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'''Dextrallorphan''' ('''DXA''') is a [[drug]] of the [[morphinan]] class known in [[scientific research]]. It acts as a [[sigma-1 receptor|σ<sub>1</sub> receptor]] [[agonist]] and [[NMDA receptor]] [[receptor antagonist|antagonist]].<ref name="pmid6290634">{{ cite journal | author = Su, T. P. | title = Evidence for Sigma Opioid Receptor: Binding of <nowiki>[3H]</nowiki>SKF-10047 to Etorphine-Inaccessible Sites in Guinea-Pig Brain | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 223 | issue = 2 | pages = 284–290 | year = 1982 | month = Nov | pmid = 6290634 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=6290634 }}</ref><ref name="pmid7562497">{{ cite journal | author = Codd, E. E,; Shank, R. P.; Schupsky, J. J.; Raffa, R. B. | title = Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 274 | issue = 3 | pages = 1263–1270 | year = 1995 | month = Sep | pmid = 7562497 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=7562497 }}</ref><ref name="pmid8996216">{{ cite journal | author = Shukla, V. K.; Lemaire, S. | title = N-methyl-D-aspartate antagonist activity of alpha- and beta-sulfallorphans | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 280 | issue = 1 | pages = 357–365 | year = 1997 | month = Jan | pmid = 8996216 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=8996216 }}</ref><ref name="pmid6834266">{{cite journal | author = Shannon, H. E. | title = Pharmacological evaluation of N-allynormetazocine (SKF 10,047) on the basis of its discriminative stimulus properties in the rat | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 225 | issue = 1 | pages = 144–152 | year = 1983 | month = Apr | pmid = 6834266 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=6834266 }}</ref> It has no significant [[affinity (pharmacology)|affinity]] for the [[sigma-2 receptor|σ<sub>2</sub>]], [[mu-opioid receptor|μ-opioid]], or [[delta-opioid receptor|δ-opioid receptor]], or for the [[serotonin transporter|serotonin]] or [[norepinephrine transporter]].<ref name="pmid8496936">{{ cite journal | author = He, X. S.; Bowen, W. D.; Lee, K. S.; Williams, W.; Weinberger, D. R.; de Costa, B. R. | title = Synthesis and binding characteristics of potential SPECT imaging agents for sigma-1 and sigma-2 binding sites | journal = Journal of Medicinal Chemistry | volume = 36 | issue = 5 | pages = 566–571 | year = 1993 | month = Mar | pmid = 8496936 | doi = 10.1021/jm00057a006 | url = }}</ref><ref name="pmid7562497">{{ cite journal | author = Codd, E. E.; Shank, R. P.; Schupsky, J. J.; Raffa, R. B. | title = Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 274 | issue = 3 | pages = 1263–1270 | year = 1995 | month = Sep | pmid = 7562497 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=7562497 }}</ref>
'''Dextrallorphan''' ('''DXA''') is a [[drug]] of the [[morphinan]] class known in [[scientific research]]. It acts as a [[sigma-1 receptor|σ<sub>1</sub> receptor]] [[agonist]] and [[NMDA receptor]] [[receptor antagonist|antagonist]].<ref name="pmid6290634">{{ cite journal | author = Su, T. P. | title = Evidence for ''Sigma'' Opioid Receptor: Binding of <nowiki>[3H]</nowiki>SKF-10047 to Etorphine-Inaccessible Sites in Guinea-Pig Brain | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 223 | issue = 2 | pages = 284–290 | year = 1982 | month = Nov | pmid = 6290634 | doi = | url = http://jpet.aspetjournals.org/content/223/2/284.full.pdf | format = pdf }}</ref><ref name="pmid7562497">{{ cite journal | author = Codd, E. E.; Shank, R. P.; Schupsky, J. J.; Raffa, R. B. | title = Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 274 | issue = 3 | pages = 1263–1270 | year = 1995 | month = Sep | pmid = 7562497 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=7562497 }}</ref><ref name="pmid8996216">{{ cite journal | author = Shukla, V. K.; Lemaire, S. | title = N-methyl-D-aspartate antagonist activity of alpha- and beta-sulfallorphans | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 280 | issue = 1 | pages = 357–365 | year = 1997 | month = Jan | pmid = 8996216 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=8996216 }}</ref><ref name="pmid6834266">{{cite journal | author = Shannon, H. E. | title = Pharmacological evaluation of N-allynormetazocine (SKF 10,047) on the basis of its discriminative stimulus properties in the rat | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 225 | issue = 1 | pages = 144–152 | year = 1983 | month = Apr | pmid = 6834266 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=6834266 }}</ref> It has no significant [[affinity (pharmacology)|affinity]] for the [[sigma-2 receptor|σ<sub>2</sub>]], [[mu-opioid receptor|μ-opioid]], or [[delta-opioid receptor|δ-opioid receptor]], or for the [[serotonin transporter|serotonin]] or [[norepinephrine transporter]].<ref name="pmid8496936">{{ cite journal | author = He, X. S.; Bowen, W. D.; Lee, K. S.; Williams, W.; Weinberger, D. R.; de Costa, B. R. | title = Synthesis and binding characteristics of potential SPECT imaging agents for sigma-1 and sigma-2 binding sites | journal = Journal of Medicinal Chemistry | volume = 36 | issue = 5 | pages = 566–571 | year = 1993 | month = Mar | pmid = 8496936 | doi = 10.1021/jm00057a006 | url = }}</ref><ref name="pmid7562497">{{ cite journal | author = Codd, E. E.; Shank, R. P.; Schupsky, J. J.; Raffa, R. B. | title = Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 274 | issue = 3 | pages = 1263–1270 | year = 1995 | month = Sep | pmid = 7562497 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=7562497 }}</ref>
As an NMDA receptor antagonist, ''[[in vivo]]'', it is approximately twice as [[potency (pharmacology)|potent]] as [[dextromethorphan]], and five-fold less potent than [[dextrorphan]].<ref name="pmid8996216">{{ cite journal | author = Shukla, V. K.; Lemaire, S. | title = N-methyl-D-aspartate antagonist activity of alpha- and beta-sulfallorphans | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 280 | issue = 1 | pages = 357–365 | year = 1997 | month = Jan | pmid = 8996216 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=8996216 }}</ref>
As an NMDA receptor antagonist, ''[[in vivo]]'', it is approximately twice as [[potency (pharmacology)|potent]] as [[dextromethorphan]], and five-fold less potent than [[dextrorphan]].<ref name="pmid8996216">{{ cite journal | author = Shukla, V. K.; Lemaire, S. | title = N-methyl-D-aspartate antagonist activity of alpha- and beta-sulfallorphans | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 280 | issue = 1 | pages = 357–365 | year = 1997 | month = Jan | pmid = 8996216 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=8996216 }}</ref>


Revision as of 01:22, 9 February 2012

Dextrallorphan
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • (+)-(13α,14α)-17-allylmorphinan-3-ol
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC19H25NO
Molar mass283.41 g/mol g·mol−1
3D model (JSmol)
  • Oc1ccc3c(c1)[C@]24[C@@H]([C@H](N(CC2)C\C=C)C3)CCCC4

Dextrallorphan (DXA) is a drug of the morphinan class known in scientific research. It acts as a σ1 receptor agonist and NMDA receptor antagonist.[1][2][3][4] It has no significant affinity for the σ2, μ-opioid, or δ-opioid receptor, or for the serotonin or norepinephrine transporter.[5][2] As an NMDA receptor antagonist, in vivo, it is approximately twice as potent as dextromethorphan, and five-fold less potent than dextrorphan.[3]

See also

References

  1. ^ Su, T. P. (1982). "Evidence for Sigma Opioid Receptor: Binding of [3H]SKF-10047 to Etorphine-Inaccessible Sites in Guinea-Pig Brain" (pdf). The Journal of Pharmacology and Experimental Therapeutics. 223 (2): 284–290. PMID 6290634. {{cite journal}}: Unknown parameter |month= ignored (help)
  2. ^ a b Codd, E. E.; Shank, R. P.; Schupsky, J. J.; Raffa, R. B. (1995). "Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception". The Journal of Pharmacology and Experimental Therapeutics. 274 (3): 1263–1270. PMID 7562497. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  3. ^ a b Shukla, V. K.; Lemaire, S. (1997). "N-methyl-D-aspartate antagonist activity of alpha- and beta-sulfallorphans". The Journal of Pharmacology and Experimental Therapeutics. 280 (1): 357–365. PMID 8996216. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  4. ^ Shannon, H. E. (1983). "Pharmacological evaluation of N-allynormetazocine (SKF 10,047) on the basis of its discriminative stimulus properties in the rat". The Journal of Pharmacology and Experimental Therapeutics. 225 (1): 144–152. PMID 6834266. {{cite journal}}: Unknown parameter |month= ignored (help)
  5. ^ He, X. S.; Bowen, W. D.; Lee, K. S.; Williams, W.; Weinberger, D. R.; de Costa, B. R. (1993). "Synthesis and binding characteristics of potential SPECT imaging agents for sigma-1 and sigma-2 binding sites". Journal of Medicinal Chemistry. 36 (5): 566–571. doi:10.1021/jm00057a006. PMID 8496936. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)


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