January 13, 1872.] 
THE PHARMACEUTICAL JOURNAL AND TRANSACTIONS 
5G7 
in a definite manner in the production of mannite from 
inverted cane-sugar by hydrogenation, a result that has 
'i>een verified by others :— 
C 12 H 12 0 li2 + H 2 = C 12 H 14 0 12 , 
or CgHjoOg + Ho = C 6 H 14 0 6 . 
Relations of the same kind appear to exist between in¬ 
serted sugar of milk (galactose) and a hexatomic alcohol 
yielding like that body mucic acid among its products 
•of oxidation, viz. dulcite, or an isomeride of dulcite. 
These relations were first indicated by M. Berthelot,* 
■and in the present paper M. Bouchardat gives the results 
of some experiments verifying this fact. 
An aqueous solution of inverted sugar of milk was kept 
in contact with 2 '5 per cent, sodium amalgam for two or 
three days, the amalgam being added bit by bit, and the 
liquid neutralized from time to time by dilute sulphuric 
ncid. The action being terminated, the solution was 
' exactly neutralized and the greater part of the sulphate 
of soda removed from it, first, by crystallization, then by 
the addition of double its volume of concentrated alcohol. 
It was then filtered and evaporated to a syrupy consist¬ 
ence. After some time small crystalline mamelons were 
formed, which were removed and drained on filter paper; 
the liquor left to itself, deposited a fresh lot of crystals. 
These were easily purified by recrystallization from 
water. 
This substance consisted of small pure crystals, gritty 
hetw’een the teeth, with a scarcely sweet taste, not fer¬ 
menting in contact with beer-yeast. It melted at 187° 
U., pure dulcite fusing at 188‘5 0 C. It was very slightly 
soluble in strong alcohol; water at 20° C. dissolved 4T 
per cent., while pure dulcite is dissolved in the pro¬ 
portion of 3-6 or 3 - 7 per cent., the difference arising pro¬ 
bably from some slight impurity. The solution had. no 
appreciable action upon polarized light, a cold saturated 
solution causing no deviation in a column of 200 milli¬ 
metres. It did not turn brown by boiling with potash, 
nor did it reduce an alkaline solution of copper salt; 
treated with nitric acid, diluted by four times its volume 
of water, it yielded crystals of mucic acid. Elemen¬ 
tary analysis gave the centesimal proportions of dulcite 
-and mannite:— 
1st time. 2nd time. Calculated. 
C. . . . 39T0 39-3 39-0 
H . . . 7-85 7-9 7-7 
This body would thus appear to be identical with dul¬ 
cite, C 12 H 14 0 12 or C 6 H 14 0 12 , the natural principle first 
obtained from the manna of Madagascar and afterwards 
in the juice of Melampyrum nemorosum. 
PHYSIOLOGICAL ACTION OF TOBACCO WHEN USED 
AS A NARCOTIC, WITH ESPECIAL REFERENCE 
TO THE CONSTITUENTS OF TOBACCO SMOEH, 
BY H. VOHL AND H. EULENBERG.f 
The authors first give a short account of the introduc¬ 
tion of tobacco and a summary of its chemical history, 
from which they conclude that the action of tobacco, 
when used as a narcotic, has been erroneously attributed 
to the nicotine it contains. This conclusion they confirm 
by analyses and experiments of their own. 
The amount of nicotine in snuff they found to be only 
from ‘0392 to *062 per cent.; in the strongest tobacco for 
chewing there was only a mere trace of nicotine, and in 
other specimens of the same kind there was none at all, 
so that nothing like nicotine-poisoning can result from 
the use of these sorts. 
They then analysed the §moke of strong tobacco con¬ 
taining 4 per cent, of nicotine, burning part of it in a 
* Traits de Chimie, fondee sur la Svnthese, vol. ii. pp. 165, 
207. 
f Arch. Pharm. [2] cxlvii. 130-166, from the Journal of 
the Chemical Society. 
pipe and part of it as cigars. The smoke was drawn by 
an aspirator first through potash-solution to collect acids, 
and then through dilute sulphuric acid to collect bases. 
Besides this, the gases given off wben cigars were smoked 
were collected and examined. These consisted of oxygen, 
nitrogen, carbonic oxide and marsh-gas. 
The potash-solution soon became brown, acquired an 
almost unbearable odour of tobacco-juice, and an oily 
substance collected on the surface which became of a 
consistence like butter when cold. This oily substance 
was removed, washed with water and dilute sulphuric 
acid, and distilled. It began to boil at 200°, but the 
boiling-point was not constant, and gradually rose. The 
distillate was at fh*st fluid and oily, but when the tem¬ 
perature rose to 300°, the substance which then passed 
over thickened on cooling to a laminated mass, which, 
after being several times recrystallized from ether, formed 
pearly-white scales, melting between 94° and 95°, and 
having a higher boiling-point- than mercury. In these 
characters, as well as in their percentage composition, 
they agree with the carbohydrate (C 19 H 18 ) discovered by 
Ivnauss, and examined by Fehling and Fritsche. The 
oily distillate, after repeated treatment with potash and 
sulphuric acid, was colourless, neutral, burned with a 
smoky flame, and had a specific gravity of 0‘8 to 0-87. 
From its percentage-composition (92 and 93 C, and 8 or 
7 per cent. H) it seems to be a mixture of different hy¬ 
drocarbons belonging to the benzene series or a series 
analogous to it. None of the nitro-compounds obtained 
by treating it with nitric acid had any definite character, 
and when they were deoxidized, no trace of aniline was 
found, showing that benzene was absent. After sepa¬ 
rating the oily substance, the potash-solution was dis¬ 
tilled, and the distillate added to the sulphuric acid 
through which the smoke had already been passed. On 
saturating the residue with excess of dilute sulphuric 
acid, keeping it well cooled, a large amount of gas was 
given off which consisted of carbon dioxide, hydrogen 
cyanide and hydrogen sulphide. The two latter gases 
were also detected directly in the potash-solution. When 
it had been used for absorption during a considerable 
time, the reaction of cyanogen disappeared, and that of 
sulphocyanogen took its place. This may be the reason 
of a recent statement that tobacco-smoke contains no 
cyanogen. 
The acid potash-solution was distilled, and acetic, 
formic, propionic, butyric, valerianic, and carbolic acids 
and creasote were discovered in the distillate ; caproic, 
caprylic and succinic acids were doubtfully present. 
The sulphuric acid which had served to absorb the 
bases had become dark brown and thick, and a dark- 
brown resin had separated. The liquid was filtered, and, 
after addition of the distillate from the potash, partially 
evaporated, cooled, and saturated with caustic potash, 
whereupon ammoniacal vapours escaped, and a brown 
oil, with an odour of tobacco-juice, collected on the sur¬ 
face. The liquid was distilled and saturated with caustic 
potash redistilled, and the most volatile bases were col¬ 
lected in a Horsford’s nitrogen-apparatus containing 
dilute hydrochloric acid. These were found to be am¬ 
monium chloride and traces of ethylamine. The dis¬ 
tillate was neutralized with dilute sulphuric acid, filtered, 
evaporated, and treated with strong potash, the bases 
taken up by ether, and the ethereal solution distilled. 
The distillate contained only ammonia. The oily residue 
was dried by caustic potash and submitted to fractional 
distillation. The resulting bodies were further separated 
by repeated distillation and crystallization of their pla¬ 
tinum-salts, and at last the w r hole series of picoline or 
pyridine bases, analogous to the aniline bases, w r ere ob¬ 
tained. 
The identity of the following bases was determined 
by the boiling-point, pei’centage-composition, and the 
composition of the platinum double salt:—Pyridine, 
C 5 H- N, boiling-point 115°-116°. Picoline, C 6 H 7 N, 
boiling-point 134°-13o° C. Lutidine, C-H 9 N, boiling- 
