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Dichloropane ((−)-2β-Carbomethoxy-3β-(3,4-dichlorophenyl)tropane, RTI-111, O-401) is a powerful SNDRI with IC50 (nM) values of 0.79, 3.13, and 18 at the DAT, SERT, and NET.〔Carroll FI, Blough BE, Nie Z, Kuhar MJ, Howell LL, Navarro HA. Synthesis and Monoamine Transporter Binding Properties of 3-(3',4'-Disubstituted phenyl)tropane-2-carboxylic Acid Methyl Esters. J Med Chem. 2005 Apr 21;48(8):2767-71. PMID 15828814〕 Methylecgonidine as the direct precursor to this compound.〔Carroll FI, Mascarella SW, Kuzemko MA, Gao Y, Abraham P, Lewin AH, Boja JW, Kuhar MJ. Synthesis, ligand binding, and QSAR (CoMFA and classical) study of 3 beta-(3'-substituted phenyl)-, 3 beta-(4'-substituted phenyl)-, and 3 beta-(3',4'-disubstituted phenyl)tropane-2 beta-carboxylic acid methyl esters. ''Journal of Medicinal Chemistry''. 1994 Sep 2;37(18):2865-73. PMID 8071935〕 In contrast to the closely related RTI-112, dichloropane is a potent stimulant drug which produces similar effects to cocaine as well as being structurally similar to cocaine. In animal studies although, dichloropane had a slower onset and longer duration of action.〔Ranaldi R, Anderson KG, Carroll FI, Woolverton WL. Reinforcing and discriminative stimulus effects of RTI 111, a 3-phenyltropane analog, in rhesus monkeys: interaction with methamphetamine. ''Psychopharmacology (Berlin)''. 2000 Dec;153(1):103-10. PMID 11255920〕〔Cook CD, Carroll IF, Beardsley PM. Cocaine-like discriminative stimulus effects of novel cocaine and 3-phenyltropane analogs in the rat. ''Psychopharmacology (Berlin)''. 2001 Dec;159(1):58-63. PMID 11797070〕 ==Transporter selectivity for disubstituted analogs== DAT: (''p''-Br, ''m''-Cl) < (''p''-I, ''m''-Br) ≈ (''p''-Br, ''m''-I) ~ (''p''-I, ''m''-Cl) ≈ p,m-Br2 < (''p''-Cl, ''m''-I) ≈ (''p''-Cl, ''m''-Br) ≈ p,m-Me2 < p,m-Cl2 < (''p''-Cl, ''m''-Me) < p,m-I2. 5HT: (''p''-I, ''m''-Br) < p,m-Br2 ~ (''p''-Cl, ''m''-Br) < (''p''-Br, ''m''-Cl) ~ (''p''-I, ''m''-Cl) < (''p''-Br, ''m''-I) < (''p''-Cl, ''m''-I) < p,m-I2 < p,m-Cl2 < (''p''-Cl, ''m''-Me) < p,m-Me2. NET: (''p''-I, ''m''-Cl) ~ (''p''-Br, ''m''-Cl) < (''p''-I, ''m''-Br) < p,m-Br2 < (''p''-Cl, ''m''-Br) < (''p''-Br, ''m''-I) < (''p''-Cl, ''m''-I) < p,m-Cl2 < (''p''-Cl, ''m''-Me) < p,m-I2 < p,m-Me2. 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Dichloropane」の詳細全文を読む スポンサード リンク
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