View source for Chemistry:Nalmexone

{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name               = (5α)-3,14-dihydroxy-17-(3-methyl-2-buten-1-yl)-4,5-epoxymorphinan-6-one
| image                    = Nalmexone.svg
| CAS_number               = 16676-26-9
| CAS_supplemental         = <br />{{CAS|16291-05-7}} ([[Chemistry:Hydrochloride|HCl]])
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = AIB278UKIG
| ATC_prefix               = None
| ATC_suffix               = 
| PubChem                  = 5360516
| ChemSpiderID             = 4514525
| C=21 | H=25 | N=1 | O=4
| smiles                   = O=C4[C@@H]5Oc1c2c(ccc1O)C[C@H]3N(CC[C@]25[C@@]3(O)CC4)C\C=C(/C)C
| StdInChI                 = 1S/C21H25NO4/c1-12(2)6-9-22-10-8-20-17-13-3-4-14(23)18(17)26-19(20)15(24)5-7-21(20,25)16(22)11-13/h3-4,6,16,19,23,25H,5,7-11H2,1-2H3/t16-,19+,20+,21-/m1/s1
| StdInChIKey              = OHKCLOQPSLQCQR-MBPVOVBZSA-N
| bioavailability          = 
| protein_bound            = 
| metabolism               = 
| elimination_half-life    = 
| excretion                = 
| pregnancy_category       = 
| legal_status             = 
| routes_of_administration = 
}}
'''Nalmexone''' (INN) (code names '''EN-1620A''', '''UM-592'''), or '''nalmexone hydrochloride''' (USAN), is a semisynthetic, [[Chemistry:Opioid|opioid]] [[Chemistry:Partial agonist|partial agonist]] or mixed [[Biology:Agonist|agonist]]-[[Biology:Receptor antagonist|antagonist]] with both [[Biology:Analgesic|analgesic]] and narcotic antagonist properties that was never marketed.<ref name="Macdonald1997">{{cite book | author = Macdonald F | title = Dictionary of Pharmacological Agents | url = https://books.google.com/books?id=A0THacd46ZsC&pg=PA1395 | access-date = 11 May 2012 | year = 1997 | publisher = CRC Press | isbn = 978-0-412-46630-4 | page = 1395}}</ref><ref name="CasyParfitt1986">{{cite book |vauthors=Casy AF, Parfitt RT | title = Opioid Analgesics: Chemistry and Receptors | url = https://books.google.com/books?id=KTWoPZdOwQAC&pg=PA55 | access-date = 11 May 2012 | year = 1986 | publisher = Springer | isbn = 978-0-306-42130-3 | page = 55}}</ref><ref name="pmid73588">{{cite journal |vauthors=Loew GH, Berkowitz DS | title = Quantum chemical studies of N-substituent variation in the oxymorphone series of opiate narcotics | journal = Journal of Medicinal Chemistry | volume = 21 | issue = 1 | pages = 101–106 | year = 1978 | pmid = 73588 | doi=10.1021/jm00199a018}}</ref><ref name="pmid4557582">{{cite journal |vauthors=Forrest WH, Shroff PF, Mahler DL | title = Analgesic and other effects of nalmexone in man | journal = Clinical Pharmacology and Therapeutics | volume = 13 | issue = 4 | pages = 520–525 | year = 1972 | pmid = 4557582 | doi = 10.1002/cpt1972134520 | s2cid = 30780581 }}</ref> In [[Engineering:Clinical trial|clinical studies]] it was found to have comparable analgesic efficacy to [[Biology:Morphine|morphine]], though with several-fold reduced [[Chemistry:Potency (pharmacology)|potency]].<ref name="DependenceDependence1969">{{cite book | author=Committee on Problems of Drug Dependence | title = Bulletin, problems of drug dependence | url = https://books.google.com/books?id=BUcrAAAAYAAJ&pg=PA5873 | access-date = 11 May 2012 | year = 1969 | publisher = National Academies | page = 5873 | id=NAP:10503}}</ref> In addition, nalmexone's [[Medicine:Side effect|side effect]]s, the most common of which were sleepiness and sweating, were reported to be similar to those of morphine, albeit with a noticeably higher degree of incidence.<ref name="DependenceDependence1969" />

==Synthesis==
[[File:Nalmexone synthesis.png|thumb|700px|center|Nalmexone synthesis: Lowenstein, M. J.; Fishman, J.; 1967, {{US Patent|3,320,262}}]]

==See also==
* [[Chemistry:Nalbuphine|Nalbuphine]]
* [[Chemistry:Oxymorphone|Oxymorphone]]
* [[Chemistry:Naloxone|Naloxone]]
* [[Chemistry:Naltrexone|Naltrexone]]
* [[Chemistry:Pentazocine|Pentazocine]]

==References==
{{Reflist|2}}

{{Analgesics}}
{{Opioidergics}}

[[Category:Tertiary alcohols]]
[[Category:Alkene derivatives]]
[[Category:Analgesics]]
[[Category:4,5-Epoxymorphinans]]
[[Category:Mu-opioid receptor agonists]]
[[Category:Semisynthetic opioids]]



{{Sourceattribution|Nalmexone}}