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{{drugbox
{{Drugbox
| IUPAC_name       = (−)−(5''R'',6''S'')--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 = (,)-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}}
{{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}}
{{Antidotes}}
{{Hallucinogens}}


[[Category:Drug]]
[[Category:Alcohols]]
[[Category:Alkenes]]
[[Category:Morphinans]]
[[Category:Opioid antagonists]]
[[Category:Opioid antagonists]]
[[Category:Drugs]]
[[Category:Phenols]]
{{WikiDoc Sources}}
[[Category:Semisynthetic opioids]]
{{WH}}

Latest revision as of 17:11, 9 April 2015

Nalorphine
Clinical data
Synonyms(−)−(5R,6S)-9α-allyl- 4,5-epoxymorphin- 7-en- 3,6-diol
AHFS/Drugs.comInternational Drug Names
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
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
FormulaC19H21NO3
Molar mass311.375 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

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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

Nalorphine synthesis:[2]

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.

See also

References