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Short description
Manifaxine Clinical data Other names GW-320,659 Routes of Oral ATC code Identifiers
(2S ,3S ,5R )-2-(3,5-difluorophenyl)-3,5-dimethylmorpholin-2-ol
CAS Number PubChem CID ChemSpider UNII Chemical and physical data Formula C 12 H 15 F 2 N O 2 Molar mass −1 3D model (JSmol )
C[C@@H]1CO[C@]([C@@H](N1)C)(C2=CC(=CC(=C2)F)F)O
InChI=1S/C12H15F2NO2/c1-7-6-17-12(16,8(2)15-7)9-3-10(13)5-11(14)4-9/h3-5,7-8,15-16H,6H2,1-2H3/t7-,8+,12-/m1/s1
N Key:OZGPVYJHWWPEFT-RGNHYFCHSA-N
N N Y (what is this?) (verify)
Manifaxine (developmental code name GW-320,659 ) is a norepinephrine–dopamine reuptake inhibitor developed by GlaxoSmithKline through structural modification of radafaxine , an isomer of hydroxybupropion and one of the active metabolites of bupropion .[1] attention deficit hyperactivity disorder (ADHD) and obesity and was found to be safe, reasonably effective, and well-tolerated for both applications.[2] [3] [1]
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The Grignard reaction between 3,5-difluorobenzonitrile [64248-63-1] (1 ) and ethylmagnesium bromide gives 3,5-difluoropropiophenone [135306-45-5] (2 ). Halogenation with molecular bromine occurs at the alpha-keto position providing 2-bromo-3',5'-difluoropropiophenone [135306-46-6] (3 ). Intermolecular ring formation with DL-Alaninol (2-Aminopropanol) [6168-72-5] completed the synthesis of Manifaxine (4 ).
See also References
↑ 1.0 1.1 "Manifaxine - AdisInsight" . https://adisinsight.springer.com/drugs/800006906 . ↑ "GW320659 for the treatment of attention-deficit/hyperactivity disorder in children". Journal of the American Academy of Child and Adolescent Psychiatry 41 (8): 914–20. August 2002. doi :10.1097/00004583-200208000-00009 . PMID 12162627 . ↑ "Pharmacogenetics and obesity: common gene variants influence weight loss response of the norepinephrine/dopamine transporter inhibitor GW320659 in obese subjects". Pharmacogenetics and Genomics 15 (12): 883–9. December 2005. doi :10.1097/01213011-200512000-00006 . PMID 16272960 . ↑ "(2 S ,3 S ,5 R )-2-(3,5-Difluorophenyl)-3,5- dimethyl-2-morpholinol: A Novel Antidepressant Agent and Selective Inhibitor of Norepinephrine Uptake". Journal of Medicinal Chemistry 39 (2): 347–349. 1 January 1996. doi :10.1021/jm950630p . PMID 8558500 . ↑ James Leroy Kelley, et al. EP0426416 (1991 to Wellcome Foundation Ltd).
↑ Frank Ivy Carroll, et al. US9562001 (2012 to Research Triangle Institute).
↑ Frank Ivy Carroll, et al. US20180215701 (Research Triangle Institute).
Adamantanes Adenosine antagonists Alkylamines Ampakines Arylcyclohexylamines Benzazepines Cholinergics Convulsants Eugeroics Oxazolines Phenethylamines
1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fuoroamphetamine 2-Fuoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fuoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-CMC 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-MMA 4-Methylpentedrone 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine , Levoamphetamine )Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzedrone Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Buphedrone Bupropion Butylone Camfetamine Cathine Cathinone Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D -DeprenylDenopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA (Dextrodopa , Levodopa )Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylnorepinephrine Ethylone Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine , Levofenfluramine )Fenproporex Feprosidnine Flephedrone Fludorex Formetorex Furfenorex Gepefrine Hexapradol Hexedrone HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L -DeprenylLefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine , Levomethamphetamine )Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylenedioxycathinone Methylone Mexedrone MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N-Ethylbuphedrone N-Ethylhexedrone N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L -NorpseudoephedrineOctopamine (drug) Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Pentedrone Pentylone Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Phthalimidopropiophenone Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol (Levosalbutamol )Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine Phenylmorpholines Piperazines Piperidines Pyrrolidines Racetams Tropanes Tryptamines Others
DAT (DRIs
NET (NRIs
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|Desmetramadol ]]]], methadone , pethidine (meperidine) , tapentadol , tramadol, Levorphanol
SERT (SRIs
VMATs Others
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