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Revision as of 12:08, 15 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit		Latest revision as of 16:07, 10 January 2025 edit undoArthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix
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			{{Short description|Chemical compound}}
	{{drugbox
			{{Distinguish|Nalbuphine}}
	| verifiedrevid = 394787358
			{{Drugbox
	| IUPAC_name = (5α,6α)-17-allyl- 7,8-didehydro- 4,5-epoxymorphinan- 3,6-diol
			| Verifiedfields = verified
	|synonyms=<small>(−)−(5''R'',6''S'')-9α-allyl- 4,5-epoxymorphin- 7-en- 3,6-diol</small>
			| Watchedfields = verified
	| image = Nalorphine.svg
			| verifiedrevid = 402503832
			| IUPAC_name = 17-allyl-7,8-didehydro-4,5α-epoxymorphinan-3,6α-diol
			| image = Nalorphine.svg
			| image_class = skin-invert-image
			| width = 225px
			<!--Clinical data-->
			| tradename = Lethidrone, Nalline
			| Drugs.com = {{drugs.com|international|nalorphine}}
			| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
			| pregnancy_US = <!-- A / B / C / D / X -->
			| pregnancy_category =
			| legal_AU = S4
			| legal_BR = A2
			| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-03 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
			| legal_CA = Schedule I
			| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
			| legal_US = Schedule III
			| legal_status =
			| routes_of_administration =
			<!--Pharmacokinetic data-->
			| bioavailability =
			| protein_bound =
			| metabolism =
			| elimination_half-life =
			| excretion =
			<!--Identifiers-->
			| CAS_number_Ref = {{cascite|correct|??}}
			| CAS_number = 62-67-9
			| ATC_prefix = V03
			| ATC_suffix = AB02
			| PubChem = 5284595
			| IUPHAR_ligand = 1629
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
			| DrugBank = DB11490
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 4447643		| ChemSpiderID = 4447643
			| UNII_Ref = {{fdacite|correct|FDA}}
	| InChI = 1/C19H21NO3/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20/h2-6,12-13,15,18,21-22H,1,7-10H2/t12-,13+,15-,18-,19-/m0/s1
			| UNII = U59WB2WRY2
	| InChIKey = UIQMVEYFGZJHCZ-SSTWWWIQBT
			| ChEBI_Ref =
	| smiles = O2\C=C/54N(CC51c3c(O12)c(O)ccc3C4)C\C=C
			| ChEBI = 7458
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
			| ChEMBL = 415284
			| KEGG_Ref =
			| KEGG = D08247
			| synonyms = ''N''-Allylnormorphine
			<!--Chemical data-->
			| C=19 | H=21 | N=1 | O=3
			| SMILES = O2\C=C/54N(CC51c3c(O12)c(O)ccc3C4)C\C=C
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C19H21NO3/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20/h2-6,12-13,15,18,21-22H,1,7-10H2/t12-,13+,15-,18-,19-/m0/s1		| StdInChI = 1S/C19H21NO3/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20/h2-6,12-13,15,18,21-22H,1,7-10H2/t12-,13+,15-,18-,19-/m0/s1
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = UIQMVEYFGZJHCZ-SSTWWWIQSA-N		| StdInChIKey = UIQMVEYFGZJHCZ-SSTWWWIQSA-N
	| CAS_number = 62-67-9
	| CASNo_Ref = {{cascite|correct|CAS}}
	| ATC_prefix = V03
	| ATC_suffix = AB02
	| PubChem = 5284595
	| IUPHAR_ligand = 1629
	| DrugBank =
	| C=19|H=21|N=1|O=3
	| molecular_weight = 311.375 g/mol
	| bioavailability =
	| protein_bound =
	| metabolism =
	| elimination_half-life =
	| excretion =
	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
	| pregnancy_US = <!-- A / B / C / D / X -->
	| pregnancy_category=
	| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
	| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
	| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
	| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
	| legal_status =
	| routes_of_administration =
	}}		}}
	'''Nalorphine''' (], also known as '''''N''-allyl-normorphine''') trade names Lethidrone and Nalline. Nalorphine acts at two opioid receptors, at the mu receptor it has antagonistic effects and at the kappa receptors it exerts agonistic characteristics. It is used to reverse opioid overdose and (starting in the 1950s) in a challenge test to determine opioid dependence.<ref>[http://www.time.com/time/magazine/article/0,9171,808859,00.html
	"Medicine: Drug Detector"], '']'', Dec. 24, 1956</ref>
			'''Nalorphine''' ({{abbrlink|INN|International Nonproprietary Name}}; also known as '''''N''-allylnormorphine'''; brand names '''Lethidrone''' and '''Nalline''') is a mixed ] ] with ] and ] properties.<ref name="Glatt2012">{{cite book| vauthors = Glatt M |title=The Dependence Phenomenon|url=https://books.google.com/books?id=rN7dBgAAQBAJ&pg=PT121|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-7457-2|pages=121–}}</ref> It was introduced in 1954<ref name="Aggrawal">{{cite book| first = Anil | last = Aggrawal | name-list-style = vanc |title=APC Essentials of Forensic Medicine and Toxicology|url=https://books.google.com/books?id=iSH8CgAAQBAJ&pg=PA554|publisher=Avichal Publishing Company|isbn=978-81-7739-441-2|pages=554–}}</ref> and was used as an ] to reverse ] and in a challenge test to determine ].<ref>{{cite magazine | url = http://www.time.com/time/magazine/article/0,9171,808859,00.html | archive-url = https://web.archive.org/web/20050726083728/http://www.time.com/time/magazine/article/0,9171,808859,00.html | url-status = dead | archive-date = July 26, 2005 | title = Medicine: Drug Detector | magazine = ] | date = 24 December 1956 }}</ref>
	==References==
	{{Reflist}}
	{{Antidotes}}
	{{Opioids}}
			Nalorphine was the second opioid antagonist to be introduced, preceded by ] (''N''-allylnorcodeine) in 1915 and followed by ] in 1960 and ] in 1963.<ref name="Aggrawal" /> Due to potent activation of the ], nalorphine produces ]s such as ], ], ], and ]s, and for this reason, is no longer used medically.<ref name="Glatt2012" /><ref name="Aggrawal" /><ref name="SatoskarRege2015">{{cite book| vauthors = Satoskar RS, Rege N, Bhandarkar SD |title=Pharmacology and Pharmacotherapeutics|url=https://books.google.com/books?id=h2drCgAAQBAJ&pg=PA166|date=27 July 2015|publisher=Elsevier Health Sciences APAC|isbn=978-81-312-4371-8|pages=166–}}</ref>
	]
	]
	]
	]
	]
			==Pharmacology==
			===Pharmacodynamics===
	{{pharmacology-stub}}
			Nalorphine acts at two ]s — the ] (MOR) where it has ]ic effects, and at the ] (KOR) (K<sub>i</sub> = 1.6 nM; ] = 483 nM; ] = 95%) where it exerts high-] ]/near-] characteristics.<ref name="GharagozlouHashemi2006">{{cite journal | vauthors = Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J | title = Pharmacological profiles of opioid ligands at kappa opioid receptors | journal = BMC Pharmacology | volume = 6 | issue = 1 | pages = 3 | date = January 2006 | pmid = 16433932 | pmc = 1403760 | doi = 10.1186/1471-2210-6-3 | doi-access = free }}</ref>
			==Chemistry==
			===Analogues===
			Nalorphine has a number of ]s including ] (the ] analogue), ] (] analogue), ] (dihydromorphine), and a number of others as well as a number of ]-based analogues.<ref>{{cite book|url=https://books.google.com/books?id=vwAHCAAAQBAJ&q=dihydronalorphine&pg=PA507|title=Opioid Analgesics: Chemistry and Receptors | vauthors = Casy AF, Parfitt RT |date=29 June 2013|publisher=Springer Science & Business Media|via=Google Books|isbn=9781489905857}}</ref>
			===Synthesis===
			]).</ref>]]{{clear-left}}
			More recently, it has become much more commonplace to use ] instead of ] for the ] demethylation step. See for example the ] or the synthesis of ] for further examples of this.
			==See also==
			* ]
			* ]
			* ]
			* ]
			==References==
			{{Reflist}}
			{{Antidotes}}
			{{Hallucinogens}}
			{{Opioid receptor modulators}}
			]
	]
			]
	]
	]		]
			]
	]
			]
			]
			]
			]
			]
			]
			]