Nalodeine

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 notable as the first opioid antagonist to be discovered.[1][2] It was first reported in 1915 and was found to block the effects of morphine in animals.[3][2] 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.[4] 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).[5] Similarly to nalorphine, nalodeine has also been found to act as an agonist of the κ-opioid receptor.[6]

Nalodeine
Clinical data
Other namesN-Allylnorcodeine
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
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC20H23NO3
Molar mass325.408 g·mol−1
3D model (JSmol)
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

See also

References
  1. Gavril Pasternak (17 April 2013). The Opiate Receptors. Springer Science & Business Media. pp. 4–. ISBN 978-1-60761-990-1.
  2. Anil Aggrawal. APC Essentials of Forensic Medicine and Toxicology. Avichal Publishing Company. pp. 554–. ISBN 978-81-7739-441-2.
  3. Gonzalez JP, Brogden RN (March 1988). "Naltrexone. A review of its pharmacodynamic and pharmacokinetic properties and therapeutic efficacy in the management of opioid dependence". Drugs. 35 (3): 192–213. doi:10.2165/00003495-198835030-00002. PMID 2836152.
  4. Robert M. Julien; Claire D. Advokat; Joseph E. Comaty (8 October 2010). Primer of Drug Action. Worth Publishers. pp. 349–. ISBN 978-1-4292-3343-9.
  5. Bentham Science Publishers (April 1995). Current Medicinal Chemistry. Bentham Science Publishers. pp. 423–.
  6. Cho N, Hirobe M, Takayanagi I (1985). "Effects of epoxidation on the actions of normorphine, norcodeine, N-allylnormorphine(nalorphine) and N-allylnorcodeine on the electrically stimulated guinea pig ileum" (PDF). Chem. Pharm. Bull. 33 (4): 1681–6. doi:10.1248/cpb.33.1681. PMID 4042244.


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