Structure via PubChem · Public domain (PubChem)
corynanthine
Sign in to saveCorynanthine, 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.
In the Vinony graph
Vinony's link graph records 1,065 inbound references to corynanthine, and connects out to tryptamines, N-methylserotonin and propranolol.
It is catalogued under topics including Alkaloids found in Rauvolfia, Alpha-1 blockers and Alpha-2 blockers.
Vinony links it to 7 Wikipedia language editions.
Chemical data
- Formula
- C21H26N2O3
- Molecular weight
- 354.4 g/mol
- IUPAC name
- methyl (1S,15R,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-DKJBZYCGSA-N
- XLogP
- 2.9
- Polar surface area
- 65.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 354.194343
Show 5 more facts
- chemical formula
- C₂₁H₂₆N₂O₃
- found in taxon
- Alstonia constricta
- 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
- canonical SMILES
- COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
- Commons category
- Corynanthine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
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.
Excerpted from Wikipedia’s “corynanthine” article, available under the CC BY-SA 4.0 licence.