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Methylethyltryptamine

From Wikipedia, the free encyclopedia
Chemical compound
For other uses, seeMethylethyltryptamine (disambiguation).

Pharmaceutical compound
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;Serotonin5-HT2A and5-HT2C receptoragonist;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
PubChemCID
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)

Methylethyltryptamine (MET), also known asN-methyl-N-ethyltryptamine (N,N-MET), is apsychedelic drug of thetryptamine family.[1][4] It is takenorally or viainhalation.[1][3]

The drug acts as anagonist of theserotonin5-HT2 receptors and to a lesser extent as aserotonin releasing agent.[5] It is closely related todimethyltryptamine (DMT) and todiethyltryptamine (DET).[6][7]

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

Use and effects

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MET was briefly mentioned inAlexander Shulgin'sTiHKAL (Tryptamines I Have Known and Loved) and other publications, where he has stated it to beorally active as apsychedelic at doses of 80 to 100 mg.[1][4][2] Itsduration,onset, and peak were not provided.[1] Thefree base of MET has been reported to be active as a psychedelic viavaporization at a dose of 15 mg per informalanecdotal reports.[2][3] Very little information is available on the effects of MET.[2] However, its effects have been reported to includehallucinations,euphoria,tactile enhancement, cognitive effects,pupil dilation,muscle cramps,teeth grinding, and increasedheart rate andblood pressure.[2]

Interactions

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

Pharmacology

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Pharmacodynamics

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MET is aserotonin5-HT2A and5-HT2C receptorpartial agonist.[5] It shows very weak activity as anagonist of the serotonin5-HT1A and5-HT2B receptors.[5] In addition to acting at the serotonin5-HT2 receptors, MET is aserotonin releasing agent with lowerpotency.[5] It produces thehead-twitch response, a behavioral proxy ofpsychedelic effects, in animals.[7][5]

Chemistry

[edit]

MET, also known asN-methyl-N-ethyltryptamine, is asubstituted tryptaminederivative.[1][4][5] It is closely related toN,N-dimethyltryptamine (DMT) and to otherN,N-dialkylated tryptamines.[1][4][5]

Analogues

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Analogues of MET besides DMT includeDET,DPT,DiPT,DBT,MiPT,MBT,EPT,EiPT, andPiPT, among others.[1][4]Derivatives of MET include4-HO-MET,5-MeO-MET,bretisilocin (5-fluoro-MET; GM-2505), and7-F-5-MeO-MET, among others.[1][4]

History

[edit]

MET appears to have first been described in the literature by 1981.[8] It was specifically mentioned in Michael Valentine Smith'sPsychedelic Chemistry.[8] Subsequently, MET was briefly described inAlexander Shulgin'sTiHKAL (Tryptamines I Have Known and Loved) in 1997.[1] MET was encountered as a noveldesigner drug inEurope in 2014.[9]

See also

[edit]

References

[edit]
  1. ^abcdefghijklmShulgin AT,Shulgin A (1997).TiHKAL: The Continuation (1st ed.). Berkeley, CA: Transform Press.ISBN 978-0-9630096-9-2.OCLC 38503252. Retrieved30 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. ^abcdeMalaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA (December 2020)."Toxicology and Analysis of Psychoactive Tryptamines".Int J Mol Sci.21 (23): 9279.doi:10.3390/ijms21239279.PMC 7730282.PMID 33291798.N-methyl-N-ethyltryptamine (MET): MET is structurally related to DMT but little scientific information is available on its pharmacology or toxicity in humans. Inhalation of 15 mg freebase MET or 80–100 mg oral freebase MET produce effects [73]. Anecdotal reports describe the most common physical and psychological effects as physical euphoria, tactile enhancement, increased heart rate and blood pressure, muscle cramps, teeth grinding, pupil dilation, hallucinations and cognitive effects [73].
  3. ^abc"That's okay, you're good" MET trip report -The Vaults of Erowid
  4. ^abcdefShulgin 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. Retrieved1 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.
  5. ^abcdefgUS 11440879, Kruegel AC, "Methods of treating mood disorders", issued 13 September 2022, assigned to Gilgamesh Pharmaceuticals Inc. 
  6. ^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.
  7. ^abHalberstadt AL, Geyer MA (2018). "Effect of Hallucinogens on Unconditioned Behavior".Behavioral Neurobiology of Psychedelic Drugs. Curr Top Behav Neurosci. Vol. 36. pp. 159–199.doi:10.1007/7854_2016_466.ISBN 978-3-662-55878-2.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).
  8. ^abcSmith MV (1981).Psychedelic Chemistry. Loompanics Unlimited.ISBN 978-0-915179-10-7. Retrieved20 February 2025.
  9. ^abEuropean Monitoring Centre for Drugs and Drug Addiction., European Police Office. (2015).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.ISBN 978-92-9168-821-0. Retrieved20 February 2025.

External links

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