Alazocine

Alazocine (developmental code name SKF-10047), also known more commonly as N-allylnormetazocine (NANM), is a synthetic opioid analgesic of the benzomorphan family related to metazocine, which was never marketed. In addition to its opioid activity, the drug is a sigma receptor agonist, and has been used widely in scientific research in studies of this receptor. Alazocine is described as a potent analgesic, psychotomimetic or hallucinogen, and opioid antagonist. Moreover, one of its enantiomers was the first compound that was found to selectively label the σ1 receptor, and led to the discovery and characterization of the receptor.

Not to be confused with N-Allylnormorphine.
Alazocine
Clinical data
Other namesSKF-10047; WIN-19631; N-Allylnormetazocine; NANM; NAN; ANMC; 2'-Hydroxy-5,9-dimethyl-2-allyl-6,7-benzomorphan
ATC code
  • None
Identifiers
  • (±)-1,2,3,4,5,6-hexahydro-6,11-dimethyl-3-(2-propen-1-yl)-2,6-methano-3-benzazocin-8-ol
CAS Number
  • 825594-24-9 Y
    34061-23-9 (hydrochloride)
    14198-28-8 ((–)-isomer)
    58640-82-7 ((+)-isomer)
    74957-58-7 ((–)-isomer HCl)
    133005-41-1 ((+)-isomer HCl)
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.162.264
Chemical and physical data
FormulaC17H23NO
Molar mass257.377 g·mol−1
3D model (JSmol)
  • CC1C2CC3=C(C1(CCN2CC=C)C)C=C(C=C3)O
  • InChI=1S/C17H23NO/c1-4-8-18-9-7-17(3)12(2)16(18)10-13-5-6-14(19)11-15(13)17/h4-6,11-12,16,19H,1,7-10H2,2-3H3 Y
  • Key:LGQCVMYAEFTEFN-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)
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