4-HO-pyr-T
Pharmaceutical compound
From Wikipedia, the free encyclopedia
4-HO-pyr-T, also known as 4-hydroxy-N,N-tetramethylenetryptamine, is a serotonin receptor modulator of the tryptamine, 4-hydroxytryptamine, and pyrrolidinylethylindole families.[1][2] It is the 4-hydroxyl analogue of pyr-T and the analogue of psilocin (4-HO-DMT) and 4-HO-DET in which the N,N-dialkyl moiety has been cyclized into a pyrrolidine ring.[2][1]
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| Other names | 4-OH-pyr-T; 4-Hydroxy-pyr-tryptamine; 4-Hydroxy-N,N-tetramethylenetryptamine; 1-[2-[3-(4-Hydroxy)indolyl]ethyl]pyrrolidine; 4-Hydroxypyrrolidyltryptamine; 3-[2-(1-Pyrrolidyl)ethyl]-4-indolol |
| Drug class | Serotonin receptor modulator |
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| Formula | C14H18N2O |
| Molar mass | 230.311 g·mol−1 |
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Use and effects
In his book TiHKAL (Tryptamines I Have Known and Loved), Shulgin gives the dose as ≥20 mg orally, its duration as unknown, and its onset as about 3 hours.[1] It was described as quite unlike psilocin and bordering on bizarre.[1] There were minimal visual disturbances and no alterations in colors or objects.[1] It was however said to heighten the intellectual process.[1] The drug was said to be more "stimulant-like" than hallucinogenic or psychedelic.[1] 4-HO-pyr-T was described as very unpleasant.[1]
Interactions
Pharmacology
Pharmacodynamics
4-HO-pyr-T has been found to interact with serotonin receptors, including the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[3] Its affinities (Ki) were 429 nM for the serotonin 5-HT2A receptor, 423 nM for the serotonin 5-HT2B receptor, and 275 to 1,772 nM for the serotonin 5-HT2C receptor.[3] Functional activities at these receptors were not assessed or reported.[3]
Chemistry
Synthesis
The chemical synthesis of 4-HO-pyr-T has been described.[1]
Analogues
Analogues of 4-HO-pyr-T include pyr-T, 5-MeO-pyr-T, and 4-F-5-MeO-pyr-T, among others.[1]
Derivatives and analogues of 4-HO-pyr-T, for instance analogues with an azetidine instead of pyrrolidine ring, have been synthesized and described.[4]
History
4-HO-pyr-T was first described in the scientific literature by David Repke and colleagues by 1977.[5] Its effects in humans were subsequently described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) in 1997.[1]