Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 6-Br-APB: Difference between pages
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Saving copy of the {{drugbox}} taken from revid 460983191 of page 6-Br-APB for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Michael7604 (talk | contribs) recategorized from Bromoarenes to Bromobenzene derivatives |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:6-Br-APB|oldid=460983191}} 460983191] of page [[6-Br-APB]] with values updated to verified values.}} |
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{{about|the dopamine D1 receptor agonist|the amphetamine derivative|6-APB}} |
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{{Drugbox |
{{Drugbox |
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| IUPAC_name = 3-allyl-6-bromo-1-phenyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol |
| IUPAC_name = 3-allyl-6-bromo-1-phenyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol |
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| image = |
| image = 6-Br-APB Structure.svg |
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| image2 = 6-Br-APB-3D-balls.png |
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<!--Clinical data--> |
<!--Clinical data--> |
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<!--Identifiers--> |
<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = |
| CAS_number = 135974-57-1 |
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| ATC_prefix = |
| ATC_prefix = |
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| ATC_suffix = |
| ATC_suffix = |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=19 | H=20 | Br=1 | N=1 | O=2 |
| C=19 | H=20 | Br=1 | N=1 | O=2 |
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| molecular_weight = 374.27 g/mol |
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| smiles = c3ccccc3C2CN(CC=C)CCc(c1Br)c2cc(O)c1O |
| smiles = c3ccccc3C2CN(CC=C)CCc(c1Br)c2cc(O)c1O |
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}} |
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'''6-Br-APB''' is a synthetic compound that acts as a [[binding selectivity|selective]] [[D1 receptor|D<sub>1</sub>]] [[receptor agonist|agonist]],<ref name="pmid1684995">{{cite journal |vauthors =Neumeyer JL |title=(+/-)-3-Allyl-6-bromo-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3- benzazepin, a new high-affinity D1 dopamine receptor ligand: synthesis and structure-activity relationship |journal=Journal of Medicinal Chemistry |volume=34 |issue=12 |pages=3366–71 |date=December 1991 |pmid=1684995 |doi= 10.1021/jm00116a004|display-authors=etal}}</ref> with the (''R'')-[[enantiomer]] being a potent [[full agonist]], while the (''S'') enantiomer retains its D<sub>1</sub> selectivity but is a weak [[partial agonist]].<ref name="pmid1533424">{{cite journal |vauthors =Neumeyer JL, Kula NS, Baldessarini RJ, Baindur N |title=Stereoisomeric probes for the D1 dopamine receptor: synthesis and characterization of R-(+) and S-(-) enantiomers of 3-allyl-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine and its 6-bromo analogue |journal=Journal of Medicinal Chemistry |volume=35 |issue=8 |pages=1466–71 |date=April 1992 |pmid=1533424 |doi= 10.1021/jm00086a016}}</ref> (''R'')-6-Br-APB and similar D<sub>1</sub>-selective full agonists like [[SKF-81,297]] and [[SKF-82,958]] produce characteristic [[anorectic]] effects, stereotyped behaviour and self-administration in animals, with a similar but not identical profile to that of dopaminergic [[stimulant]]s such as [[amphetamine]].<ref name="pmid7862937">{{cite journal |vauthors =Rosenzweig-Lipson S, Hesterberg P, Bergman J |title=Observational studies of dopamine D1 and D2 agonists in squirrel monkeys |journal=Psychopharmacology |volume=116 |issue=1 |pages=9–18 |date=September 1994 |pmid=7862937 |doi= 10.1007/BF02244865|s2cid=24204026 }}</ref><ref name="pmid8531104">{{cite journal |vauthors =Weed MR, Woolverton WL |title=The reinforcing effects of dopamine D1 receptor agonists in rhesus monkeys |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=275 |issue=3 |pages=1367–74 |date=December 1995 |pmid=8531104 }}</ref><ref name="pmid15464142">{{cite journal |vauthors =Barrett AC, Miller JR, Dohrmann JM, Caine SB |title=Effects of dopamine indirect agonists and selective D1-like and D2-like agonists and antagonists on cocaine self-administration and food maintained responding in rats |journal=Neuropharmacology |volume=47 |pages=256–73 |year=2004 |issue=Suppl 1 |pmid=15464142 |doi=10.1016/j.neuropharm.2004.07.007 |s2cid=2959198 }}</ref> |
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== References == |
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{{Reflist}} |
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{{Stimulants}} |
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{{Anorectics}} |
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{{Dopaminergics}} |
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[[Category:1-Phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines]] |
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[[Category:Dopamine agonists]] |
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[[Category:Bromobenzene derivatives]] |
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[[Category:Allylamines]] |
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[[Category:Benzazepanes]] |
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{{gastrointestinal-drug-stub}} |
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