Norcocaine
Cocaine is catalyzed primarily by BChE to yield ecgonine methyl ester (EME); hydrolysis catalyzed by hepatic carboxylesterase 1 (CES1) to form benzoylecgonine (BZE); oxidation via liver cytochrome P450 3A4 to produce norcocaine (NC). Among these, benzoylecgonine is the primary metabolite, accounting for ~45% of cocaine breakdown and exhibiting a significantly prolonged half-life relative to cocaine.
General
Type : Natural, Alkaloid, Benzoate, Azabicyclo
Chemical_Nomenclature : methyl (1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2-carboxylate
Canonical SMILES : COC(=O)[C@@H]1[C@H]2CC[C@H](N2)C[C@@H]1OC(=O)C3=CC=CC=C3
InChI : InChI=1S\/C16H19NO4\/c1-20-16(19)14-12-8-7-11(17-12)9-13(14)21-15(18)10-5-3-2-4-6-10\/h2-6,11-14,17H,7-9H2,1H3\/t11-,12+,13-,14+\/m0\/s1
InChIKey : AYDBLCSLKNTEJL-RFQIPJPRSA-N
Other name(s) : (-)-Norcocaine || N-Demethylcocaine || 3SL7BR2M1E || RefChem:166578 || CHEBI:178585 || SCHEMBL328855
MW : 289.33
Formula : C16H19NO4
CAS_number : 18717-72-1
PubChem : 644007
UniChem : AYDBLCSLKNTEJL-RFQIPJPRSA-N
Target
Structures : No structure
Families : No family
References (7)
| Title : Substrate Specificity and In Vivo Efficacy of Engineered Cocaine Esterases toward Cocaine and its Toxic Metabolites - Li_2026_Chem.Biol.Interact__112088 |
| Author(s) : Li Z , Hu Q , Deng X , Chen C , Ren Z , Mo N , Huang Z , Wang B , Fang L , Wang J , Hou S , Chen X |
| Ref : Chemico-Biological Interactions , :112088 , 2026 |
| Abstract : |
| PubMedSearch : Li_2026_Chem.Biol.Interact__112088 |
| PubMedID: 42000102 |
| Gene_locus related to this paper: human-BCHE , rhosm-cocE |
| Title : Simultaneous analysis of cocaine and its metabolites in urine by capillary electrophoresis-electrospray mass spectrometry using a pressurized liquid junction nanoflow interface - Hezinova_2012_Electrophoresis_33_653 |
| Author(s) : Hezinova V , Aturki Z , Kleparnik K , D'Orazio G , Foret F , Fanali S |
| Ref : Electrophoresis , 33 :653 , 2012 |
| Abstract : |
| PubMedSearch : Hezinova_2012_Electrophoresis_33_653 |
| PubMedID: 22451058 |
| Title : The ability of bacterial cocaine esterase to hydrolyze cocaine metabolites and their simultaneous quantification using high-performance liquid chromatography-tandem mass spectrometry - Brim_2011_Mol.Pharmacol_80_1119 |
| Author(s) : Brim RL , Noon KR , Collins GT , Nichols J , Narasimhan D , Sunahara RK , Woods JH |
| Ref : Molecular Pharmacology , 80 :1119 , 2011 |
| Abstract : |
| PubMedSearch : Brim_2011_Mol.Pharmacol_80_1119 |
| PubMedID: 21885621 |
| Gene_locus related to this paper: rhosm-cocE |
| Title : Major and minor metabolites of cocaine in human plasma following controlled subcutaneous cocaine administration - Kolbrich_2006_J.Anal.Toxicol_30_501 |
| Author(s) : Kolbrich EA , Barnes AJ , Gorelick DA , Boyd SJ , Cone EJ , Huestis MA |
| Ref : J Anal Toxicol , 30 :501 , 2006 |
| Abstract : |
| PubMedSearch : Kolbrich_2006_J.Anal.Toxicol_30_501 |
| PubMedID: 17132243 |
| Title : Human liver carboxylesterase hCE-1: binding specificity for cocaine, heroin, and their metabolites and analogs - Brzezinski_1997_Drug.Metab.Dispos_25_1089 |
| Author(s) : Brzezinski MR , Spink BJ , Dean RA , Berkman CE , Cashman JR , Bosron WF |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 25 :1089 , 1997 |
| Abstract : |
| PubMedSearch : Brzezinski_1997_Drug.Metab.Dispos_25_1089 |
| PubMedID: 9311626 |
| Gene_locus related to this paper: human-CES1 |
| Title : Analysis of cocaine, benzoylecgonine, ecgonine methyl ester, ethylcocaine and norcocaine in human urine using HPLC with post-column ion-pair extraction and fluorescence detection - Roy_1992_J.Pharm.Biomed.Anal_10_943 |
| Author(s) : Roy IM , Jefferies TM , Threadgill MD , Dewar GH |
| Ref : J Pharm Biomed Anal , 10 :943 , 1992 |
| Abstract : |
| PubMedSearch : Roy_1992_J.Pharm.Biomed.Anal_10_943 |
| PubMedID: 1298401 |
| Title : Cocaine metabolism: cocaine and norcocaine hydrolysis by liver and serum esterases - Stewart_1979_Clin.Pharmacol.Ther_25_464 |
| Author(s) : Stewart DJ , Inaba T , Lucassen M , Kalow W |
| Ref : Clinical Pharmacology & Therapeutics , 25 :464 , 1979 |
| Abstract : |
| PubMedSearch : Stewart_1979_Clin.Pharmacol.Ther_25_464 |
| PubMedID: 428191 |