Nalodeine

Nalodeine

Identifiers
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
Synonyms	N-Allylnorcodeine
CAS Number	56195-50-7
PubChem CID	5486632
ChemSpider	4588998
Chemical and physical data
Formula	C20H23NO3
Molar mass	325.40152 g/mol
3D model (Jmol)	Interactive image
SMILES COC1=C2C3=C(CC4C5C3(CCN4CC=C)C(O2)C(C=C5)O)C=C1
InChI 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. 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.Nalmefene (6-desoxy-6-methylene-naltrexone), another structurally related opioid antagonist derivative, was also subsequently introduced, in 1996. 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). Similarly to nalorphine, nalodeine has also been found to act as an agonist of the κ-opioid receptor.