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Nalodeine

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Nalodeine
Clinical data
Other namesN-Allylnorcodeine
Identifiers
  • (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
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H23NO3
Molar mass325.408 g·mol−1
3D model (JSmol)
  • 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 asN-allylnorcodeine, is anopioid antagonist (specifically, anantagonist of theμ-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 ofmorphine in animals.[3][2] This was followed by the clinical introduction ofnalorphine (N-allylnormorphine) in 1954,naloxone (N-allyloxymorphone) in 1960, andnaltrexone (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 reversesmorphine- andheroin-inducedrespiratory depression and acts as arespiratory stimulant in its own right (i.e., when given alone).[5] Similarly to nalorphine, nalodeine has also been found to act as anagonist of theκ-opioid receptor.[6]

See also

[edit]

References

[edit]
  1. ^Martin WR (17 April 2013)."The Evolution of Concepts of Opioid Receptors". In Pasternak G (ed.).The Opiate Receptors. Springer Science & Business Media. pp. 4–.ISBN 978-1-60761-990-1.
  2. ^abcAggrawal A."Identification".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.S2CID 195697174.
  4. ^Julien RM, Advokat CD, Comaty JE (8 October 2010).Primer of Drug Action. Worth Publishers. pp. 349–.ISBN 978-1-4292-3343-9.
  5. ^Furst S, Hosztafi S, Friedmann T (April 1995)."Structure-Activity Relationships of Synthetic and Semisynthetic opioid agonist and antagonists".Current Medicinal Chemistry.6 (1). Bentham Science Publishers:423–440.doi:10.2174/092986730106220216112120.S2CID 99996951.
  6. ^Cho N, Hirobe M, Takayanagi I (April 1985)."Effects of epoxidation on the actions of normorphine, norcodeine, N-allylnormorphine(nalorphine) and N-allylnorcodeine on the electrically stimulated guinea pig ileum".Chemical & Pharmaceutical Bulletin.33 (4):1681–1686.doi:10.1248/cpb.33.1681.PMID 4042244.
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others


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