Dichloropane

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Dichloropane
Phenyltropane 17c.svg
Clinical data
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C16H19Cl2NO2
Molar mass 328.23356 g/mol
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.[1] In animal studies, dichloropane had a slower onset and longer duration of action compared to cocaine.[2][3]

Methylecgonidine is the direct precursor to this compound.[4]

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. ^ Carroll, F. Ivy; Blough, Bruce E.; Nie, Zhe; Kuhar, Michael J.; Howell, Leonard L.; Navarro, Hernan A. (21 April 2005). "Synthesis and Monoamine Transporter Binding Properties of 3β-(3',4'-Disubstituted phenyl)tropane-2β-carboxylic Acid Methyl Esters". Journal of Medicinal Chemistry. 48 (8): 2767–2771. doi:10.1021/jm040185a. PMID 15828814. 
  2. ^ Ranaldi, Robert; Anderson, Karen G.; Carroll, F. Ivy; Woolverton, William L. (December 2000). "Reinforcing and discriminative stimulus effects of RTI 111, a 3-phenyltropane analog, in rhesus monkeys: interaction with methamphetamine". Psychopharmacology. 153 (1): 103–110. doi:10.1007/s002130000602. ISSN 1432-2072. PMID 11255920. 
  3. ^ Cook, Charles D.; Carroll, Ivy F.; Beardsley, Patrick M. (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. ISSN 1432-2072. PMID 11797070. 
  4. ^ Carroll, F. Ivy; Mascarella, S. Wayne; Kuzemko, Michael A.; Gao, Yigong; Abraham, Philip; Lewin, Anita H.; Boja, John W.; Kuhar, Michael J. (2 September 1994). "Synthesis, Ligand Binding, and QSAR (CoMFA and Classical) Study of 3β-(3'-Substituted phenyl)-, 3β-(4'-Substituted phenyl)-, and 3β-(3',4'-Disubstituted phenyl)tropane-2β-carboxylic Acid Methyl Esters". Journal of Medicinal Chemistry. 37 (18): 2865–2873. doi:10.1021/jm00044a007. PMID 8071935.