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Pilocarpine, chemical structure

Carbachol (Figure 3.12), and the closely related bethane-chol, is a powerful cholinergic agent (used to induce miosis). Its structure is similar to that of choline and its precursor, DMAE. Other muscarinic agents (e.g. pilocarpine), have a completely different chemical structure to choline. [Pg.21]

The isolation of pilocarpine was reported in 1875 [1], separately by Byasson and Gerrard, and some chemical information was obtained subsequently [2]. The two-dimensional structure of the alkaloid was reported at the beginning of the twentieth century [3]. The absolute chemical structure and the total synthesis were reported subsequently [4,5]. [Pg.157]

In 1900 Jowett (38) suggested that the differences between pilocarpine and isopilocarpine had their origin in the steric structures. This was in contrast to the opinion of Pinner et al. who assumed the differences to be caused by N-methylation at different sites in the imidazole ring (39). Lan-genbeck in 1924 assumed on the basis of chemical reactions, such as the formation of quaternary salts and ozonolysis, that the differences were of a steric nature (40,41). Preobrazhenski et al. in 1936 (42) supposed on the basis of different stability and optical rotation that pilocarpine and isopilocarpine should possess the cis and trans configuration, respectively. An identical conclusion was drawn by Zavyalov (43) in 1952, on the basis of... [Pg.285]

In 1973, Khuong-Huu et al. isolated three alkaloids anantine (94), cyno-metrine (95), and cynodine (96), from the leaves of Cynometra ananta, a plant of the Leguminoseae family native to Zaire. The structures were deduced on the basis of spectral and chemical evidence (752). The structures bear some similarity to that of pilocarpine (7), which contains a lactone ring instead of a lactam ring. Treatment of cynometrine with polyphosphoric acid yielded the N-methylated anantine (97). The latter compound could not be prepared by a simple N-methylation of anantine. Hydrolysis of cynodine afforded cynometrine and benzoic acid. [Pg.307]

Pilosinine is a monoacidic base, and is optically active, the rotatory power falling rapidly in aqueous solution. It gives no color with diazo-benzenesulfonic acid and does not immediately decolorize permanganate. In its physical and chemical properties it closely resembles pilocarpine and isopilocarpine, and accordingly Pyman (46) proposed structures I and II for pilosine and pilosinine respectively, the alkaline degradation of pilosine being attributed to a reversed aldol condensation of a known type (177). On this basis, anhydropilosine has structure III. As pilosine... [Pg.232]

Initially, pilocarpine structure was incorrectly attributed as a betaine derivative of a pyridine-lactic acid compound. Further research, based rai chemical degradation, synthesis, and X-ray analysis, provided pilocarpine structure as (25,3/ )-2-ethyl-3-[(l-methyIimidazol-5-yl)methyl]-4-butanolide, as extensively described in previous reviews [8],... [Pg.869]


See other pages where Pilocarpine, chemical structure is mentioned: [Pg.645]    [Pg.362]    [Pg.1343]    [Pg.1343]    [Pg.206]    [Pg.38]    [Pg.37]    [Pg.198]    [Pg.874]    [Pg.197]   
See also in sourсe #XX -- [ Pg.74 ]




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