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4-HO-pyr-T

Field	Value
Verifiedfields	verified
Watchedfields	verified
verifiedrevid	477222092
image	4-HO-pyr-T.png
image_class	skin-invert-image
width	200px
image2	4-HO-pyr-T 3D.png
image_class2	bg-transparent
width2	200px
class	Serotonin receptor modulator
ATC_prefix	None
CAS_number_Ref
CAS_number	63097-26-7
PubChem	21854226
ChemSpiderID_Ref
ChemSpiderID	10579820
UNII_Ref
UNII	55L8SYC7EQ
ChEMBL_Ref
ChEMBL	364061
synonyms	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
IUPAC_name	3-[2-(pyrrolidin-1-yl)ethyl]-1H-indol-4-ol
C	14	H=18	N=2	O=1
SMILES	Oc2cccc3[nH]cc(CCN1CCCC1)c23
StdInChI_Ref
StdInChI	1S/C14H18N2O/c17-13-5-3-4-12-14(13)11(10-15-12)6-9-16-7-1-2-8-16/h3-5,10,15,17H,1-2,6-9H2
StdInChIKey_Ref
StdInChIKey	XASLPZWIPBCAPF-UHFFFAOYSA-N

| Drugs.com =

| elimination_half-life =

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. 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.

Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved), Shulgin gives the dose as ≥20mg orally, its duration as unknown, and its onset as about 3hours. It was described as quite unlike psilocin and bordering on bizarre. There were minimal visual disturbances and no alterations in colors or objects. It was however said to heighten the intellectual process. The drug was said to be more "stimulant-like" than hallucinogenic or psychedelic. 4-HO-pyr-T was described as very unpleasant.

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. Its affinities (Ki) were 429nM for the serotonin 5-HT2A receptor, 423nM for the serotonin 5-HT2B receptor, and 275 to 1,772nM for the serotonin 5-HT2C receptor. Functional activities at these receptors were not assessed or reported.

Chemistry

Synthesis

The chemical synthesis of 4-HO-pyr-T has been described.

Analogues

Analogues of 4-HO-pyr-T include pyr-T, 5-MeO-pyr-T, and 4-F-5-MeO-pyr-T, among others.

Derivatives and analogues of 4-HO-pyr-T, for instance analogues with an azetidine instead of pyrrolidine ring, have been synthesized and described.

History

4-HO-pyr-T was first described in the scientific literature by David Repke and colleagues by 1977. Its effects in humans were subsequently described by Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved) in 1997.

References

"Erowid Online Books: "TIHKAL" - #24 4-HO-PYR-T".
(2003). "Hallucinogens: A Forensic Drug Handbook". Elsevier Science.
(October 2005). "SAR of psilocybin analogs: discovery of a selective 5-HT 2C agonist". Bioorganic & Medicinal Chemistry Letters.
(2025). "Towards "unmakable" psychedelics: SAR exploration of psilocin analogs obtained by a HATU-mediated amide coupling strategy". European Journal of Medicinal Chemistry Reports.
(1977). "Psilocin analogs. 1. Synthesis of 3‐[2‐(dialkylamino)ethyl] ‐and 3‐[2‐(cycloalkylamino)ethyl] indol‐4‐ols". Journal of Heterocyclic Chemistry.

Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

david-repke n,n-dialkyltryptamines 4-hydroxytryptamines 1-pyrrolidinyl-compounds pyrrolidinylethylindoles serotonin-receptor-modulators tihkal

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