Pyr-T
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| _other_data=3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole
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Pyr-T, also known as N,N-tetramethylenetryptamine or as 3-(2-pyrrolidinoethyl)indole, is a lesser-known serotonin receptor modulator of the tryptamine family.[1][2] It is the cyclized derivative of diethyltryptamine (DET) in which the N,N-diethyl groups have been fused into a pyrrolidine ring.[2]
Use and effects
In his 1997 book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin reported neither the dose range nor the duration of the drug.[1][3] However, individual experiments employed 25 to 50Script error: No such module "String".mg orally and 70Script error: No such module "String".mg smoked.[1] Pyr-T produced effects including malaise, feeling sick, unpleasantness, salivation, muscle and joint pains, dizziness, feeling high, and uncomfortableness.[1] Hallucinogenic effects, for instance visuals, were either absent or minor.[1]
Pharmacology
Pyr-T has been found to show affinity for serotonin receptors, including the serotonin 5-HT1A, 5-HT2A and 5-HT2C receptors.[4][5] Its affinities (IC50) for these receptors were 30Script error: No such module "String".nM for the serotonin 5-HT1A receptor, 110Script error: No such module "String".nM for the 5-HT2A receptor, and 750Script error: No such module "String".nM for the serotonin 5-HT2B receptor.[4][5] The affinities of pyr-T for the serotonin 5-HT2A and 5-HT2B receptors were similar to but slightly lower than those of dimethyltryptamine (DMT), whereas its affinity for the serotonin 5-HT1A receptor was 5.7-fold higher than that of DMT and was intermediate between those of DMT and 5-MeO-DMT.[4][5] The serotonin 5-HT1A to 5-HT2A receptor affinity ratios in the study were about 0.27 for pyr-T, 0.5 for 5-MeO-DMT, 1.4 for bufotenin, 2.3 for DMT, and 32 for psilocin.[5]
Pyr-T has been found to produce behavioral changes in animal tests.[2][6][7] It was described as being as potent as diethyltryptamine (DET) in rodents, cats, and primates, but that it also had a poor margin of activity relative to toxicity and was unlikely to be tested in humans.[2] It has been found to produce hypolocomotion in rodents.[7] Conversely, pyr-T (3Script error: No such module "String".mg/kg) failed to acutely produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[7]
Chemistry
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Pyr-T is a substituted tryptamine in which the amine moiety has been replaced with a pyrrolidine ring. It can be thought of as a cyclized derivative of diethyltryptamine (DET) in which the N,N-ethyl groups have been connected to form the pyrrolidine ring present in pyr-T.
Derivatives of pyr-T include 4-HO-pyr-T, 5-MeO-pyr-T, and 4-F-5-MeO-pyr-T. Analogues of pyr-T include pip-tryptamine, 10,11-secoergoline (α,N-Pip-T), MPMI, and SN-22, among others.
History
Pyr-T was first characterized by Mitzal by 1962.[8] Animal toxicity testing was later performed by Hunt and Brimblecombe by 1967.[2][6] The effects of pyr-T in humans were described by Alexander Shulgin in his book TiHKAL in 1997.[1]
References
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External links
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