dichloropane

{{Short description|Chemical compound}}

{{multiple issues|

{{primary sources|date=February 2016}}

{{technical|date=February 2016}}

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{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 450843376

| IUPAC_name = Methyl (1R,2S,3S,5S)-3-(3,4-dichlorophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate

| image = Phenyltropane 17c.svg

| image_class = skin-invert-image

| width = 220

| tradename =

| legal_status =

| legal_UK = PSA

| legal_US = Schedule II

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 146725-34-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = V7SQE82R87

| ATC_prefix = none

| PubChem = 127024

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 112783

| C = 15

| H = 17

| Cl = 2

| N = 1

| O = 2

| smiles = COC(=O)[C@@H]1[C@H]2CC[C@H](N2C)C[C@@H]1C3=CC(=C(C=C3)Cl)Cl

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = JFUNLJPTPCQLIR-PJQZNRQZSA-N

}}

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.{{cite journal | vauthors = Carroll FI, Blough BE, Nie Z, Kuhar MJ, Howell LL, Navarro HA | title = Synthesis and monoamine transporter binding properties of 3beta-(3',4'-disubstituted phenyl)tropane-2beta-carboxylic acid methyl esters | journal = Journal of Medicinal Chemistry | volume = 48 | issue = 8 | pages = 2767–71 | date = April 2005 | pmid = 15828814 | doi = 10.1021/jm040185a }} In animal studies, dichloropane had a slower onset and longer duration of action compared to cocaine.{{cite journal | vauthors = Ranaldi R, Anderson KG, Carroll FI, Woolverton WL | title = Reinforcing and discriminative stimulus effects of RTI 111, a 3-phenyltropane analog, in rhesus monkeys: interaction with methamphetamine | journal = Psychopharmacology | volume = 153 | issue = 1 | pages = 103–10 | date = December 2000 | pmid = 11255920 | doi = 10.1007/s002130000602 | s2cid = 29716872 }}{{cite journal | vauthors = Cook CD, Carroll IF, Beardsley PM | title = Cocaine-like discriminative stimulus effects of novel cocaine and 3-phenyltropane analogs in the rat | journal = Psychopharmacology | volume = 159 | issue = 1 | pages = 58–63 | date = December 2001 | pmid = 11797070 | doi = 10.1007/s002130100891 | s2cid = 25696981 }}

Methylecgonidine is the direct precursor to this compound.{{cite journal | vauthors = Carroll FI, Mascarella SW, Kuzemko MA, Gao Y, Abraham P, Lewin AH, Boja JW, Kuhar MJ | display-authors = 6 | title = 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 = Journal of Medicinal Chemistry | volume = 37 | issue = 18 | pages = 2865–73 | date = September 1994 | pmid = 8071935 | doi = 10.1021/jm00044a007 }}