777. Arecaidine

Nomenclature

CAS number: 499-04-7
1,2,5,6-Tetrahydro-1-methyl-3-pyridinecarboxylic acid; 1,2,5,6-tetrahydro-1-methylnicotinic acid; arecaine; methylguvacine.
C7H11NO2; mol wt 141.17.
C 59.56%, H 7.85%, N 9.92%, O 22.67%.

Description and references

From seeds of Areca catechu L., Palmaceae (betel nuts). Synthesis: Wohl, Johnson, Ber. 40, 4712 (1907); Hess, Leibbrandt, ibid. 51, 806 (1918); Freudenberg, ibid. 976; Maurit, Preobrazhenskii, Zh. Obshch. Khim. 28, 968 (1958), C.A. 52, 17263 (1958); Merck, DE 485139 C.A. 24, 919 (1930).

Chemical structure

Properties

Plates from dil alc, dec 232° (after drying at 102°). pH of 0.1 molar soln 5.6. Freely soluble in water, and dilute alc; almost insol in abs alc, chloroform, ether, benzene.

Derivative

Hydrochloride.
C7H11NO2.HCl; mol wt 177.63.
C 47.33%, H 6.81%, N 7.89%, O 18.01%, Cl 19.96%.

Properties

mp 251°; needles, dec 263° (rapid heating). Freely sol in water.

Derivative

Hydrobromide.
C7H11NO2.HBr; mol wt 222.08.
C 37.86%, H 5.45%, N 6.31%, O 14.41%, Br 35.98%.

Properties

Crystals from methanol, dec 249°.