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Dichloropane
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 none
PubChem 127024
Chemical data
Formula C15H17Cl2NO2 
Mol. mass 314.207
SMILES eMolecules & PubChem
Therapeutic considerations
Pregnancy cat.  ?
Legal status

Dichloropane ((-)-2β-Carbomethoxy-3β-(3,4-dichlorophenyl)tropane, RTI-111, O-401) is a powerful SNDRI with IC50 (nM) values of 0.79, 3.13, and 18 at the DAT, SERT, and NET.[1]

Methylecgonidine as the direct precursor to this compound.[2]

In contrast to the closely related RTI-112, 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.[3][4]

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.

Transporter selectivity for disubstituted analogs

MAT IC50 (Ki) nM for 3',4'-Disubstituted Phenyltropanes.
RTI P M [3H]WIN 35,428 [3H]Paroxetine [3H]Nisoxetine
111 Cl Cl 0.79 3.13 (0.29) 18 (11)
112 Cl Me 0.82 ± 0.05 10.5 ± 0.41 (0.95 ± 0.04) 36.2 ± 1.02 (21.8 ± 0.62)
Cl Br 0.42 ± 0.02 0.78 ± 0.04 (0.19 ± 0.01) 7.24 ± 0.69 (3.62 ± 0.34)
Cl I 0.41 ± 0.09 1.39 ± 0.23 (0.34 ± 0.06) 15.1 ± 0.59 (7.74 ± 0.29)
Br Cl 0.12 ± 0.04 0.94 ± 0.09 (0.23 ± 0.02) 1.31 ± 0.13 (0.65 ± 0.07)
Br Br 0.27 ± 0.01 0.71 ± 0.03 (0.18 ± 0.01) 2.80 ± 0.16 (1.10 ± 0.08)
Br I 0.21 ± 0.06 1.14 ± 0.26 (0.25 ± 0.04) 10.4 ± 1.5 (5.12 ± 0.77)
I Cl 0.26 ± 0.05 1.04 ± 0.14 (0.63 ± 0.05) 1.26 ± 0.09 (0.63 ± 0.05)
I Br 0.20 ± 0.04 0.58 ± 0.07 (0.14 ± 0.02) 1.96 ± 0.17 (0.98 ± 0.09)
I I 0.98 ± 0.05 2.0 ± 0.56 (0.19 ± 0.05) 40.4 ± 3.56 (24 ± 2.1)
Me Me 0.43 ± 0.07 9.88 ± 1.11 (2.42 ± 0.27) 107 ± 11 (44 ± 4.7)

DAT: (p-Br, m-Cl) < (p-I, m-Br) ≈ (p-Br, m-I) ~ (p-I, m-Cl) ≈ p,m-Br2 < (p-Cl, m-I) ≈ (p-Cl, m-Br) ≈ p,m-Me2 < p,m-Cl2 < (p-Cl, m-Me) < p,m-I2.

5HT: (p-I, m-Br) < p,m-Br2 ~ (p-Cl, m-Br) < (p-Br, m-Cl) ~ (p-I, m-Cl) < (p-Br, m-I) < (p-Cl, m-I) < p,m-I2 < p,m-Cl2 < (p-Cl, m-Me) < p,m-Me2.

NET: (p-I, m-Cl) ~ (p-Br, m-Cl) < (p-I, m-Br) < p,m-Br2 < (p-Cl, m-Br) < (p-Br, m-I) < (p-Cl, m-I) < p,m-Cl2 < (p-Cl, m-Me) < p,m-I2 < p,m-Me2.

See also

References

  1. ^ Carroll FI, Blough BE, Nie Z, Kuhar MJ, Howell LL, Navarro HA. Synthesis and Monoamine Transporter Binding Properties of 3-(3',4'-Disubstituted phenyl)tropane-2-carboxylic Acid Methyl Esters. J Med Chem. 2005 Apr 21;48(8):2767-71. PMID 15828814
  2. ^ 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
  3. ^ 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
  4. ^ 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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