9774. Tropacocaine

Nomenclature

CAS number: 537-26-8
exo-8-Methyl-8-azabicyclo[3.2.1]octan-3-ol benzoate (ester); 1αH,5αH-tropan-3β-ol benzoate; benzoylpseudotropeine; benzoyl-ψ-tropeine; pseudotropine benzoate; ψ-tropine benzoate; tropacaine.
C15H19NO2; mol wt 245.32.
C 73.44%, H 7.81%, N 5.71%, O 13.04%.

Description and references

From Javanese coca leaves. Prepared by heating pseudotropine with water and benzoic anhydride: Wilsttter, Ber. 29, 943 (1896). Stereochemistry: Beyerman et al., Rec. Trav. Chim. 75, 1445 (1956).

Chemical structure

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).

Derivative

Hydrochloride.
C15H19NO2.HCl; mol wt 281.78.
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.