Rescinnamine

Rescinnamine occnrs in the roots of a nnm-ber of Rauwolfia species. Therapentically, it is used as an antihypertensive agent. 

Crystalline solid, crystallized as needles from benzene melts at 238°C (460.4°F) insoluble in water, moderately soluble in methanol, benzene, and chloroform. 

The pharmacological properties of rescinnamine are similar to those of reserpine, bnt 

Chemical Name 11,l7a-dimethoxy-18 3-[[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]-oxy]-3/3,20a-yohimban-16 3-carboxylic acid methyl ester 

Trede Name Manufacturer Country Year Introduced 

0 grams of 3,4,5-trimethoxycinnamic acid, MP 125.5° to 127°C was refluxed for 35 minutes under anhydrous conditions with 6.0 parts by volume of redistilled thionyl chloride. 

The excess thionyl chloride was removed under vacuum and by distilling from the residue two portions of dry benzene. The crystalline residue was crystallized twice from hexane-ether to yield 3,4,5-trimethoxycinnamoyl chloride which was obtained in the form of bright yellow prisms, MP 95° to 96°C. 

5-trimethoxycinnamic ester of methyl reserpate is also present in Rauwolfia plants and obtainable in purified form therefrom by extraction as described in U.S, Patents 2,974,144 and 2,876,228. 

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The alkaloid reserpiae [50-55-5] which is isolated from the roots of Kauwoljia serpentina T., contains a gaUate trimethyl ether moiety. Reserpiae is used as an antihypertensive and a tranquilizer. A vinylogue of reserpiae, rescinnamine [24815-24-5] is also an antihypersensitive (75). Methoxsalen [298-81-7] (8-methoxypsoralen 7JT-9-methoxy-furo [3,2- ] [l]benzopyran-7-one) (21), a furocoumatia that occurs ia plants, eg, l eguminosae and Umbelliferae is used ia the treatment of vitiligo, as a suntanning promoter, and as a sunburn protectant. It is also available by synthesis (76). 

Racemoramide 1, 82 Racemorphan 293 Ranitidine 2 131 Reproterol 3, 231 Rescinnamine U 319 Rimantadine 19... 

Rauwolfia plants, by extraction Deserpidine Rescinnamine Reserpine... 

Frdns has demonstrated this possibility with reserpine and rescinnamine hy irradiating at the start zone for two hours and obtaining a characteristic zone pattern (fingerprint) after TLC separation of the photochemically produced derivatives [20J. Huck and Dworcak exposed developed chromatograms with vanilmandelic acid and homovanillic acid zones to diffuse daylight and observed the formation of fluorescent metabolites that were suitable for direct quantitative analysis [21]. 

Alkaloids, e.g. reserpine, rescinnamine 105 C, 2 h Induced fluorescence (Xn > 500 nm, cut off filter). Possibly formation of 3-dehydro derivatives. [19]... 

The previously known reserpine-type alkaloids (3) are shown below. They are reserpine (109), deserpidine (110), rescinnamine (111), veneserpine (112), pseudoreserpine (113), raunescine (114), rescidine (115), raugustine (116), and isoraunescine (117). It should be mentioned that all reserpine-type alkaloids are trisubstituted at ring E and that the substituents at C-16, C-17, and C-18 are all in equatorial positions on the epiallo yohimbane ring system existing predominantly... 

Rescinnamine-type derivatives containing differently substituted cin-namoyloxy functions at C-18 have been investigated extensively by Japanese researchers (371-376). Rescimetol (623), an effective antihypertensive agent... 

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