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Dichloropane ATC code Legal status
Methyl (1R ,2S ,3S ,5S )-3-(3,4-dichlorophenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate
CAS Number PubChem CID ChemSpider CompTox Dashboard (EPA ) Formula C 15 H 17 Cl 2 N O 2 Molar mass −1 3D model (JSmol )
COC(=O)[C@@H]1[C@H]2CC[C@H](N2C)C[C@@H]1C3=CC(=C(C=C3)Cl)Cl
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 N Y (what is this?)
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, 0.79 and 18 nM, respectively.[1] cocaine .[2] [3]
Methylecgonidine is the direct precursor to this compound.[4]
Trans -CO2 Me group [ ] The thermodynamic isomer with a trans -CO2 Me group is still active. This isomer was used by Neurosearch to make three different phenyltropanes which were tested in clinical trials.
See also [ ] 3,4-DCMP O-2390 List of cocaine analogues List of phenyltropanes 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 .
Stimulants
Adamantanes
Adapromine Amantadine Bromantane Memantine Rimantadine Adenosine antagonists Alkylamines
Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Levopropylhexedrine Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane Ampakines Arylcyclohexylamines Benzazepines
6-Br-APB SKF-77434 SKF-81297 SKF-82958 Cathinones Cholinergics Convulsants Eugeroics Oxazolines Phenethylamines Phenylmorpholines Piperazines
2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP oMPP Vanoxerine Piperidines Pyrrolidines Racetams
Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide Tropanes Tryptamines Others ATC code : N06B
Monoamine reuptake inhibitors
DAT (DRIs
Piperazines: DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 Nefazodone Vanoxerine
Pyrrolidines: Diphenylprolinol MDPV Naphyrone Prolintane Pyrovalerone
NET (NRIs
Norepinephrine–dopamine reuptake inhibitors: Amineptine Bupropion Fencamine Fencamfamin Hydroxybupropion Lefetamine Levophacetoperane LR-5182 Manifaxine Methylphenidate Nomifensine O-2172 Radafaxine Serdexmethylphenidate Solriamfetol
Tricyclic antidepressants: Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Melitracen Nortriptyline Protriptyline Trimipramine
Tetracyclic antidepressants: Amoxapine Maprotiline Mianserin Oxaprotiline Setiptiline
Others: Antihistamines (e.g., brompheniramine , chlorphenamine , pheniramine , tripelennamine )Antipsychotics (e.g., loxapine , ziprasidone )Arylcyclohexylamines (e.g., ketamine , phencyclidine )Dopexamine Ephenidine Ginkgo biloba Indeloxazine Nefazodone Opioids (e.g., desmetramadol , methadone , pethidine (meperidine) , tapentadol , tramadol , levorphanol )
SERT (SRIs
Selective serotonin reuptake inhibitors and serotonin receptor modulators: Etoperidone Litoxetine Lubazodone LY-393558 Quipazine SB-649915 TGBA01AD Trazodone Vilazodone Vortioxetine
Tricyclic antidepressants: Amitriptyline Cianopramine Clomipramine Cyanodothiepin Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Nortriptyline Pipofezine Protriptyline
Others: Amoxapine Antihistamines (e.g., brompheniramine , chlorphenamine , dimenhydrinate , diphenhydramine , mepyramine (pyrilamine) , pheniramine , tripelennamine )Antipsychotics (e.g., loxapine , ziprasidone )Arylcyclohexylamines (e.g., 3-MeO-PCP , esketamine , ketamine , methoxetamine , phencyclidine )Cyclobenzaprine Delucemine Dextromethorphan Dextrorphan Efavirenz Hypidone Medifoxamine Mesembrine Mifepristone MIN-117 (WF-516) N-Me-5-HT Opioids (e.g., dextropropoxyphene , methadone , pethidine (meperidine) , levorphanol , tapentadol , tramadol )Roxindole
VMATs
Amiodarone Amphetamines (e.g., amphetamine , methamphetamine , MDMA )Bietaserpine Deserpidine Deutetrabenazine Dihydrotetrabenazine Efavirenz GBR-12935 Ibogaine Ketanserin Lobeline Reserpine Rose bengal Tetrabenazine Valbenazine Vanoxerine (GBR-12909) Others
DAT modulators: Agonist-like: SoRI-9804 ; Antagonist-like: SoRI-20041 See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
Phenyltropanes (classifications )
2-Carboxymethyl Esters (3,4-Disubstituted Phenyl)-tropanes Arylcarboxy Carboxyalkyl Acyl β,α Stereochemistry α,β Stereochemistry Heterocycles: 3-Substituted-isoxazol-5-yl Heterocycles: 3-Substituted-1,2,4-oxadiazole N-alkyl N-replaced (S,O,C) Irreversible Nortropanes (N-demethylated)
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