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
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)
