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

Description

This Rauwolfia alkaloid is found in the barks of R. serpentina and R. vomitora and was originally given the name Reserpinine, this being altered to avoid confusion with another alkaloid of the same name (q.v.). The base has [α]17D - 99.2° (c 1.3, CHCI3). From chemical degradation and spectroscopic analysis, the structure has been established as the 3:4: 5-trimethoxycinnamoyl ester of reserpic acid.

Chemical Properties

white to cream powder

Uses

Different sources of media describe the Uses of 24815-24-5 differently. You can refer to the following data:
1. Rescinnamine occurs in the roots of a num ber of Rauwolfia species. Therapeutically, itis used as an antihypertensive agent.
2. Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug.

Brand name

Moderil (Pfizer).

General Description

Odorless white to cream colored crystalline powder.

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

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

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.