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{{Short description|Psychoactive drug}}
{{DISPLAYTITLE:''alpha''-''N'',''N''-Trimethyltryptamine}}
{{DISPLAYTITLE:α,''N'',''N''-Trimethyltryptamine}}
{{Drugbox
{{Drugbox
| verifiedrevid = 447733427
| verifiedrevid = 447733427
| IUPAC_name = (2-(1H-indol-3-yl)-1-methyl-ethyl)dimethylamine
| IUPAC_name = (2-(1''H''-Indol-3-yl)-1-methyl-ethyl)dimethylamine
| image = α,N,N-TMT.png
| image = A,N,N-TMT.svg
| width = 200
| image2 = A,A,N-TMT.png
| imagename = α,N,N-TMT
| drug_name = α,''N'',''N''-Trimethyltryptamine
| drug_name = α,''N'',''N''-Trimethyltryptamine

<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 4761-32-4
| PubChem = 134080494
| ChemSpiderID = 59718639
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8AV9QTP9HK


<!--Chemical data-->
<!--Chemical data-->
| C=13 | H=18 | N=2
| C=13 | H=18 | N=2
| smiles = CN(C)C(C)Cc2c[nH]c1ccccc12
| molecular_weight = 202.30 g/mol
| StdInChI = 1S/C13H18N2/c1-10(15(2)3)8-11-9-14-13-7-5-4-6-12(11)13/h4-7,9-10,14H,8H2,1-3H3
| StdInChIKey = XQFCCTPWINMCQJ-UHFFFAOYSA-N
}}
}}


'''α,''N'',''N''-Trimethyltryptamine''' ('''α,''N'',''N''-TMT''', '''α-TMT''', '''ATMT''') is a [[psychoactive drug]] of the [[tryptamine]] [[chemical class]] which acts as a [[psychedelic drug|psychedelic]] [[hallucinogen]]. It is similar in [[chemical structure|structure]] to the other psychedelics of the tryptamine class such as [[dimethyltryptamine]] (DMT) and [[alpha-Methyltryptamine|α-methyltryptamine]] (α-MT).
'''α,''N'',''N''-Trimethyltryptamine''' ('''α,''N'',''N''-TMT''', '''α-TMT''', '''ATMT''') is a [[psychoactive drug]] of the [[tryptamine]] [[chemical class]] which acts as a [[psychedelic drug|psychedelic]] [[hallucinogen]]. It is similar in [[chemical structure|structure]] to the other psychedelics of the tryptamine class such as [[dimethyltryptamine]] (DMT) and [[alpha-Methyltryptamine|α-methyltryptamine]] (α-MT).


α-TMT has been animal tested in comparison with α-MT, and was found to produce similar effects to α-MT but with only around half the potency.<ref>Kalir A, Szara S. Synthesis and pharmacological activity of alkylated tryptamines. ''Journal of Medicinal Chemistry''. 1966 May;9(3):341-4.</ref> Anecdotal reports from human users suggest that it produces psychedelic effects similar to those of other tryptamine derivatives when taken orally at a dose of around 80–120&nbsp;mg, however it does not appear to have been widely sold or used, and its safety profile has not been studied.
α-TMT has been tested in animals in comparison with α-MT and was found to produce similar effects, but with only around half the potency.<ref>{{cite journal | vauthors = Kalir A, Szara S | title = Synthesis and pharmacological activity of alkylated tryptamines | journal = Journal of Medicinal Chemistry | volume = 9 | issue = 3 | pages = 341–4 | date = May 1966 | pmid = 5960901 | doi = 10.1021/jm00321a017 }}</ref>


==See also==
== See also ==
* [[AAZ-A-154]]
* [[alpha-Methyltryptamine|α-Methyltryptamine]]
* [[Ciclindole]]
* [[Ciclindole]]
* [[MPMI (drug)|MPMI]]


==References==
== References ==
{{Reflist|2}}
{{Reflist}}


{{Hallucinogens}}
{{Hallucinogens}}
{{Serotonergics}}
{{Serotonergics}}
{{Tryptamines}}
{{Tryptamines}}
{{TiHKAL}}


{{DEFAULTSORT:Trimethyltryptamine, A,N,N-}}
{{DEFAULTSORT:Trimethyltryptamine, A, N, N-}}
[[Category:Psychedelic tryptamines]]
[[Category:Psychedelic tryptamines]]
[[Category:Dimethylamino compounds]]




Latest revision as of 14:11, 5 February 2024

α,N,N-Trimethyltryptamine
Identifiers
  • (2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H18N2
Molar mass202.301 g·mol−1
3D model (JSmol)
  • CN(C)C(C)Cc2c[nH]c1ccccc12
  • InChI=1S/C13H18N2/c1-10(15(2)3)8-11-9-14-13-7-5-4-6-12(11)13/h4-7,9-10,14H,8H2,1-3H3
  • Key:XQFCCTPWINMCQJ-UHFFFAOYSA-N
  (verify)

α,N,N-Trimethyltryptamine (α,N,N-TMT, α-TMT, ATMT) is a psychoactive drug of the tryptamine chemical class which acts as a psychedelic hallucinogen. It is similar in structure to the other psychedelics of the tryptamine class such as dimethyltryptamine (DMT) and α-methyltryptamine (α-MT).

α-TMT has been tested in animals in comparison with α-MT and was found to produce similar effects, but with only around half the potency.[1]

See also

[edit]

References

[edit]
  1. ^ Kalir A, Szara S (May 1966). "Synthesis and pharmacological activity of alkylated tryptamines". Journal of Medicinal Chemistry. 9 (3): 341–4. doi:10.1021/jm00321a017. PMID 5960901.


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