# Methylethyltryptamine

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Methylethyltryptamine
> Markdown URL: https://mediated.wiki/source/Methylethyltryptamine.md
> Source: https://en.wikipedia.org/wiki/Methylethyltryptamine
> Source revision: 1338066521
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Chemical compound}}
{{Other uses|Methylethyltryptamine (disambiguation)}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Infobox drug
| verifiedrevid = 400309782
| image = MET image.svg
| image_class = skin-invert-image
| width = 185px
| image2 = MET 3D.png
| image_class2 = bg-transparent
| width2 = 225px

<!-- Clinical data -->
| pronounce = 
| tradename = 
| Drugs.com = 
| MedlinePlus = 
| licence_CA = 
| licence_EU = 
| DailyMedID = 
| licence_US = 
| pregnancy_AU = 
| pregnancy_category = 
| dependency_liability = 
| addiction_liability = 
| routes_of_administration = [Oral](/source/Oral_administration); [Vaporized](/source/Vaporization)/[inhaled](/source/inhalational_administration)<ref name="TiHKAL1997" /><ref name="MalacaLoFaroTamborra2020" /><ref name="Erowid2011" />
| class = [Serotonergic psychedelic](/source/Serotonergic_psychedelic); [Hallucinogen](/source/Hallucinogen); [Serotonin](/source/Serotonin) [5-HT<sub>2A</sub>](/source/5-HT2A_receptor) and [5-HT<sub>2C</sub> receptor](/source/5-HT2C_receptor) [agonist](/source/agonist); [Serotonin releasing agent](/source/Serotonin_releasing_agent)
| ATC_prefix = None
| ATC_suffix = 

<!-- Legal status -->
| legal_status = 

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
| metabolism = 
| metabolites = 
| onset = Unknown<ref name="TiHKAL1997" />
| elimination_half-life = 
| duration_of_action = Unknown<ref name="TiHKAL1997" />
| excretion = 

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 5599-69-9
| CAS_supplemental = 
| PubChem = 824845
| PubChemSubstance = 
| IUPHAR_ligand = 
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 720502
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4KX1J1D3RD
| KEGG = 
| ChEBI = 
| ChEMBL = 
| NIAID_ChemDB = 
| PDB_ligand = 
| 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 [psychedelic drug](/source/psychedelic_drug) of the [tryptamine](/source/substituted_tryptamine) family.<ref name="TiHKAL1997" /><ref name="Shulgin2003" /> It is taken [orally](/source/oral_administration) or via [inhalation](/source/inhalational_administration).<ref name="TiHKAL1997" /><ref name="Erowid2011" />

The drug acts as an [agonist](/source/agonist) of the [serotonin](/source/serotonin) [5-HT<sub>2</sub> receptor](/source/5-HT2_receptor)s and to a lesser extent as a [serotonin releasing agent](/source/serotonin_releasing_agent).<ref name="US11440879B2" /> It is closely related to [dimethyltryptamine](/source/dimethyltryptamine) (DMT) and to [diethyltryptamine](/source/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 book | vauthors = Halberstadt AL, Geyer MA | title = Behavioral Neurobiology of Psychedelic Drugs | chapter = Effect of Hallucinogens on Unconditioned Behavior | series = Curr Top Behav Neurosci | volume = 36 | pages = 159–199 | date = 2018 | pmid = 28224459 | pmc = 5787039 | doi = 10.1007/7854_2016_466 | isbn = 978-3-662-55878-2 | chapter-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>

MET appears to have been first described in the literature in 1981.<ref name="Smith1981" /> It was only briefly mentioned in [Alexander Shulgin](/source/Alexander_Shulgin)'s 1997 book ''[TiHKAL](/source/TiHKAL)'' (''Tryptamines I Have Known and Loved'').<ref name="TiHKAL1997" /> The drug was encountered as a novel [designer drug](/source/designer_drug) in [Europe](/source/Europe) in 2014.<ref name="EMCDDA2015">{{cite book | author1=European Monitoring Centre for Drugs and Drug Addiction. | author2=European Police Office. | 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. | date=2015 | publisher=Publications Office | doi=10.2810/112317 | url=https://data.europa.eu/doi/10.2810/112317 | access-date=20 February 2025 | page= | isbn=978-92-9168-821-0 }}</ref>

==Use and effects==
MET was briefly mentioned in [Alexander Shulgin](/source/Alexander_Shulgin)'s ''[TiHKAL](/source/TiHKAL)'' (''Tryptamines I Have Known and Loved'') and other publications, where he has stated it to be [orally active](/source/oral_administration) as a [psychedelic](/source/psychedelic_drug) at doses of 80 to 100{{nbsp}}mg.<ref name="TiHKAL1997">{{cite book | vauthors = [Shulgin AT](/source/Alexander_T._Shulgin), [Shulgin A](/source/Ann_Shulgin) | 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><ref name="MalacaLoFaroTamborra2020">{{cite journal | vauthors = Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA | title = Toxicology and Analysis of Psychoactive Tryptamines | journal = Int J Mol Sci | volume = 21 | issue = 23 | date = December 2020 | page = 9279 | pmid = 33291798 | pmc = 7730282 | doi = 10.3390/ijms21239279 | doi-access = free | url = | quote = 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].}}</ref> Its [duration](/source/duration_of_action), [onset](/source/onset_of_action), and peak were not provided.<ref name="TiHKAL1997" /> The [free base](/source/free_base) of MET has been reported to be active as a psychedelic via [vaporization](/source/vaporization) at a dose of 15{{nbsp}}mg per informal [anecdotal report](/source/anecdotal_report)s.<ref name="MalacaLoFaroTamborra2020" /><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> Very little information is available on the effects of MET.<ref name="MalacaLoFaroTamborra2020" /> However, its effects have been reported to include [hallucination](/source/hallucination)s, [euphoria](/source/euphoria), [tactile](/source/touch) enhancement, cognitive effects, [pupil dilation](/source/pupil_dilation), [muscle cramp](/source/muscle_cramp)s, [teeth grinding](/source/teeth_grinding), and increased [heart rate](/source/heart_rate) and [blood pressure](/source/blood_pressure).<ref name="MalacaLoFaroTamborra2020" />

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

==Pharmacology==
===Pharmacodynamics===
MET is a [serotonin](/source/serotonin) [5-HT<sub>2A</sub>](/source/5-HT2A_receptor) and [5-HT<sub>2C</sub> receptor](/source/5-HT2C_receptor) [partial agonist](/source/partial_agonist).<ref name="US11440879B2" /> It shows very weak activity as an [agonist](/source/agonist) of the serotonin [5-HT<sub>1A</sub>](/source/5-HT1A_receptor) and [5-HT<sub>2B</sub> receptor](/source/5-HT2B_receptor)s.<ref name="US11440879B2" /> In addition to acting at the serotonin [5-HT<sub>2</sub> receptor](/source/5-HT2_receptor)s, MET is a [serotonin releasing agent](/source/serotonin_releasing_agent) with lower [potency](/source/potency_(pharmacology)).<ref name="US11440879B2" /> It produces the [head-twitch response](/source/head-twitch_response), a behavioral proxy of [psychedelic](/source/psychedelic_drug) effects, in animals.<ref name="HalberstadtGeyer2018" /><ref name="US11440879B2" />

==Chemistry==
MET, also known as ''N''-methyl''-N''-ethyltryptamine, is a [substituted tryptamine](/source/substituted_tryptamine) [derivative](/source/chemical_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 [''N'',''N''-dimethyltryptamine](/source/dimethyltryptamine) (DMT) and to other ''N'',''N''-di[alkylated](/source/alkyl_group) tryptamines.<ref name="TiHKAL1997" /><ref name="Shulgin2003" /><ref name="US11440879B2" />

===Analogues===
Analogues of MET besides DMT include [DET](/source/N%2CN-diethyltryptamine), [DPT](/source/N%2CN-dipropyltryptamine), [DiPT](/source/N%2CN-diisopropyltryptamine), [DBT](/source/N%2CN-dibutyltryptamine), [MiPT](/source/N-methyl-N-isopropyltryptamine), [MBT](/source/N-methyl-N-butyltryptamine), [EPT](/source/N-ethyl-N-propyltryptamine), [EiPT](/source/N-ethyl-N-isopropyltryptamine), and [PiPT](/source/N-propyl-N-isopropyltryptamine), among others.<ref name="TiHKAL1997" /><ref name="Shulgin2003" /> [Derivative](/source/Chemical_derivative)s of MET include [4-HO-MET](/source/4-HO-MET), [5-HO-MET](/source/5-HO-MET), [5-MeO-MET](/source/5-MeO-MET), [bretisilocin](/source/bretisilocin) (5-fluoro-MET; GM-2505), and [7-F-5-MeO-MET](/source/7-F-5-MeO-MET), among others.<ref name="TiHKAL1997" /><ref name="Shulgin2003" />

==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](/source/Alexander_Shulgin)'s ''[TiHKAL](/source/TiHKAL)'' (''Tryptamines I Have Known and Loved'') in 1997.<ref name="TiHKAL1997" /> MET was encountered as a novel [designer drug](/source/designer_drug) in [Europe](/source/Europe) in 2014.<ref name="EMCDDA2015" />

==Society and culture==
===Legal status===
====Canada====
MET is not a [controlled substance](/source/controlled_substance) in [Canada](/source/Canada) as of 2025.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>

====United States====
MET is not an explicitly [controlled substance](/source/controlled_substance) in the [United States](/source/United_States).<ref name="OrangeBook2026">{{citation | title = Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) | date = January 2026 | publisher = U.S. [Department of Justice](/source/Department_of_Justice): [Drug Enforcement Administration](/source/Drug_Enforcement_Administration) (DEA): Diversion Control Division | location = [United States](/source/United_States) | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf}}</ref> However, it could be considered a [controlled substance](/source/controlled_substance) under the [Federal Analogue Act](/source/Federal_Analogue_Act) if intended for human consumption.

==See also==
* [Substituted tryptamine](/source/Substituted_tryptamine)
* [Bretisilocin](/source/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

---
Adapted from the Wikipedia article [Methylethyltryptamine](https://en.wikipedia.org/wiki/Methylethyltryptamine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Methylethyltryptamine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.