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 ;
	(verify)

Norcocaine is a minor metabolite of cocaine. It is the only confirmed pharmacologically active metabolite of cocaine,^[1] 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,^[2]^[3] 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.^[4]^[5]

^ "Virtual Mass Spectrometry Laboratory: Cocaine in Hair". Archived from the original on 2007-09-01. Retrieved 2008-01-14.
^ Wang Q, Simpao A, Sun L, Falk JL, Lau CE (January 2001). "Contribution of the active metabolite, norcocaine, to cocaine's effects after intravenous and oral administration in rats: pharmacodynamics". Psychopharmacology. 153 (3): 341–52. doi:10.1007/s002130000568. PMID 11271407. S2CID 10708670.
^ Just WW, Hoyer J (January 1977). "The local anesthetic potency of norcocaine, a metabolite of cocaine". Experientia. 33 (1). Birkhäuser: 70–1. doi:10.1007/BF01936761. PMID 836425. S2CID 32483810.
^ Stenberg VI, Narain NK, Singh SP, Parmar SS (April 1976). "An improved synthesis of norcocaine". Journal of Heterocyclic Chemistry. 13 (2): 363–364. doi:10.1002/jhet.5570130231.
^ Lazer ES, Aggarwal ND, Hite GJ, Nieforth KA, Kelleher RT, Spealman RD, et al. (December 1978). "Synthesis and biological activity of cocaine analogs I: N-alkylated norcocaine derivatives". Journal of Pharmaceutical Sciences. 67 (12): 1656–8. doi:10.1002/jps.2600671204. PMID 102759.

[1] "Virtual Mass Spectrometry Laboratory: Cocaine in Hair". Archived from the original on 2007-09-01. Retrieved 2008-01-14.

[2] Wang Q, Simpao A, Sun L, Falk JL, Lau CE (January 2001). "Contribution of the active metabolite, norcocaine, to cocaine's effects after intravenous and oral administration in rats: pharmacodynamics". Psychopharmacology. 153 (3): 341–52. doi:10.1007/s002130000568. PMID 11271407. S2CID 10708670.

[3] Just WW, Hoyer J (January 1977). "The local anesthetic potency of norcocaine, a metabolite of cocaine". Experientia. 33 (1). Birkhäuser: 70–1. doi:10.1007/BF01936761. PMID 836425. S2CID 32483810.

[4] Stenberg VI, Narain NK, Singh SP, Parmar SS (April 1976). "An improved synthesis of norcocaine". Journal of Heterocyclic Chemistry. 13 (2): 363–364. doi:10.1002/jhet.5570130231.

[5] Lazer ES, Aggarwal ND, Hite GJ, Nieforth KA, Kelleher RT, Spealman RD, et al. (December 1978). "Synthesis and biological activity of cocaine analogs I: N-alkylated norcocaine derivatives". Journal of Pharmaceutical Sciences. 67 (12): 1656–8. doi:10.1002/jps.2600671204. PMID 102759.

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[5]

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
(verify)