α-yohimbine

Also known as corynanthidine, isoyohimbine, mesoyohimbine, 17alpha-hydroxy-20alpha-yohimban-16beta-carboxylic acid methyl ester, alpha-yohimbine, rauwolscine, methyl (16beta,17alpha,20alpha)-17-hydroxyyohimban-16-carboxylate

Rauwolscine, also known as isoyohimbine, α-yohimbine, and corynanthidine, is an alkaloid found in various species within the genera Rauvolfia and Corynanthe (including Pausinystalia). It is a stereoisomer of yohimbine. Rauwolscine is a central nervous system stimulant, a local anesthetic and a vague aphrodisiac.

Chemical data

Formula: C21H26N2O3
Molecular weight: 354.4 g/mol
IUPAC name: methyl (1S,15S,18S,19S,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-DIRVCLHFSA-N
XLogP: 2.9
Polar surface area: 65.6 Å²
H-bond donors: 2
H-bond acceptors: 4
Formal charge: 0

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Drug data · ChEMBL

Molecule type: Small molecule

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Wikidata facts

Mass: 354.194343

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chemical formula: C₂₁H₂₆N₂O₃
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
Commons category: Rauwolscine

Sources (3)

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Encyclopedic overview

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Contents

See also
References

Rauwolscine acts predominantly as a α2-adrenergic receptor antagonist. It has also been shown to function as a 5-HT1A receptor partial agonist and 5-HT2A and 5-HT2B receptor antagonist.

Excerpted from Wikipedia’s “α-yohimbine” article, available under the CC BY-SA 4.0 licence.

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