Structure via PubChem · Public domain (PubChem)
yohimbine
Sign in to saveAlso 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 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
25,136 papers- Yohimbine.Pediatric emergency care · 2000
- Yohimbine as a pharmacological probe for alcohol research: a systematic review of rodent and human studies.Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology · 2022
- Multifaced Nature of Yohimbine-A Promising Therapeutic Potential or a Risk?International journal of molecular sciences · 2024
- A literature perspective on the pharmacological applications of yohimbine.Annals of medicine · 2022
- [Yohimbine in therapy of erectile dysfunction].Fortschritte der Medizin · 1998
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 354.194343
- Has use
- medication
Show 10 more facts
- chemical formula
- C₂₁H₂₆N₂O₃
- World Health Organisation international non-proprietary name
- yohimbine
- medical condition treated
- hypoactive sexual desire disorder
- canonical SMILES
- COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
- isomeric 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
- found in taxon
- Apocynaceae
- defined daily dose
- 15
- route of administration
- oral administration
- has characteristic
- bitterness
- Commons category
- Yohimbine
Sources (6)
via Wikidata · CC0
~15 min read
Encyclopedic overview
22 sectionsContents
- 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
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.
Excerpted from Wikipedia’s “yohimbine” article, available under the CC BY-SA 4.0 licence.