| 词条 | Dichloropane |
| 释义 |
}}{{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 | width = 220 | tradename = | legal_status = | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 146725-34-0 | ATC_prefix = none | PubChem = 9797476[1] | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 112783 | C=16 | H=19 | Cl=2 | N=1 | O=2 | molecular_weight = 328.23356 g/mol | 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, 0.79 and 18 nM, respectively.[2] In animal studies, dichloropane had a slower onset and longer duration of action compared to cocaine.[3][4]Methylecgonidine is the direct precursor to this compound.[5] Trans -CO2Me groupThe 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.
See also
References1. ^{{Cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/9797476#section=Top | title=Amihuyqknjhxpt-Drabbmoasa-N}} {{Stimulants}}{{Monoamine reuptake inhibitors}}{{Phenyltropanes}}2. ^{{cite journal|first1=F. Ivy|last1=Carroll|first2=Bruce E.|last2=Blough|first3=Zhe|last3=Nie|first4=Michael J.|last4=Kuhar|title=Synthesis and Monoamine Transporter Binding Properties of 3β-(3',4'-Disubstituted phenyl)tropane-2β-carboxylic Acid Methyl Esters|journal=Journal of Medicinal Chemistry|date=21 April 2005|pages=2767–2771|volume=48|issue=8|doi=10.1021/jm040185a|pmid=15828814|first5=Leonard L.|last5=Howell|first6=Hernan A.|last6=Navarro}} 3. ^{{cite journal|first1=Robert|last1=Ranaldi|first2=Karen G.|last2=Anderson|first3=F. Ivy|last3=Carroll|first4=William L.|last4=Woolverton|title=Reinforcing and discriminative stimulus effects of RTI 111, a 3-phenyltropane analog, in rhesus monkeys: interaction with methamphetamine|journal=Psychopharmacology|issn=1432-2072|pages=103–110|volume=153|issue=1|doi=10.1007/s002130000602|pmid=11255920|date=December 2000}} 4. ^{{cite journal|first1=Charles D.|last1=Cook|first2=Ivy F.|last2=Carroll|first3=Patrick M.|last3=Beardsley|title=Cocaine-like discriminative stimulus effects of novel cocaine and 3-phenyltropane analogs in the rat|journal=Psychopharmacology|date=December 2001|issn=1432-2072|pages=58–63|volume=159|issue=1|doi=10.1007/s002130100891|pmid=11797070}} 5. ^{{cite journal|first1=F. Ivy|last1=Carroll|first2=S. Wayne|last2=Mascarella|first3=Michael A.|last3=Kuzemko|first4=Yigong|last4=Gao|title=Synthesis, Ligand Binding, and QSAR (CoMFA and Classical) Study of 3β-(3'-Substituted phenyl)-, 3β-(4'-Substituted phenyl)-, and 3β-(3',4'-Disubstituted phenyl)tropane-2β-carboxylic Acid Methyl Esters|journal=Journal of Medicinal Chemistry|date=2 September 1994|pages=2865–2873|volume=37|issue=18|doi=10.1021/jm00044a007|pmid=8071935|first5=Philip|last5=Abraham|first6=Anita H.|last6=Lewin|first7=John W.|last7=Boja|first8=Michael J.|last8=Kuhar}} 6 : Chloroarenes|Designer drugs|RTI compounds|Serotonin-norepinephrine-dopamine reuptake inhibitors|Stimulants|Tropanes |
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