET produce effects [73]. Anecdotal reports describe the most common physical and psychological effects as physical euphoria, tactile enhancement, increased heart rate and blood pressure, muscle cramps, teeth grinding, pupil dilation, hallucinations and cognitive effects [73].
- ^ a b c "That's okay, you're good" MET trip report - The Vaults of Erowid
- ^ a b c d e f Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025.
Table 3.19 N,N-Dialkyl homologues of DMT: [...] R1: Me-. R2: Et-. common name: methyl-ethyltryptamine. code: MET. potency: mg: 80–100. x-DMT: 1.
- ^ a b c d e f g US 11440879, Kruegel AC, "Methods of treating mood disorders", issued 13 September 2022, assigned to Gilgamesh Pharmaceuticals Inc.
- ^ Schifano F, Orsolini L, Papanti D, Corkery J (2016). "NPS: Medical Consequences Associated with Their Intake". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. Vol. 32. pp. 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. PMID 27272067.
- ^ a b Halberstadt AL, Geyer MA (2018). "Effect of Hallucinogens on Unconditioned Behavior". Behavioral Neurobiology of Psychedelic Drugs. Curr Top Behav Neurosci. Vol. 36. pp. 159–199. doi:10.1007/7854_2016_466. ISBN 978-3-662-55878-2. PMC 5787039. PMID 28224459.
The HTR has also been observed in rodents treated with N-methyl-N-ethyltryptamine (MET), N,N-diethyltryptamine (DET), N,N-dipropyltryptamine (DPT), N,N-diisopropyltryptamine (DIPT), and N,N-diallyltryptamine (DALT) (Fantegrossi et al. 2008; Smith et al. 2014; Carbonaro et al. 2015; Halberstadt and Klein, unpublished observations).
- ^ a b c Smith MV (1981). Psychedelic Chemistry. Loompanics Unlimited. ISBN 978-0-915179-10-7. Retrieved 20 February 2025.
- ^ a b European Monitoring Centre for Drugs and Drug Addiction., European Police Office. (2015). EMCDDA–Europol 2014 annual report on the implementation of Council Decision 2005/387/JHA: in accordance with Article 10 of Council Decision 2005/387/JHA on the information exchange, risk assessment and control of new psychoactive substances: implementation reports. Publications Office. doi:10.2810/112317. ISBN 978-92-9168-821-0. Retrieved 20 February 2025.