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| | RESCINNAMINE Basic information |
| Product Name: | RESCINNAMINE | | Synonyms: | Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]oxy]-, methyl ester, (3β,16β,17α,18β,20α)-;METHYL RESERPATE-3,4,5-TRIMETHOXY CINNAMIC ACID ESTER;ANAPREL;3,4,5-TRIMETHOXYCINNAMOYLRESERPATE;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 | | CAS: | 24815-24-5 | | MF: | C35H42N2O9 | | MW: | 634.73 | | EINECS: | 246-471-8 | | Product Categories: | | | Mol File: | 24815-24-5.mol |  |
| | 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) | | pka | pKa 6.4 (Uncertain) | | form | Solid | | 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) |
| | 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]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) |
| | RESCINNAMINE Preparation Products And Raw materials |
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