Dichloropane

Chemical compound
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Legal statusLegal status
Identifiers
IUPAC name
  • Methyl (1R,2S,3S,5S)-3-(3,4-dichlorophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number
  • 146725-34-0 checkY
PubChem CID
  • 127024
ChemSpider
  • 112783 ☒N
UNII
  • V7SQE82R87
CompTox Dashboard (EPA)
  • DTXSID20932894 Edit this at Wikidata
Chemical and physical dataFormulaC15H17Cl2NO2Molar mass314.21 g·mol−13D model (JSmol)
  • Interactive image
SMILES
  • COC(=O)[C@@H]1[C@H]2CC[C@H](N2C)C[C@@H]1C3=CC(=C(C=C3)Cl)Cl
InChI
  • InChI=1S/C16H19Cl2NO2/c1-19-10-4-6-14(19)15(16(20)21-2)11(8-10)9-3-5-12(17)13(18)7-9/h3,5,7,10-11,14-15H,4,6,8H2,1-2H3/t10-,11+,14+,15-/m0/s1 ☒N
  • Key:JFUNLJPTPCQLIR-PJQZNRQZSA-N ☒N
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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, 18, and 0.79 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

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. ^ 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.
  2. ^ 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. S2CID 29716872.
  3. ^ 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. S2CID 25696981.
  4. ^ 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.
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ATC code: N06B
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DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
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2-Carboxymethyl Esters
(3,4-Disubstituted Phenyl)-tropanes
Arylcarboxy
Carboxyalkyl
Acyl
  • PTT/WF-11
  • WF-23
  • PIT/WF-21
  • WF-33
β,α Stereochemistry
α,β Stereochemistry
Heterocycles: 3-Substituted-isoxazol-5-yl
Heterocycles: 3-Substituted-1,2,4-oxadiazole
N-alkyl
  • FP-β-CPPIT
  • FE-β-CPPIT
  • Altropane
  • Ioflupane (123I)
N-replaced (S,O,C)
Irreversible
Nortropanes (N-demethylated)