Norcocaine

Norcocaine
Clinical data
Addiction; liability	High
ATC code	none;
Legal status
Legal status	US: Schedule II;
Identifiers
	IUPAC name methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate;
CAS Number	18717-72-1 ;
PubChem CID	644007;
ChemSpider	559083 ;
UNII	3SL7BR2M1E;
CompTox Dashboard (EPA)	DTXSID80912319 ;
ECHA InfoCard	100.161.803
Chemical and physical data
Formula	C16H19NO4
Molar mass	289.331 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:AYDBLCSLKNTEJL-RFQIPJPRSA-N ;
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Norcocaine is a minor metabolite of cocaine. It is the only confirmed pharmacologically active metabolite of cocaine, although salicylmethylecgonine is also speculated to be an active metabolite. The local anesthetic potential of norcocaine has been shown to be higher than that of cocaine, however cocaine continues to be more widely used. Norcocaine used for research purposes is typically synthesized from cocaine. Several methods for the synthesis have been described.

Clinical data

Addiction liability	High
ATC code	none
Legal status
Legal status	US: Schedule II
Identifiers
IUPAC name methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number	18717-72-1^Y
PubChem CID	644007
ChemSpider	559083^Y
UNII	3SL7BR2M1E
CompTox Dashboard (EPA)	DTXSID80912319
ECHA InfoCard	100.161.803
Chemical and physical data
Formula	C₁₆H₁₉NO₄
Molar mass	289.331 g·mol⁻¹
3D model (JSmol)	Interactive image
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^Y Key:AYDBLCSLKNTEJL-RFQIPJPRSA-N^Y
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