Title: Arecoline
CAS Registry Number: 63-75-2
CAS Name: 1,2,5,6-Tetrahydro-1-methyl-3-pyridinecarboxylic acid methyl ester
Additional Names: methyl 1,2,5,6-tetrahydro-1-methylnicotinate; methyl 1-methyl-D3,4-tetrahydro-3-pyridinecarboxylate; methyl N-methyltetrahydronicotinate; arecaline; arecholine; methylarecaidin
Molecular Formula: C8H13NO2
Molecular Weight: 155.19
Percent Composition: C 61.91%, H 8.44%, N 9.03%, O 20.62%
Literature 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.
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).
Boiling point: bp 209°; bp7 92-93°; bp12 105°
pKa: pK 6.84
Index of refraction: nD20 1.4302
Density: d20 1.0495
Toxicity data: LD50 in mice, dogs (mg/kg): 100, 5 s.c. (Burrows)
Derivative Type: Hydrobromide
CAS Registry Number: 300-08-3
Molecular Formula: C8H13NO2.HBr
Molecular Weight: 236.11
Percent Composition: 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.
Melting point: mp 169-171°
Derivative Type: Compd with acetarsone
CAS Registry Number: 900-77-6
Additional Names: Arecoline-acetarsone; arecoline-acetarsol; drocarbil
Trademarks: Nemural
Molecular Formula: C8H13NO2.C8H10AsNO5
Molecular Weight: 430.28
Percent Composition: 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 Type: Compd with p-stibonobenzoic acid
CAS Registry Number: 17162-36-6
Additional Names: Arecoline p-stibonobenzoic acid
Trademarks: Anthelin
Molecular Formula: C8H13NO2.C7H7O5Sb
Molecular Weight: 448.08
Percent Composition: C 40.21%, H 4.50%, N 3.13%, O 24.99%, Sb 27.17%
Literature References: Prepn: Kartsonis, Austin, US 2557353 (1951 to Jensen-Salsbery Labs.).
Therap-Cat-Vet: Anthelmintic (Cestodes); cathartic.

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