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N-Methyl-N-ethyltryptamine

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N-Methyl-N-ethyltryptamine
Clinical data
Other namesMET; Methylethyltryptamine
Routes of
administration		Oral; Vaporized/inhaled
Drug classSerotonergic psychedelic; Hallucinogen; Serotonin 5-HT2A and 5-HT2C receptor agonist; Serotonin releasing agent
Identifiers
  • N-ethyl-2-(1H-indol-3-yl)-N-methylethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H18N2
Molar mass202.301 g·mol−1
3D model (JSmol)
  • c1cccc2c1c(c[nH]2)CCN(CC)C
  • InChI=1S/C13H18N2/c1-3-15(2)9-8-11-10-14-13-7-5-4-6-12(11)13/h4-7,10,14H,3,8-9H2,1-2H3 checkY
  • Key:MYEGVMLMDWYPOA-UHFFFAOYSA-N checkY
  (verify)

N-Methyl-N-ethyltryptamine (MET) is a serotonergic psychedelic of the tryptamine family.[1][2] It is closely related to dimethyltryptamine (DMT) and to diethyltryptamine (DET).[3][4] The drug acts as an agonist of the serotonin 5-HT2 receptors and to a lesser extent as a serotonin releasing agent.[5]

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 freebase of MET is active as a psychedelic via vaporization at a dose of 15 mg per a 2011 Erowid trip report.[6] The drug was encountered as a novel designer drug in Europe in 2014.[7]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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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.[4][5]

Chemistry

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MET, also known as N-methyl-N-ethyltryptamine, is a substituted tryptamine derivative.[1][2][5] It is closely related to N,N-dimethyltryptamine (DMT) and to other N,N-dialkylated tryptamines.[1][2][5]

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, 5-fluoro-MET, and 7-F-5-MeO-MET.

The lysergamide counterpart of MET is ETH-LAD, an analogue of LSD that was first developed and characterized by Alexander Shulgin.[citation needed]

History

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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.[7]

See also

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References

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  1. ^ a b c d e f 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.
  2. ^ a b c d e 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.
  3. ^ 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.
  4. ^ a b Halberstadt AL, Geyer MA (2018). "Effect of Hallucinogens on Unconditioned Behavior". Curr Top Behav Neurosci. 36: 159–199. doi:10.1007/7854_2016_466. 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).
  5. ^ 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. 
  6. ^ "That's okay, you're good" MET trip report - The Vaults of Erowid
  7. ^ a b 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. Retrieved 20 February 2025.
  8. ^ a b Smith MV (1981). Psychedelic Chemistry. Loompanics Unlimited. ISBN 978-0-915179-10-7. Retrieved 20 February 2025.
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