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

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

  1. Gavril Pasternak (17 April 2013). The Opiate Receptors. Springer Science & Business Media. pp. 4–. ISBN 978-1-60761-990-1.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  2. 2.0 2.1 Anil Aggrawal. APC Essentials of Forensic Medicine and Toxicology. Avichal Publishing Company. pp. 554–. ISBN 978-81-7739-441-2.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  3. 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.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  4. Bentham Science Publishers (April 1995). Current Medicinal Chemistry. Bentham Science Publishers. pp. 423–.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  5. 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. PMID 4042244.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>