Methylethyltryptamine

Methylethyltryptamine
Clinical data
Other names	MET; N-Methyl-N-ethyltryptamine; N,N-MET
Routes of; administration	Oral; Vaporized/inhaled
Drug class	Serotonergic psychedelic; Hallucinogen; Serotonin 5-HT2A and 5-HT2C receptor agonist; Serotonin releasing agent
Identifiers
	IUPAC name N-ethyl-2-(1H-indol-3-yl)-N-methylethan-1-amine;
CAS Number	5599-69-9 ;
PubChem CID	824845;
ChemSpider	720502 ;
UNII	4KX1J1D3RD;
CompTox Dashboard (EPA)	DTXSID901024010 ;
Chemical and physical data
Formula	C13H18N2
Molar mass	202.301 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1cccc2c1c(c[nH]2)CCN(CC)C;
	InChI 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 ; Key:MYEGVMLMDWYPOA-UHFFFAOYSA-N ;
	(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] It was encountered as a novel designer drug in Europe in 2014.^[6]

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 freebase of MET is active as a psychedelic via vaporization at a dose of 15 mg per a 2011 Erowid trip report.^[7]

Interactions

Pharmacology

MET is a serotonin 5-HT_2A and 5-HT_2C receptor partial agonist.^[5] It shows very weak activity as an agonist of the serotonin 5-HT_1A and 5-HT_2B 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.^[6]

References

^ ^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.
^ ^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.
^ 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". 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).
^ ^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.
^ ^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.
^ "That's okay, you're good" MET trip report - The Vaults of Erowid
^ ^a ^b Smith MV (1981). Psychedelic Chemistry. Loompanics Unlimited. ISBN 978-0-915179-10-7. Retrieved 20 February 2025.

External links

[TiHKAL1997-1] ^ ^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.

[Shulgin2003-2] 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.

[SchifanoOrsoliniPapanti2016-3] 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.

[HalberstadtGeyer2018-4] 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).

[US11440879B2-5] ^ ^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.

[EMCDDA2015-6] 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.

[Erowid2011-7] "That's okay, you're good" MET trip report - The Vaults of Erowid

[Smith1981-8] Smith MV (1981). Psychedelic Chemistry. Loompanics Unlimited. ISBN 978-0-915179-10-7. Retrieved 20 February 2025.

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