Norcocaine

Not to be confused with Nocaine.
Norcocaine
Clinical data
Addiction
liability		High
ATC code
  • none
Legal status
Legal status
Identifiers
  • methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.161.803 Edit this at Wikidata
Chemical and physical data
FormulaC16H19NO4
Molar mass289.331 g·mol−1
3D model (JSmol)
  • COC(=O)[C@@H]1[C@H]2CC[C@H](N2)C[C@@H]1OC(=O)C3=CC=CC=C3
  • 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 checkY
  • Key:AYDBLCSLKNTEJL-RFQIPJPRSA-N checkY
  (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]

  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.