SKF-81,297

SKF-81,297
Clinical data
ATC code	none;
Identifiers
	IUPAC name 6-chloro-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7,8-diol;
CAS Number	253446-15-0 ;
PubChem CID	16219952;
ChemSpider	1181;
UNII	J494DH8JRC;
CompTox Dashboard (EPA)	DTXSID3058743 ;
Chemical and physical data
Formula	C16H16ClNO2
Molar mass	289.76 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1c(O)c(O)cc2c1CCNCC2c3ccccc3;

SKF-81,297 is a synthetic drug of the benzazepine chemical class that acts as a selective dopamine D₁/D₅ receptor full agonist, and produces a characteristic stimulant-like pattern of anorexia, hyperactivity and self-administration in animals.^[1] This profile is shared with several related drugs such as 6-Br-APB and SKF-82,958,^[2] but not with certain other D₁ full agonists such as A-77,636, reflecting functional selectivity of D₁ activation.^[3]^[4]^[5] Newer findings reveal that SKF-81,297 additionally acts as a partial agonist at D₁-D₂ receptor heteromers.^[6]

References[]

^ Weed MR, Vanover KE, Woolverton WL (1993). "Reinforcing effect of the D1 dopamine agonist SKF 81297 in rhesus monkeys". Psychopharmacology. 113 (1): 51–2. doi:10.1007/BF02244333. PMID 7862828. S2CID 7292320.
^ Weed MR, Paul IA, Dwoskin LP, Moore SE, Woolverton WL (October 1997). "The relationship between reinforcing effects and in vitro effects of D1 agonists in monkeys". The Journal of Pharmacology and Experimental Therapeutics. 283 (1): 29–38. PMID 9336305.
^ Chausmer AL, Katz JL (January 2002). "Comparison of interactions of D1-like agonists, SKF 81297, SKF 82958 and A-77636, with cocaine: locomotor activity and drug discrimination studies in rodents". Psychopharmacology. 159 (2): 145–53. doi:10.1007/s002130100896. PMID 11862342. S2CID 6788631.
^ Graham DL, Hoppenot R, Hendryx A, Self DW (April 2007). "Differential ability of D1 and D2 dopamine receptor agonists to induce and modulate expression and reinstatement of cocaine place preference in rats". Psychopharmacology. 191 (3): 719–30. doi:10.1007/s00213-006-0473-5. PMID 16835769. S2CID 21192319.
^ Delfino M, Kalisch R, Czisch M, Larramendy C, Ricatti J, Taravini IR, Trenkwalder C, Murer MG, Auer DP, Gershanik OS (September 2007). "Mapping the effects of three dopamine agonists with different dyskinetogenic potential and receptor selectivity using pharmacological functional magnetic resonance imaging". Neuropsychopharmacology. 32 (9): 1911–21. doi:10.1038/sj.npp.1301329. PMID 17287822.
^ 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. Bibcode:2007PNAS..104..654R. doi:10.1073/pnas.0604049104. PMC 1766439. PMID 17194762.

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[pmid7862828-1] Weed MR, Vanover KE, Woolverton WL (1993). "Reinforcing effect of the D1 dopamine agonist SKF 81297 in rhesus monkeys". Psychopharmacology. 113 (1): 51–2. doi:10.1007/BF02244333. PMID 7862828. S2CID 7292320.

[pmid9336305-2] Weed MR, Paul IA, Dwoskin LP, Moore SE, Woolverton WL (October 1997). "The relationship between reinforcing effects and in vitro effects of D1 agonists in monkeys". The Journal of Pharmacology and Experimental Therapeutics. 283 (1): 29–38. PMID 9336305.

[pmid11862342-3] Chausmer AL, Katz JL (January 2002). "Comparison of interactions of D1-like agonists, SKF 81297, SKF 82958 and A-77636, with cocaine: locomotor activity and drug discrimination studies in rodents". Psychopharmacology. 159 (2): 145–53. doi:10.1007/s002130100896. PMID 11862342. S2CID 6788631.

[pmid16835769-4] Graham DL, Hoppenot R, Hendryx A, Self DW (April 2007). "Differential ability of D1 and D2 dopamine receptor agonists to induce and modulate expression and reinstatement of cocaine place preference in rats". Psychopharmacology. 191 (3): 719–30. doi:10.1007/s00213-006-0473-5. PMID 16835769. S2CID 21192319.

[pmid17287822-5] Delfino M, Kalisch R, Czisch M, Larramendy C, Ricatti J, Taravini IR, Trenkwalder C, Murer MG, Auer DP, Gershanik OS (September 2007). "Mapping the effects of three dopamine agonists with different dyskinetogenic potential and receptor selectivity using pharmacological functional magnetic resonance imaging". Neuropsychopharmacology. 32 (9): 1911–21. doi:10.1038/sj.npp.1301329. PMID 17287822.

[6] 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. Bibcode:2007PNAS..104..654R. doi:10.1073/pnas.0604049104. PMC 1766439. PMID 17194762.

[1]

[2]

[3]

[4]

[5]

[6]

v t 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 Levopropylhexedrine 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-Fluoromethcathinone 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 Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine 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 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 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

Clinical data

ATC code	none
Identifiers
IUPAC name 6-chloro-1-phenyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine-7,8-diol
CAS Number	253446-15-0^Y
PubChem CID	16219952
ChemSpider	1181
UNII	J494DH8JRC
CompTox Dashboard (EPA)	DTXSID3058743
Chemical and physical data
Formula	C₁₆H₁₆ClNO₂
Molar mass	289.76 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Clc1c(O)c(O)cc2c1CCNCC2c3ccccc3