RESCINNAMINE Chemical Properties

Melting point:

238-239°C

alpha 

D24 -97° (c = 1 in chloroform)

Boiling point:

669.26°C (rough estimate)

Density 

1.2161 (rough estimate)

refractive index 

1.5300 (estimate)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly, Heated)

form 

Solid

pka

pKa 6.4 (Uncertain)

color 

Pale Beige to Pale Brown

Stability:

Stable, but darkens slowly in light. Incompatible with strong oxidizing agents.

EPA Substance Registry System

Rescinnamine (24815-24-5)

Safety Information

Hazard Codes 

Xn

Risk 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)

RESCINNAMINE Usage And Synthesis

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]¹⁷_D - 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

Rescinnamine occurs in the roots of a num ber of Rauwolfia species. Therapeutically, itis used as an antihypertensive agent.

Uses

Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug.

Definition

ChEBI: Rescinnamine is a methyl ester, an organic heteropentacyclic compound and an indole alkaloid. It has a role as an antihypertensive agent. It derives from a hydride of a yohimban.

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/kg
The 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)

RESCINNAMINE(24815-24-5)Related Product Information

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