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Deserpidine

Deserpidine structure

CAS No:
131-01-1
Formula:
C32H38N2O8
Chemical Name:
Deserpidine
Synonyms:
Yohimban-16-carboxylic acid,17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-,methyl ester,(3β,16β,17α,18β,20α)-;3β,20α-Yohimban-16β-carboxylic acid,18β-hydroxy-17α-methoxy-,methyl ester,3,4,5-trimethoxybenzoate (ester);Deserpidine;Deserpidic acid,methyl ester,3,4,5-trimethoxybenzoate;Benz[g]indolo[2,3-a]quinolizine,yohimban-16-carboxylic acid deriv.;Canescine;11-Desmethoxyreserpine;Harmonyl;Raunormine;Recanescine;Reserpidine;11-Demethoxyreserpine;Deserpidin;Recanescin;Raunormin;Canescin;Deserpic acid,methyl ester,3,4,5-trimethoxybenzoate;NSC 72138;Canescine (Rauwolfia);(-)-Deserpidine;13079-12-4;438621-53-5;439669-81-5;855395-45-8;1195636-91-9
Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs

Description

Crystalline solid; exists in three crystallineforms; mp 228–232°C (442.4–449.6°F); soluble in chloroform and methanol, insolublein water; pK 6.68 in saturated solution of40% methanol in water.

Solid

Deserpidine is an alkaloid ester, a methyl ester, a benzoate ester, an organic heteropentacyclic compound and a yohimban alkaloid. It derives from a hydride of a yohimban.|Deserpidine is an ester alkaloid drug isolated from Rauwolfia canescens (family Apocynaceae) with antipsychotic and antihypertensive properties that has been used for the control of high blood pressure and for the relief of psychotic behavior.|Deserpidine is a Catecholamine-depleting Sympatholytic. The physiologic effect of deserpidine is by means of Decreased Sympathetic Activity.|Deserpidine is an ester alkaloid derived from Rauwolfia canescens with antihypertensive activity. Deserpidine is a competitive inhibitor of the angiotensin converting enzyme (ACE). By competing with angiotensin I for ACE, deserpidine blocks the conversion of angiotensin I to angiotensin II, which is a potent vasoconstrictor. Reduced level of serum angiotensin II causes a decrease in blood pressure. Deserpidine also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex.

Deserpidine Basic Attributes

Molecular Weight：

578.65272

Exact Mass：

578.65

EC Number：

205-004-8

UNII：

9016E3VB47

NSC Number：

72138

DSSTox ID：

DTXSID8020383

NCI Thesaurus Code：

C61699

ATC Code：

C - Cardiovascular system

Characteristics

PSA：

109

XLogP3：

3.3

Appearance：

Solid

Density：

1.2277 (rough estimate)

Melting Point：

230.5 °C

Boiling Point：

638.28°C (rough estimate)

Flash Point：

362.7±31.5 °C

Refractive Index：

1.6260 (estimate)

Water Solubility：

H2O: slightly soluble

Vapor Pressure：

3.87E-18mmHg at 25°C

Specific rotation：

D20 -163° (c = 0.5 in pyridine)

Safety Information

Transport codes：

UN 9111

wgk germany：

Toxicity

Toxicity Summary：

Symptoms of overdose include dizziness or drowsiness (severe), flushing of skin, pinpoint pupils of eyes and slowed pulse.

Drug Information

Drug Indication：

For the treatment of hypertension.

Pharmacology：

Deserpidine, an alkaloid of Rauwolfia canescens, 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/Mg²⁺ 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.

MeSH Entry Terms：

deserpidine

Deserpidine Use and Manufacturing

Uses

Deserpidine is found and extracted fromthe roots of Rauwolfia canescens L., andApocyanaceae. Therapeutically, it is used asan antihypertensive agent.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:578.7
XLogP3:4.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:9
Exact Mass:578.26281617
Monoisotopic Mass:578.26281617
Topological Polar Surface Area:109
Heavy Atom Count:42
Complexity:953
Defined Atom Stereocenter Count:6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Extract from the above information

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Dishepin
Manufacturer	Jilin Aodong--Taonan Pharnalentical Company Ltd

Registered Holders

Jilin Aodong--Taonan Pharnalentical Company Ltd

China
Active
ROUSSELL UCLAF

United States
Inactive
SB PENICK AND CO

United States
Inactive

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