Dichloropane

Quality 0.50 · 0 views · Updated 2 months ago

Chemical compound

title: "Dichloropane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["chloroarenes", "designer-drugs", "rti-compounds", "serotonin–norepinephrine–dopamine-reuptake-inhibitors", "stimulants", "tropanes"] description: "Chemical compound" topic_path: "general/chloroarenes" source: "https://en.wikipedia.org/wiki/Dichloropane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| 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 = | CAS_number = 146725-34-0 | UNII_Ref = | UNII = V7SQE82R87 | ATC_prefix = none | PubChem = 127024 | ChemSpiderID_Ref = | ChemSpiderID = 112783 | C = 15 | H = 17 | Cl = 2 | N = 1 | O = 2 | smiles = COC(=O)[C@@H]1[C@H]2CCC@HC[C@@H]1C3=CC(=C(C=C3)Cl)Cl | StdInChI_Ref = | 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 = | 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. In animal studies, dichloropane had a slower onset and longer duration of action compared to cocaine.

Methylecgonidine is the direct precursor to this compound.

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

References

  1. (April 2005). "Synthesis and monoamine transporter binding properties of 3beta-(3',4'-disubstituted phenyl)tropane-2beta-carboxylic acid methyl esters". Journal of Medicinal Chemistry.
  2. (December 2000). "Reinforcing and discriminative stimulus effects of RTI 111, a 3-phenyltropane analog, in rhesus monkeys: interaction with methamphetamine". Psychopharmacology.
  3. (December 2001). "Cocaine-like discriminative stimulus effects of novel cocaine and 3-phenyltropane analogs in the rat". Psychopharmacology.
  4. (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.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

chloroarenesdesigner-drugsrti-compoundsserotonin–norepinephrine–dopamine-reuptake-inhibitorsstimulantstropanes