N-Methylconiine
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Names | |
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IUPAC name
1-Methyl-2-propylpiperidine
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Identifiers | |
3D model (JSmol)
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3DMet | |
79936 | |
ChEBI | |
ChemSpider | |
KEGG | |
PubChem CID
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UNII | |
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Properties | |
C9H19N | |
Molar mass | 141.258 g·mol−1 |
Density | (d) 0.8318 g cm−3 at 24.3 °C (l) 0.8349 g cm−3 at 20 °C |
Boiling point | 173 to 174 °C (343 to 345 °F; 446 to 447 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Infobox references | |
N-Methylconiine is a poisonous alkaloid found in poison hemlock in small quantities.
Isolation and properties[]
The d-(+)-stereoisomer of N-methylconiine is reported to occur in hemlock in small quantities,[1] and methods for its isolation are described by Wolffenstein[2] and by von Braun.[3] It is a colourless, oily, coniine-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[4] 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. 191–192 °C; the monohydrobromide in leaflets, mp. 189–190 °C; the platinichloride in orange crystals, mp. 153–154 °C; the aurichloride in leaflets, mp. 77–78 °C; and the picrate in long needles, mp. 121–122 °C.
Synthesis[]
N-Methyl-d-coniine was prepared by the action of potassium methyl sulfate on coniine by Passon.[5] Hess and Eichel[6] 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 150–170 °C.
References[]
- Piperidine alkaloids
- Neurotoxins