Dichloropane

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Dichloropane
Dichloropane.svg
Systematic (IUPAC) name
methyl (1R,2S,3S,5S)-3-(3,4-dichlorophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate
Legal status
Legal status
  • Legal
Identifiers
CAS Number 146725-34-0 YesY
ATC code none
PubChem CID 127024
ChemSpider 112783
Chemical data
Formula C15H17Cl2NO2
Molar mass 314.207 g/mol
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Dichloropane ((−)-2β-Carbomethoxy-3β-(3,4-dichlorophenyl)tropane, RTI-4229-111, O-401) is a powerful SNDRI with IC50 (nM) values of 0.79, 3.13, and 18 at the DAT, SERT, and NET.[1]

Methylecgonidine as the direct precursor to this compound.[2]

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.[3][4]

Trans -CO2Me group[edit]

The thermodynamic isomer with a trans -CO2Me group is still active. This isomer was used by Neurosearch to make 3 different phenyltropanes, and all 3 were tested in clinical trials.

See also[edit]

References[edit]

  1. ^ 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
  2. ^ 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
  3. ^ 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
  4. ^ 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