24815-24-5

Basic information

• Product Name: RESCINNAMINE
• Synonyms: 17alpha-dimethoxy-18beta-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-1;3,4,5-Trimethoxycinnamic acid, methyl reserpate;3,4,5-Trimethoxycinnamoyl methyl reserpate;3,4,5-trimethoxycinnamoylmethylreserpate;3,4,5-Trimethylcinnamic acid, ester with methyl reserpate;3,4,5-trimethylcinnamicacid,esterwithmethylreserpate;3,4,5-Trimethylcinnamoyl methyl reserpate;3,4,5-trimethylcinnamoylmethylreserpate
• CAS NO: 24815-24-5
• Molecular Formula: C₃₅H₄₂N₂O₉
• Molecular Weight: 634.72
• EINECS: 246-471-8
• Mol File: 24815-24-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 238-239°C
• Boiling Point: 669.26°C (rough estimate)
• Flash Point: 411.5°C
• Appearance: white to cream powder
• Density: 1.2161 (rough estimate)
• Vapor Pressure: 8.5E-23mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• PKA: pKa 6.4 (Uncertain)
• Stability: Stable, but darkens slowly in light. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: RESCINNAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: RESCINNAMINE(24815-24-5)
• EPA Substance Registry System: RESCINNAMINE(24815-24-5)

Safety Data

• Hazard Codes: Xn
• Statements: 25-20/21/22
• Safety Statements: 22-45-36
• RIDADR: 1544
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 24815-24-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
RESCINNAMINE is used as an antihypertensive agent for the treatment of high blood pressure. It functions as an angiotensin-converting enzyme (ACE) inhibitor, which helps in regulating blood pressure by blocking the conversion of angiotensin I to angiotensin II, a potent vasoconstrictor. This action leads to vasodilation and a subsequent decrease in blood pressure.
Used in Cardiovascular Applications:
In the cardiovascular field, RESCINNAMINE is utilized as a therapeutic agent to manage hypertension and its associated complications, such as heart disease and stroke. Its ACE inhibitory activity contributes to the prevention and treatment of cardiovascular disorders by reducing the strain on the heart and improving blood flow.
Brand Name:
RESCINNAMINE is commercially available under the brand name Moderil, manufactured by Pfizer. This brand name facilitates the identification and prescription of the drug by healthcare professionals for the treatment of hypertension.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

The neat material darkens slowly on exposure to light. In solution this occurs more rapidly. .

Health Hazard

The pharmacological properties of rescinnamine are similar to those of reserpine, butthe side effects are low. It acts as a sedativeand hypotensive. A dose of 0.25 mg/day mayproduce the effect of sleepiness in humans.Excessive doses may produce depression,nightmare, nausea, diarrhea, and hypotension.LD50 value, oral (rats): 1000 mg/kgThe carcinogenicity of rescinnamine inanimals or humans is unknown.

Fire Hazard

Flash point data for RESCINNAMINE are not available. RESCINNAMINE is probably combustible.

Purification Methods

Crystallise it from *benzene, MeOH or aqueous Me2CO. The hydrochloride has m 232o(dec) (from MeOH) and [] D -74o (MeOH). It is an antihypertensive. [Klohs et al. J Am Chem Soc 77 2241 1955, Beilstein 25 III/IV 1323.]

References

Haack e tal., Naturwiss., 41, 214 (1954) Klohs, Draper, Keller.,J. Amer. Chem. Soc., 77,2241 (1955) Kidd., Chem. & Ind., 1481 (1955) Popelak, Lettenbauer., Arch. Pharm., 296,261 (1963)

InChI:InChI=1/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/b10-7+/t20-,24+,26-,29-,31+,34+/m1/s1

Upstream product

• 10263-19-1 (E)-3-(3,4,5-trimethoxyphenyl)acryloyl chloride 
• 2901-66-8 methyl reserpate 

Downstream Products

• 110222-52-1 ent-11,17β-dimethoxy-18α-[3-(3,4,5-trimethoxy-phenyl)-propionyloxy]-15β-yohimban-16α-carboxylic acid methyl ester 
• 2901-66-8 methyl reserpate 

Relevant articles and documents

Pharmaceutical composition containing N-(3-diethyl-aminopropyl)-4-nitro-1-oxide-pyridine-2-carboxamide and process for the treatment of hypertension therewith

This invention relates to a process for the treatment of hypertension and of the disorders derived therefrom, comprising administering to a patient suffering from hypertension a therapeutically effective amount of a compound selected from N-(3-diethyl-aminopropyl)-4-nitro-1-oxide-pyridine-2-carboxamide and its acid addition salts with therapeutically acceptable acids.