rescinnamine

Also known as 3,4,5-Trimethoxycinnamoyl methyl reserpate, Trimethoxy cinnamoyl reserpate de methyl, Tsuruselpi S

Rescinnamine, known by the brand names Moderil, Cinnasil, and Anaprel, is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug.

Chemical data

Formula: C35H42N2O9
Molecular weight: 634.7 g/mol
IUPAC name: methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]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=C4C=CC(=C5)OC)OC(=O)/C=C/C6=CC(=C(C(=C6)OC)OC)OC
InChIKey: SZLZWPPUNLXJEA-QEGASFHISA-N
XLogP: 4.5
Polar surface area: 118 Å²
H-bond donors: 1
H-bond acceptors: 10
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1956
Admin. routes: oral
Indications: hypertension

via ChEMBL · EBI

Wikidata facts

Mass: 634.289031
Has use: medication

Show 4 more facts

chemical formula: C₃₅H₄₂N₂O₉
found in taxon: Rauvolfia afra
canonical SMILES: COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C=CC6=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=C4C=CC(=C5)OC)OC(=O)/C=C/C6=CC(=C(C(=C6)OC)OC)OC

Sources (2)

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Encyclopedic overview

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Contents

References

{{Drugbox | verifiedrevid = 464380960 | IUPAC_name = methyl (3β,16β,17α,18β,20α)-11,17-dimethoxy-18-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}yohimban-16-carboxylate | image = Rescinnamine.svg | image_class = skin-invert-image | width = 250px | image2 = Rescinnamine.png | image_class2 = bg-transparent | width2 = 250px

| tradename = Moderil, Cinnasil, Anaprel | pregnancy_category = | legal_status = Rx-only | routes_of_administration = By mouth

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

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