Amfonelic Acid - 1.0 Grams, ≥98%

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AMFONELIC ACID ≥99%
Chemical Name: 1-ethyl-4-oxo-7-(phenylmethyl)-1,8-naphthyridine-3-carboxylic acid

Synonyms: WIN 25,978, D-044, Amfonelinsaeure, 15180-02-6, 7-Benzyl-1-ethyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, Acide amfonelique, Amofolic acid

CAS #: 15180-02-6

Selective Dopamine Reuptake Inhibitor (DRI). Stimulant.

Form: Pale yellow powder
Molecular Formula:  C18H16N2O3

Molecular Weight:    308.33 g/mol
Solubility:    Insoluble in water; Very slightly soluble in ethanol, Soluble to 5 mg / mL in 0.1M NaOH aqueous solution.

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AMFONELIC ACID, 1.0 Grams, ≥99%

Chemical Information:

CAS Number: 15180-02-6
Purity: ≥99%
Molecular Weight: 308.33 g/mol
Melting Point: 160-163°C
Molecular Formula: C18H16N2O3
Synonyms: WIN 25,978, D-044, Amfonelinsaeure, 15180-02-6, 7-Benzyl-1-ethyl-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, Acide amfonelique, Amofolic acid
PubChem CID: 2137
SMILES: CCN1C=C(C(=O)C2=C1N=C(C=C2)CC3=CC=CC=C3)C(=O)O


Technical Information:

Application: Amfonelic acid is a selective, potent dopamine reuptake inhibitor with stimulant properties.
Appearance: Pale yellow powder
Physical State: Solid
Solubility: Insoluble in water; Very slightly soluble in ethanol, Soluble to 5 mg / mL in 0.1M NaOH aqueous solution.
Storage: Store at room temperature or cooler, in a sealed airtight container, protected from heat, light and humidity.
Stability: Stable for at least two years when stored as above.

 

Biochemical Activity:

Amfonelic acid is a selective, potent dopamine reuptake inhibitor, with a unique structure differing from better known classes of DAT inhibitors. Unlike more common DA reuptake inhibitors, AFA has few effects on the noradrenergic system. AFA is used in neuroscience studies of the Dopamine Transporter and in research related to CNS stimulants with reduced physical side effects.

A large number of studies relating to the dopaminergic system have been carried out with Amfonelic acid in animal models.

AFA produces significant DA uptake blockade for about 12 hours after administration (half life 8h-12h) and produces no toxic effects in rats at up to 2.5 mg / kg1.

Amfonelic acid was shown to enhance maternal behaviors and decrease maternal agression in gestationally treated rat dams, and oxytocin levels were significantly increased in the amygdala of AFA treated dams administed 0.625 mg / kg - 1.5 mg/kg of AFA1. In contrast, the non-selective serotonergic, dopaminergic and noradrenergic reuptake inhibitor, cocaine, resulted in a significant down-regulation of oxytocin receptors.

In the Japanese quail, AFA increased aspects of both appetitive and consummatory sexual behavior.2

AFA completely blocked the degeneration of dopaminergic nerve terminals, astrogliosis and reduction of dopamine content induced by methamphetamine in the rat neostriatum.3

Unlike cocaine, AFA did not produce adverse effects such as neophobia, aggressive behavior and hypoactivity in the offspring of rat dams given 1.5 mg / kg AFA daily during gestation.4, 5,6

In comparisons of AFA to other dopaminergic stimulants, AFA was found to have an ED50 of 0.11 mg/kg (i.p.) in rats7, and was found to be approximately 1.5 times as potent as d-amphetamine8

However, unlike amphetamine, AFA was found to have much less toxicity, both in isolated mice and in aggregate groups of mice9. In isolated mice, an LD50 for AFA could not be determined; no deaths occurred up to 1024 mg / kg p.o. and there was a 7% lethality rate at 2048 mg / kg p.o., whereas amphetamine produced 100% death at 256 mg / kg p.o.

References:

  • 1. Johns JM, Joyner PW, McMurray MS, Elliott DL, Hofler VE, Middleton CL, Knupp K, Greenhill KW, Lomas LM, Walker CH. (2005). "The effects of dopaminergic/serotonergic reuptake inhibition on maternal behavior, maternal aggression, and oxytocin in the rat". Pharmacol Biochem Behav. 81(4): 769-85. http://dx.doi.org/10.1016/j.pbb.2005.06.001. PMID 15996723
  • 2. Castagna C1, Ball GF, Balthazart J. (1997). "Effects of dopamine agonists on appetitive and consummatory male sexual behavior in Japanese quail.". Pharmacol Biochem Behav. 58(2):403-14. http://dx.doi.org/10.1016/S0091-3057(97)00243-8. PMID 9300599
  • 3. Pu C1, 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 Res. 649(1-2): 217-24. PMID 7953636
  • 4. Johns JM, Means MJ, Bass EW, Means LW, Zimmerman LI, McMillen BA. (1994). "Prenatal exposure to cocaine: effects on aggression in Sprague-Dawley rats.". Dev Psychobiol. 27(4): 227-39. PMID 7913451
  • 5. Johns JM, Means MJ, Anderson DR, Means LW, McMillen BA. (1992). "Prenatal exposure to cocaine. II: Effects on open-field activity and cognitive behavior in Sprague-Dawley rats.". Neurotoxicol Teratol. 14(5): 343-9. PMID 1454043
  • 6. Johns JM, Means LW, Means MJ, McMillen BA. (1992). "Prenatal exposure to cocaine. I: Effects on gestation, development, and activity in Sprague-Dawley rats.". Neurotoxicol Teratol. 14(5): 337-42. PMID 1454042
  • 7. Schechter MD. (1987). "Amfonelic acid: similarity to other dopamine agonists.". Pharmacol Biochem Behav. 26(2): 413-6. PMID 3575360
  • 8. Aceto MD, Rosecrans JA, Young R, Glennon RA. (1984). "Similarity between (+)-amphetamine and amfonelic acid.". Pharmacol Biochem Behav. 20(4): 635-7. PMID 6728880
  • 9. Aceto MD, Botton I, Martin R, Levitt M, Bentley HC, Speight PT. (1970). "Pharmacologic properties and mechanism of action of amfonelic acid.". Eur J Pharmacol. 10(3): 344-54. PMID 4393073

Precautions and Disclaimer:
This Material is Sold For Laboratory and Research Use Only.  Not for Diagnostic or Therapeutic, Drug, or Other Household Uses.

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