Dichloropane

Dichloropane
Clinical data
ATC code	none;
Legal status
Legal status	UK: Under Psychoactive Substances Act; US: Schedule II;
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 ;
PubChem CID	127024;
ChemSpider	112783 ;
UNII	V7SQE82R87;
CompTox Dashboard (EPA)	DTXSID20932894 ;
Chemical and physical data
Formula	C15H17Cl2NO2
Molar mass	314.21 g·mol−1
3D 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 ; Key:JFUNLJPTPCQLIR-PJQZNRQZSA-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.

References

^ 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.
^ 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.
^ 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.
^ 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.

[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.

[1]

[2]

[3]

[4]

Clinical data

ATC code	none
Legal status
Legal status	UK: Under Psychoactive Substances Act US: Schedule II
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^Y
PubChem CID	127024
ChemSpider	112783^N
UNII	V7SQE82R87
CompTox Dashboard (EPA)	DTXSID20932894
Chemical and physical data
Formula	C₁₅H₁₇Cl₂NO₂
Molar mass	314.21 g·mol⁻¹
3D 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
^NY (what is this?) (verify)

Dichloropane

Trans -CO2Me group

See also

References

Trans -CO₂Me group