Methyl reserpate Rescinnamine

The 400-MHz NMR chemical shifts and most of the main coupling constants of reserpine (109), deserpidine (110), rescinnamine (111), and methyl reserpate (121) have been reported by Lounasmaa et al. (400). 

In contrast to the oxidative reactions discussed above, the only reported biotransformations of reserpine (21) and rescinnamine (23) (42-44) appear to involve hydrolytic processes. Reserpine is readily metabolized by liver homogenates from the mouse (43), rat, guinea pig, dog, and cat (44) to yield methyl reserpate (22) and 3,4,5-trimethoxybenzoic acid in yields of up to 70% (43). The use of reserpine labeled with tritium in the 2 and 6 positions of the trimethoxybenzoate residue indicated that no significant metabolism of reserpine by another route occurred before hydrolysis, reserpine and 3,4,5-trimethoxybenzoic acid being the only detectable radioactive components of the incubation mixture at the conclusion of the reaction (44). An... 

In the yohimbine group, reserpine Nfoxide has been found in the aerial parts of Melodinus balansae Baillon var. paucivenosus (S. Moore) Boiteau, and yohimbine, 18-hydroxy-yohimbine, reserpine, and rescinnamine in the stem bark of Rauwolfia cumminsii. Other extractions have resulted in the isolation of yohimbine, methyl reserpate, and (possibly) 18-hydroxy-yohimbine from the stem bark of R. vomitoria. ... 

Other reserpine derivatives which have been used in psychiatry include 11-demethoxyreserpine (deserpidine, Harmonyl) and methyl 0-3,4,5-tri-methoxycinnamoyl reserpate (rescinnamine, Anaprel, Moderil). The compound tetrabenazine (Nitoman VI)) which lacks an indole nucleus has similar pharmacological actions to reserpine but its side effects are milder, perhaps because it has few peripheraljactions. 

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