deserpidine

Also known as Harmonyl®, recanescin, (3beta,16beta,17alpha,18beta,20alpha)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester, 11-demethoxyreserpine, 11-desmethoxyreserpine, canescine, recanescine, Harmonyl

Deserpidine (INN) or reserpidine (USAN) is an antihypertensive drug structurally related to reserpine differing only by the absence of a methoxy group on the indole ring. It is a naturally occurring alkaloid from Rauvolfia spp.

Chemical data

Formula: C32H38N2O8
Molecular weight: 578.7 g/mol
IUPAC name: methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
SMILES: CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=CC=CC=C45)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
InChIKey: CVBMAZKKCSYWQR-WCGOZPBSSA-N
XLogP: 4.1
Polar surface area: 109 Å²
H-bond donors: 1
H-bond acceptors: 9
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1957
Admin. routes: oral
Indications: hypertension

via ChEMBL · EBI

Wikidata facts

Mass: 578.263
Has use: medication

Show 7 more facts

chemical formula: C₃₂H₃₈N₂O₈
found in taxon: Rauvolfia tetraphylla
medical condition treated: arterial hypertension
subject has role: adrenergic uptake inhibitors
canonical SMILES: COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=CC=CC=C45)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
isomeric SMILES: CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=CC=CC=C45)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
Commons category: Deserpidine

Sources (4)

via Wikidata · CC0

~1 min read

Encyclopedic overview

1 sections

Contents

References

==References==

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

Available in 8 languages

via Wikidata sitelinks · CC0