Rescinnamine

• " Reserpinin " (revised)
• Methyl [ 11,17 α -dimethoxy- 18β - (3,4,5- trimethoxyphenyl -2- propenyloxy) - 3β, 20α - 16β -carboxylate yohimbane ]

C02AA01

Fine needles

238-239 ° C

Easily in chloroform, glacial acetic acid and benzene, slightly in ethanol, insoluble in water

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Rescinnamine is an indole alkaloid that is found in various Rauvolfia species, particularly in the Indian snake root, for their hypotensive and sedative effect is mainly responsible next reserpine. From this it differs in its chemical structure only by the esterification of the C-18 pendant hydroxyl group of the substrate with 3,4,5- Trimethoxyzimtsäure ( TMZS ) instead of 3,4,5- trimethoxy ( TMBS ).

Rescinnamine is not Reserpinin

Thanks to these common tasks Erich Haack and his colleagues to their level of 1954 new alkaloid isolated the trivial names " Reserpinin ". However, since the research group led by Emil sledders this name almost the same for the Haack et al. " Raubasinin " said Reserpinin awarded and this name was also adopted by others, they changed the name in favor of the uniqueness in " rescinnamine ". Notwithstanding this, nor the names of both alkaloids mixed with each other to this day.

Application

Rescinnamine found in total extracts of Rauvolfia serpentina and, through moderate lowering of dopamine, norepinephrine and serotonin levels to their soothing and blood pressure lowering effect in. Corresponds qualitatively to be pharmacological profile so that of reserpine, the differences are rather quantitative in nature: While its sedative and bradycardic effect significantly lighter than that of reserpine fails, its hypotensive effect compared to this is only a little weaker. The effect of rescinnamine does not last as long. In Germany it was among other Rauvolfia alkaloids in Modenol ® ( Hoffmann-La Roche) and Diuraupur ® (then Giulini Pharma) included in the United States, there are numerous mono-preparations.

Besides the use for therapeutic purposes rescinnamine place in research as compared to reserpine substance use.

Analysis

The specific rotation angle is -87 ° to -97 ° (c = 1, chloroform ). The additional double bond of TMZS - against the TMBS ester allows for a distinction between rescinnamine and reserpine by bromination, as an electrophilic addition of bromine is possible to her. The resulting change in the absorption spectrum characteristic of rescinnamine.

Itemization

• ATC -C02
• Antihypertensive
• Piperidine
• Carboxylic acid esters
• Ether
• Indole alkaloid
• Phenol
• Tetrahydropyridine
• Alkene