(-)-2β-Carbomethoxy-3β-(3,4-dichlorophenyl)tropane

Drugbox
IUPAC_name = methyl (1R,2S,3S,5S)-3-(3,4-dichlorophenyl)-8-azabicyclo [3.2.1] octane-2-carboxylate


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CAS_number= 146725-34-0
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PubChem= 127024
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C=15 | H=17 | Cl=2 | N=1 | O=2
molecular_weight = 314.207
smiles = COC(=O) [C@@H] 1 [C@H] 2CC [C@H] (N2)C [C@@H] 1C3=CC(=C(C=C3)Cl)Cl
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(-)-2β-Carbomethoxy-3β-(3,4-dichlorophenyl)tropane (Dichloropane, RTI-111, O-401) is a phenyltropane derivative synthesised from methylecgonidine, which acts as a dopamine reuptake inhibitor. [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]

Dichloropane is a potent stimulant drug which produces similar effects to cocaine in animal studies, although with 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]

It is not explicitly illegal anywhere in the world as of 2008, but might be considered to be a controlled substance analogue of cocaine on the grounds of its related chemical structure, in some jurisdictions such as the USA, Canada, Australia and New Zealand.

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