Alpha,N,O-TMS

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Alpha,N,O-TMS
A,N,O-TMS.svg
Identifiers
  • [1-(5-methoxy-1H-indol-3-yl)propan-2-yl](methyl)amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C13H18N2O
Molar mass 218.300 g·mol−1
3D model (JSmol)
  • O(c1cc2c(cc1)[nH]cc2CC(NC)C)C
  • InChI=1S/C13H18N2O/c1-9(14-2)6-10-8-15-13-5-4-11(16-3)7-12(10)13/h4-5,7-9,14-15H,6H2,1-3H3 Yes check.svgY
  • Key:IYEMYZOLBLHKFE-UHFFFAOYSA-N Yes check.svgY
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Alpha,N,O-TMS, or α,N-dimethyl-5-methoxy tryptamine , is a lesser-known psychedelic drug. 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 10-20 mg when taken orally, and the duration as 6–8 hours. [1]

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<span class="mw-page-title-main">5-MeO-DET</span> Chemical compound

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<span class="mw-page-title-main">4-HO-MiPT</span> Chemical compound

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<span class="mw-page-title-main">MiPT</span> Chemical compound

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<span class="mw-page-title-main">Ethylisopropyltryptamine</span> Chemical compound

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<span class="mw-page-title-main">5-MeO-2-TMT</span> Chemical compound

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<span class="mw-page-title-main">Dibutyltryptamine</span> Chemical compound

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<span class="mw-page-title-main">4-HO-DBT</span> Chemical compound

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<span class="mw-page-title-main">Methylbutyltryptamine</span> Chemical compound

MBT, or N-methyl-N-butyltryptamine, is a lesser-known psychedelic drug. MBT was first synthesized by Alexander Shulgin. In his book TiHKAL, the minimum dosage is listed as 250-400 mg, and the duration listed as 4–6 hours. MBT produces a heavy body load with dehydration, and causes visuals similar to those of DMT. Very little data exists about the pharmacological properties, metabolism, and toxicity of MBT.

<span class="mw-page-title-main">Pyr-T</span> Chemical compound

Pyr-T (N,N-tetramethylenetryptamine) is a lesser-known, possible psychedelic drug. Pyr-T was first characterized by S. Mitzal. Toxicity testing was later performed by Hunt and Brimblecombe, and although a lethal dosage was found in rats, a value is not given. In the book TiHKAL, neither the dosage nor the duration are reported.

<span class="mw-page-title-main">4-MeO-MiPT</span> Chemical compound

4-MeO-MiPT, or 4-methoxy-N-methyl-N-isopropyltryptamine, is a lesser-known psychedelic drug. It is the 4-methoxy analog of MiPT. 4-MeO-MiPT was first synthesized by Alexander Shulgin and is mentioned in his book TiHKAL. Subsequent testing by Shulgin on human test subjects showed the effective dose as 20-30 mg ; the onset time between ingestion and the first noticeable effects was 45-60 min, with sensations lasting between 2-2.5 hours. The sensation were significantly milder than those of 4-HO-MiPT, with 4-MeO-MiPT producing erotic-enhancing effects, and few of the visuals common with tryptamines. Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-MeO-MiPT.

<span class="mw-page-title-main">5-MeO-pyr-T</span> Chemical compound

5-MeO-pyr-T (5-methoxy-N,N-tetramethylenetryptamine) is a lesser-known psychedelic drug. It is the 5-methoxy analog of pyr-T. 5-MeO-pyr-T was first synthesized by Hunt & Brimblecombe, who credited S. Mitzal for characterization of chemical properties. Later human tests were reported by Alexander Shulgin, in his book TiHKAL. An oral dosage of 0.5 to 2 mg, and an inhaled dosage of 2–3 mg are reported. 5-MeO-pyr-T causes varying reactions, such as amnesia, tinnitus, vomiting, and a 5-MeO-DMT-like rushing sensation. At the highest dosage reported in TiHKAL, the subject describes awakening from an apparent fugue state during which they were wandering the streets, with complete amnesia upon awakening.

<span class="mw-page-title-main">5,6-MeO-MiPT</span> Chemical compound

5,6-MeO-MiPT, or 5,6-dimethoxy-N-methyl-N-isopropyltryptamine, is a lesser-known psychedelic drug. It is the 5,6-dimethoxy analog of MiPT. 5,6-MeO-MiPT was first synthesized by Alexander Shulgin. In his book TiHKAL, 5,6-MeO-MiPT produces no noticeable psychoactive effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of 5,6-MeO-MiPT.

<span class="mw-page-title-main">5,6-MDO-DiPT</span> Chemical compound

5,6-MDO-DiPT, or 5,6-methylenedioxy-N,N-diisopropyltryptamine, is a lesser-known psychedelic drug. It is the 5,6-methylenedioxy analog of DiPT. 5,6-MDO-DiPT was first synthesized by Alexander Shulgin. It is mentioned in his book TiHKAL, but 5,6-MDO-DiPT was never tested to determine what effects it produces, if any. Very little data exists about the pharmacological properties, metabolism, and toxicity of 5,6-MDO-DiPT.

<span class="mw-page-title-main">2,α-Dimethyltryptamine</span> Chemical compound

2,α-Dimethyltryptamine (2,α-DMT) is a tryptamine and a lesser-known psychedelic drug. It is the 2,α-dimethyl analog of DMT. Its synthesis was first reported in 1965. Alexander Shulgin lists the dosage as 300-500 mg, and the duration as 7–10 hours in his book TiHKAL. 2,α-DMT causes mydriasis and paresthesia. It also produces a calm, drunk-like feeling. Very little data exists about the pharmacological properties, metabolism, and toxicity of 2,α-DMT.

<span class="mw-page-title-main">Alpha,N-DMT</span> Chemical compound

Alpha,N-DMT, or α,N-dimethyltryptamine, is a lesser-known psychedelic drug. It is the α,N-dimethyl analog of DMT. α,N-DMT was first synthesized by Alexander Shulgin. In his book TiHKAL, Shulgin lists the dosage as 50-100 mg, and the duration as 6–8 hours. α,N-DMT causes an unpleasant body load. Very little data exists about the pharmacological properties, metabolism, and toxicity of α,N-DMT. α,N-DMT is known to be a potent monoamine oxidase inhibitor

<span class="mw-page-title-main">4-HO-αMT</span> Chemical compound

4-Hydroxy-α-methyltryptamine (4-HO-αMT) is a psychedelic drug of the tryptamine class. It is a close structural analogue of α-methyltryptamine (αMT) and produces similar effects to it, but with exacerbated side effects similarly to 5-MeO-αMT. Alexander Shulgin describes 4-HO-αMT briefly in his book TiHKAL:

The 4-hydroxy analogue of αMT has been looked at in human subjects. It is reported to be markedly visual in its effects, with some subjects reporting dizziness and a depressed feeling. There were, however, several toxic signs at doses of 15 to 20 milligrams orally, including abdominal pain, tachycardia, increased blood pressure and, with several people, headache and diarrhea.

<i>N</i>-<i>t</i>-Butyltryptamine Chemical compound

N-t-Butyltryptamine (NTBT) is a tryptamine derivative which has serotonergic effects. It is described by Alexander Shulgin as producing "a light-headed intoxication that is a totally pleasant buzz, but nothing more profound than that" at a dosage range of 5 to 20 mg, along with the related sec-butyl isomer NSBT which is similar in effects but slightly less potent.

References

  1. Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. p. 425. ISBN   0-9630096-9-9. OCLC   38503252.