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; N,N-Dimethyl-5-MeO-AMT
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 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]

Use and effects

α,N,N,O-TeMS 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, dose, and duration are all unknown.[1]

α,N,N,O-TeMS is the N,N-dimethylated derivative of 5-MeO-αMT (α,O-DMS) and the N-methylated derivative of 5-MeO-α,N-DMT (α,N,O-TMS).[1][2][3] 5-MeO-α,N-DMT is less potent and shorter in duration than 5-MeO-αMT, with 5-MeO-α,N-DMT having a dose range of 10 to 20 mg and a duration of 6 to 8 hours versus 5-MeO-αMT having a dose range of 2.5 to 4.5 mg and a duration of 12 to 18 hours.[1][4] Similarly, α,N-DMT (α,N-dimethyltryptamine) is less potent than αMT, with doses of 50 to 100 mg for α,N-DMT and doses of 15 to 30 mg for αMT.[4] Hence, of potential relevance to α,N,N,O-TeMS, it appears that N-methylation of α-alkyltryptamines may reduce their activity by several-fold.[1][4]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Chemistry

Analogues of α,N,N,O-TeMS (N,N-dimethyl-5-MeO-AMT) include α-methyltryptamine (AMT), α,N-DMT (N-methyl-AMT), α,N,N-TMT (N,N-dimethyl-AMT), α-methylserotonin (5-HO-AMT), 5-MeO-AMT (α,O-DMS), and α,N,O-TMS (N-methyl-5-MeO-AMT), among others.[1] Another compound, zalsupindole ((R)-N,N-dimethyl-5-MeO-isoAMT), is a close isotryptamine analogue of α,N,N,O-TeMS.[5]

History

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

References

  1. ^ a b c d e f g h i j 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.
  5. ^ Agrawal R, Gillie D, Mungenast A, Chytil M, Engel S, Wu MC, et al. (October 2025). "Zalsupindole is a Nondissociative, Nonhallucinogenic Neuroplastogen with Therapeutic Effects Comparable to Ketamine and Psychedelics". ACS Chem Neurosci. doi:10.1021/acschemneuro.5c00667. PMID 41078264.
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