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

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(-)-2β-Carbomethoxy-3β-(3,4-dichlorophenyl)tropane
Systematic (IUPAC) name
methyl (1R,2S,3S,5S)-3-(3,4-dichlorophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate
Identifiers
CAS number 146725-34-0
ATC code  ?
PubChem 127024
Chemical data
Formula C15H17Cl2NO2 
Mol. mass 314.207
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

?
Legal status
Routes  ?

(-)-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.[1]

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.[2][3]

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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[edit] References

  1. ^ 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
  2. ^ 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
  3. ^ 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


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