Α,N,N,O-TeMS

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. It is the combined derivative of α-methyltryptamine (αMT) and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).

The drug was described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) as a putative psychedelic drug. 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 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 20 mg and a duration of 6 to 8 hours versus 5-MeO-αMT having doses of 2.5 to 4.5 mg and a duration of 12 to 18 hours. Similarly, α,N-dimethyltryptamine (α,N-DMT) 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. 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, 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.