Yohimbine

Yohimbine
Clinical data
Pronunciation/jˈhɪmbn/
Other namesQuebrachine
Routes of
administration
By mouth
Drug classα2-Adrenergic receptor antagonist
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • US: Unscheduled
Pharmacokinetic data
Bioavailability7-86% (mean 33%)
Elimination half-life0.25–2.5 hours
ExcretionUrine (as metabolites)
Identifiers
  • 17α-hydroxyyohimban-16α-carboxylic acid methyl ester
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.157
Chemical and physical data
FormulaC21H26N2O3
Molar mass354.450 g·mol−1
3D model (JSmol)
  • [H][C@@]15CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@@]4([H])c3[nH]c2ccccc2c3CCN4C5
  • InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1 Y
  • Key:BLGXFZZNTVWLAY-SCYLSFHTSA-N Y
  (verify)

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.

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.

In the United States, it is illegal to market an over-the-counter (OTC) supplement product containing yohimbine as a treatment for any supposed health effect without having approval from the Food and Drug Administration (FDA). In the United Kingdom, yohimbine is an unlicensed drug, rarely and specifically compounded as a "prescription-only medicine", while yohimbine herbal supplements are banned from manufacturing as dangerous substances.