N-Methylconiine

N-Methylconiine is a poisonous alkaloid found in poison hemlock in small quantities.

N-Methylconiine

Names
IUPAC name 1-Methyl-2-propylpiperidine
Identifiers
CAS Number	35305-13-6 Y
3D model (JSmol)	Interactive image
3DMet	B03672
Beilstein Reference	79936
ChEBI	CHEBI:32
ChemSpider	148393
KEGG	C10159
PubChem CID	338921
UNII	KO6UG4YXE1 Y
CompTox Dashboard (EPA)	DTXSID901310152
InChI InChI=1S/C9H19N/c1-3-6-9-7-4-5-8-10(9)2/h9H,3-8H2,1-2H3 Key: CUBHREGSQFAWDJ-UHFFFAOYSA-N
SMILES CCCC1CCCCN1C
Properties
Chemical formula	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). Y verify (what is YN ?) Infobox references

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

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.
5. Ber., 1891, 24, 1678.
6. Ber., 1917, 50, 1386; 1919, 52, 1622; 1920, 53, 129.