N-Methylconiine
Encyclopedia
N-Methylconiine is a poisonous alkaloid
found in poison hemlock
in small quantities.
-like liquid, specific rotation [α]D +81.33° at 24.3 °C. The salts are crystalline ("B" marks one molecule of the base): the hydrochloride
, B•HCl, forms masses of needles, mp. 188 °C; the platinichloride, B2•H2PtCl6, has mp. 158 °C.
The L-(-)-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 °C/767 mmHg, specific rotation [α]D -81.92° at 20 °C. The monohydrochloride crystallises in leaflets, mp. 191-2 °C; the monohydrobromide in leaflets, mp. 189-190 °C; the platinichloride in orange crystals, mp. 153-4 °C; the aurichloride in leaflets, mp. 77-8 °C; and the picrate
in long needles, mp. 121-2 °C.
by Passon.
Hess and Eichel have shown that D-coniine with formaldehyde and formic acid yields an active N-methyl-D-coniine, and that methyl-isopelletierine hydrazone yields N-methyl-DL-coniine when heated with sodium ethoxide
at 150-70 °C.
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
found in poison hemlock
Conium
Conium is a genus of two species of highly poisonous perennial herbaceous flowering plants in the family Apiaceae, native to Europe and the Mediterranean region as Conium maculatum, and to southern Africa as Conium chaerophylloides....
in small quantities.
Isolation and properties
The D-(+)-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, coniineConiine
Coniine is a poisonous alkaloid found in poison hemlock and the yellow pitcher plant, and contributes to hemlock's fetid smell. It is a neurotoxin which disrupts the peripheral nervous system. It is toxic to humans and all classes of livestock; less than 0.2g is fatal to humans, with death caused...
-like liquid, specific rotation [α]D +81.33° at 24.3 °C. The salts are crystalline ("B" marks one molecule of the base): the hydrochloride
Hydrochloride
In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base . This is also known as muriate, derived from hydrochloric acid's other name: muriatic acid....
, B•HCl, forms masses of needles, mp. 188 °C; the platinichloride, B2•H2PtCl6, has mp. 158 °C.
The L-(-)-stereoisomer was obtained by Ahrens from residues left in the isolation of coniine as hydrobromide or by removing coniine as the nitroso
Nitroso
Nitroso refers to a functional group in organic chemistry which has the general formula RNO. Nitroso compounds are a class of organic compounds containing the nitroso functional group, R−N=O....
-compound. It is a colourless, coniine-like liquid, bp. 175.6 °C/767 mmHg, specific rotation [α]D -81.92° at 20 °C. The monohydrochloride crystallises in leaflets, mp. 191-2 °C; the monohydrobromide in leaflets, mp. 189-190 °C; the platinichloride in orange crystals, mp. 153-4 °C; the aurichloride in leaflets, mp. 77-8 °C; and the picrate
Picrate
A picrate is a salt or an ester of picric acid . But it could also be an additional compound which picric acid forms with many aromatic hydrocarbons, aromatic amines, aliphatic amines, alkalines, and other compounds. These additional compounds are also called picrates even though they are not a...
in long needles, mp. 121-2 °C.
Synthesis
N-Methyl-D-coniine was prepared by the action of potassium methyl sulfate on coniineConiine
Coniine is a poisonous alkaloid found in poison hemlock and the yellow pitcher plant, and contributes to hemlock's fetid smell. It is a neurotoxin which disrupts the peripheral nervous system. It is toxic to humans and all classes of livestock; less than 0.2g is fatal to humans, with death caused...
by Passon.
Hess and Eichel have shown that D-coniine with formaldehyde and formic acid yields an active N-methyl-D-coniine, and that methyl-isopelletierine hydrazone yields N-methyl-DL-coniine when heated with sodium ethoxide
Sodium ethoxide
Sodium ethoxide is an alkoxide salt with the chemical formula C2H5ONa.-Preparation:It is commercially available as a white solid, or as a solution in ethanol. It is easily prepared in the laboratory by reacting sodium metal with ethanol:...
at 150-70 °C.