Chemistry:Methylethyltryptamine

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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][2] 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.[4] It is closely related to dimethyltryptamine (DMT) and to diethyltryptamine (DET).[5][6]

MET appears to have been first described in the literature in 1981.[7] 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.[8]

Use and effects

MET has been 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][2] The free base of MET has been reported to be active as a psychedelic via vaporization at a dose of 15 mg, at least per an informal 2011 Erowid trip report.[3]

Interactions

Pharmacology

Pharmacodynamics

MET is a serotonin 5-HT2A and 5-HT2C receptor partial agonist.[4] It shows very weak activity as an agonist of the serotonin 5-HT1A and 5-HT2B receptors.[4] In addition to acting at the serotonin 5-HT2 receptors, MET is a serotonin releasing agent with lower potency.[4] It produces the head-twitch response, a behavioral proxy of psychedelic effects, in animals.[6][4]

Chemistry

MET, also known as N-methyl-N-ethyltryptamine, is a substituted tryptamine derivative.[1][2][4] It is closely related to N,N-dimethyltryptamine (DMT) and to other N,N-dialkylated tryptamines.[1][2][4]

Analogues

Analogues of MET besides DMT include DET, DPT, DiPT, DBT, MiPT, MBT, EPT, EiPT, and PiPT, among others.[1][2] 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][2]

History

MET appears to have first been described in the literature by 1981.[7] It was specifically mentioned in Michael Valentine Smith's Psychedelic Chemistry.[7] 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.[8]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 TiHKAL: The Continuation (1st ed.). Berkeley, CA: Transform Press. 1997. ISBN 978-0-9630096-9-2. OCLC 38503252. https://books.google.com/books?id=jl_ik66IumUC. 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." 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6. 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." 
  3. ↑ 3.0 3.1 "That's okay, you're good" MET trip report - The Vaults of Erowid
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 Kruegel AC, "Methods of treating mood disorders", US patent 11440879, issued 13 September 2022
  5. ↑ "NPS: Medical Consequences Associated with Their Intake". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. 32. 2016. pp. 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. 
  6. ↑ 6.0 6.1 "Effect of Hallucinogens on Unconditioned Behavior". Behavioral Neurobiology of Psychedelic Drugs. Curr Top Behav Neurosci. 36. 2018. pp. 159–199. doi:10.1007/7854_2016_466. ISBN 978-3-662-55878-2. "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)." 
  7. ↑ 7.0 7.1 7.2 Psychedelic Chemistry. Loompanics Unlimited. 1981. ISBN 978-0-915179-10-7. https://books.google.com/books?id=WYzZAAAAMAAJ. Retrieved 20 February 2025. 
  8. ↑ 8.0 8.1 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. https://data.europa.eu/doi/10.2810/112317. Retrieved 20 February 2025. 

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