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Chemical compound
Pharmaceutical compound
GYKI 52895 Other names 4-(8,9-Dihydro-8-methyl-7H -1,3-dioxolo[4,5-h ][2,3]benzodiazepin-5-yl)benzenamine
4-{13-methyl-4,6-dioxa-11,12-diazatricyclo[7.5.0.03,7 ]tetradeca-1,3(7),8,10-tetraen-10-yl}aniline
CAS Number PubChem CID ChemSpider UNII KEGG ChEMBL CompTox Dashboard (EPA ) Formula C 17 H 17 N 3 O 2 Molar mass −1 3D model (JSmol )
O1c2c(OC1)cc3c(c2)C(=N/NC(C3)C)\c4ccc(N)cc4
InChI=1S/C17H17N3O2/c1-10-6-12-7-15-16(22-9-21-15)8-14(12)17(20-19-10)11-2-4-13(18)5-3-11/h2-5,7-8,10,19H,6,9,18H2,1H3
Y Key:AQTITSBNGSVQNZ-UHFFFAOYSA-N
Y (verify)
GYKI 52895 is a drug which is a 2,3-benzodiazepine derivative that also shares the 3,4-methylenedioxyamphetamine pharmacophore . Unlike other similar drugs, GYKI 52895 is a selective dopamine reuptake inhibitor (DARI),[ 1] [ 2] [ 3] amphetamine and its derivatives (e.g. dextromethamphetamine ), cocaine , and methylphenidate and its derivatives (e.g. ethylphenidate ). However, dopaminergic drugs are also prone to producing emetic effects such as in the case of apomorphine .
Egis Pharmaceuticals began clinical development of the drug in 1997 for major depressive disorder and Parkinson's disease , but it was discontinued in 2001.[ 4]
^ Horváth K, Szabó H, Pátfalusi M, Berzsenyi P, Andrási F (1990). "Pharmacological Effects of GYKI 52895, a New Selective Dopamine Uptake Inhibitor". European Journal of Pharmacology . 183 (4): 1416– 1417. doi :10.1016/0014-2999(90)94548-C . ^ Huang CL, Chen HC, Huang NK, Yang DM, Kao LS, Chen JC, et al. (June 1999). "Modulation of dopamine transporter activity by nicotinic acetylcholine receptors and membrane depolarization in rat pheochromocytoma PC12 cells" . Journal of Neurochemistry . 72 (6): 2437– 44. doi :10.1046/j.1471-4159.1999.0722437.x PMID 10349853 . ^ Vaarmann A, Gandhi S, Gourine AV, Abramov AY (2010). "Novel pathway for an old neurotransmitter: dopamine-induced neuronal calcium signalling via receptor-independent mechanisms". Cell Calcium . 48 (2– 3): 176– 82. doi :10.1016/j.ceca.2010.08.008 . PMID 20846720 . ^ "GYKI 52895" . Adis Insight.
DAT Tooltip Dopamine transporter (DRIs Tooltip Dopamine reuptake inhibitors )
NET Tooltip Norepinephrine transporter (NRIs Tooltip Norepinephrine reuptake inhibitors )
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SERT Tooltip Serotonin transporter (SRIs Tooltip Serotonin reuptake inhibitors )
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VMATs Tooltip Vesicular monoamine transporters Others
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Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted
1-Aminomethylindanes (e.g., 2CB-Ind , AMMI , jimscaline )2-ADN 2-Benzhydrylpyrrolidine 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g., 3-phenylpiperidine , OSU-6162 (PNU-96391) , LPH-5 , LPH-48 )6-AB AL-1095 Benzazepines (e.g., fenoldopam , lorcaserin , SCHEMBL5334361 )Benzocyclobutenes (e.g., 2CBCB-NBOMe , S33005 , TCB-2 , tomscaline )Benzoxepins (e.g., BBOX , IBOX , TFMBOX )Butyltolylquinuclidine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g., LSD )GYKI-52895 HDMP-29 Ivabradine Lumateperone and analogues (e.g., IHCH-7079 , IHCH-7086 , IHCH-7113 , ITI-1549 )Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g., NDTDI , RU-27849 , DEIMDHPCA , DEMPDHPCA , RU-27251 )PF-592,379 Phenylcyclopropylamines (e.g., DMCPA , TMT , tranylcypromine )Tricyclics (e.g., benzoctamine , dizocilpine )Z3517967757 ZC-B
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2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g., 1,3-DMBA Tooltip 1,3-dimethylbutylamine , 1,4-DMAA Tooltip 1,4-dimethylamylamine , heptaminol , iproheptine , isometheptene , methylhexanamine/1,3-DMAA , octodrine , oenethyl , tuaminoheptane )Benzylamines (e.g., benzylamine , α-methylbenzylamine , MDM1EA , ALPHA , M-ALPHA , pargyline )Benzylpiperazines (e.g., benzylpiperazine , MDBZP , fipexide )Cyclohexylaminopropanes (e.g., propylhexedrine , norpropylhexedrine )Cyclopentylaminopropanes (e.g., isocyclamine , cyclopentamine )Phenylalkenylamines (e.g., phenylbutenamine )Phenylalkynylamines (e.g., phenylbutynamine )Phenylpiperazines (e.g., 1-phenylpiperazine , mCPP Tooltip meta-chlorophenylpiperazine , TFMPP Tooltip trifluoromethylphenylpiperazine , oMPP Tooltip ortho-methylphenylpiperazine , pFPP Tooltip para-fluorophenylpiperazine , pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g., phenylpropylamine , homo-MDA , homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g., thiopropamine , methiopropamine , thiothinone )
