Chemistry:CGS-15943

CGS-15943
Clinical data
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 9-chloro-2-(furan-2-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine;
CAS Number	104615-18-1 ;
PubChem CID	2690;
IUPHAR/BPS	384;
ChemSpider	2589 ;
UNII	Y5A5D5E2AQ;
ChEBI	CHEBI:131351 ;
ChEMBL	ChEMBL16687 ;
Chemical and physical data
Formula	C13H8ClN5O
Molar mass	285.69 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES ClC1=CC=C2N=C(N)N3N=C(C4=CC=CO4)N=C3C2=C1;
	InChI InChI=1S/C13H8ClN5O/c14-7-3-4-9-8(6-7)12-17-11(10-2-1-5-20-10)18-19(12)13(15)16-9/h1-6H,(H2,15,16) ; Key:MSJODEOZODDVGW-UHFFFAOYSA-N ;
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Short description: Chemical compound

CGS-15943 is a drug which acts as a potent and reasonably selective antagonist for the adenosine receptors A₁ and A_2A, having a K_i of 3.3nM at A_2A and 21nM at A₁. It was one of the first adenosine receptor antagonists discovered that is not a xanthine derivative, instead being a triazoloquinazoline.^[1]^[2] Consequently, CGS-15943 has the advantage over most xanthine derivatives that it is not a phosphodiesterase inhibitor, and so has more a specific pharmacological effects profile. It produces similar effects to caffeine in animal studies, though with higher potency.^[3]^[4]^[5]^[6]^[7]

References

↑ "Biochemical characterization of the triazoloquinazoline, CGS 15943, a novel, non-xanthine adenosine antagonist". The Journal of Pharmacology and Experimental Therapeutics 241 (2): 415–20. May 1987. PMID 2883298.
↑ "Pharmacological characterization of CGS 15943A: a novel nonxanthine adenosine antagonist". The Journal of Pharmacology and Experimental Therapeutics 242 (3): 784–90. September 1987. PMID 3656113.
↑ Holtzman SG (1991). "CGS 15943, a nonxanthine adenosine receptor antagonist: effects on locomotor activity of nontolerant and caffeine-tolerant rats". Life Sciences 49 (21): 1563–70. doi:10.1016/0024-3205(91)90329-A. PMID 1943461.
↑ "Comparison of the behavioural effects of an adenosine A1/A2-receptor antagonist, CGS 15943A, and an A1-selective antagonist, DPCPX". Psychopharmacology 103 (4): 541–4. 1991. doi:10.1007/bf02244256. PMID 2062988.
↑ "Effects of CGS 15943, a nonxanthine adenosine antagonist, on behavior in the squirrel monkey". The Journal of Pharmacology and Experimental Therapeutics 267 (1): 432–9. October 1993. PMID 8229772.
↑ Holtzman SG (May 1996). "Discriminative effects of CGS 15943, a competitive adenosine receptor antagonist, in monkeys: comparison to methylxanthines". The Journal of Pharmacology and Experimental Therapeutics 277 (2): 739–46. PMID 8627553.
↑ "The adenosine receptor antagonist CGS15943 reinstates cocaine-seeking behavior and maintains self-administration in baboons". Psychopharmacology 168 (1–2): 155–63. July 2003. doi:10.1007/s00213-003-1410-5. PMID 12669180.

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[pmid2883298-1] "Biochemical characterization of the triazoloquinazoline, CGS 15943, a novel, non-xanthine adenosine antagonist". The Journal of Pharmacology and Experimental Therapeutics 241 (2): 415–20. May 1987. PMID 2883298.

[pmid3656113-2] "Pharmacological characterization of CGS 15943A: a novel nonxanthine adenosine antagonist". The Journal of Pharmacology and Experimental Therapeutics 242 (3): 784–90. September 1987. PMID 3656113.

[pmid1943461-3] Holtzman SG (1991). "CGS 15943, a nonxanthine adenosine receptor antagonist: effects on locomotor activity of nontolerant and caffeine-tolerant rats". Life Sciences 49 (21): 1563–70. doi:10.1016/0024-3205(91)90329-A. PMID 1943461.

[pmid2062988-4] "Comparison of the behavioural effects of an adenosine A1/A2-receptor antagonist, CGS 15943A, and an A1-selective antagonist, DPCPX". Psychopharmacology 103 (4): 541–4. 1991. doi:10.1007/bf02244256. PMID 2062988.

[pmid8229772-5] "Effects of CGS 15943, a nonxanthine adenosine antagonist, on behavior in the squirrel monkey". The Journal of Pharmacology and Experimental Therapeutics 267 (1): 432–9. October 1993. PMID 8229772.

[pmid8627553-6] Holtzman SG (May 1996). "Discriminative effects of CGS 15943, a competitive adenosine receptor antagonist, in monkeys: comparison to methylxanthines". The Journal of Pharmacology and Experimental Therapeutics 277 (2): 739–46. PMID 8627553.

[pmid12669180-7] "The adenosine receptor antagonist CGS15943 reinstates cocaine-seeking behavior and maintains self-administration in baboons". Psychopharmacology 168 (1–2): 155–63. July 2003. doi:10.1007/s00213-003-1410-5. PMID 12669180.

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v t e Stimulants
Adamantanes	Adapromine Amantadine Bromantane Memantine Rimantadine
Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan 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
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 Haldol 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-Fuoroamphetamine 2-Fuoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fuoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-CMC 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-MMA 4-Methylpentedrone 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone 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 Benzedrone Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Buphedrone Bupropion Butylone Camfetamine Cathine Cathinone Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylnorepinephrine Ethylone Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine Flephedrone Fludorex Formetorex Furfenorex Gepefrine Hexapradol Hexedrone HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylenedioxycathinone Methylone Mexedrone MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N-Ethylbuphedrone N-Ethylhexedrone N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine (drug) Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Pentedrone Pentylone Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Phthalimidopropiophenone 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 5-DBFPV α-PPP α-PBP 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

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Clinical data

ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 9-chloro-2-(furan-2-yl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine
CAS Number	104615-18-1^Y
PubChem CID	2690
IUPHAR/BPS	384
ChemSpider	2589^Y
UNII	Y5A5D5E2AQ
ChEBI	CHEBI:131351^N
ChEMBL	ChEMBL16687^Y
Chemical and physical data
Formula	C₁₃H₈ClN₅O
Molar mass	285.69 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES ClC1=CC=C2N=C(N)N3N=C(C4=CC=CO4)N=C3C2=C1
InChI InChI=1S/C13H8ClN5O/c14-7-3-4-9-8(6-7)12-17-11(10-2-1-5-20-10)18-19(12)13(15)16-9/h1-6H,(H2,15,16)^Y Key:MSJODEOZODDVGW-UHFFFAOYSA-N^Y
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