Misplaced Pages

Nalodeine

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Chemical compound

Pharmaceutical compound
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-methanobenzofuroisoquinoline-7-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H23NO3
Molar mass325.408 g·mol
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

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. It was first reported in 1915 and was found to block the effects of morphine in animals. 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.

See also

References

  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. ^ Aggrawal 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.
Opioid receptor modulators
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
  • Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)


Stub icon

This analgesic-related article is a stub. You can help Misplaced Pages by expanding it.

Categories: