Identification | Back Directory | [Name]
RESCINNAMINE | [CAS]
24815-24-5 | [Synonyms]
Rozex Tuareg Rescin Apolon Cartric Anapral ANAPREL Resipal Moderil Raupyrol Rescamin Rescidan Rescisan Tenamine Cinnasil Cinamine Cinatabs Apoterin REPIN(P) NSC 15628 Cinnaloid Rescinpal Rescitens Resealoid Paresinan Rescaloid Raurescin Raurescine Reserpinin Scinnamina Apoterin S RESERPININE Reskinnamin Reserpinene Rescinnamin Recinnamine Recitensina rscinnamine Normorescina RESCINNAMINE RESCINNAMINE(RG) Rescinnamine,98% resepinine(c35alkaloid) reserpinine[c35alkaloid] Reserpinine (C35 alkaloid) trimethoxycinnamoylmethylreserpate methyltrimethoxycinnamoylreserpate 3,4,5-TRIMETHOXYCINNAMOYLRESERPATE Methyl trimethoxycinnamoylreserpate trimethoxycinnamoylreserpatedemethyl Trimethoxycinnamoyl methyl reserpate 3,4,5-trimethylcinnamoylmethylreserpate 3,4,5-trimethoxycinnamoylmethylreserpate 3,4,5-Trimethylcinnamoyl methyl reserpate 3,4,5-Trimethoxycinnamoyl methyl reserpate METHYL-3,4,5-TRIMETHOXYCINNAMOYL RESERPATE methyl18-o-(3,4,5-trimethoxycinnamoylreserpate methyl18-o-(3,4,5-trimethoxycinnamoyl)reserpate 3,4,5-Trimethoxycinnamic acid, methyl reserpate Methyl 18-O-(3,4,5-trimethoxycinnamoyl)reserpate 3,4,5-trimethylcinnamicacid,esterwithmethylreserpate methylester,3,4,5-trimethoxycinnamate(ester),(e)-oxy Reserpic acid methyl ester 3,4,5-trimethoxycinnamate O-(3,4,5-Trimethoxy-trans-cinnamoyl) methyl reserpate METHYL RESERPATE-3,4,5-TRIMETHOXY CINNAMIC ACID ESTER imethoxy-,methylester,3,4,5-trimethoxycinnamate(ester) 3beta,20alpha-yohimban-16beta-carboxylicacidmethylester 3,4,5-Trimethylcinnamic acid, ester with methyl reserpate 17alpha-dimethoxy-18beta-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-1 3beta,20alpha-yohimban-16beta-carboxylicacid,18beta-hydroxy-11,17alpha-dimeth yohimban-16-carboxylicacid,11,17-dimethoxy-18-((1-oxo-3-(3,4,5-trimethoxyphen Methyl 18beta-hydroxy-11,17alpha-dimethoxy-3beta,20alpha-yohimban-16beta-carboxylate Methyl 11,17-dimethoxy-18-([(2E)-3-(3,4,5-trimethoxyphenyl)-2-propenoyl]oxy)yohimban-16-carboxylate (3β,20α)-11,17α-Dimethoxy-18β-[[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]yohimban-16β-carboxylic acid methyl (3β,20α)-11,17α-Dimethoxy-18β-[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyloxy]yohimban-16β-carboxylic acid methyl ester (3β,20α)-11,17α-Dimethoxy-18β-[[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]yohimban-16β-carboxylic acid methyl ester 3b,20a-Yohimban-16b-carboxylic acid, 18b-hydroxy-11,17a-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester) (8CI) 3-beta,20-alpha-Yohimban-16-beta-carboxylic acid, 18-beta-hydroxy-11,17-alpha-dimethoxy-,methyl ester, 3,4,5-trimethoxycinnamate 3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester) Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-, methyl ester, (3b,16b,17a,18b,20a)- Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-, methyl ester, (3b,16b,17a,18b,20a)- (9CI) Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha) Benz(g)indolo(2,3-a)quinolizine-1-carboxylic acid, 1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-3-hydroxy-2,11-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate | [EINECS(EC#)]
246-471-8 | [Molecular Formula]
C35H42N2O9 | [MDL Number]
MFCD00005092 | [MOL File]
24815-24-5.mol | [Molecular Weight]
634.72 |
Chemical Properties | Back Directory | [Appearance]
white to cream powder | [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) |
Hazard Information | Back Directory | [Chemical Properties]
white to cream powder | [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. . | [Fire Hazard]
Flash point data for RESCINNAMINE are not available. RESCINNAMINE is probably combustible. | [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. | [Uses]
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. | [Brand name]
Moderil (Pfizer). | [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. | [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) |
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