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Serotonin receptor agonist · Serotonergic psychedelic

O-Pivalylbufotenine

Original Wikipedia articleen.wikipedia.org/wiki/O-Pivalylbufotenine revision used (24 October 2026)

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Overview

O-Pivalylbufotenine, or bufotenine O-pivalate, also known as 5-pivaloxy-N,N-dimethyltryptamine (5-t-BuCO-DMT) or as O-pivalyl-N,N-dimethylserotonin, is a synthetic tryptamine derivative and putative serotonergic psychedelic. It is the O-pivalyl analogue of the naturally occurring but peripherally selective serotonergic tryptamine bufotenine (5-hydroxy-N,N-dimethyltrypamine or N,N-dimethylserotonin) and is thought to act as a centrally penetrant prodrug of bufotenine.[1–4] WP

Drug class

Serotonin receptor agonist Serotonergic psychedelic WP

From the Wikipedia article's infobox.

Pharmacology

Pharmacology

O-Pivalylbufotenine is thought to be a prodrug of bufotenin and shows psychedelic-like effects in animal. However, it is less active than anticipated, perhaps due to its high lipophilicity and, by extension, high plasma protein binding and ester hydrolysis into bufotenin prior to crossing the blood–brain barrier. In addition to theoretically acting as a prodrug of bufotenine, which is a non-selective serotonin receptor agonist, O-pivalylbufotenine may also interact directly with certain serotonin receptors.[3–7] WP

History

History

O-Pivalylbufotenine was first described in the scientific literature by 1979.[4] WP

Chemistry

Formula
C17H24N2O2 PC
Molar mass (g/mol)
288.4 PC
IUPAC name (computed by PubChem)
[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl] 2,2-dimethylpropanoate PC
SMILES
CC(C)(C)C(=O)OC1=CC2=C(C=C1)NC=C2CCN(C)C PC
InChIKey
AFACMZRKVDGTKP-UHFFFAOYSA-N PC
PubChem CID
44339071

Harm reduction information

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Sources

  1. Journal / agency Glennon RA, Rosecrans JA. Indolealkylamine and phenalkylamine hallucinogens: a brief overview. Neurosci Biobehav Rev. 1982. doi:10.1016/0149-7634(82)90030-6 · PMID 6757811
  2. Other Nichols DE, Glennon RA. Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. 1984
  3. Journal / agency Glennon RA, Rosecrans JA. Speculations on the mechanism of action of hallucinogenic indolealkylamines. Neurosci Biobehav Rev. 1981. doi:10.1016/0149-7634(81)90002-6 · PMID 7022271
  4. Journal / agency Glennon RA, Gessner PK, Godse DD, Kline BJ. Bufotenine esters. J Med Chem. November 1979. doi:10.1021/jm00197a025 · PMID 533890
  5. Journal / agency McBride MC. Bufotenine: toward an understanding of possible psychoactive mechanisms. J Psychoactive Drugs. 2000. doi:10.1080/02791072.2000.10400456 · PMID 11061684
  6. Journal / agency Plazas E, Faraone N. Indole Alkaloids from Psychoactive Mushrooms: Chemical and Pharmacological Potential as Psychotherapeutic Agents. Biomedicines. February 2023. doi:10.3390/biomedicines11020461 · PMID 36830997 · PMC9953455
  7. Journal / agency Neumann J, Dhein S, Kirchhefer U, Hofmann B, Gergs U. Effects of hallucinogenic drugs on the human heart. Front Pharmacol. 2024. doi:10.3389/fphar.2024.1334218 · PMID 38370480 · PMC10869618

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.