6-Br-APB

Chemical compound

This article is about the dopamine D1 receptor agonist. For the amphetamine derivative, see 6-APB.

Pharmaceutical compound

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 ^☒N
PubChem CID	11957483
ChemSpider	8627436 ^checkY
ChEMBL	ChEMBL34095 ^checkY
CompTox Dashboard (EPA)	DTXSID40474680 Edit this at Wikidata
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^checkY Key:KKZGFVAZUKHFAC-MRXNPFEDSA-N^checkY
^☒NcheckY (what is this?) (verify)

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

[edit ]

^ 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.200407007. PMID 15464142. S2CID 2959198.

v t e Stimulants
Adamantanes	Adapromine Amantadine Bromantane Memantine Rimantadine
Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Istradefylline Paraxanthine SCH-58261 Theobromine Theophylline
Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane
Ampakines	CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram
Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine
Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958
Cathinones	3-FMC 3-MMC 3,4-DMMC 4-BMC 4-CMC 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-Methylpentedrone Amfepramone Benzedrone Buphedrone Bupropion Butylone Cathinone Dimethylcathinone Ethcathinone Ethylone Flephedrone Hexedrone Isoethcathinone Mephedrone Methcathinone Methedrone Methylenedioxycathinone Methylone Mexedrone N-Ethylbuphedrone N-Ethylhexedrone Pentedrone Pentylone Phthalimidopropiophenone
Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538
Convulsants	Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone
Eugeroics	Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil
Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-MMA 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Camfetamine Cathine Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethylnorepinephrine Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Fludorex Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methoxyphenamine MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Pyr-AI Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine
Phenylmorpholines	3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine
Piperazines	2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 JJC8-088 MeOPP MBZP oMPP Vanoxerine
Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate Serdexmethylphenidate SCH-5472
Pyrrolidines	2-Diphenylmethylpyrrolidine 4-Cl-PVP 5-DBFPV α-PPP α-PBP α-PCYP α-PHiP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone
Racetams	Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide
Tropanes	4-fluorotropacocaine 4'-Fluorococaine Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33
Tryptamines	4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT
Others	2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine
ATC code: N06B

v
t
e

Antiobesity agents/Anorectics (A08)

Stimulants

Amphetamines and phenethylamines	4-Methylamphetamine ^‡ Amfecloral Amfepentorex Amfepramone Amphetamine Amphetaminil Benzphetamine Cathine Cathinone Chlorphentermine Clobenzorex Cloforex Clortermine Dextroamphetamine Dimethylcathinone Ephedrine Ephedra ^‡ Etilamfetamine Etolorex Fenethylline Fenproporex Fludorex Furfenorex ^‡ Khat Lisdexamfetamine Mefenorex Methamphetamine Norfenfluramine Pentorex Phentermine (+topiramate) Xylopropamine Zylofuramine
Adrenergic agonists	Albuterol Clenbuterol ^§ Ephedrine Ephedra ^‡ Levopropylhexedrine Synephrine Terbutaline Yohimbine (Yohimbe)
Other	Aminorex ^‡ Atomoxetine Benfluorex ^‡ Bupropion (+naltrexone) Dexfenfluramine ^‡ Dexmethylphenidate Difemetorex ^‡ Fenbutrazate Fenfluramine (+phentermine ^‡) Manifaxine Mazindol Methylphenidate Phendimetrazine Phenethylamine Phenmetrazine Phenylpropanolamine Pipradrol Propylhexedrine Pyrovalerone Sibutramine ^‡ Tesofensine

Cannabinoid
antagonists

GLP-1, GIP, and / or
glucagon agonists

DACRAs

Cagrilintide (+semaglutide ^†)

5-HT2C
receptor agonists

5-HTP
Lorcaserin ^‡

Absorption inhibitors

Uncouplers

2,4-Dinitrophenol ^‡

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

v
t
e

Dopamine receptor modulators

D₁-like

Agonists	Benzazepines: 6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959 Trepipam Zelandopam Ergolines: Cabergoline CY-208,243 Dihydroergocryptine LEK-8829 Lisuride Pergolide Terguride Dihydrexidine derivatives: A-77636 A-86929 Adrogolide (ABT-431, DAS-431) Dihydrexidine Dinapsoline Dinoxyline Doxanthrine Phenethylamines: BCO-001 Deoxyepinephrine (N-methyldopamine, epinine) Dopexamine Etilevodopa Ibopamine L-DOPA (levodopa) Melevodopa L-Phenylalanine L-Tyrosine XP21279 Others: A-68930 Apomorphine Isocorypalmine Nuciferine PF-6649751 PF 6669571 Propylnorapomorphine Rotigotine SKF-89,145 SKF-89,626 Stepholidine Tavapadon Tetrahydropalmatine
PAMs	Tetrahydroisoquinolines: DETQ DPTQ Mevidalen
Antagonists	Typical antipsychotics: Butaclamol Chlorpromazine Chlorprothixene Flupentixol (flupenthixol) (+melitracen) Fluphenazine Loxapine Perphenazine (+amitriptyline) Pifluthixol Thioridazine Thiothixene Trifluoperazine (+tranylcypromine) Zuclopenthixol Atypical antipsychotics: Asenapine Clorotepine Clotiapine Clozapine DHA-clozapine Fluperlapine Iloperidone Norclozapine Norquetiapine Olanzapine (+fluoxetine) Paliperidone Quetiapine Risperidone Tefludazine Zicronapine Ziprasidone Zotepine Others: Berupipam Ecopipam EEDQ Metitepine (methiothepin) Odapipam Perlapine SCH-23390