Methylethyltryptamine

Chemical compound From Wikipedia, the free encyclopedia

Methylethyltryptamine (MET), also known as N-methyl-N-ethyltryptamine (N,N-MET), is a psychedelic drug of the tryptamine family.[1][4] It is taken orally or via inhalation.[1][3]

Other namesMET; N-Methyl-N-ethyltryptamine; N,N-MET
ATC code
  • None
Quick facts Clinical data, Other names ...
Methylethyltryptamine
Clinical data
Other namesMET; N-Methyl-N-ethyltryptamine; N,N-MET
Routes of
administration
Oral; Vaporized/inhaled[1][2][3]
Drug classSerotonergic psychedelic; Hallucinogen; Serotonin 5-HT2A and 5-HT2C receptor agonist; Serotonin releasing agent
ATC code
  • None
Pharmacokinetic data
Onset of actionUnknown[1]
Duration of actionUnknown[1]
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)
Close

The drug acts as an agonist of the serotonin 5-HT2 receptors and to a lesser extent as a serotonin releasing agent.[5] It is closely related to dimethyltryptamine (DMT) and to diethyltryptamine (DET).[6][7]

MET appears to have been first described in the literature in 1981.[8] It was only briefly mentioned in Alexander Shulgin's 1997 book TiHKAL (Tryptamines I Have Known and Loved).[1] The drug was encountered as a novel designer drug in Europe in 2014.[9]

Use and effects

MET was 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][4][2] Its duration, onset, and peak were not provided.[1] The free base of MET has been reported to be active as a psychedelic via vaporization at a dose of 15 mg per informal anecdotal reports.[2][3] Very little information is available on the effects of MET.[2] However, its effects have been reported to include hallucinations, euphoria, tactile enhancement, cognitive effects, pupil dilation, muscle cramps, teeth grinding, and increased heart rate and blood pressure.[2]

Interactions

Pharmacology

Pharmacodynamics

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.[7][5]

Chemistry

MET, also known as N-methyl-N-ethyltryptamine, is a substituted tryptamine derivative.[1][4][5] It is closely related to N,N-dimethyltryptamine (DMT) and to other N,N-dialkylated tryptamines.[1][4][5]

Analogues

Analogues of MET besides DMT include DET, DPT, DiPT, DBT, MiPT, MBT, EPT, EiPT, and PiPT, among others.[1][4] Derivatives of MET include 4-HO-MET, 5-HO-MET, 5-MeO-MET, bretisilocin (5-fluoro-MET; GM-2505), and 7-F-5-MeO-MET, among others.[1][4]

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.[9]

Society and culture

Canada

MET is not a controlled substance in Canada as of 2025.[10]

United States

MET is not an explicitly controlled substance in the United States.[11] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

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