Menispermum Canadense.

Botanical name: 


From an Inaugural Essay.

The rhizome examined upon transverse section showed the thickness of the bark to be one-sixteenth the diameter, in some specimens even less. It is formed of two irregular layers, the inner one (liber) being about twice the thickness of the outer covering, and consisting of roundish or lengthened cells of parenchyma, and the elongated bast fibres. The outer layer is entirely parenchyma. The medullary rays are in the shape of an elongated wedge, curved at the pith, and united at the top by a circular zone of polyhedral parenchyma tissue pale brown in color, and separated from the liber by a darker line. The rays are about equal in width to the wood wedges, and are about fourteen in number, but varied from twelve to twenty-six. The pith is about one-fifth the whole diameter, and consists entirely of polyhedral parenchyma. The wood wedges are semicircular on the outer extremity, being capped by a tissue having a semi-lunar form; they consist of ducts and pleurenchyma, and are invariably truncated and tapering towards the centre. The overground stem consists of about one-half pith. The bark is in two layers, structure similar to the rhizome, but the layers proportionately thinner. The wood wedges are oval, being separated by narrow medullary rays, and the cells of the medulla are large and polyhedral.

Analysis.—None of the constituents were soluble in benzin with the exception of a very minute quantity of two yellowish, resinous bodies, one of which was lighter in color, and soluble in ether. No fatty material was dissolved by the action of the benzin.

The ether percolate evaporated left a brownish yellow, soft, resinous mass. This was entirely soluble in alcohol, partially so in water. The residue from tills aqueous solution dissolves entirely in chloroform and benzin, and has all the characteristics of a resin. It is tasteless, inodorous, hard and brittle, brownish in color, and corresponds to the soluble resin of the benzin operation. The aqueous solution responded to the general alkaloidal tests. A tannin (menispermo-tannic acid) was also found in this, giving, with test solution of ferric chloride, a dark green color.

The ground rhizome was next heated to about 40°C. to expel the ether, and was then percolated with 94 per cent. alcohol. This on evaporation also gave a resinous residue, yellowish brown in color, slightly soluble in ether and partially so in water, a brown resin remaining. Hydrochloric acid was added to this aqueous solution, a yellowish precipitate being thrown down, which was soluble in hot alcohol, and answered all the tests for hydrochlorate of berberine.

On the addition of carbonate of sodium to the mother liquor from the berberine precipitate, a grayish white powder was thrown down, which reacted with various group tests for alkaloids (see "Amer. Jour. Phar.," 1863, p. 302). The precipitate was dissolved in hydrochloric acid, and filtered through animal charcoal. Ammonia was added to the solution, producing a precipitate which on being shaken thoroughly with ether dissolved. This etherial solution was evaporated, the residue being dissolved in water acidulated with HCl, this solution again being precipitated. The above process was repeated several times, in order to attain the highest degree of purity. The alkaloid was at length procured in the form of a whitish, amorphous powder.

The aqueous percolate of the rhizome gave alkaloidal precipitates, and green ones with ferric chloride, showing presence of the tannin before mentioned.

The percolate with diluted hydrochloric acid gave, with ammonia and general group reagents, alkaloidal reactions corresponding to the previous tests, some coloring matter, and a small quantity of pectin.

The ammoniacal percolate gave no evidence of alkaloidal presence, but a large amount of coloring matter was extracted, the color of this percolate being much darker than any of the preceding ones. Nothing important was found in this operation.

The decoction was concentrated. This gave on addition of absolute alcohol, a flocculent precipitate of gummy matter. Test solution of iodine yielded a bluish coloration indicating starch. Test solution of iodo-hydrargyrate of potassium gave here slight evidences of alkaloidal reaction.

On distilling the rhizome with water, a milky-white liquid resulted, separating after long standing, a very minute portion of volatile oil which was colorless, and aromatic, the odor resembling that of oil of erigeron.

Carefully heating the powdered rhizome, without charring, at or near 100°C., the moisture was found to be 3.2 per cent. On incineration it yielded 7.07 per cent. of ash containing K., Ca., Mg. and Si., with traces of Fe.

The second alkaloid (We propose for this alkaloid the name of menispine.—ED.) obtained from the rhizome was in the form of a whitish amorphous powder, gradually becoming darker on exposure to the air and light; when first precipitated it was supposed to be either oxyacanthine or menispermine. Solutions of the alkaloid were made containing one part in one hundred, in two hundred and fifty, in five hundred, in seven hundred and fifty, and in one thousand parts. These five degrees of strength were taken that the exact limit of precipitation and sensitiveness could be ascertained. The behavior of oxyacanthine is that described by Mr. H. B. Parsons.

Oxyacanthine. Menispermine. Menispine.
Color White, yell. on expos. White, yell. on expos. White, yell. on expos.
Taste Bitter. Tasteless, entirely. Very bitter.
Water Nearly insoluble. Insoluble. 1 part in 75.
Alcohol, abs. Soluble. 1 part in 200. Very soluble.
Alcohol, com. 1 part in 30. 1 part in 200. 1 part in 6.
Ether 1 part in 125. 1 part in 60. 1 part in 40.
Chloroform Freely soluble. 1 part in 170. 1 part in 20.
Benzol Soluble. 1 part in 200. Insoluble.
Ammonia Sparingly soluble. Insoluble. Insoluble.
Sol. Soda Moderately soluble. Insoluble. Insoluble.
Sol. Soda Carb. Nearly insoluble. Insoluble. Insoluble.

It will be noticed that the alkaloid resembles oxyacanthine in color and influence of air. The bitter taste was distinctly noticeable in a solution of one part in fifteen hundred; it is to be remarked in this connection, that it was not nauseous, but agreeable, like that of gentian.

A marked difference in the solubilities is seen, the alkaloid being five times more soluble in alcohol than oxyacanthine, and over three times in ether. While oxyacanthine is more or less soluble in ammonia, solution of soda, and solution carbonate of sodium, the alkaloid in question is entirely insoluble in all three.

It was also noticed that menispermine was entirely insoluble in and unchanged by hydrochloric acid, but menispine is freely soluble without residue. Other marked differences are that menispermine is perfectly devoid of taste, the other persistently bitter, even in very dilute solutions. Menispermine is insoluble in water, and barely soluble in excess of alcohol and chloroform.

The following experiments prove, in the opinion of the writer, the alkaloid to be distinct from either oxyacanthine or menispermine. The solutions used in this case were in alcohol, 94 per cent., the strengths being one part in two hundred. The reactions of the white alkaloid of Menispermum canadense are identical in both water and alcohol; the table given by the author describing the precipitates obtained from the weaker solutions as being of a paler color, but as being distinctly observable in a 1/1000 solution, the reactions with potassio-mercuric iodide, phospho-molybdic acid and tannin being faintest. Menispermine was examined at the suggestion of Prof. Maisch, to whom the writer is indebted for the sample used in the experimentation.

Menispermine. Oxyacanthine. Menispine.
Tr. Iodine Yellow ppt. Dark brown red ppt. Dark red ppt.
Iodine in KI Yellow ppt. Dark brown red ppt. Dark red ppt.
Potass. Merc. Iod. White ppt. Yellowish ppt. Yellowish white ppt.
Ac. Phospho-molyb. White ppt. Brown ppt. insol. in but dark blue by NH4OH Yellow ppt. sol. in NH4OH with't ch'nge
Potass. cadm. Iod. White ppt. White ppt. Grayish ppt.
Acid, picric Yellow ppt. Insol. in HC2H3O2. Yellowish ppt. Sol. in HC2H3O2. Yellowish ppt.
Platinic chloride Yellow ppt. Insol. in HCl. Yellowish ppt. Insol. in HCl. Yellow ppt.
Gold chloride Yellow ppt. Insol. in HCl. Orange ppt. Insol. in HCl. Orange ppt.
Acid, tannic Yellow ppt. Brownish ppt., insol. in HC2H3O2 and dil. HCl. Whitish ppt., insol. in HC2H3O2 and dil. HCl.
Acid, sulph. conc. Yellow coloration. Brownish purple, darker on standing. Brown, fades on standing.
Acid, sulpho-molybdic Yellowish coloration. Purple, fades slowly, becomes yellow, then green. Brown, fades to yellow.
Acid, nicric, conc. No change. Orange red, effervesces color permanent. Effervesces, yellow, permanent.
Zinc chloride, fused No change. Chocolate brown. Brownish yellow.

The four last mentioned reagents were applied to the powdered alkaloids.

The American Journal of Pharmacy, Vol. 56, 1884, was edited by John M. Maisch.