Methylethyltryptamine

Nowadays, Methylethyltryptamine has become a very important issue in society. With the advancement of technology and globalization, Methylethyltryptamine has taken a fundamental role in our lives, influencing everything from our way of communicating to our political decisions. That is why it is crucial to thoroughly analyze the impact of Methylethyltryptamine on different aspects of our daily lives, as well as the challenges and opportunities it presents. In this article, we will explore the relevance of Methylethyltryptamine in today's world, offering a complete overview that seeks not only to inform, but also to generate reflection and debate on this significant topic.

For other uses, see Methylethyltryptamine (disambiguation).

Methylethyltryptamine
Clinical data
Other namesMET; N-Methyl-N-ethyltryptamine; N,N-MET
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(c2)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)

Methylethyltryptamine (MET), also known as N-methyl-N-ethyltryptamine (N,N-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

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

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. ^ 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.