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 Synthetic may refer to: Science * Synthetic biology * Synthetic chemical or compound, produced by the process of chemical synthesis * Synthetic elements, chemical elements that are not naturally found on Earth and therefore have to be created in ...

compound Compound may refer to: Architecture and built environments * Compound (enclosure), a cluster of buildings having a shared purpose, usually inside a fence or wall ** Compound (fortification), a version of the above fortified with defensive struc ...

of the

tryptamine Tryptamine is an indolamine metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the firs ...

α-alkyltryptamine Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine analogues), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all trypt ...

, and

5-methoxytryptamine 5-Methoxytryptamine (5-MT, 5-MeO-T, or 5-OMe-T), also known as serotonin methyl ether or ''O''-methylserotonin and as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. It has been shown to oc ...

families. It is the combined

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

of α-methyltryptamine (αMT) and 5-methoxy-''N'',''N''-dimethyltryptamine (5-MeO-DMT). The drug was described by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

in his book ''

TiHKAL ''TiHKAL: The Continuation'' is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to '' PiHKAL: A Chemical Love Story'', ''TiHKAL'' is an acronym that stands for "Trypt ...

'' (''Tryptamines I Have Known and Loved'') as a putative

psychedelic drug Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluc ...

. However, Shulgin does not appear to have ever synthesized or assayed it. As such, α,''N'',''N'',''O''-TeMS's effects, dosage, and duration are all unknown. α,''N'',''N'',''O''-TeMS is also the ''N'',''N''- dimethylated derivative of

5-methoxy-α-methyltryptamine 5-MeO-αMT, also known as 5-methoxy-α-methyltryptamine or as α,''O''-dimethylserotonin (α,''O''-DMS or Alpha-O), is a serotonergic psychedelic of the tryptamine, α-alkyltryptamine, and 5-methoxytryptamine families. It is a derivative of α- ...

(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). 5-MeO-α,''N''-DMT is less potent and long-lasting than 5-MeO-αMT, with 5-MeO-α,''N''-DMT having doses of 10 to 20mg and a duration of 6 to 8hours versus 5-MeO-αMT having doses of 2.5 to 4.5mg and a duration of 12 to 18hours. Similarly, α,''N''-dimethyltryptamine (α,''N''-DMT) is less potent than αMT, with doses of 50 to 100mg for α,''N''-DMT and doses of 15 to 30mg for αMT. Hence, it appears that ''N''-methylation of α-alkyltryptamines may reduce their activity and potency, by about 3- or 4-fold. α,''N'',''N'',''O''-TeMS was first described in the literature, specifically in ''TiHKAL'', by 1997. It is known to have been made at

Edgewood Arsenal Aberdeen Proving Ground (APG) is a U.S. Army facility located adjacent to Aberdeen, Harford County, Maryland, United States. More than 7,500 civilians and 5,000 military personnel work at APG. There are 11 major commands among the tenant units, ...

, but the facility never published anything on the compound. α,''N'',''N'',''O''-TeMS does not appear to have been otherwise described in the literature.

References

External links

5-MeO-α-methyl-DMT - Isomer Design
Alpha-Alkyltryptamines N,N-Dialkyltryptamines Dimethylamino compounds 5-Methoxytryptamines {{Psychoactive-stub

See also

References

External links