778. Arecoline

Nomenclature

CAS number: 63-75-2
1,2,5,6-Tetrahydro-1-methyl-3-pyridinecarboxylic acid methyl ester; methyl 1,2,5,6-tetrahydro-1-methylnicotinate; methyl 1-methyl-Δ3,4-tetrahydro-3-pyridinecarboxylate; methyl N-methyltetrahydronicotinate; arecaline; arecholine; methylarecaidin.
C8H13NO2; mol wt 155.19.
C 61.91%, H 8.44%, N 9.03%, O 20.62%.

Description and references

Cholinergic alkaloid from seeds of the betel nut palm Areca catechu L., Palmaceae (catechu). Isoln: E. Johns, Arch. Pharm. 229, 673 (1891). Synthesis: F. Chemnitius, J. Prakt. Chem. 117, 147 (1926); Mannich, Ber. 75B, 1480 (1942); Knox, US 2506458 (1950 to Nopco). Improved synthesis from nicotinic acid: I. A. Kozello et al., Khim. Farm. Zh. 10, 90 (1976), C.A. 86, 171205a (1977). Effect on human serial learning: N. Sitaram et al., Science 201, 274 (1978). Clinical evaluation in Alzheimer's disease: T. T. Soncrant et al., Psychopharmacology 112, 421 (1993). Review: R. B. Burrows, Progress in Drug Research vol. 17, E. Jucker, Ed. (Birkhaüser Verlag, Basel, 1973) pp 108-210.

Chemical structure

Properties

Oily liquid, bp 209°, bp7 92-93°, bp12 105°. Volatile with steam. Strong base. pK 6.84. nD20 1.4302. d20 1.0495. Miscible with water, alc, ether. Soluble in chloroform. LD50 in mice, dogs (mg/kg): 100, 5 s.c. (Burrows).

Derivative

Hydrobromide.

Nomenclature

CAS number: 300-08-3
C8H13NO2.HBr; mol wt 236.11.
C 40.70%, H 5.98%, N 5.93%, O 13.55%, Br 33.84%.

Properties

Bitter, optically inactive crystals, mp 169-171°. One gram dissolves in about 1 ml water, 10 ml alc, 2 ml boiling alc; slightly soluble in chloroform, ether. The aq soln is practically neutral.

Derivative

Compd with acetarsone.

Nomenclature

CAS number: 900-77-6
Arecoline-acetarsone; arecoline-acetarsol; drocarbil; Nemural.
C8H13NO2.C8H10AsNO5; mol wt 430.28.
C 44.66%, H 5.39%, N 6.51%, O 26.03%, As 17.41%.

Properties

White to pale-yellow powder. Stable when kept dry. Freely sol in water.

Derivative

Compd with p-stibonobenzoic acid.

Nomenclature

CAS number: 17162-36-6
Arecoline p-stibonobenzoic acid; Anthelin.
C8H13NO2.C7H7O5Sb; mol wt 448.08.
C 40.21%, H 4.50%, N 3.13%, O 24.99%, Sb 27.17%.

Description and references

Prepn: Kartsonis, Austin, US 2557353 (1951 to Jensen-Salsbery Labs.).

Therapeutic Category (Veterinary)

Anthelmintic (Cestodes); cathartic.