Amfonelic acid

Top

Home > Library > Miscellaneous > Wikipedia

Amfonelic acid

Systematic (IUPAC) name
1-ethyl-4-oxo-7-(phenylmethyl)-1,8-naphthyridine-3-carboxylic acid;
Clinical data
Pregnancy cat.	?
Legal status	Uncontrolled
Identifiers
CAS number	15180-02-6^N
ATC code	None
PubChem	CID 2137
ChemSpider	2052^Y
UNII	RR302AR19Y^N
KEGG	D02897^Y
ChEMBL	CHEMBL35337^Y
Chemical data
Formula	C₁₈H₁₆N₂O₃
Mol. mass	308.331 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C18H16N2O3/c1-2-20-11-15(18(22)23)16(21)14-9-8-13(19-17(14)20)10-12-6-4-3-5-7-12/h3-9,11H,2,10H2,1H3,(H,22,23)^Y Key:WHHHJDGNBVQNAU-UHFFFAOYSA-N^Y
N (what is this?) (verify)

Amfonelic acid (AFA; WIN 25,978; Oxaprozin) is a drug used in scientific studies. It was discovered while researchers were investigating novel antibiotics.^[1]In studies it was found a potent and highly selective dopamine reuptake inhibitor (DRI) in rat brain preparations.^[2]^[3] A study found a moderately long half-life of approximately 12 hours and a dopaminergic potency approximately 50 fold that of methylphenidate in rat brain preparations.^[4]

References

^ US patent 3590036, "Naphthyridine-3-carboxylic Acids, Their Derivatives and Preparation Thereof"
^ Fuller, R. W.; Perry, K. W.; Bymaster, F. P.; Wong, D. T. (1978). "Comparative effects of pemoline, amfonelic acid and amphetamine on dopamine uptake and release in vitro and on brain 3,4-dihydroxyphenylacetic acid concentration in spiperone-treated rats.". Journal of Pharmacy and Pharmacology 30 (3): 197–198. PMID 24701.
^ McMillen, B. A.; Shore, P. A. (1978). "Amfonelic acid, a non-amphetamine stimulant, has marked effects on brain dopamine metabolism but not noradrenaline metabolism: Association with differences in neuronal storage systems". Journal of Pharmacy and Pharmacology 30 (7): 464–466. PMID 27622.
^ Izenwasser, S.; Werling, L. L.; Cox, B. M. (1990). "Comparison of the effects of cocaine and other inhibitors of dopamine uptake in rat striatum, nucleus accumbens, olfactory tubercle, and medial prefrontal cortex". Brain Research 520 (1–2): 303–309. PMID 2145054.

v t e Stimulants (N06B)

Adamantanes	Adaphenoxate Adapromine Amantadine Bromantane Chlodantane Gludantane Memantine Midantane

Adenosine antagonists	8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Paraxanthine SCH-58261 Theobromine Theophylline

Alkylamines	Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane

Arylcyclohexylamines	Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine

Benzazepines	6-Br-APB SKF-77434 SKF-81297 SKF-82958

Cholinergics	A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 TC-5619 Tebanicline UB-165 Varenicline WAY-317,538

Convulsants	Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone

Eugeroics	Adrafinil Armodafinil CRL-40941 Modafinil

Oxazolines	4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone

Phenethylamines	1-(4-Methylphenyl)-2-aminobutane 1-Phenyl-2-(piperidin-1-yl)pentan-3-one 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2-Phenyl-3-methylaminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-Ethylamphetamine 4-FA 4-FMA 4-MA 4-MMA 4-MTA 6-FNE Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone Amidephrine Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine ß-Methylphenethylamine ß-Phenylmethamphetamine Benfluorex Benzedrone Benzphetamine BDB BOH BPAP Buphedrone Bupropion Butylone Cathine Cathinone Chlorphentermine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylamphetamine Ethylnorepinephrine Ethylone Etilefrine Famprofazone Fenbutrazate Fencamine Fenethylline Fenfluramine (Dexfenfluramine) Fenmetramide Fenproporex Flephedrone Fludorex Furfenorex Gepefrine Hexapradol HMMA Hordenine Hydroxyamphetamine Ibopamine IMP Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lophophine Manifaxine MBDB MDA MDBU MDEA MDMA MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylone MMDA MMDMA MMMA Morazone N-Benzyl-1-phenethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine Octopamine Orciprenaline Ortetamine Oxilofrine PBA PCA PHA Pargyline Pentorex Pentylone Phenatine Phendimetrazine Phenmetrazine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Radafaxine Ropinirole Salbutamol (Levosalbutamol) Sibutramine Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xamoterol Xylopropamine Zylofuramine

Piperazines	2C-B-BZP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 MeOPP MBZP Vanoxerine

Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 1-(3,4-Dichlorophenyl)-1-(piperidin-2-yl)butane 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylphenidate Methylnaphthidate Methylphenidate (Dexmethylphenidate) N-Methyl-3ß-propyl-4ß-(4-chlorophenyl)piperidine Nocaine Phacetoperane Pipradrol SCH-5472

Pyrrolidines	2-Diphenylmethylpyrrolidine a-PPP a-PBP a-PVP Diphenylprolinol MDPPP MDPBP MDPV MPBP MPHP MPPP MOPPP Naphyrone PEP Prolintane Pyrovalerone

Tropanes	3-CPMT 3'-Chloro-3a-(diphenylmethoxy)tropane 3-Pseudotropyl-4-fluorobenzoate 4'-Fluorococaine AHN-1055 Altropane (IACFT) Brasofensine CFT (WIN 35,428) ß-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-ß-CPPIT FP-ß-CPPIT Ioflupane (¹²³I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-105 RTI-112 RTI-113 RTI-117 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-154 RTI-171 RTI-177 RTI-183 RTI-193 RTI-194 RTI-199 RTI-202 RTI-204 RTI-229 RTI-241 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (ß-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33 WF-60

Others	1-(Thiophen-2-yl)-2-aminopropane 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 2-Aminotetralin 2-MDP 2-Phenylcyclohexylamine 2-Phenyl-3,6-dimethylmorpholine 3-Benzhydrylmorpholine 3,3-Diphenylcyclobutanamine 5-(2-Aminopropyl)indole 5-Iodo-2-aminoindane AL-1095 Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Camfetamine Carphedon Ciclazindol Cilobamine Clofenciclan Cropropamide Crotetamide Cypenamine D-161 Diclofensine Dimethocaine Efaroxan Etamivan EXP-561 Fencamfamine Fenpentadiol Feprosidnine G-130 Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 JZ-IV-10 Lazabemide Leptacline Levopropylhexedrine Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Mesocarb Methastyridone Methiopropamine N-Methyl-3-phenylnorbornan-2-amine Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline Phthalimidopropiophenone PNU-99,194 Propylhexedrine PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Trazium UH-232 Yohimbine

See also Sympathomimetic amines

Dopaminergics

Receptor ligands

Agonists	Adamantanes: Amantadine Memantine Rimantadine; Aminotetralins: 7-OH-DPAT 8-OH-PBZI Rotigotine UH-232; Benzazepines: 6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959; Ergolines: Bromocriptine Cabergoline Dihydroergocryptine Epicriptine Lisuride LSD Pergolide; Dihydrexidine derivatives: 2-OH-NPA A-86,929 Ciladopa Dihydrexidine Dinapsoline Dinoxyline Doxanthrine; Others: A-68,930 A-77636 A-412,997 ABT-670 ABT-724 Aplindore Apomorphine Aripiprazole Bifeprunox BP-897 CY-208,243 Dizocilpine Etilevodopa Flibanserin Ketamine Melevodopa Modafinil Pardoprunox Phencyclidine PD-128,907 PD-168,077 PF-219,061 Piribedil Pramipexole Propylnorapomorphine Pukateine Quinagolide Quinelorane Quinpirole RDS-127 Ro10-5824 Ropinirole Rotigotine Roxindole Salvinorin A SKF-89,145 Sumanirole Terguride Umespirone WAY-100,635

Antagonists	Typical antipsychotics: Acepromazine Azaperone Benperidol Bromperidol Clopenthixol Chlorpromazine Chlorprothixene Droperidol Flupentixol Fluphenazine Fluspirilene Haloperidol Loxapine Mesoridazine Methotrimeprazine Nemonapride Penfluridol Perazine Periciazine Perphenazine Pimozide Prochlorperazine Promazine Sulforidazine Sulpiride Sultopride Thioridazine Thiothixene Trifluoperazine Triflupromazine Trifluperidol Zuclopenthixol; Atypical antipsychotics: Amisulpride Asenapine Blonanserin Cariprazine Carpipramine Clocapramine Clorotepine Clozapine Gevotroline Iloperidone Lurasidone Melperone Molindone Mosapramine Olanzapine Paliperidone Perospirone Piquindone Quetiapine Remoxipride Risperidone Sertindole Tiospirone Ziprasidone Zotepine; Antiemetics: AS-8112 Alizapride Bromopride Clebopride Domperidone Metoclopramide Thiethylperazine; Others: Amoxapine Buspirone Butaclamol Ecopipam EEDQ Eticlopride Fananserin L-745,870 Nafadotride Nuciferine PNU-99,194 Raclopride Sarizotan SB-277,011-A SCH-23,390 SKF-83,959 Sonepiprazole Spiperone Spiroxatrine Stepholidine Tetrahydropalmatine Tiapride UH-232 Yohimbine

Reuptake inhibitors

Plasmalemmal

DAT inhibitors

Piperazines: DBL-583
GBR-12,935
Nefazodone
Vanoxerine; Piperidines: BTCP
Desoxypipradrol
Dextromethylphenidate
Difemetorex
Ethylphenidate
Methylnaphthidate
Methylphenidate
Phencyclidine
Pipradrol; Pyrrolidines: Diphenylprolinol
MDPV
Naphyrone
Prolintane
Pyrovalerone; Tropanes: Altropane
Brasofensine
CFT
Cocaine
Dichloropane
Difluoropine
FE-β-CPPIT
FP-β-CPPIT
Ioflupane (¹²³I)
Iometopane
RTI-112
RTI-113
RTI-121
RTI-126
RTI-150
RTI-177
RTI-229
RTI-336
Tenocyclidine
Tesofensine
Troparil
Tropoxane
WF-11
WF-23
WF-31
WF-33; Others: Adrafinil
Armodafinil
Amfonelic acid
Amineptine
Benzatropine
Bromantane
BTQ
BTS-74,398
Bupropion
Ciclazindol
Diclofensine
Dimethocaine
Diphenylpyraline
Dizocilpine
DOV-102,677
DOV-21,947
DOV-216,303
Etybenzatropine
EXP-561
Fencamine
Fencamfamine
Fezolamine
GYKI-52,895
Indatraline
Ketamine
Lefetamine
Levophacetoperane
LR-5182
Manifaxine
Mazindol
Medifoxamine
Mesocarb
Modafinil
Nefopam
Nomifensine
NS-2359
O-2172
Pridefrine
Propylamphetamine
Radafaxine
SEP-225,289
SEP-227,162
Sertraline
Sibutramine
Tametraline
Tedatioxetine
Tripelennamine

Vesicular

VMAT inhibitors	Deserpidine Ibogaine Reserpine Tetrabenazine

Releasing agents

Morpholines: Fenbutrazate
Morazone
Phendimetrazine
Phenmetrazine; Oxazolines: 4-MAR
Aminorex
Clominorex
Cyclazodone
Fenozolone
Fluminorex
Pemoline
Thozalinone; Phenethylamines (also amphetamines, cathinones, etc): 2-OH-PEA
4-CAB
4-FA
4-FMA
4-MA
4-MMA
Alfetamine
Amfecloral
Amfepentorex
Amfepramone
Amphetamine (Dextroamphetamine
Levoamphetamine)
Amphetaminil
β-Me-PEA
BDB
BOH
Benzphetamine
Buphedrone
Butylone
Cathine
Cathinone
Clobenzorex
Clortermine
D-Deprenyl
DMA
DMMA
Dimethylamphetamine
Dimethylcathinone
Ethcathinone
Ethylamphetamine
EBDB
Ethylone
Famprofazone
Fenethylline
Fenproporex
Flephedrone
Fludorex
Furfenorex
Hordenine
Hydroxyamphetamine
Iofetamine
Lophophine
Mefenorex
Mephedrone
Methamphetamine (Dextromethamphetamine, Levomethamphetamine)
Methcathinone
Methedrone
MMDA
MMDMA
MBDB
MDA
MDEA
MDMA
MDMPEA
MDOH
MDPEA
Methylone
Ortetamine
pBA
pCA
pIA
Pholedrine
Phenethylamine
Pholedrine
Phenpromethamine
Prenylamine
Propylamphetamine
Tiflorex
Tyramine
Xylopropamine
Zylofuramine; Piperazines: 2C-B-BZP
BZP
MBZP
MDBZP
MeOPP; Others: 2-ADN
2-AI
2-AT
4-BP
5-IAI
Clofenciclan
Cyclopentamine
Cypenamine
Cyprodenate
Feprosidnine
Gilutensin
Heptaminol
Hexacyclonate
IAP
Indanorex
Isometheptene
Methylhexanamine
Naphthylisopropylamine
Octodrine
Phthalimidopropiophenone
Propylhexedrine (Levopropylhexedrine)
Tuaminoheptane

Allosteric modulators

Quinazolinamines: SoRI-9804 SoRI-20040 SoRI-20041

Enzyme inhibitors

Anabolism

PAH inhibitors	3,4-Dihydroxystyrene

TH inhibitors	3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

AAAD/DDC inhibitors	Benserazide Carbidopa DFMD Genistein Methyldopa

Catabolism

MAO inhibitors	Nonselective: Benmoxin Caroxazone Echinopsidine Furazolidone Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivalylbenzhydrazine Procarbazine Safrazine Tranylcypromine; MAO-A selective: Amiflamine Bazinaprine Befloxatone Befol Brofaromine Cimoxatone Clorgiline Esuprone Harmala alkaloids Methylene Blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone Tyrima; MAO-B selective: D-Deprenyl L-Deprenyl (Selegiline) Ladostigil Lazabemide Milacemide Pargyline Rasagiline Safinamide

COMT inhibitors	Entacapone Tolcapone

DBH inhibitors	Disulfiram Dopastin Fusaric acid Nepicastat Tropolone

Others

Precursors	L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa)

Cofactors	Ferrous iron (Fe²⁺) Tetrahydrobiopterin Vitamin B₃ (Niacin Nicotinamide → NADPH) Vitamin B₆ (Pyridoxine Pyridoxamine Pyridoxal → Pyridoxal phosphate) Vitamin B₉ (Folic acid → Tetrahydrofolic acid) Vitamin C (Ascorbic acid) Zinc (Zn²⁺)

Others	Activity enhancers: BPAP PPAP; Toxins: 6-OHDA

List of dopaminergic drugs

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

This entry is from Wikipedia, the leading user-contributed encyclopedia. It may not have been reviewed by professional editors (see full disclaimer)

Donate to Wikimedia

Help us answer these

Which acid is more strong stearic acid or citric acid?

How are sulfuric acid and nitric acid related to acid precipitation?

What acid is worst phosphoric acid or food acid?

acid dissociations for maleic acid and fumaric acid?

Post a question - any question - to the WikiAnswers community:

Copyrights:

Cite

Wikipedia on Answers.com This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article Amfonelic acid. Read