Dichloropane

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.[3] In animal studies, dichloropane had a slower onset and longer duration of action compared to cocaine.[4][5]

Dichloropane
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC16H19Cl2NO2
Molar mass328.23356 g/mol g·mol−1
3D model (JSmol)
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Methylecgonidine is the direct precursor to this compound.[6]

Trans -CO2Me group

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

References
  1. "Amihuyqknjhxpt-Drabbmoasa-N".
  2. "Amihuyqknjhxpt-Drabbmoasa-N".
  3. 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.
  4. 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.
  5. 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.
  6. 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.
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