Methylethyltryptamine

For other uses, see Methylethyltryptamine (disambiguation).

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]

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 Y
PubChem CID	824845
ChemSpider	720502 Y
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 Y Key:MYEGVMLMDWYPOA-UHFFFAOYSA-N Y
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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-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.^[7]

See also

• Bretisilocin (5-fluoro-MET; GM-2505)