View source for Methylethyltryptamine

{{Short description|Chemical compound}}
{{Other uses|Methylethyltryptamine (disambiguation)}}
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{{Infobox drug
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| image = MET image.svg
| width = 225px
| caption = 

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| routes_of_administration = [[Oral administration|Oral]]; [[Vaporization|Vaporized]]/[[inhalational administration|inhaled]]
| class = [[Serotonergic psychedelic]]; [[Hallucinogen]]; [[Serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub>]] and [[5-HT2C receptor|5-HT<sub>2C</sub> receptor]] [[agonist]]; [[Serotonin releasing agent]]
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| CAS_number = 5599-69-9
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| PubChem = 824845
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| ChemSpiderID = 720502
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| UNII = 4KX1J1D3RD
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| synonyms = MET; ''N''-Methyl-''N''-ethyltryptamine; ''N'',''N''-MET

<!-- Chemical data -->
| IUPAC_name = ''N''-ethyl-2-(1''H''-indol-3-yl)-''N''-methylethan-1-amine
| C=13 | H=18 | N=2
| SMILES = c1cccc2c1c(c[nH]2)CCN(CC)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MYEGVMLMDWYPOA-UHFFFAOYSA-N
}}

'''Methylethyltryptamine''' ('''MET'''), also known as '''''N''-methyl-''N''-ethyltryptamine''' ('''''N'',''N''-MET'''), is a [[serotonergic psychedelic]] of the [[substituted tryptamine|tryptamine]] family.<ref name="TiHKAL1997" /><ref name="Shulgin2003" /> It is closely related to [[dimethyltryptamine]] (DMT) and to [[diethyltryptamine]] (DET).<ref name="SchifanoOrsoliniPapanti2016">{{cite book | doi = 10.1007/7854_2016_15| chapter = NPS: Medical Consequences Associated with Their Intake| title = Neuropharmacology of New Psychoactive Substances (NPS)| series = Current Topics in Behavioral Neurosciences| date = 2016| vauthors = Schifano F, Orsolini L, Papanti D, Corkery J | volume = 32| pages = 351–380| pmid = 27272067| isbn = 978-3-319-52442-9}}</ref><ref name="HalberstadtGeyer2018">{{cite journal | vauthors = Halberstadt AL, Geyer MA | title = Effect of Hallucinogens on Unconditioned Behavior | journal = Curr Top Behav Neurosci | volume = 36 | issue = | pages = 159–199 | date = 2018 | pmid = 28224459 | pmc = 5787039 | doi = 10.1007/7854_2016_466 | url = | quote = 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).}}</ref> The drug acts as an [[agonist]] of the [[serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> receptor]]s and to a lesser extent as a [[serotonin releasing agent]].<ref name="US11440879B2" /> It was encountered as a novel [[designer drug]] in [[Europe]] in 2014.<ref name="EMCDDA2015">{{cite book | title=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. | publisher=Publications Office | doi=10.2810/112317 | url=https://data.europa.eu/doi/10.2810/112317 | access-date=20 February 2025 | page=}}</ref>

==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 [[oral administration|orally active]] as a psychedelic at doses of 80 to 100{{nbsp}}mg.<ref name="TiHKAL1997">{{cite book | vauthors = [[Alexander T. Shulgin|Shulgin AT]], [[Ann Shulgin|Shulgin A]] | title = TiHKAL: The Continuation | publisher = Transform Press | date = 1997 | edition = 1st | location = Berkeley, CA | isbn = 978-0-9630096-9-2 | oclc = 38503252 | url = https://books.google.com/books?id=jl_ik66IumUC | access-date = 30 January 2025 | pages = | quote = 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.}}</ref><ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | chapter=Basic Pharmacology and Effects | pages=67–137 | veditors = Laing RR | title=Hallucinogens: A Forensic Drug Handbook | publisher=Elsevier Science | series=Forensic Drug Handbook Series | year=2003 | isbn=978-0-12-433951-4 | url=https://books.google.com/books?id=l1DrqgobbcwC | chapter-url=https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6 | access-date=1 February 2025 | quote = 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.}}</ref> The freebase of MET is active as a psychedelic via [[vaporization]] at a dose of 15{{nbsp}}mg per a 2011 [[Erowid]] trip report.<ref name="Erowid2011">[http://www.erowid.org/experiences/exp_info7.shtml "That's okay, you're good" MET trip report] - ''The Vaults of Erowid''</ref>

==Interactions==
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

==Pharmacology==
MET is a [[serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub>]] and [[5-HT2C receptor|5-HT<sub>2C</sub> receptor]] [[partial agonist]].<ref name="US11440879B2" /> It shows very weak activity as an agonist of the serotonin [[5-HT1A receptor|5-HT<sub>1A</sub>]] and [[5-HT2B receptor|5-HT<sub>2B</sub> receptor]]s.<ref name="US11440879B2" /> In addition to acting at the serotonin [[5-HT2 receptor|5-HT<sub>2</sub> receptor]]s, MET is a [[serotonin releasing agent]] with lower [[potency (pharmacology)|potency]].<ref name="US11440879B2" /> It produces the [[head-twitch response]], a behavioral proxy of [[psychedelic drug|psychedelic]] effects, in animals.<ref name="HalberstadtGeyer2018" /><ref name="US11440879B2" />

==Chemistry==
MET, also known as ''N''-methyl''-N''-ethyltryptamine, is a [[substituted tryptamine]] [[chemical derivative|derivative]].<ref name="TiHKAL1997" /><ref name="Shulgin2003" /><ref name="US11440879B2">{{cite patent | title=Methods of treating mood disorders | country = US | number = 11440879 | inventor = Kruegel AC | assign = Gilgamesh Pharmaceuticals Inc. | gdate = 13 September 2022 | url=https://patents.google.com/patent/US11440879B2 }}</ref> It is closely related to [[dimethyltryptamine|''N'',''N''-dimethyltryptamine]] (DMT) and to other ''N'',''N''-di[[alkyl group|alkylated]] tryptamines.<ref name="TiHKAL1997" /><ref name="Shulgin2003" /><ref name="US11440879B2" />

Analogues of MET besides DMT include [[N,N-diethyltryptamine|DET]], [[N,N-dipropyltryptamine|DPT]], [[N,N-diisopropyltryptamine|DiPT]], [[N,N-dibutyltryptamine|DBT]], [[N-methyl-N-isopropyltryptamine|MiPT]], [[N-methyl-N-butyltryptamine|MBT]], [[N-ethyl-N-propyltryptamine|EPT]], [[N-ethyl-N-isopropyltryptamine|EiPT]], and [[N-propyl-N-isopropyltryptamine|PiPT]], among others.<ref name="TiHKAL1997" /><ref name="Shulgin2003" /> [[Chemical derivative|Derivative]]s 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 [[Lysergic Acid Diethylamide|LSD]] that was first developed and characterized by [[Alexander Shulgin]].{{Citation needed|date=February 2025}}

==History==
MET appears to have first been described in the literature by 1981.<ref name="Smith1981">{{cite book | vauthors = Smith MV | title=Psychedelic Chemistry | publisher=Loompanics Unlimited | year=1981 | isbn=978-0-915179-10-7 | url=https://books.google.com/books?id=WYzZAAAAMAAJ | access-date=20 February 2025 | page=}}</ref> It was specifically mentioned in Michael Valentine Smith's ''Psychedelic Chemistry''.<ref name="Smith1981" /> Subsequently, MET was briefly described in [[Alexander Shulgin]]'s ''[[TiHKAL]]'' (''Tryptamines I Have Known and Loved'') in 1997.<ref name="TiHKAL1997" /> MET was encountered as a novel [[designer drug]] in [[Europe]] in 2014.<ref name="EMCDDA2015" />

==See also==
* [[Bretisilocin]] (5-fluoro-MET; GM-2505)

==References==
{{Reflist}}

==External links==
* [https://isomerdesign.com/pihkal/explore/5174 MET - Isomer Design]
* [https://psychonautwiki.org/wiki/MET MET - Psychonaut Wiki]
* [https://www.erowid.org/chemicals/met/met.shtml MET - Erowid]
* [https://www.bluelight.org/community/threads/the-big-dandy-met-thread.255405/ The Big & Dandy MET Thread - Bluelight]
* [https://www.bluelight.org/community/threads/met-scraps.287757/ MET scraps - Bluelight]

{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Monoamine releasing agents}}
{{Tryptamines}}

[[Category:5-HT2A agonists]]
[[Category:5-HT2C agonists]]
[[Category:Designer drugs]]
[[Category:N,N-Dialkyltryptamines]]
[[Category:Entheogens]]
[[Category:Psychedelic tryptamines]]
[[Category:Serotonin releasing agents]]