Nalorphine: Difference between revisions

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Nalorphine
Clinical data
Synonyms	(−)−(5R,6S)-9α-allyl- 4,5-epoxymorphin- 7-en- 3,6-diol
AHFS/Drugs.com	International Drug Names
ATC code	V03AB02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only) ;
Identifiers
	IUPAC name (5α,6α)-17-allyl- 7,8-didehydro- 4,5-epoxymorphinan- 3,6-diol;
CAS Number	62-67-9 ;
PubChem CID	5284595;
IUPHAR/BPS	1629;
ChemSpider	4447643 ;
UNII	U59WB2WRY2;
ChEMBL	ChEMBL415284 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C19H21NO3
Molar mass	311.375 g/mol
3D model (JSmol)	Interactive image;
	SMILES O[C@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(O)ccc3C4)C\C=C;
	InChI InChI=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 ; Key:UIQMVEYFGZJHCZ-SSTWWWIQSA-N ;
(what is this?) (verify)

VisualWikitext

Latest revision as of 17:11, 9 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Nalorphine (INN; Lethidrone, Nalline), also known as N-allyl-normorphine, is a mixed opioid agonist–antagonist. It acts at two opioid receptors, at the mu receptor it has antagonistic effects and at the kappa receptors it exerts high-efficacy agonistic characteristics. It is used to reverse opioid overdose and (starting in the 1950s) in a challenge test to determine opioid dependence.^[1]

Synthesis

More recently, it has become much more commonplace to use ethyl chloroformate instead of cyanogen bromide for the Von Braun degradation demethylation step. See for example the list of phenyltropanes or the synthesis of paroxetine for further examples of this.

References

↑ "Medicine: Drug Detector", Time, Dec. 24, 1956
↑ Template:Cite doi

[1] "Medicine: Drug Detector", Time, Dec. 24, 1956

[2] Template:Cite doi

[1]

[2]

@@ Line 1: / Line 1: @@
-{{drugbox
+{{Drugbox
-| IUPAC_name        = (−)−(5''R'',6''S'')-9α-allyl-4,5-epoxymorphin-7-en-3,6-diol
+| Verifiedfields = changed
-| image             = Nalorphine.svg
+| Watchedfields = changed
-| CAS_number        = 62-67-9
+| verifiedrevid = 402503832
-| ATC_prefix        = V03
+| IUPAC_name = (5α,6α)-17-allyl- 7,8-didehydro- 4,5-epoxymorphinan- 3,6-diol
-| ATC_suffix        = AB02
+| image =Nalorphine.png
-| PubChem           = 5284595
-| DrugBank          =
+<!--Clinical data-->
-| C=19|H=21|N=1|O=3
+| tradename =
-| molecular_weight  = 311.375 g/mol
+| Drugs.com = {{drugs.com|international|nalorphine}}
-| bioavailability   =
+| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
-| protein_bound     =
+| pregnancy_US = <!-- A / B            / C / D / X -->
-| metabolism        =
+| pregnancy_category =
-| elimination_half-life =
+| legal_AU = S4
-| excretion         =
+| legal_CA = <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
-| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
+| legal_UK = <!-- GSL         / P       / POM / CD / Class A, B, C -->
-| pregnancy_US      =  <!-- A / B            / C / D / X -->
+| legal_US = <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
-| pregnancy_category=
+| legal_status =
-| legal_AU          =  <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
+| routes_of_administration =
-| legal_CA          =  <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
-| legal_UK          =  <!-- GSL         / P       / POM / CD / Class A, B, C -->
+<!--Pharmacokinetic data-->
-| legal_US          =  <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
+| bioavailability =
-| legal_status      =
+| protein_bound =
-| routes_of_administration =
+| metabolism =
+| elimination_half-life =
+| excretion =
+<!--Identifiers-->
+| CASNo_Ref = {{cascite|correct|CAS}}
+| 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 =
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 4447643
+| UNII_Ref = {{fdacite|changed|FDA}}
+| UNII = U59WB2WRY2
+| ChEMBL_Ref = {{ebicite|changed|EBI}}
+| ChEMBL = 415284
+<!--Chemical data-->
+| C=19 | H=21 | N=1 | O=3
+| molecular_weight = 311.375 g/mol
+| smiles = O[C@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(O)ccc3C4)C\C=C
+| 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
+| InChIKey = UIQMVEYFGZJHCZ-SSTWWWIQBT
+| 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
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = UIQMVEYFGZJHCZ-SSTWWWIQSA-N
+| synonyms = <small>(−)−(5''R'',6''S'')-9α-allyl- 4,5-epoxymorphin- 7-en- 3,6-diol</small>
 }}
-{{EH}}
+__Notoc__
 {{SI}}
+{{CMG}}
+==Overview==
+'''Nalorphine''' ([[International Nonproprietary Name|INN]]; '''Lethidrone''', '''Nalline'''), also known as '''''N''-allyl-normorphine''', is a mixed [[opioid]] [[agonist–antagonist]]. It acts at two opioid receptors, at the [[mu receptor]] it has antagonistic effects and at the [[kappa receptor]]s it exerts high-efficacy 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"], ''[[Time (magazine)|Time]]'', Dec. 24, 1956</ref>
+==Synthesis==
+[[File:Nalorphine synthesis.png|thumb|center|700px|Nalorphine synthesis:<ref>{{Cite doi|10.1021/ja01256a036}}</ref>]]
+More recently, it has become much more commonplace to use [[ethyl chloroformate]] instead of [[cyanogen bromide]] for the [[Von Braun reaction|Von Braun degradation]] demethylation step. See for example the [[list of phenyltropanes]] or the synthesis of [[paroxetine]] for further examples of this.
+==See also==
+==References==
+{{Reflist|2}}
-==Overview==
-'''Nalorphine''' ([[International Nonproprietary Name|INN]], also known as '''''N''-allyl-normorphine''') is a [[narcotic]] antagonist.
-{{SIB}}
 {{Antidotes}}
+{{Hallucinogens}}
+[[Category:Drug]]
+[[Category:Alcohols]]
+[[Category:Alkenes]]
+[[Category:Morphinans]]
 [[Category:Opioid antagonists]]
-[[Category:Drugs]]
+[[Category:Phenols]]
-{{WikiDoc Sources}}
+[[Category:Semisynthetic opioids]]
-{{WH}}

Nalorphine: Difference between revisions

Latest revision as of 17:11, 9 April 2015

Overview

Synthesis

See also

References

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