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COCAINE, C17H21NO4

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Originally appearing in Volume V06, Page 615 of the 1911 Encyclopedia Britannica.

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COCAINE, C17H21NO4

COCAINE, C17H21NO4 , an See also:

ALKALOID

alkaloid occurring to the extent of about 1% in the leaves of Erythroxylon See also:

COCA, or CUCA (Erythroxylon coca)

coca (see above). It is associated with many other alkaloids: cinnamyl cocaine, C19H23NO4; a-truxilline (C19H23N04)2; /3-truxilline, (C19H23N04)2; benzoylecgonine, C,6H,9NO2; tropa-cocaine, C13H19NO2; hygrine, C8H15NO; cuscohygrine, C,3H24NO2. These substances, which may be collectively termed " cocaines," are all derivatives of See also:

ECGONINE

ecgonine (q.v.). Cocaine is benzoylmethyl ecgonine. It crystallizes from See also:

ALCOHOL

alcohol in prisms, which are sparingly soluble in See also:

WATER

water. Its See also:

SOLUTION (from Lat. solvere, to loosen, dissolve)

solution has a See also:

BITTER, KARL THEODORE FRANCIS (1867– )

bitter See also:

TASTE (from Lat. taxare, to touch sharply; tangere, to touch)

taste, alkaline reaction, and is laevorotatory. Its use as a See also:

LOCAL

local anaesthetic (see See also:

ANAESTHESIA

ANAESTHESIA) makes it the most valuable of the coca alkaloids, and it is much used in ophthalmic practice. Applied to the conjunctiva it causes anaesthesia, See also:

DILATATION (from Lat. dis-, distributive, and lotus, wide)

dilatation of the See also:

PUPIL (Lat. pupillus, orphan, minor, dim. of pupus, boy, allied to puer, from root pm- or peu-, to beget, cf. "pupa," Lat. for " doll," the name given to the stage intervening between the larval and imaginal stages in certain insects)

pupil, diminution of the intraocular tension, and some interference with See also:

ACCOMMODATION (Lat. accommodare, to make fit, from ad, to, cum, with, and modus, measure)

accommodation. The See also:

CONVERSION (Lat. conversio, from convertere, to turn or ,change)

conversion of the mixture obtained by extracting coca-leaves into cocaine is effected by saponifying the See also:

ESTERS

esters into ecgonine and the respective acids, and then benzoylating and methylating the ecgonine. Homologues of cocaine—ethylbenzoylecgonine, &c.— have been prepared; they closely resemble natural cocaine. Cinnamyl cocaine is cinnamylmethylecgonine, i.e. cocaine in which the benzoyl See also:

GROUP

group is replaced by the cinnamyl group. a- and fl-truxillines, named from their See also:

ISOLATION

isolation from a coca of Truxillo .(See also:

Peru), are two isomeric alkaloids which hydrolyse to ecgonine, methyl alcohol, and two isomeric acids, the truxillic acids, C18H1604. T'he alkaloids are therefore methyl truxillylecgonines.

The truxillic acids have been studied by K. See also:

LIEBERMANN, MAX (1849– )

Liebermann and his students (Ber., vols. 21-27, and 31), and are See also:

DIPHENYL (phenyl benzene), C6H5

diphenyl tetra-methylene dicarboxylic acids.

End of Article: COCAINE, C17H21NO4

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