Amfonelic acid

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Amfonelic acid
Amfonelic acid.png
Systematic (IUPAC) name
1-ethyl-4-oxo-7-(phenylmethyl)-1,8-naphthyridine-3-carboxylic acid;
Clinical data
Legal status
  • Uncontrolled
Identifiers
CAS number 15180-02-6 N
ATC code None
PubChem CID 2137
ChemSpider 2052 YesY
UNII RR302AR19Y N
KEGG D02897 YesY
ChEMBL CHEMBL35337 YesY
Chemical data
Formula C18H16N2O3 
Mol. mass 308.3329 g/mol
 N (what is this?)  (verify)

Amfonelic acid (AFA; WIN 25,978) is a research chemical with highly selective dopaminergic stimulant and antibiotic properties.[1]

Pharmacology[edit]

In studies it proved to be 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] Despite lack of direct serotonin activity, rats treated with subchronic doses of amfonelic acid display subsequent decreases in 5HT and 5HIAA.[5] Amfonelic acid displays no activity in the norepinephrine system.[6]

Despite a greatly different mechanism of action, amfonelic acid displays discriminatory substitution with 150% the stimulant potency of dextroamphetamine.[7]

Amfonelic acid has been shown to be neuroprotective against methamphetamine damage to dopamine neurons.[8] It also increases the effects of the antipsychotic drugs haloperidol, trifluoperazine and spiperone.[9]

Rats are shown to self-administer amfonelic acid in a dose-dependent manner, thus it may have recreational abuse potential in humans.[10]

Legal Status[edit]

Amfonelic acid is not a controlled substance in the United States, and thus is legal to possess.

See also[edit]

References[edit]

  1. ^ US patent 3590036, "Naphthyridine-3-carboxylic Acids, Their Derivatives and Preparation Thereof" 
  2. ^ 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. doi:10.1111/j.2042-7158.1978.tb13201.x. PMID 24701. 
  3. ^ 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. doi:10.1111/j.2042-7158.1978.tb13293.x. PMID 27622. 
  4. ^ 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. doi:10.1016/0006-8993(90)91719-W. PMID 2145054. 
  5. ^ McMillen, BA; Scott, SM; Williams, HL (1991). "Effects of subchronic amphetamine or amfonelic acid on rat brain dopaminergic and serotonergic function". Journal of neural transmission. General section 83 (1–2): 55–66. doi:10.1007/BF01244452. PMID 2018630. 
  6. ^ Agmo, A; Belzung, C; Rodríguez, C (1997). "A rat model of distractibility: Effects of drugs modifying dopaminergic, noradrenergic and GABAergic neurotransmission". Journal of neural transmission (Vienna, Austria : 1996) 104 (1): 11–29. doi:10.1007/BF01271291. PMID 9085190. 
  7. ^ Aceto, MD; Rosecrans, JA; Young, R; Glennon, RA (1984). "Similarity between (+)-amphetamine and amfonelic acid". Pharmacology, Biochemistry, and Behavior 20 (4): 635–7. doi:10.1016/0091-3057(84)90316-2. PMID 6728880. 
  8. ^ Pu, C; Fisher, JE; Cappon, GD; Vorhees, CV (1994). "The effects of amfonelic acid, a dopamine uptake inhibitor, on methamphetamine-induced dopaminergic terminal degeneration and astrocytic response in rat striatum". Brain Research 649 (1–2): 217–24. doi:10.1016/0006-8993(94)91067-7. PMID 7953636. 
  9. ^ Waldmeier, PC; Huber, H; Heinrich, M; Stoecklin, K (1985). "Discrimination of neuroleptics by means of their interaction with amfonelic acid: An attempt to characterize the test". Biochemical pharmacology 34 (1): 39–44. doi:10.1016/0006-2952(85)90097-8. PMID 2857083. 
  10. ^ Porrino, LJ; Goodman, NL; Sharpe, LG (1988). "Intravenous self-administration of the indirect dopaminergic agonist amfonelic acid by rats". Pharmacology, Biochemistry, and Behavior 31 (3): 623–6. doi:10.1016/0091-3057(88)90240-7. PMID 2908003. 

External links[edit]