α,N,N,O-TeMS

α,N,N,O-TeMS
Clinical data
Other names5-Methoxy-α-methyl-N,N-dimethyltryptamine; 5-Methoxy-α,N,N-trimethyltryptamine; α,N,N,O-Tetramethylserotonin; 5-MeO-α,N,N-TMT; 5-MeO-α-methyl-DMT; 5-MeO-α-Me-DMT; α,N,N,O-TeMS
Identifiers
  • 1-(5-methoxy-1H-indol-3-yl)-N,N-dimethylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H20N2O
Molar mass232.327 g·mol−1
3D model (JSmol)
  • CC(CC1=CNC2=C1C=C(C=C2)OC)N(C)C
  • InChI=1S/C14H20N2O/c1-10(16(2)3)7-11-9-15-14-6-5-12(17-4)8-13(11)14/h5-6,8-10,15H,7H2,1-4H3
  • Key:WDKDEBAFCKHQPF-UHFFFAOYSA-N

α,N,N,O-Tetramethylserotonin (α,N,N,O-TeMS), also known as 5-methoxy-α,N,N-trimethyltryptamine (5-MeO-α,N,N-TMT), is a little-known synthetic compound of the tryptamine, α-alkyltryptamine, and 5-methoxytryptamine families.[1][2][3] It is the combined derivative of α-methyltryptamine (αMT) and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).[1][2][3]

The drug was described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) as a putative psychedelic drug.[1] However, Shulgin does not appear to have ever synthesized or assayed it.[1] As such, α,N,N,O-TeMS's effects, dosage, and duration are all unknown.[1]

α,N,N,O-TeMS is also the N,N-dimethylated derivative of 5-methoxy-α-methyltryptamine (5-MeO-αMT or α,O-DMS) and the N-methylated derivative of 5-methoxy-α,N-dimethyltryptamine (5-MeO-α,N-DMT or α,N,O-TMS).[1][2][3] 5-MeO-α,N-DMT is less potent and long-lasting than 5-MeO-αMT, with these psychedelics having doses and durations of 2.5–4.5 mg and 12–18 hours versus 10–20 mg and 6–8 hours, respectively.[1][4] Similarly, α,N-dimethyltryptamine (α,N-DMT) is less potent than αMT (dose ranges of 50–100 mg and 15–30 mg, respectively).[4] Hence, it appears that N-methylation of α-alkyltryptamines may be detrimental to activity and potency, reducing it by about 3- or 4-fold.[1][4]

α,N,N,O-TeMS was first described in the literature, specifically in TiHKAL, by 1997.[1] It is known to have been made at Edgewood Arsenal, but the facility never published anything on the compound.[2] α,N,N,O-TeMS does not appear to have been otherwise described in the literature.[2][3]

See also

[edit]

References

[edit]
  1. ^ a b c d e f g h i Shulgin A (1997). Tihkal: The Continuation. Transform Press. #55. α,N,O-TMS. ISBN 978-0-9630096-9-2. Retrieved 17 August 2024. With this, now, as a challenge, predict for me the potency of α,N,N,O-tetramethylserotonin. Here is a compound that has not been yet synthesized, but which carries the second N-methyl group (yet closer to DMT at the nitrogen atom and probably more potent) and yet a structural kiss of death (as to potency) in the MDA/MDMA world. Will it be up? Will it be down? I am afraid that the "make 'em and taste 'em" procedure is the only one that I can trust.
  2. ^ a b c d e "N,N-Dimethyl-5-methoxy-alpha-methyltryptamine". PubChem. Retrieved 10 January 2025. 8 Literature: 8.1 Consolidated References: U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals., NX#12314.
  3. ^ a b c d "5-MeO-α-methyl-DMT". Isomer Design. 11 November 2024. Retrieved 26 November 2024.
  4. ^ a b c Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137 (102). ISBN 978-0-12-433951-4.
[edit]



Stub icon

This psychoactive drug-related article is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Α,N,N,O-TeMS&oldid=1284992558"