N-Methylconiine is a poisonous alkaloid found in poison hemlock in small quantities.
The -(+)-stereoisomer of N-methylconiine is reported to occur in hemlock in small quantities, and methods for its isolation are described by Wolffenstein and by von Braun. It is a colourless, oily, coniine-like liquid, specific rotation [ñ]<sub>D</sub> +81.33ð at 24.3 ðC. The salts are crystalline ("B" marks one molecule of the base): the hydrochloride, Bâ¢HCl, forms masses of needles, mp. 188 ðC; the platinichloride, B<sub>2</sub>â¢H<sub>2</sub>PtCl<sub>6</sub>, has mp. 158 ðC.
The -(âÂÂ)-stereoisomer was obtained by Ahrens from residues left in the isolation of coniine as hydrobromide or by removing coniine as the nitroso-compound. It is a colourless, coniine-like liquid, bp. 175.6 ðC/767 mmHg, specific rotation [ñ]<sub>D</sub> âÂÂ81.92ð at 20 ðC. The monohydrochloride crystallises in leaflets, mp. 191âÂÂ192 ðC; the monohydrobromide in leaflets, mp. 189âÂÂ190 ðC; the platinichloride in orange crystals, mp. 153âÂÂ154 ðC; the aurichloride in leaflets, mp. 77âÂÂ78 ðC; and the picrate in long needles, mp. 121âÂÂ122 ðC.
N-Methyl--coniine was prepared by the action of potassium methyl sulfate on coniine by Passon. Hess and Eichel have shown that -coniine with formaldehyde and formic acid yields an active N-methyl--coniine, and that methyl-isopelletierine hydrazone yields N-methyl--coniine when heated with sodium ethoxide at 150âÂÂ170 ðC.