N2279
Norcocaine
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About This Item
Empirical Formula (Hill Notation):
C16H19NO4
CAS Number:
Molecular Weight:
289.33
UNSPSC Code:
41116107
drug control
USDEA Schedule II; Home Office Schedule 2; regulated under CDSA - not available from Sigma-Aldrich Canada
General description
Norcocaine is a hepatotoxicant and a metabolite of cocaine. It is synthesized in the liver due to microsomal mixed function oxidases.
Biochem/physiol Actions
Minor metabolite of cocaine.
Biologically active.
Biologically active.
signalword
Danger
Hazard Classifications
Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Repr. 1B - Skin Sens. 1
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Regulatory Information
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Handbook of Substance Abuse: Neurobehavioral Pharmacology (1998)
B W LeDuc et al.
Toxicology and applied pharmacology, 125(2), 322-332 (1994-04-01)
Cocaine (COC) causes liver damage in several species, including man. Chicken embryo hepatocyte cultures were evaluated as a model system to investigate the mechanism of cocaine-mediated hepatotoxicity. Parameters used to assess toxicity were: (1) release of lactate dehydrogenase (LDH); (2)
Cocaine: Pharamacology, Physiology, and Clinical Strategies (1991)
Biological effects of cocaine derivatives I: Improved synthesis and pharmacological evaluation of norcocaine.
Borne R F, et al.
Journal of Pharmaceutical Sciences, 66(1), 119-120 (1977)
J W Boja et al.
Journal of medicinal chemistry, 37(8), 1220-1223 (1994-04-15)
N-Norcocaine (2) and six N-nor-3 beta-(4'-substituted phenyl)tropane-2 beta-carboxylic acid esters (4a-f) were synthesized by N-demethylation of cocaine (1) and the appropriate 3 beta-(substituted phenyl)-tropane analogues (3a-f) with alpha-chloroethyl chloroformate. Radioligand binding affinities of 2 and 4a-f at the DA, 5-HT
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