RESCINNAMINE

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

The Uses of RESCINNAMINE

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

The Uses of RESCINNAMINE

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

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.

Indications

For the treatment of hypertension.

Background

Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug. It is an alkaloid obtained from Rauwolfia serpentina and other species of Rauwolfia.

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.

Pharmacokinetics

Used to treat hypertension. Rescinnamine inhibits angiotensin-converting enzyme. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor substance, angiotensin II. Angiotensin II also stimulates aldosterone secretion by the adrenal cortex and general vasoconstriction, both of which lead to increases vascular resistance. By inhibiting angiotensin II, aldosterone reabsorption is decreased as well as vasoconstriction. This combined effect serves to decrease blood pressure.

Metabolism

Not Available

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)