Dichloropane

Dichloropane
Phenyltropane 17c.svg
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
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Chemical and physical data
FormulaC16H19Cl2NO2
Molar mass328.23356 g/mol g·mol−1
3D model (JSmol)
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Dichloropane ((−)-2β-Carbomethoxy-3β-(3,4-dichlorophenyl)tropane, RTI-111, O-401) is a stimulant of the phenyltropane class that acts as a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI) with IC50 values of 3.13, 0.79 and 18 nM, respectively.[2] In animal studies, dichloropane had a slower onset and longer duration of action compared to cocaine.[3][4]

Methylecgonidine is the direct precursor to this compound.[5]

Trans -CO2Me group[edit]

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

See also[edit]

References[edit]

  1. ^ "Amihuyqknjhxpt-Drabbmoasa-N".
  2. ^ Carroll FI, Blough BE, Nie Z, Kuhar MJ, Howell LL, Navarro HA (April 2005). "Synthesis and monoamine transporter binding properties of 3beta-(3',4'-disubstituted phenyl)tropane-2beta-carboxylic acid methyl esters". Journal of Medicinal Chemistry. 48 (8): 2767–71. doi:10.1021/jm040185a. PMID 15828814.
  3. ^ Ranaldi R, Anderson KG, Carroll FI, Woolverton WL (December 2000). "Reinforcing and discriminative stimulus effects of RTI 111, a 3-phenyltropane analog, in rhesus monkeys: interaction with methamphetamine". Psychopharmacology. 153 (1): 103–10. doi:10.1007/s002130000602. PMID 11255920.
  4. ^ Cook CD, Carroll IF, Beardsley PM (December 2001). "Cocaine-like discriminative stimulus effects of novel cocaine and 3-phenyltropane analogs in the rat". Psychopharmacology. 159 (1): 58–63. doi:10.1007/s002130100891. PMID 11797070.
  5. ^ Carroll FI, Mascarella SW, Kuzemko MA, Gao Y, Abraham P, Lewin AH, et al. (September 1994). "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. 37 (18): 2865–73. doi:10.1021/jm00044a007. PMID 8071935.