Chemistry:Corynanthine

Short description: Chemical compound

Corynanthine

Clinical data
Other names	Rauhimbine
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name (16β,17α)-17-hydroxy-yohimban-16-carboxylic acid methyl ester
CAS Number	483-10-3
PubChem CID	92766
IUPHAR/BPS	5345
ChemSpider	83744
UNII	F5Z7C9RK8U
Chemical and physical data
Formula	C21H26N2O3
Molar mass	354.450 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(OC)[C@H]5[C@H]4C[C@H]3c2[nH]c1ccccc1c2CCN3C[C@@H]4CC[C@@H]5O

Corynanthine, also known as rauhimbine, is an alkaloid found in the Rauvolfia and Corynanthe (including Pausinystalia) genera of plants. It is one of the two diastereoisomers of yohimbine, the other being rauwolscine. It is also related to ajmalicine.

Corynanthine acts as an α₁-adrenergic and α₂-adrenergic receptor antagonist with approximately 10-fold selectivity for the former site over the latter. This is in contrast to yohimbine and rauwolscine which have around 30-fold higher affinity for the α₂-adrenergic receptor over the α₁-adrenergic receptor. As a result, corynanthine is not a stimulant (or an aphrodisiac for that matter), but a depressant, and likely plays a role in the antihypertensive properties of Rauvolfia extracts. Like yohimbine and rauwolscine, corynanthine has also been shown to possess some activity at serotonin receptors.

See also

• Ajmalicine
• Rauwolscine
• Spegatrine
• Yohimbine