Basic information
- CAS
131-01-1- Standard SMILES
COC(=O)[C@H]1[C@H]2C[C@@H]3c4[nH]c5ccccc5c4CCN3C[C@H]2C[C@@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)[C@@H]1OC- InChIKey
CVBMAZKKCSYWQR-WCGOZPBSSA-N- Molecular formula
- C32H38N2O8
- Average molar mass
- 578.7 g/mol
- Monoisotopic mass
- 578.26281617
Overview
Deserpidine is a methyl ester, a yohimban alkaloid, a benzoate ester, an organic heteropentacyclic compound and an alkaloid ester. It derives from a hydride of a yohimban.
Names & identifiers
- Preferred name
- Deserpidine
- IUPAC
- 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
- English name
- Deserpidine
- Molecular formula
- C32H38N2O8
- Molecular weight
- 578.65
Names & synonyms
DESERPIDINE131-01-1HarmonylRaunormineRecanescineRecanescinCanescine11-Demethoxyreserpine11-DesmethoxyreserpineDeserpidinaDeserpidinumHalmonyl
Show more names
ReserpidineDi She PingDeserpidine (7CI)Reserpine Impurity 3Deserpidine USP/EP/BP
Deserpidine, (-)-DTXSID8020383methyl (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-carboxylateNSC-72138CHEBI:274789016E3VB47DTXCID80383(3beta,16beta,17alpha,18beta,20alpha)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester
Database identifiers
- CAS
131-01-1- PubChem CID
- 8550
- DTXSID
DTXSID8020383- ChEMBL
CHEMBL1200515- ChEBI
CHEBI:27478- UNII
- 9016E3VB47
- EC Number
- 205-004-8
Properties
Computed structural properties
- XLogP
- 4.1
- Topological polar surface area
- 109 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 9
- Heavy atoms
- 42
- Formal charge
- 0
- Complexity
- 953
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP3.3
Solubility1.11e-02 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point
228-232
230.5 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 228 · 228-232°; mp 230-232°; mp 138° and 226-232° with resolidification at 175°
- alpha
- 20 · D20 -163° (c = 0.5 in pyridine)
- Boiling point
- 638.28 °C · 638.28°C (rough estimate)
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Pharmacodynamics
Deserpidine, an alkaloid of <i>Rauwolfia canescens</i>, is used as an antihypertensive. Rauwolfia alkaloids work by controlling nerve impulses along certain nerve pathways. As a result, they act on the heart and blood vessels to lower blood pressure.
Mechanism of Action
Deserpidine's mechanism of action is through inhibition of the ATP/Mg<sup>2+</sup> pump responsible for the sequestering of neurotransmitters into storage vesicles located in the presynaptic neuron. The neurotransmitters that are not sequestered in the storage vesicle are readily metabolized by monoamine oxidase (MAO) causing a reduction in catecholamines.
FDA Pharmacological Classification
9016E3VB47
DESERPIDINE
Established Pharmacologic Class [EPC] - Catecholamine-depleting Sympatholytic
Physiologic Effects [PE] - Decreased Sympathetic Activity
Deserpidine is a Catecholamine-depleting Sympatholytic. The physiologic effect of deserpidine is by means of Decreased Sympathetic Activity.
Cellular LocationsCytoplasm
Applications
UsesDeserpidine, is an antihypertensive drug related to Reserpine (R144600). It is naturally found in Rauvolfia spp.
UsesDeserpidine is found and extracted fromthe roots of Rauwolfia canescens L., andApocyanaceae. Therapeutically, it is used asan antihypertensive agent.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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