6-Br-APB

6-Br-APB
Identifiers
	IUPAC name 3-allyl-6-bromo-1-phenyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol;
CAS Number	135974-57-1 ;
PubChem CID	11957483;
ChemSpider	8627436 ;
ChEMBL	ChEMBL34095 ;
CompTox Dashboard (EPA)	DTXSID40474680 ;
Chemical and physical data
Formula	C19H20BrNO2
Molar mass	374.278 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c3ccccc3C2CN(CC=C)CCc(c1Br)c2cc(O)c1O;
	InChI InChI=1S/C19H20BrNO2/c1-2-9-21-10-8-14-15(11-17(22)19(23)18(14)20)16(12-21)13-6-4-3-5-7-13/h2-7,11,16,22-23H,1,8-10,12H2/t16-/m1/s1 ; Key:KKZGFVAZUKHFAC-MRXNPFEDSA-N ;
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6-Br-APB is a synthetic compound that acts as a selective D₁ agonist,^[1] with the (R)-enantiomer being a potent full agonist, while the (S) enantiomer retains its D₁ selectivity but is a weak partial agonist.^[2] (R)-6-Br-APB and similar D₁-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 stimulants such as amphetamine.^[3]^[4]^[5]

References

^ Neumeyer JL, et al. (December 1991). "(+/-)-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 of Medicinal Chemistry. 34 (12): 3366–71. doi:10.1021/jm00116a004. PMID 1684995.
^ Neumeyer JL, Kula NS, Baldessarini RJ, Baindur N (April 1992). "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 of Medicinal Chemistry. 35 (8): 1466–71. doi:10.1021/jm00086a016. PMID 1533424.
^ Rosenzweig-Lipson S, Hesterberg P, Bergman J (September 1994). "Observational studies of dopamine D1 and D2 agonists in squirrel monkeys". Psychopharmacology. 116 (1): 9–18. doi:10.1007/BF02244865. PMID 7862937. S2CID 24204026.
^ Weed MR, Woolverton WL (December 1995). "The reinforcing effects of dopamine D1 receptor agonists in rhesus monkeys". The Journal of Pharmacology and Experimental Therapeutics. 275 (3): 1367–74. PMID 8531104.
^ Barrett AC, Miller JR, Dohrmann JM, Caine SB (2004). "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". Neuropharmacology. 47 (Suppl 1): 256–73. doi:10.1016/j.neuropharm.2004.07.007. PMID 15464142. S2CID 2959198.

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[pmid1684995-1] Neumeyer JL, et al. (December 1991). "(+/-)-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 of Medicinal Chemistry. 34 (12): 3366–71. doi:10.1021/jm00116a004. PMID 1684995.

[pmid1533424-2] Neumeyer JL, Kula NS, Baldessarini RJ, Baindur N (April 1992). "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 of Medicinal Chemistry. 35 (8): 1466–71. doi:10.1021/jm00086a016. PMID 1533424.

[pmid7862937-3] Rosenzweig-Lipson S, Hesterberg P, Bergman J (September 1994). "Observational studies of dopamine D1 and D2 agonists in squirrel monkeys". Psychopharmacology. 116 (1): 9–18. doi:10.1007/BF02244865. PMID 7862937. S2CID 24204026.

[pmid8531104-4] Weed MR, Woolverton WL (December 1995). "The reinforcing effects of dopamine D1 receptor agonists in rhesus monkeys". The Journal of Pharmacology and Experimental Therapeutics. 275 (3): 1367–74. PMID 8531104.

[pmid15464142-5] Barrett AC, Miller JR, Dohrmann JM, Caine SB (2004). "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". Neuropharmacology. 47 (Suppl 1): 256–73. doi:10.1016/j.neuropharm.2004.07.007. PMID 15464142. S2CID 2959198.

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Identifiers


IUPAC name 3-allyl-6-bromo-1-phenyl-1,2,4,5-tetrahydro-3-benzazepine-7,8-diol
CAS Number	135974-57-1^N
PubChem CID	11957483
ChemSpider	8627436^Y
ChEMBL	ChEMBL34095^Y
CompTox Dashboard (EPA)	DTXSID40474680
Chemical and physical data
Formula	C₁₉H₂₀BrNO₂
Molar mass	374.278 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c3ccccc3C2CN(CC=C)CCc(c1Br)c2cc(O)c1O
InChI InChI=1S/C19H20BrNO2/c1-2-9-21-10-8-14-15(11-17(22)19(23)18(14)20)16(12-21)13-6-4-3-5-7-13/h2-7,11,16,22-23H,1,8-10,12H2/t16-/m1/s1^Y Key:KKZGFVAZUKHFAC-MRXNPFEDSA-N^Y
^NY (what is this?) (verify)