TROPINE, C8H15NO

This article appears in Volume V27, Page 307 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: TOO-TUM

TROPINE, C8H15NO , a base formed together with tropic acid, C9H1003, in the

hydrolysis

HYDROLYSIS (Gr. 6Swp, water, Anew, to loosen)

of the alkaloid atropine (K. Kraut, Ann., 1863, 128, p. 28o; 1865, 133, p. 87). It crystallizes in plates which melt at 63 C. and boil at 233 C.; it is very hygroscopic and easily soluble in water. It is an optically inactive, strongly alkaline tertiary base. On

heating

HEATING

with sodium in amyl alcoholic solution it it sransformed into a stereo-isomer, identical with the '-

tropine

TROPINE, C8H15NO

obtained by hydrolysing tropa-cocaine with hydrochloric acid. It possesses alcoholic properties, since it forms esters, the so-called " tropeines." On

distillation

DISTILLATION (from the Lat. distillare, more correctly destillare, to drop or trickle down)

with

caustic

CAUSTIC (Gr. rcavvraubs, burning)

baryta or soda lime it decomposes into methylamine and tropilidine, C7H8 (A. Ladenburg, Ann. 1883, 217, p. 74), the same 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 fourth species, P. indieus, has been described from the Gulf of Oman, but doubt has been expressed as to its validity (

Legge

LEGGE
LEGGE, JAMES (1815-1897)

,
PP. 1173, 1174).
' Sulidae (

Gannet

GANNET (O.E. gavot)

), Pelecanidae (Pelican), Plotidae (Snake-bird). Phalacrocoracidae (

Cormorant

CORMORANT (from the Lat. corvus
marinus
- MARINUS
,' through the Fr., in some patois of which it is still " cor marin "; in certain Ital. dialects are the forms " corvo marin " or " corvo marino ")

,) and Fregatidae (Frigate-bird).
iodo-compound, C8H15NI2, which, on reduction with zinc and hydrochloric acid, is converted into hydrotropidine, C8H15N. It yields various oxidation products. With an alkaline solution of 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(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

DISTILLATION (from the Lat. distillare, more correctly destillare, to drop or trickle down)

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 (Arch. Pharm., 1901, 239, p. 663) by means of its cinchonine salt. It is a dibasic acid, and the methiodide of its dimethyl ester on fusion with

caustic

CAUSTIC (Gr. rcavvraubs, burning)

alkalis yields n-adipic acid. It is apparently a derivative of Nmethyl pyrrollidine, since it may be oxidized ultimately to Nmethyl succinimide. Tropigenine, C7H13NO, is a secondary base.
The most important of the oxidation products of

tropine

TROPINE, C8H15NO

is tropinone, C3H13NO, which is a ketone containing the grouping --CH2COCH2since 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 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

chain

CHAIN (through the O. Fr. citable, chcene, &c., from Lat. catena)

of seven carbon atoms and Incidentally determine the constitution of the other various oxidation products, &c. (R. Willstatter, Ber., 1895-1901). These compounds may consequently be represented as

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