Alazocine

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 checkY
    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 Edit this at Wikidata
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 checkY
  • Key:LGQCVMYAEFTEFN-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.[1][2][3] 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.[4][5] Alazocine is described as a potent analgesic, psychotomimetic or hallucinogen, and opioid antagonist.[2] 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.[4][5]

  1. ^ Casy AF, Parfitt RT (29 June 2013). Opioid Analgesics: Chemistry and Receptors. Springer Science & Business Media. pp. 176–178, 420–421. ISBN 978-1-4899-0585-7.
  2. ^ a b Keats AS, Telford J (1964). "Narcotic Antagonists as Analgesics". Molecular Modification in Drug Design. Advances in Chemistry. Vol. 45. pp. 170–176. doi:10.1021/ba-1964-0045.ch014. ISBN 0-8412-0046-7. ISSN 0065-2393.
  3. ^ Iwamoto ET (February 1981). "Pharmacologic effects of N-allylnormetazocine (SKF-10047)". NIDA Research Monograph. 34: 82–8. PMID 6783955.
  4. ^ a b Narayanan S, Bhat R, Mesangeau C, Poupaert JH, McCurdy CR (January 2011). "Early development of sigma-receptor ligands". Future Medicinal Chemistry. 3 (1): 79–94. doi:10.4155/fmc.10.279. PMID 21428827.
  5. ^ a b Hayashi T, Su TP (2004). "Sigma-1 receptor ligands: potential in the treatment of neuropsychiatric disorders". CNS Drugs. 18 (5): 269–84. doi:10.2165/00023210-200418050-00001. PMID 15089113. S2CID 72726251.