Α,N,N,O-TMS

α,N,N,O-TMS
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-TMS
Identifiers
IUPAC name
  • 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)
SMILES
  • CC(CC1=CNC2=C1C=C(C=C2)OC)N(C)C
InChI
  • 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

5-Methoxy-α,N,N-trimethyltryptamine (5-MeO-α,N,N-TMT), also known as α,N,N,O-tetramethylserotonin (α,N,N,O-TMS), is a little-known synthetic substituted tryptamine and the combined derivative of 5-MeO-DMT and α-methyltryptamine (αMT or AMT).[1][2][3] It 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] The compound was described by Alexander Shulgin in TiHKAL as a putative psychedelic drug, but does not appear to have ever been synthesized or assayed.[1][2][3]

See also

References

  1. 1 2 3 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. 1 2 3 "N,N-Dimethyl-5-methoxy-alpha-methyltryptamine". PubChem. Retrieved 10 January 2025.
  3. 1 2 3 "5-MeO-α-methyl-DMT". Isomer Design. 11 November 2024. Retrieved 26 November 2024.



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