Description
This alkaloid occurs in the bark of Punica Granatum L. and was first isolated by Piccinini under the name of isomethylpelletierine. The base is an oily liquid with
an alkaline reaction, miscible with H20 and optically inactive. The hydrochloride
has m.p. lS6°C; the hydrobromide, m.p. lSI-2°C; the aurichloride forms
rosettes of orange-yellow needles, m.p. lIS-7°C and the picrate has m.p.
lS7-8°C. The alkaloid may be resolved into its optically active components.
(+)-methy1isopelletierine (+)-hydrogen tartrate has m.p. 133-4°C; [α]
20D +
22.7°, the corresponding figures for the antipode being m.p. 132-40c;~aH)S -
20.83° while the two hydrochlorides have [α]
18D + 11.08° and - 10.64°
respectively.
The base gives a semicarbazone as colourless crystals, m.p. 169°C; an oxime,
b.p. 1600C/12 mm and a hydrazone, b.p. lS4-SoC/29 mm. The methiodide
yields cubic crystals, m.p. lS6°C. Oxidation with chromic acid in H2S04
furnishes N-methylpiperidine-2-carboxylic acid.
Definition
ChEBI: N-Methylpelletierine is a citraconoyl group.
References
Piccinini., Gazzetta, 29, ii, 311 (1899)
Hess et al., Ber., SO, 344, 1386 (1917)
Hess et al., ibid, 51,741 (1918)
Hess et al., ibid, 52, 964, 100S (1919)
