Title: Tropacocaine
CAS Registry Number: 537-26-8
CAS Name: exo-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol benzoate (ester)
Additional Names: 1aH,5aH-tropan-3b-ol benzoate; benzoylpseudotropeine; benzoyl-y-tropeine; pseudotropine benzoate; y-tropine benzoate; tropacaine
Molecular Formula: C15H19NO2
Molecular Weight: 245.32
Percent Composition: C 73.44%, H 7.81%, N 5.71%, O 13.04%
Literature References: From Javanese coca leaves. Prepared by heating pseudotropine with water and benzoic anhydride: Wilstätter, Ber. 29, 943 (1896). Stereochemistry: Beyerman et al., Rec. Trav. Chim. 75, 1445 (1956).
Properties: Plates, tablets, mp 49°. Distills in vacuo without dec. pK (15°) 4.72. pH of 0.06M soln 8.4. Freely sol in alc, ether, chloroform, benzene, petr ether, dil acids; slightly sol in water. MLD i.v. in rats: 15-20 mg/kg, Hirschfelder, Physiol. Rev. 12, 262 (1932).
Melting point: mp 49°
pKa: pK (15°) 4.72
Toxicity data: MLD i.v. in rats: 15-20 mg/kg, Hirschfelder, Physiol. Rev. 12, 262 (1932)
Derivative Type: Hydrochloride
Molecular Formula: C15H19NO2.HCl
Molecular Weight: 281.78
Percent Composition: C 63.94%, H 7.15%, N 4.97%, O 11.36%, Cl 12.58%
Properties: Strongly refractive prisms from alcohol, dec 283°. Sol in water, slightly in abs alc, practically insol in ether. Aq solns are stable to boiling water for ~20 minutes. pH of 0.1M soln 5.8.
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