SCOPOLAMINE. 
§§ 469-472.] 
403 
converted into an inactive crystalline derivative—isoscopolamine, C 17 H 21 N0 4 + H 2 0 ; 
m.p. 56°. 
By warming isoscopolamine to 54°-55° an anhydrous isoscopolamine may be 
obtained, m.p. 82°-83°. Hesse 1 has found an inactive alkaloid in commercial 
scopolamine hydrobromide which he called atroscine, C 17 H 21 N0 4 +2H 2 0 ; m.p. 37°-38°. 
Wolffenstein proposes to call these different derivatives {-scopolamine, {-scopolamine 
monohydrate and dihydrate. Thus we have— 
Scopolamine, C 17 H 21 N0 4 +H 2 0, laevo-rotatory ; m.p. 59°. 
{-scopolamine, C 17 H 21 N0 4 , inactive ; m.p. 82°-83°. 
{-scopolamine monohydrate (or isoscopolamine), C 17 H 21 N0 4 + H 2 0, inactive; 
m.p. 56°. 
{-scopolamine dihydrate (or atroscine), C 17 H 21 N0 4 + 2H 2 0, inactive; m.p. 37°-38°. 
According to experiments on animals, the heart is first slowed, then quickened ; 
the first effect being due to a stimulation of the inhibitory nervous apparatus, the 
second to a paralysing action on the same. The temperature is not altered. The 
pupils are dilated, the saliva diminished. The irritability of the brain is lessened. 2 
Scopolamine hydrobromide, C 17 H 21 N0 4 HBr3H 2 0, under the synonym of hyoscine 
hydrobromide, is official, and is thus described in the B.P. :—Small, colourless, 
transparent, non-deliquescent, rhombic crystals, soluble in 4 parts of water. Loses 
about 12 per cent, of its weight when dried at 100°. Yields the reactions 
characteristic of bromides. An aqueous solution (5 in 100) yields, with solution 
of sodium hydroxide, a white precipitate soluble in excess of the reagent, but no 
precipitate with solution of ammonia. The alkaloid removed from the ammoniacal 
solution by shaking with chloroform, separating and evaporating the chloroformic 
solution, when dissolved in dilute hydrochloric acid, yields, with solution of auric 
chloride, a yellow precipitate which, recrystallised from water acidified with 
hydrochloric acid and dried, melts at 198°-200°. Treated with nitric acid as described 
under Atropine, a violet colour is developed. No appreciable ash. 
§ 469. Pseudo-hyoscyamine, C 17 H 23 N0 3 , isolated by Merck from Duboisia myo- 
poroides, crystallises from ether and chloroform in needles, melting at 133°-134°. 
Lsevo-rotatory. Soluble in alcohol and chloroform. A little solu ble in ether and water. 
Saponified with baryta water, it yields tropic acid and a base of the same formula 
as, but not identical with, tropine. 
Not a very active poison, but causes dilation of the pupil. 
§ 470. Atropamine, C 17 H 23 N0 2 , occurs in roots of belladonna, and may be formed 
by dehydrating atropine or hyoscyamine with sulphuric acid. On heating it forms 
belladonnine 
Crystallises from ether in prisms melting at 60°-62°. Soluble in alcohol, ether, 
and chloroform ; a little soluble in water and methyl alcohol. It is optically inactive, 
and has no mydriatic action. 
On saponification with baryta it first forms belladonnine, then splits up into 
atropic acid and tropine. 
§ 471. Belladonnine, C 17 H 21 N0 2 , is found in the belladonna; it is a yellow 
resinous mass ; a little soluble in water, and readily soluble in alcohol, ether, 
chloroform, etc. 
CH 2 . CH . CH 2 C 6 H 5 
ill I 
§ 472. Nor-hyoscyamine, C 16 H n N0 3 = | NH CH . O . CO . CH 
ill 1 
CH 2 . CH CH 2 CHjOH 
Nor-hyoscyamine is an alkaloid which is contained witli hyoscyamine in certain 
plants of the Solanaceous order, such as Scopolia japonica, Duboisia myoporoides, Datura 
metel, and Datura meteloides ; it was isolated from the alkaloids of Scopolia japonica 
by F. H. Carr and W. C. Reynolds ( J . Chem. Soc., T., 1912), and its constitution and 
salts investigated. 
1 Liebig's Ann. der Chemie und Pharm ., ccxxi. 100. 
2 Parloff. St Petersburg Med. Chem. Acad., Dissert., No. 9, 1899-90. 
