Yohimbine

Yohimbine

Clinical data
Routes of administration	Oral
ATC code	G04BE04 (WHO) QV03AB93 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: Dietary supplement
Pharmacokinetic data
Bioavailability	7-86% (mean 33%)
Biological half-life	0.25-2.5 hours
Excretion	Urine (as metabolites)
Identifiers
IUPAC name 17α-hydroxy-yohimban-16α- carboxylic acid methyl ester
CAS Number	146-48-5 Y
PubChem (CID)	8969
IUPHAR/BPS	102
DrugBank	DB01392 Y
ChemSpider	8622 Y
UNII	2Y49VWD90Q Y
ChEBI	CHEBI:10093 Y
ChEMBL	CHEMBL15245 Y
ECHA InfoCard	100.005.157
Chemical and physical data
Formula	C21H26N2O3
Molar mass	354.44 g/mol (base) 390.90 g/mol (hydrochloride)
3D model (Jmol)	Interactive image
SMILES O=C(OC)[C@@H]5[C@H]4C[C@H]3c2nc1ccccc1c2CCN3C[C@@H]4CC[C@@H]5O
InChI 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

Yohimbine (/joʊˈhɪmbiːn/) is an indole alkaloid derived from the bark of the Pausinystalia yohimbe tree in Central Africa. It is a veterinary drug used to reverse sedation in dogs and deer. Yohimbine has been studied as a potential treatment for erectile dysfunction but there is insufficient evidence to rate its effectiveness. Extracts from yohimbe have been marketed as dietary supplements for improving sexual function.

Yohimbine is a drug used in veterinary medicine to reverse the effects of xylazine in dogs and deer.

Yohimbe extracts, which contain yohimbine, have been used in traditional medicine and marketed as dietary supplements.

Depending on dosage, yohimbine can either increase or decrease systemic blood pressure (through vasoconstriction or vasodilation, respectively). Because yohimbine has highest affinity for the α₂ receptor, small doses can increase blood pressure by causing a relatively selective α₂ blockade. Yohimbine also, however, interacts with α₁ receptors, albeit with lower affinity; therefore, at higher doses an α₁ blockade can occur and supersede the effects of the α₂ blockade, leading to a potentially dangerous drop in blood pressure. Higher doses of oral yohimbine may create numerous side effects, such as rapid heart rate, overstimulation, anomalous blood pressure, cold sweating, and insomnia.

Yohimbe (Pausinystalia johimbe) is a tree that grows in western and central Africa; yohimbine was originally extracted from the bark of yohimbe in 1896 by Adolph Spiegel. In 1943 the correct constitution of yohimbine was proposed by Witkop. Fifteen years later, Van Tamelen used a 23-step synthesis to become the first person to achieve the synthesis of yohimbine.