yohimbine

Also known as Actibine®, corynine, quebrachin, yohimbin, quebrachine, aphrodine, (+)-yohimbine, 17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester

Yohimbine, also known as quebrachine, is an indole alkaloid derived from the bark of the African tree Pausinystalia johimbe (yohimbe) and from the bark of the unrelated South American tree Aspidosperma quebracho-blanco. It is a veterinary drug used to reverse xylazine.

Chemical data

Formula: C21H26N2O3
Molecular weight: 354.4 g/mol
IUPAC name: methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
SMILES: COC(=O)[C@H]1[C@H](CC[C@@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O
InChIKey: BLGXFZZNTVWLAY-SCYLSFHTSA-N
XLogP: 2.9
Polar surface area: 65.6 Å²
H-bond donors: 2
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

25,136 papers

Article

22 sections

Contents

Uses
Poison warning and variable content in over-the-counter supplements
FDA warning letters
Sexual dysfunction and aphrodisiac
Other uses
Adverse effects
Drug interactions
Pharmacology
Chemistry
Related compounds
Natural occurrence
''Pausinystalia johimbe''
''Aspidosperma quebracho-blanco''
Other plants
History
Society and culture
Doping in sport
Research
Post-traumatic stress disorder
Veterinary use
References
External links

Substances purported to be extracts from the yohimbe tree have been marketed as dietary supplements for various purposes, especially for erectile dysfunction, but they contain highly variable amounts of yohimbine, if any; no published clinical evidence supports their efficacy for treating sexual dysfunction or any disease.