Tropine
Title: Tropine
CAS Registry Number: 120-29-6
CAS Name: endo-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol
Additional Names: 1aH,5aH-tropan-3a-ol; 2,3-dihydro-3a-hydroxy-8-methylnortropidine; 2,3-dihydro-3a-hydroxytropidine
Molecular Formula: C8H15NO
Molecular Weight: 141.21
Percent Composition: C 68.04%, H 10.71%, N 9.92%, O 11.33%
Literature References: Prepd by reaction of tropidine and HBr, followed by hydrolysis and separation of isomers, tropine and pseudotropine: Ladenburg, Ber. 35, 1159 (1902); by hydrogenation of tropinone in the presence of Raney nickel: Van de Kamp, Sletzinger, US 2366760 (1945 to Merck & Co.); Stoll et al., US 2746976 (1956 to Sandoz). Yield of tropine and pseudotropine under varying conditions of reduction: Beckett et al., Tetrahedron 6, 319 (1959). Separation of tropine and pseudotropine by gold salt formation: Ladenburg, loc. cit.; by fractional distillation under reduced pressure: Friess et al., Toxicol. Appl. Pharmacol. 2, 574 (1960). Stereochemistry: Beyerman et al., Rec. Trav. Chim. 75, 1445 (1956).
Properties: Hygroscopic plates from ether, mp 63°. bp 233°. pK at 15° = 3.80. pH of 0.05 molar soln 11.5. Freely sol in water and alcohol; sol in ether and chloroform.
Melting point: mp 63°
Boiling point: bp 233°
pKa: pK at 15° = 3.80
NOTE: Esters of tropine are known as tropeines.

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