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Industrial
And Engineering Chemistry
- [News Edition] - Vol. 31, (or 17) Feb. 20, 1939 - pp-117
Marihuana
Preliminary Note
on Investigation
Herbert J. Wollner
Treasury
Department, Washington, D. C.
THE structure of the
chemical entity responsible for the typical "hashish" action of the
plant Cannabis sativa or marihuana and its preparations is unknown.
There is no qualitative chemical test for it, nor is there any
quantitative measure of it save only a bioassay of value so doubtful that it was
deleted from the U. S. Pharmacopoeia XI.
The
activity is resident in a so-called resin which may be prepared rather readily
from the plant itself. This
substance is a complex mixture, from which only a single pure compound has been
directly crystallized---a paraffin hydrocarbon containing 29 carbon atoms.
The substance possesses no "hashish" activity, hence is of
little interest.
Following
removal of the hydrocarbon, the resin, which obstinately resists partition by
other means, may be separated into fractions by vacuum distillation.
The high-boiling fraction, sometimes referred to
as the "red oil," or "crude cannabinol," contains the
active material and possesses so many of the attributes of a pure compound that
it has been regarded as such by a number of investigators.
Others have definitely shown it to be, on the contrary, a complex mixture
from which only one pure compound has as yet been separated.
This is pure cannabinol which separates crystalline as the acetate
following treatment of the mixture with acetic anhydride or, better, acetyl
chloride and pyridine.
Pure
cannabinol has no "hashish" activity. Its reactions have shown it to possess the structure of a
substituted dibenzopyran.
The
mixture from which cannabinol has been separated, either as acetate or as p-nitrobenzoate,
retains the typical physiological activity.
It has been found resistant to the usual techniques of partition, but a
preliminary note indicates that it may be fractionated by chromatographic
analysis. No details have been
published, except that certain of the fractions are physiologically active.
Since continuing
progress in the administration of the Marihuana Tax Act of 1937 must be
dependent, in a large measure, on accumulation of knowledge concerning the
growth, preparation, distribution, and effect of the drug, there has been
initiated in the Treasury Department laboratories a broad program of research
which includes, as one of its principal objectives, the isolation and
characterization of the substance or substances responsible for the
characteristic action.
In
Pursuance of this objective, it is proposed at the outset to take advantage of
the sharper fractionation possible under conditions of molecular distillation.
To this end the drug has been extracted with alcohol, and the alcohol
solution extracted with low-boiling petroleum ether.
Removal of the petroleum ether leaves a very viscous, dark green oil
which is separated into two parts by "flash" distillation of the
volatile portion. The apparatus is
operated at a pressure of 0.1 to 0.2 mm. Distillation
is effected in four chambers maintained at 220º, 240º, 250º, and 250º,
through which the oil flows progressively.
The combined distillate collects in one receiver and the tar, which
amounts in the present case to somewhat more than 60 per cent of the total, is
received in another.
The
distilled portion is a reddish brown oil, very viscous at room temperature.
It contains sensibly all the physiologically active material present in
the original alcohol extract.
The
crude oil,[1] so obtained, is introduced into a molecular distillation apparatus
of the static rather than cyclic type and separated into ten fractions at a
pressure of 2 X 10-4 mm. Certain of
these have been found extremely active, and it is proposed, by further
distillation of these active fractions under the same or lower pressures, to
concentrate the activity to a greater extent than has heretofore been attained.
When
no further concentration can be effected in this manner the mixture will be
treated chemically to form an acyl derivative, probably the acetate, which will
then be fractionated as before.
From
the fractions in which the activity is most concentrated by these procedures it
is hoped to isolate the pure active principle or principles by one or more of a
number of processes, many of which have proved unsuccessful with the "red
oil"--- for example, low temperature crystallization, precipitation of
derivatives, chromatographic analysis, and others.
Physiological
activity of the various products obtained is being followed through bioassay on
the dog and mouse, conducted by S. Loewe, of the Cornell University Medical
College.
Further
reports of the progress of this investigation, and others, will be made from
time to time as conditions warrant.
[1]
This mixture has been found to contain, in addition to the active
principle, the substances responsive to the Duquenois test, the Ghamrawy test,
and the alkaline (but not the acid) Beam test.
Results obtained thus far indicate rather definitely that more than one
compound present in the resin contributes to response to the Duquenois test, and
that the compound responsive to the alkaline Beam test is not the
physiologically active principle.
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