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C17H21NO4 See also: alkaloid occurring to the extent of about 1% in the leaves of Erythroxylon See also: coca (see above)
.
It is associated with many other alkaloids: cinnamyl
See also: 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 (q.v.)
.
Cocaine is benzoylmethyl ecgonine
.
It crystallizes from See also: alcohol in prisms, which are sparingly soluble in See also: water
.
Its solution has a bitter taste, alkaline reaction, and is laevorotatory
.
Its use as a See also: local anaesthetic (see See also: 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, dilatation of the pupil, diminution of the intraocular tension, and some interference with accommodation
.
The conversion of the mixture obtained by extracting coca-leaves into cocaine is effected by saponifying the See also: 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 is replaced by the cinnamyl group. a- and fl-truxillines, named from their See also: 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 and his students (Ber., vols
.
21-27, and 31), and are See also: diphenyl tetra-methylene dicarboxylic acids
.
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