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.
Rescinnamine occurs in the roots of a num ber of Rauwolfia species. Therapeutically, itis used as an antihypertensive agent.
Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug.
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.
Odorless white to cream colored crystalline powder.
The neat material darkens slowly on exposure to light. In solution this occurs more rapidly. .
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.
Flash point data for RESCINNAMINE are not available. RESCINNAMINE is probably combustible.
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.]
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)
