N-Methyl-N-ethyltryptamine

Last updated
N-Methyl-N-ethyltryptamine
MET image.svg
Clinical data
Other namesMET; Methylethyltryptamine
Routes of
administration 		Oral; Vaporized/inhaled
Drug class Serotonergic 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
Formula C13H18N2
Molar mass 202.301 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 Yes check.svgY
  • Key:MYEGVMLMDWYPOA-UHFFFAOYSA-N Yes check.svgY
   (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]

Contents

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]

Pharmacology

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

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

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

References

  1. 1 2 3 4 5 6 Alexander T. Shulgin; Ann Shulgin (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. 1 2 3 4 5 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, Fabrizio; Orsolini, Laura; Papanti, Duccio; Corkery, John (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. 1 2 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. 1 2 3 4 5 6 7 "Methods of treating mood disorders". Google Patents. 2022. Retrieved 14 November 2024.
  6. ↑ "That's okay, you're good" MET trip report - The Vaults of Erowid
  7. 1 2 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. 1 2 Smith, M.V. (1981). Psychedelic Chemistry. Loompanics Unlimited. ISBN   978-0-915179-10-7 . Retrieved 20 February 2025.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.