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N2279

Norcocaine

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About This Item

Empirical Formula (Hill Notation):
C16H19NO4
CAS Number:
18717-72-1
Molecular Weight:
289.33
UNSPSC Code:
41116107

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drug control

USDEA Schedule II; Home Office Schedule 2; regulated under CDSA - not available from Sigma-Aldrich Canada

General description

Norcocaine is a hepatotoxicant[1] and a metabolite of cocaine.[2] It is synthesized in the liver due to microsomal mixed function oxidases.[3]

Biochem/physiol Actions

Minor metabolite of cocaine.
Biologically active.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
129H4054
077H4116
128H4084
127H4166
088H4058

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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)
Handbook of Substance Abuse: Neurobehavioral Pharmacology (1998)
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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