Yohimbine

Yohimbine
Clinical data
Pronunciation	/joʊˈhɪmbiːn/
Other names	Quebrachine
Routes of; administration	By mouth
Drug class	α2-Adrenergic receptor antagonist
ATC code	G04BE04 (WHO) QV03AB93 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; US: Unscheduled;
Pharmacokinetic data
Bioavailability	7-86% (mean 33%)
Elimination half-life	0.25–2.5 hours
Excretion	Urine (as metabolites)
Identifiers
	IUPAC name 17α-hydroxyyohimban-16α-carboxylic acid methyl ester;
CAS Number	146-48-5 ;
PubChem CID	8969;
IUPHAR/BPS	102;
DrugBank	DB01392 ;
ChemSpider	8622 ;
UNII	2Y49VWD90Q;
KEGG	D08685 ;
ChEBI	CHEBI:10093 ;
ChEMBL	ChEMBL15245 ;
CompTox Dashboard (EPA)	DTXSID9040130 ;
ECHA InfoCard	100.005.157
Chemical and physical data
Formula	C21H26N2O3
Molar mass	354.450 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [H][C@@]15CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@@]4([H])c3[nH]c2ccccc2c3CCN4C5;
	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 ; Key:BLGXFZZNTVWLAY-SCYLSFHTSA-N ;
	(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.^[3]^[4] It is a veterinary drug used to reverse sedation in dogs and deer.

Substances that have purported to be extracts from the yohimbe tree have been marketed as dietary supplements for various purposes, but they contain highly variable amounts of yohimbine, if any; no published scientific evidence supports their efficacy for treating sexual dysfunction or any disease.^[3]^[4]^[5]

^ "Yohimbine. (n.d.)". Collins English Dictionary – Complete and Unabridged. (1991, 1994, 1998, 2000, 2003). Retrieved 27 January 2015.
^ Hedner T, Edgar B, Edvinsson L, Hedner J, Persson B, Pettersson A (1992). "Yohimbine pharmacokinetics and interaction with the sympathetic nervous system in normal volunteers". European Journal of Clinical Pharmacology. 43 (6): 651–6. doi:10.1007/BF02284967. PMID 1493849. S2CID 12346330.
^ ^a ^b "Yohimbe". National Center for Complementary and Integrative Health, US National Institutes of Health. April 2025. Retrieved 20 June 2025.
^ ^a ^b "Yohimbe". Drugs.com. 26 June 2024. Retrieved 20 June 2025.
^ EFSA Panel on Food Additives and Nutrient Sources Added to Food, European Food Safety Authority (2013). "Scientific Opinion on the evaluation of the safety in use of Yohimbe (Pausinystalia yohimbe (K. Schum.) Pierre ex Beille)". EFSA Journal. 7. 11: 3302 (1–46). doi:10.2903/j.efsa.2013.3302.

[1] "Yohimbine. (n.d.)". Collins English Dictionary – Complete and Unabridged. (1991, 1994, 1998, 2000, 2003). Retrieved 27 January 2015.

[2] Hedner T, Edgar B, Edvinsson L, Hedner J, Persson B, Pettersson A (1992). "Yohimbine pharmacokinetics and interaction with the sympathetic nervous system in normal volunteers". European Journal of Clinical Pharmacology. 43 (6): 651–6. doi:10.1007/BF02284967. PMID 1493849. S2CID 12346330.

[nccih-3] "Yohimbe". National Center for Complementary and Integrative Health, US National Institutes of Health. April 2025. Retrieved 20 June 2025.

[drugs-4] "Yohimbe". Drugs.com. 26 June 2024. Retrieved 20 June 2025.

[EFSA2013-5] EFSA Panel on Food Additives and Nutrient Sources Added to Food, European Food Safety Authority (2013). "Scientific Opinion on the evaluation of the safety in use of Yohimbe (Pausinystalia yohimbe (K. Schum.) Pierre ex Beille)". EFSA Journal. 7. 11: 3302 (1–46). doi:10.2903/j.efsa.2013.3302.

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