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N-Methylconiine

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N-Methylconiine
N-Methylconiine
Names
IUPAC name 1-Methyl-2-propylpiperidine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 79936
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H19N/c1-3-6-9-7-4-5-8-10(9)2/h9H,3-8H2,1-2H3Key: CUBHREGSQFAWDJ-UHFFFAOYSA-N
SMILES
  • CCCC1CCCCN1C
Properties
Chemical formula C9H19N
Molar mass 141.258 g·mol
Density (d) 0.8318 g cm at 24.3 °C

(l) 0.8349 g cm 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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, and methods for its isolation are described by Wolffenstein and by von Braun. It is a colourless, oily, coniine-like liquid, specific rotation 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 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. 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 150–170 °C.

References

  1. Planta and Kekulé, Annalen, 1854, 89, 150.
  2. Ber., 1894, 27, 2615; 1895, 28, 302
  3. Ber., 1905, 38, 3108; 1917, 50, 1477.
  4. Ber., 1902, 35, 1330; cf. Löffler and Friedrich, ibid., 1909, 42, 107.
    Constructs such as ibid., loc. cit. and idem are discouraged by Misplaced Pages's style guide for footnotes, as they are easily broken. Please improve this article by replacing them with named references (quick guide), or an abbreviated title. (August 2019) (Learn how and when to remove this message)
  5. Ber., 1891, 24, 1678.
  6. Ber., 1917, 50, 1386; 1919, 52, 1622; 1920, 53, 129.
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