7912. Pseudococaine

Nomenclature

CAS number: 478-73-9
[1R-(2-endo,3-exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester; 3β-hydroxy-1αH,5αH-tropane-2α-carboxylic acid methyl ester benzoate; 2α-carbomethoxy-3β-benzoxytropane; depsococaine; dextrocaine; isococaine; Delcaine.
C17H21NO4; mol wt 303.35.
C 67.31%, H 6.98%, N 4.62%, O 21.10%.

Description and references

Cocaine diastereomer with greater local anesthetic activity than the natural substance. Synthesis: Einhorn, Marquardt, Ber. 23, 468, 981 (1890); Willst"atter, Bode, Ann. 326, 42 (1903); Willst"atter, Bommer, ibid. 422, 34 (1921); Willst"atter et al., ibid. 434, 138 (1923); GB 210050 (1923 to E. Merck). Configuration: S. P. Findlay, J. Am. Chem. Soc. 76, 2855 (1954). Conformational analysis and 1H, 13C NMR studies: F. I. Carroll et al., J. Org. Chem. 1982, 13. Pharmacokinetics: A. L. Misra et al., Experientia 32, 895 (1976). Interaction with sodium channels: J C. Matthews, A. Collins, Biochem. Pharmacol. 32, 455 (1983). Pharmacology of cocaine and pseudococaine: G. Schmidt et al., Arch. Exp. Pathol. Pharmakol. 240, 523 (1961).

Chemical structure

Properties

Prisms, mp 47°. [α]D20 +42° (c = 5 in chloroform). Freely sol in ether, chloroform, benzene, petr ether. Slightly sol in water.

Derivative

Hydrochloride.

Nomenclature

CAS number: 6363-57-1
C17H21NO4.HCl; mol wt 339.81.
C 60.09%, H 6.53%, N 4.12%, O 18.83%, Cl 10.43%.

Properties

Crystals from alcohol, mp 210°. [α]D20 +41° (c = 5), less sol in water than cocaine hydrochloride.

Derivative

Tartrate.

Nomenclature

CAS number: 1176-03-0
Psicaine.
C17H21NO4.C4H6O6; mol wt 453.44.
C 55.62%, H 6.00%, N 3.09%, O 35.28%.

Properties

Crystals, mp 139°. [α]D20 +43° (c = 5 in water). Sol in 4 parts water, in alcohol. The aq soln is stable and may be sterilized by boiling, without decompn. pH about 3.7 (2% soln).

Derivative

Sodium tartrate.

Nomenclature

Psicaine N.

Properties

More sol in water than the tartrate; esp useful where a neutral soln is desired.

Derivative

n-Propyl ester analog.

Nomenclature

CAS number: 55608-72-5
Neopsicaine.
C19H25NO4; mol wt 331.41.
C 68.86%, H 7.60%, N 4.23%, O 19.31%.

Therapeutic Category

Formerly as anesthetic (local).

Keywords

Anesthetic (Local)