Α,N,O-TMS
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| Other names | α,N,O-Trimethylserotonin; α,N,O-TMS; 5-Methoxy-α,N-dimethyltryptamine; 5-MeO-α,N-DMT; 5-MeO-α-Me-NMT |
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| Formula | C13H18N2O |
| Molar mass | 218.300 g·mol−1 |
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α,N,O-Trimethylserotonin (α,N,O-TMS), also known as 5-methoxy-α,N-dimethyltryptamine (5-MeO-α,N-DMT), is a lesser-known psychedelic drug of the tryptamine family. Its abbreviated nomenclature is derived from its structure, as it is α,N,O-trimethyl serotonin.
α,N,O-TMS was first synthesized by Alexander Shulgin. In his book TiHKAL (Tryptamines I Have Known and Loved), Shulgin lists the dosage as 10 to 20 mg when taken orally, and the duration as 6 to 8 hours. The drug is significantly less potent than its non-N-methylated parent compound 5-MeO-AMT (5-methoxy-α-methyltryptamine), which has a dose range of 2.5 to 4.5 mg and a duration of 12 to 18 hours.
A derivative of α,N,O-TMS, α,N,N,O-tetramethylserotonin (α,N,N,O-TeMS), also known as 5-methoxy-α-methyl-N,N-dimethyltryptamine (5-MeO-α-Me-DMT), has also been described. However, it was not synthesized or described and its dosage, duration, and effects are unknown.