48 
NOTES ON ALKALOIDS AND OTHER SUBSTANCES. 
also fonud in tlie flowers of Crataegus oxyacantlia, Crataegus 
monogyna, Pyrus aucuparia and communis, Chenopodium vulvaria, 
and in some odorous fungi, especially in Ergot of rye, and in putre- 
fying yeast. Probably Phallus impudicus and Clathrus cancellatus 
owe their odor to trimethylamine. 
The formula of trimethylamine is N (CH3)3 or Cg Hg N. This 
group itself forms the nucleus of a series of alkaloids differing from 
one another by two atoms of hydrogen : — 
Betaine, Cg Hg [N (CHg)3] Og or C5 NOg. 
Muscarine, Cg Hg [N (CHg)g] (OH)g or C5 H^g NOg. 
Amanitine, CgH^[N (CHg)g] (OH)g or C5 H^g NOg. 
Betaine occurs in Beta vulgaris and Lycium barbarum, but has 
not yet been found in fungi. 
Muscarine, C^ H^g NOg, was discovered by Schmeideberg about 
1873. In the ‘‘ Chemische Centralblatt ” of 1876, p. 554, occurs 
his paper establishing its composition and artiflcial production. It 
occurs together with amanitine in Am. muscaria. The juice is 
evaporated, treated with alcohol, and then with lead acetate. After 
a long and complicated process the hydrochlorides of muscarine and 
amanitine are obtained, and are separated by pressing with paper, 
which absorbs the more deliquescent muscarine salt, and leaves the 
amanitine. The yield is verj small, as 2 lbs. of the alcoholic ex- 
tract (representing a very much larger quantity of the fungus, per- 
haps about 40 or 50 lbs.) gave only about ^ oz. of muscarine. 
Muscarine forms a colorless inodorous syrup, crystallizing with 
great difficulty, easily soluble in water and alcohol, sparingly in 
chloroform, and not soluble in ether. It is strongly alkaline, 
forms crystallizable deliquescent salts, and is a strong narcotic, in 
some respects antagonistic to atropia. [Later researches show 
that this antagonism of physiological effect is not complete ; there 
are lateral actions of each poison which may make a combined dose 
of each more fatal than the same quantity of either separately, so 
that its action as an antidote must be carefully watched.] Mus- 
carine has not been obtained from any other natural source, but can 
be made artificially from amanitine. 
Amanitine, Cg H^g NOg is identical with the animal bases 
choline and neurine. Its sources are : — 
1. Am. muscaria, hence the name amanitine. 
2. Bile, hence the name choline (Strecker). 
3. Brain and nerve tissue, hence the name neurine. 
4. From eggs and the milt of the salmon, &c. 
5. It can be prepared artificially by a complicated process. 
It is only of late years that the identity of these products has 
been proved. Amanitine is chemically called — 
“ Trimethyloxethylammonium hydrate.” 
It is a white crystalline substance similar to muscarine, but not 
so deliquescent, and not so poisonous. 
By oxidizing agents, such as strong nitric acid, amanitine is con- 
verted into muscarine by the loss of two atoms of hydrogen. By 
