Methylethyltryptamine: Difference between revisions
imported>AlyInWikiWonderland Section. |
imported>Wolren added 3D image |
||
| Line 5: | Line 5: | ||
| verifiedrevid = 400309782 | | verifiedrevid = 400309782 | ||
| image = MET image.svg | | image = MET image.svg | ||
| image_class = skin-invert-image | |||
| width = 225px | | width = 225px | ||
| caption = | | caption = | ||
| image2 = MET 3D.png | |||
| image_class2 = bg-transparent | |||
| width2 = 200px | |||
<!-- Clinical data --> | <!-- Clinical data --> | ||
| Line 21: | Line 25: | ||
| dependency_liability = | | dependency_liability = | ||
| addiction_liability = | | addiction_liability = | ||
| routes_of_administration = [[Oral administration|Oral]]; [[Vaporization|Vaporized]]/[[inhalational administration|inhaled]] | | routes_of_administration = [[Oral administration|Oral]]; [[Vaporization|Vaporized]]/[[inhalational administration|inhaled]]<ref name="TiHKAL1997" /><ref name="MalacaLoFaroTamborra2020" /><ref name="Erowid2011" /> | ||
| 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]] | | 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]] | ||
| ATC_prefix = | | ATC_prefix = None | ||
| ATC_suffix = | | ATC_suffix = | ||
| Line 34: | Line 38: | ||
| metabolism = | | metabolism = | ||
| metabolites = | | metabolites = | ||
| onset = | | onset = Unknown<ref name="TiHKAL1997" /> | ||
| elimination_half-life = | | elimination_half-life = | ||
| duration_of_action = | | duration_of_action = Unknown<ref name="TiHKAL1997" /> | ||
| excretion = | | excretion = | ||
| Line 68: | Line 72: | ||
}} | }} | ||
'''Methylethyltryptamine''' ('''MET'''), also known as '''''N''-methyl-''N''-ethyltryptamine''' ('''''N'',''N''-MET'''), is a [[ | '''Methylethyltryptamine''' ('''MET'''), also known as '''''N''-methyl-''N''-ethyltryptamine''' ('''''N'',''N''-MET'''), is a [[psychedelic drug]] of the [[substituted tryptamine|tryptamine]] family.<ref name="TiHKAL1997" /><ref name="Shulgin2003" /> It is taken [[oral administration|orally]] or via [[inhalational administration|inhalation]].<ref name="TiHKAL1997" /><ref name="Erowid2011" /> | ||
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 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 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]]'s 1997 book ''[[TiHKAL]]'' (''Tryptamines I Have Known and Loved'').<ref name="TiHKAL1997" /> The drug was encountered as a novel [[designer drug]] in [[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== | ==Use and effects== | ||
MET | 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 [[oral administration|orally active]] as a [[psychedelic drug|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><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 of action|duration]], [[onset of action|onset]], and peak were not provided.<ref name="TiHKAL1997" /> The [[free base]] of MET has been reported to be active as a psychedelic via [[vaporization]] at a dose of 15{{nbsp}}mg per informal [[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]]s, [[euphoria]], [[touch|tactile]] enhancement, cognitive effects, [[pupil dilation]], [[muscle cramp]]s, [[teeth grinding]], and increased [[heart rate]] and [[blood pressure]].<ref name="MalacaLoFaroTamborra2020" /> | ||
==Interactions== | ==Interactions== | ||
| Line 77: | Line 85: | ||
==Pharmacology== | ==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" /> | ===Pharmacodynamics=== | ||
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== | ==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" /> | 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 | ===Analogues=== | ||
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]], [[bretisilocin]] (5-fluoro-MET; GM-2505), and [[7-F-5-MeO-MET]], among others.<ref name="TiHKAL1997" /><ref name="Shulgin2003" /> | |||
==History== | ==History== | ||
| Line 90: | Line 98: | ||
==See also== | ==See also== | ||
* [[Substituted tryptamine]] | |||
* [[Bretisilocin]] (5-fluoro-MET; GM-2505) | * [[Bretisilocin]] (5-fluoro-MET; GM-2505) | ||
Latest revision as of 12:55, 23 November 2025
Template:Short description Script error: No such module "other uses". Template:Cs1 config Template:Short description <templatestyles src="Infobox drug/styles.css"/> Script error: No such module "Infobox".Template:Template otherScript error: No such module "TemplatePar".{{Infobox drug/maintenance categoriesTemplate:Yesno | drug_name = | INN = | _drugtype =
| _has_physiological_data= | _has_gene_therapy=
| vaccine_type= | mab_type= | _number_of_combo_chemicals=Script error: No such module "ParameterCount". | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data=13182c1cccc2c1c(c[nH]2)CCN(CC)C1S/C13H18N2/c1-3-15(2)9-8-11-10-14-13-7-5-4-6-12(11)13/h4-7,10,14H,3,8-9H2,1-2H3MYEGVMLMDWYPOA-UHFFFAOYSA-NTemplate:StdinchiciteTemplate:Stdinchicite | _combo_data= | _physiological_data= | _clinical_data= Oral; Vaporized/inhaled[1][2][3]Serotonergic psychedelic; Hallucinogen; Serotonin 5-HT2A and 5-HT2C receptor agonist; Serotonin releasing agentNone | _legal_data=
| _other_data=N-ethyl-2-(1H-indol-3-yl)-N-methylethan-1-amine
| _image_0_or_2 = MET image.svgMET 3D.png | _image_LR =
| _datapage = Methylethyltryptamine (data page) | _vaccine_target=_type_not_vaccine | _legal_all= | _ATC_prefix_supplemental=None | _has_EMA_link = | CAS_number=5599-69-9 | PubChem=824845 | ChemSpiderID=720502 | ChEBI= | ChEMBL= | DrugBank= | KEGG= | _hasInChI_or_Key=yes | UNII=4KX1J1D3RD | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =
| _countSecondIDs=Script error: No such module "ParameterCount". | _countIndexlabels=Script error: No such module "ParameterCount". | _trackListSortletter= |QID = |QID2 = |Verifiedfields= |Watchedfields= |verifiedrevid=400309782}}
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]
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 100Script error: No such module "String".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 15Script error: No such module "String".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
Script error: No such module "Labelled list hatnote".
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-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]
See also
- Substituted tryptamine
- Bretisilocin (5-fluoro-MET; GM-2505)
References
<templatestyles src="Reflist/styles.css" />
- ↑ a b c d e f g h i j k Script error: No such module "citation/CS1".
- ↑ a b c d e Script error: No such module "Citation/CS1".
- ↑ a b c "That's okay, you're good" MET trip report - The Vaults of Erowid
- ↑ a b c d e f Script error: No such module "citation/CS1".
- ↑ a b c d e f g <templatestyles src="Citation/styles.css"/>Template:Citation/make link, Kruegel AC, "Methods of treating mood disorders", issued Script error: No such module "auto date formatter"., assigned to Gilgamesh Pharmaceuticals Inc.Script error: No such module "Check for unknown parameters".
- ↑ Script error: No such module "citation/CS1".
- ↑ a b Script error: No such module "citation/CS1".
- ↑ a b c Script error: No such module "citation/CS1".
- ↑ a b Script error: No such module "citation/CS1".
Script error: No such module "Check for unknown parameters".
External links
- MET - Isomer Design
- MET - Psychonaut Wiki
- MET - Erowid
- The Big & Dandy MET Thread - Bluelight
- MET scraps - Bluelight
Template:Psychedelics Template:Serotonin receptor modulators Template:Monoamine releasing agents Script error: No such module "Navbox".