SKF-83,959: Difference between revisions

SKF-83,959
Identifiers
	IUPAC name 6-chloro-7,8-dihydroxy-3-methyl-1-(3-methylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine;
PubChem CID	24278699;
ChemSpider	10131933 ;
ChEMBL	ChEMBL520992 ;
Chemical and physical data
Formula	C18H20ClNO2
Molar mass	317.810 g/mol
3D model (JSmol)	Interactive image;
	SMILES Br.Clc1c3c(cc(O)c1O)C(c2cccc(c2)C)CN(CC3)C;
	InChI InChI=1S/C18H20ClNO2.BrH/c1-11-4-3-5-12(8-11)15-10-20(2)7-6-13-14(15)9-16(21)18(22)17(13)19;/h3-5,8-9,15,21-22H,6-7,10H2,1-2H3;1H ; Key:FHYWNBUFNGHNCP-UHFFFAOYSA-N ;
	(verify)

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Revision as of 12:26, 28 June 2012

SKF-83,959 is a synthetic benzazepine derivative used in scientific research which acts as an agonist at the D₁-D₂ dopamine receptor.^[1] It behaves as a full agonist at the D₁ protomer and a high-affinity partial agonist at the D₂ protomer. SKF-83,959 is a racemate that consists of the R-(+)- and S-(-)-enantiomers MCL 202 and MCL 201, respectively. SKF-83,959 inhibits sodium channels^[2] as well as delayed rectifier potassium channels^[3].

References

^ Rashid AJ, So CH, Kong MM; et al. (2007). "D1-D2 dopamine receptor heterooligomers with unique pharmacology are coupled to rapid activation of Gq/11 in the striatum". Proc. Natl. Acad. Sci. U.S.A. 104 (2): 654–9. doi:10.1073/pnas.0604049104. PMC 1766439. PMID 17194762. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
^ Chu HY, Wu Q, Zhou S; et al. (2011). "SKF83959 suppresses excitatory synaptic transmission in rat hippocampus via a dopamine receptor-independent mechanism". J. Neurosci. Res. 89 (8): 1259–66. doi:10.1002/jnr.22653. PMID 21538463. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
^ Chen XQ, Zhang J, Neumeyer JL; et al. (2009). "Arylbenzazepines are potent modulators for the delayed rectifier K+ channel: a potential mechanism for their neuroprotective effects". PLoS ONE. 4 (6): e5811. doi:10.1371/journal.pone.0005811. PMC 2690691. PMID 19503734. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)

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[1] Rashid AJ, So CH, Kong MM; et al. (2007). "D1-D2 dopamine receptor heterooligomers with unique pharmacology are coupled to rapid activation of Gq/11 in the striatum". Proc. Natl. Acad. Sci. U.S.A. 104 (2): 654–9. doi:10.1073/pnas.0604049104. PMC 1766439. PMID 17194762. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)

[2] Chu HY, Wu Q, Zhou S; et al. (2011). "SKF83959 suppresses excitatory synaptic transmission in rat hippocampus via a dopamine receptor-independent mechanism". J. Neurosci. Res. 89 (8): 1259–66. doi:10.1002/jnr.22653. PMID 21538463. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)

[3] Chen XQ, Zhang J, Neumeyer JL; et al. (2009). "Arylbenzazepines are potent modulators for the delayed rectifier K+ channel: a potential mechanism for their neuroprotective effects". PLoS ONE. 4 (6): e5811. doi:10.1371/journal.pone.0005811. PMC 2690691. PMID 19503734. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)

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-'''SKF-83,959''' is a [[chemical synthesis|synthetic]] [[benzazepine]] [[chemical derivative|derivative]] used in [[scientific research]] which acts as a [[binding selectivity|selective]] [[D1_receptor|D<sub>1</sub> receptor]] [[receptor antagonist|antagonist]] and [[D5_receptor|D<sub>5</sub> receptor]] [[full agonist]], as evidenced by the fact that it has high [[affinity (pharmacology)|affinity]] for both receptors and stimulates the D<sub>5</sub>-linked [[phospholipase C|PLC]]/[[phosphatidylinositol|PI]] [[second messenger system|second messenger pathway]] without affecting the [[Cyclic adenosine monophosphate|cAMP]]/[[adenylyl cyclase|AC]] pathway which is linked to D<sub>1</sub>.<ref name="pmid12675914">{{cite journal |author=Jin LQ, Goswami S, Cai G, Zhen X, Friedman E |title=SKF83959 selectively regulates phosphatidylinositol-linked D1 dopamine receptors in rat brain |journal=Journal of Neurochemistry |volume=85 |issue=2 |pages=378–86 |year=2003 |month=April |pmid=12675914 |doi= |url=}}</ref><ref name="pmid15820529">{{cite journal |author=Zhen X, Goswami S, Friedman E |title=The role of the phosphatidyinositol-linked D1 dopamine receptor in the pharmacology of SKF83959 |journal=Pharmacology, Biochemistry, and Behavior |volume=80 |issue=4 |pages=597–601 |year=2005 |month=April |pmid=15820529 |doi=10.1016/j.pbb.2005.01.016 |url=}}</ref><ref name="pmid15911136">{{cite journal |author=Zhang ZJ, Jiang XL, Zhang SE, Hough CJ, Li H, Chen JG, Zhen XC |title=The paradoxical effects of SKF83959, a novel dopamine D1-like receptor agonist, in the rat acoustic startle reflex paradigm |journal=Neuroscience Letters |volume=382 |issue=1-2 |pages=134–8 |year=2005 |pmid=15911136 |doi=10.1016/j.neulet.2005.03.001 |url=}}</ref><ref name="pmid19047479">{{cite journal | author = Sahu A, Tyeryar KR, Vongtau HO, Sibley DR, Undieh AS | title = D5 dopamine receptors are required for dopaminergic activation of phospholipase C | journal = Molecular Pharmacology | volume = 75 | issue = 3 | pages = 447–53 | year = 2009 | month = March | pmid = 19047479 | doi = 10.1124/mol.108.053017 | url = http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=19047479}}</ref>
+'''SKF-83,959''' is a [[chemical synthesis|synthetic]] [[benzazepine]] [[chemical derivative|derivative]] used in [[scientific research]] which acts as an agonist at the [[D1-D2 Dopamine receptor heteromer|D<sub>1</sub>-D<sub>2</sub> dopamine receptor]].<ref>{{cite journal |author=Rashid AJ, So CH, Kong MM, ''et al.'' |title=D1-D2 dopamine receptor heterooligomers with unique pharmacology are coupled to rapid activation of Gq/11 in the striatum |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=104 |issue=2 |pages=654–9 |year=2007 |pmid=17194762 |pmc=1766439 |doi=10.1073/pnas.0604049104 |url=}}</ref> It behaves as a full agonist at the D<sub>1</sub> [[protomer]] and a high-affinity partial agonist at the D<sub>2</sub> protomer. SKF-83,959 is a racemate that consists of the ''R''-(+)- and ''S''-(-)-enantiomers MCL 202 and MCL 201, respectively. SKF-83,959 inhibits [[sodium channel]]s<ref>{{cite journal |author=Chu HY, Wu Q, Zhou S, ''et al.'' |title=SKF83959 suppresses excitatory synaptic transmission in rat hippocampus via a dopamine receptor-independent mechanism |journal=J. Neurosci. Res. |volume=89 |issue=8 |pages=1259–66 |year=2011 |pmid=21538463 |doi=10.1002/jnr.22653 |url=}}</ref> as well as delayed rectifier [[potassium channel]]s<ref>{{cite journal |author=Chen XQ, Zhang J, Neumeyer JL, ''et al.'' |title=Arylbenzazepines are potent modulators for the delayed rectifier K+ channel: a potential mechanism for their neuroprotective effects |journal=PLoS ONE |volume=4 |issue=6 |pages=e5811 |year=2009 |pmid=19503734 |pmc=2690691 |doi=10.1371/journal.pone.0005811 |url=}}</ref>.
 == References ==