9781. Tropine

Nomenclature

CAS number: 120-29-6
endo-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol; 1αH,5αH-tropan-3α-ol; 2,3-dihydro-3α-hydroxy-8-methylnortropidine; 2,3-dihydro-3α-hydroxytropidine.
C8H15NO; mol wt 141.21.
C 68.04%, H 10.71%, N 9.92%, O 11.33%.

Description and 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).

Chemical structure

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.

Note

Esters of tropine are known as tropeines.