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TROPINE, C8H15NO

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Originally appearing in Volume V27, Page 307 of the 1911 Encyclopedia Britannica.
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TROPINE, C8H15NO , a See also:base formed together with tropic See also:acid, C9H1003, in the See also:hydrolysis of the See also:alkaloid atropine (K. Kraut, See also:Ann., 1863, 128, p. 28o; 1865, 133, p. 87). It crystallizes in plates which melt at 63° C. and See also:boil at 233° C.; it is very hygroscopic and easily soluble in See also:water. It is an optically inactive, strongly alkaline See also:tertiary base. On See also:heating with See also:sodium in amyl alcoholic See also:solution it it sransformed into a stereo-isomer, identical with the '-tropine obtained by hydrolysing tropa-See also:cocaine with hydrochloric acid. It possesses alcoholic properties, since it forms See also:esters, the so-called " tropeines." On See also:distillation with See also:caustic baryta or soda See also:lime it decomposes into methylamine and tropilidine, C7H8 (A. Ladenburg, Ann. 1883, 217, p. 74), the same See also:hydrocarbon being also obtained when it is destructively methylated, a certain amount of tropiline, C7H100, being produced simultaneously When heated with fuming hydrochloric acid to 150--18o° C. it yields tropidine, C3H13N, and with hydriodic acid 'similarly forms an 3 A See also:fourth See also:species, P. indieus, has been described from the Gulf of See also:Oman, but doubt has been expressed as to its validity (See also:Legge, PP. 1173, 1174).

' Sulidae (See also:

Gannet), Pelecanidae (See also:Pelican), Plotidae (Snake-See also:bird). Phalacrocoracidae (See also:Cormorant,) and Fregatidae (See also:Frigate-bird). iodo-See also:compound, C8H15NI2, which, on reduction with See also:zinc and hydrochloric acid, is converted into hydrotropidine, C8H15N. It yields various oxidation products. With an alkaline solution of See also:potassium permanganate it yields tropigenine, C7H13NO; with chromic acid in the presence of acetic acid it yields tropinone, C8H13NO; and with chromic acid in the presence of sulphuric acid it yields tropinic acid, C6H11N(See also:CO2H)2. Tropidine, C8H13N, is a liquid having an odour resembling that of confine. It is a strong tertiary base, and is an unsaturated compound, forming addition products with the halogen acids. Hydrotropidine, C8H15N, is also a liquid. Its hydrochloride on distillation loses methyl chloride and yields norhydrotropidine, C7H13N, a compound which is a secondary base, and whose hydro-chloride when distilled over zinc dust yields a-ethylpyridine. Tropinic acid, C6H11N(CO2H)2, obtained as above, is inactive; it was resolved by J. Gadamer (See also:Arch. Pharm., 1901, 239, p.

663) by means of its cinchonine See also:

salt. It is a dibasic acid, and the methiodide of its dimethyl ester on See also:fusion with caustic alkalis yields n-adipic acid. It is apparently a derivative of N—methyl pyrrollidine, since it may be oxidized ultimately to N—methyl succinimide. Tropigenine, C7H13NO, is a secondary base. The most important of the oxidation products of tropine is tropinone, C3H13NO, which is a ketone containing the grouping --See also:CH2•CO•CH2—since it yields a di-isonitroso derivative, a dibenzal derivative, and also forms mono- and di-oxalic esters. It is a strong base and has a powerful reducing See also:action. Its constitution is determined by the above facts and also because tropinic acid on destructive methylation yields a diolefine dicarboxylic acid which on reduction is converted into n-pimelic acid. These data point to tropine possessing an unbranched See also:chain of seven See also:carbon atoms and Incidentally determine the constitution of the other various oxidation products, &c. (R. Willstatter, Ber., 1895-1901).

End of Article: TROPINE, C8H15NO

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