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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1417131Generated: October 26, 2026

Ammonia → Benzoic Acid

https://huagongshe.com/reaction/1417131

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmoniaHCID 222—
Reactant3-(Benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acidHCID 2340—
ReactantCocaineHCID 446220—
Reactant(-)-NorcocaineHCID 644007—
SolventMethanolHCID 887—
SolventWaterHCID 962—
SolventChloroformHCID 6212—
SolventTriethylamineHCID 8471—
SolventEthyl AcetateHCID 8857—
ProductBenzoic AcidHCID 243—
Product3-(Benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acidHCID 2340—
ProductCocaineHCID 446220—
Product(-)-NorcocaineHCID 644007—

Reaction Steps

Plasma samples were aliquoted and non-radioactive cocaine, benzoyl ecgonine, and norcocaine were added in order to assist in the UV visualization of the compounds. Samples were then applied to silica TLC plates which were developed in two solvent systems: methanol, chloroform, and triethylamine (3:1:0.1); and ethyl acetate, methanol, water, and concentrated ammonia (85:10:3:1). Metabolites were identified by reference to control compounds run on the same plates. The bands were scraped off the plates and 3H-containing compounds were detected through scintillation counting. From the counts obtained the amount of cocaine, benzoyl ecgonine, benzoic acid, and norcocaine as percent of total counts was determined. The total radioactivity in the plasma was determined by scintillation counting of whole plasma. Benzoic acid is detected as a metabolite when cocaine degrades into ecgonine methyl ester and benzoic acid, and so is equimolar to the ecgonine methyl ester metabolite.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05876727
Source datasetuspto-grants-1999_03
ORD IDord-da5712f4266540978fd6a448e0d421a0
Source noteuspto-grants-1999_03