Adrafinil - CAS 63547-13-7
Catalog number: 63547-13-7
Category: Inhibitor
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Molecular Formula:
C15H15NO3S
Molecular Weight:
289.35
COA:
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Targets:
Others
Description:
Adrafinil, prodrug of modafinil, is a mild central nervous system stimulant drug used to relieve excessive sleepiness and inattention. It is believed to serve as an alpha-1 adrenoceptor agonist.
Purity:
>98%
Synonyms:
CRL 40028; Olmifon
MSDS:
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InChIKey:
CGNMLOKEMNBUAI-UHFFFAOYSA-N
InChI:
InChI=1S/C15H15NO3S/c17-14(16-18)11-20(19)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15,18H,11H2,(H,16,17)
Canonical SMILES:
C1=CC=C(C=C1)C(C2=CC=CC=C2)S(=O)CC(=O)NO
1. Effect of noradrenergic system on the anxiolytic-like effect of DOI (5-HT2A/2C agonists) in the four-plate test
Fabienne Massé . Martine Hascoët . Eric Dailly . Michel Bourin. Psychopharmacology (2006) 183: 471–481
The α1-adrenoceptors have been extensively studied in anxiety. Prazosin (0.25 to 8 mg/kg) and adrafinil (0.25 to 8 mg/kg) was found to have no action in the FPT when they were administered alone (unpublished results). Contradictory results were observed in the literature; many studies demonstrated anxiolytic-like or no effect of α1-adrenoceptor ligands (La Marca and Dunn 1994; Zarrindast et al. 2000), but an anxiogenic-like action following α1-adrenoceptor activation is predominant in animal model of anxiety including EPM, elevated X-maze and Vogel’s drinking conflict test in rat (Cecchi et al. 2002a,b; Handley and Mithani 1984; Soderpalm and Engel 1990). Bortolozzi et al. 2003 observed an increase in 5-HT release after local injection of DOI in the medial prefrontal cortex in mice. This increase was reversed by co-perfusion of prazosin (Bortolozzi et al. 2003). However, in the present study, the α1-adrenoceptor agonist adrafinil, at doses of 0.25 and 4 mg/kg, and the α1-adrenoceptor antagonist prazosin, at doses of 0.5 and 2 mg/kg, did not potentiate nor antagonize the activity of DOI in the FPT in mice.
2. Prevalence of legal and illegal stimulating agents in sports
K. Deventer & K. Roels & F. T. Delbeke & P. Van Eenoo. Anal Bioanal Chem (2011) 401:421–432
Detection of modafinil and adrafinil in urine should be performed by monitoring their common metabolite modafinil acid. However the distinction between the use of either modafinil and adrafinil can only be made by detecting both the metabolite and the parent drug. GC–MS detection of intact modafinil has been achieved without derivatisation. No GC–MS method for detection of adrafinil has been described. LC–MS detection of the parent drug has been described by several authors. Deventer et al. observed uncommon positive electrospray ionization with an abundant sodium adduct and an in-source fragment with m/z 167 assigned to benzyltropylium which originates from neutral loss of the sulfonyl side chain. Good sensitivity could be observed when the sodium adduct is chosen as precursor ion for MS–MS experiments. This uncommon behaviour has also been observed by other research groups, suggesting selected ion monitoring (SIM) of the [M+H]+ ion or selected reaction monitoring of the fragment ions from m/z 167.
3. Thin-layer chromatography enantioseparations on chiral stationary phases: a review
Massimo Del Bubba & Leonardo Checchini & Luciano Lepri. Anal Bioanal Chem (2013) 405:533–554
The separation of adrafinil and modafinil, which have very similar structures, confirms the importance of the presence of a carbonyl group at the β-position with respect to the stereogenic centre for the separation on MCTA. The enantiomers of methiocarb sulfoxide (Fig. 3, plots M) and chlorbensid sulfoxide (Fig. 3, plots N), which are both oxidative degradation products of the corresponding sulfur-containing pesticides and are used as pesticides, were baseline-resolved using 60 % and 40 % aqueous propanol. For methyl phenyl sulfoxides differently substituted at the para and meta positions of the aromatic ring, successful resolutionswere obtained for (4-chlorophenyl)methyl sulfoxide (Fig. 3, plots B) and 3-(methylsulfinyl)phenylacetic acid (Fig. 3, plots F),whereas for methyl phenyl sulfoxide (Fig. 3, plots A) and 1-methyl-4- (methylsulfinyl)benzene (Fig. 3, plots E) the enantioresolution failed, suggesting a positive role of electron-withdrawing substituents on the aromatic ring in the enantioseparation on MCTA. In this regard, a more in-depth investigation of structurally closely related molecules should be performed.
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CAS 63547-13-7 Adrafinil

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