Nalodeine

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Nalodeine
Nalodeine.svg
Systematic (IUPAC) name
(4R,4aR,7S,7aR,12bS)-9-methoxy-3-prop-2-enyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol
Identifiers
CAS Number 56195-50-7
PubChem CID: 5486632
ChemSpider 4588998
Synonyms N-Allylnorcodeine
Chemical data
Formula C20H23NO3
Molecular mass 325.40152 g/mol
  • COC1=C2C3=C(CC4C5C3(CCN4CC=C)C(O2)C(C=C5)O)C=C1
  • InChI=1S/C20H23NO3/c1-3-9-21-10-8-20-13-5-6-15(22)19(20)24-18-16(23-2)7-4-12(17(18)20)11-14(13)21/h3-7,13-15,19,22H,1,8-11H2,2H3/t13-,14+,15-,19-,20-/m0/s1
  • Key:XAOWELGMJQTJQR-WYIOCLOVSA-N

Nalodeine, also known more commonly as N-allylnorcodeine, is an opioid antagonist (specifically, an antagonist of the μ-opioid receptor) that was never marketed but is of notability in having been the first opioid antagonist to have been discovered.[1][2] It was first reported in 1915, and this was followed by the clinical introduction of nalorphine (N-allylnormorphine) in 1954, naloxone (N-allyloxymorphone) in 1960, and naltrexone (N-methylcyclopropyloxymorphone) in 1963.[2] Nalmefene (6-desoxy-6-methylene-naltrexone), another structurally related opioid antagonist derivative, was also subsequently introduced, in 1996.[3] In animals, nalodeine both reverses morphine- and heroin-induced respiratory depression and acts as a respiratory stimulant in its own right (i.e., when given alone).[4] Similarly to nalorphine, nalodeine has also been found to act as an agonist of the κ-opioid receptor.[5]

See also

References

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