Pseudococaine
Title: Pseudococaine
CAS Registry Number: 478-73-9
CAS Name: [1R-(2-endo,3-exo)]-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester
Additional Names: 3b-hydroxy-1aH,5aH-tropane-2a-carboxylic acid methyl ester benzoate; 2a-carbomethoxy-3b-benzoxytropane; depsococaine; dextrocaine; isococaine
Trademarks: Delcaine
Molecular Formula: C17H21NO4
Molecular Weight: 303.35
Percent Composition: C 67.31%, H 6.98%, N 4.62%, O 21.10%
Literature References: Cocaine diastereomer with greater local anesthetic activity than the natural substance. Synthesis: Einhorn, Marquardt, Ber. 23, 468, 981 (1890); Willstätter, Bode, Ann. 326, 42 (1903); Willstätter, Bommer, ibid. 422, 34 (1921); Willstätter 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).
Properties: Prisms, mp 47°. [a]D20 +42° (c = 5 in chloroform). Freely sol in ether, chloroform, benzene, petr ether. Slightly sol in water.
Melting point: mp 47°
Optical Rotation: [a]D20 +42° (c = 5 in chloroform)
 
Derivative Type: Hydrochloride
CAS Registry Number: 6363-57-1
Molecular Formula: C17H21NO4.HCl
Molecular Weight: 339.81
Percent Composition: C 60.09%, H 6.53%, N 4.12%, O 18.83%, Cl 10.43%
Properties: Crystals from alcohol, mp 210°. [a]D20 +41° (c = 5), less sol in water than cocaine hydrochloride.
Melting point: mp 210°
Optical Rotation: [a]D20 +41° (c = 5)
 
Derivative Type: Tartrate
CAS Registry Number: 1176-03-0
Trademarks: Psicaine
Molecular Formula: C17H21NO4.C4H6O6
Molecular Weight: 453.44
Percent Composition: C 55.62%, H 6.00%, N 3.09%, O 35.28%
Properties: Crystals, mp 139°. [a]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).
Melting point: mp 139°
Optical Rotation: [a]D20 +43° (c = 5 in water)
 
Derivative Type: Sodium tartrate
Trademarks: Psicaine N
Properties: More sol in water than the tartrate; esp useful where a neutral soln is desired.
 
Derivative Type: n-Propyl ester analog
CAS Registry Number: 55608-72-5
Trademarks: Neopsicaine
Molecular Formula: C19H25NO4
Molecular Weight: 331.41
Percent Composition: C 68.86%, H 7.60%, N 4.23%, O 19.31%
 
Therap-Cat: Formerly as anesthetic (local).
Keywords: Anesthetic (Local).

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