(R)-(-)-Modafinic acid - CAS 112111-45-2
Catalog number: 112111-45-2
Category: Inhibitor
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Molecular Formula:
C15H14O3S
Molecular Weight:
274.33
COA:
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Targets:
Others
Description:
(R)-(-)-Modafinic acid(Armodafinic acid) is the major metabolite of Modafinil(HY-10521A), which is a central nervous system vigilance promoting agent, which posseses neuroprotective properties.
Purity:
>98%
MSDS:
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InChIKey:
QARQPIWTMBRJFX-LJQANCHMSA-N
InChI:
InChI=1S/C15H14O3S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H,16,17)/t19-/m1/s1
Canonical SMILES:
C1=CC=C(C=C1)C(C2=CC=CC=C2)S(=O)CC(=O)O
1.An enantioselective assay for (+/-)-modafinil.
Cass QB1, Kohn CK, Calafatti SA, Aboul-Enein HY. J Pharm Biomed Anal. 2001 Aug;26(1):123-30.
Enantiomers of modafinil, (diphenylmethyl)sulphinyl-2-acetamide, were separated by an amylose tris[(S)-1-phenylethylcarbamate] chiral stationary phase, using acetonitrile: water (25:75 v/v) as mobile phase, with excellent selectivity (alpha=1.4) and resolution factors (R(s)=1.5). The assay involved a solid-phase extraction of the enantiomers of modafinil from plasma using a C(18) Cartridge. A good linear relationship was obtained in the concentration of 0.15-3 microg ml(-1) for each enantiomer. The method developed is sufficiently accurate and precise to be used for clinical samples and has a good selectivity with the two main circulating metabolites: the (diphenylmethyl)sulphinyl-2-acetic acid and (diphenylmethyl)sulphonyl-2-acetamide. The use of a polysaccharide-based column on multimodal elution was explored in developing the method.
2.Evaluation of (R)-(-)-α-methoxy phenyl acetic acid as a chiral shift reagent for resolution and determination of R and S enantiomers of modafinil in bulk drugs and formulations by 1H NMR spectroscopy.
Rao RN1, Ramachandra B, Santhakumar K. Chirality. 2012 Apr;24(4):339-44. doi: 10.1002/chir.22002. Epub 2012 Feb 17.
(R)-(-)-α-Methoxy phenyl acetic acid, (S)-(-)-1,1'-(2-naphthol), and (R)-(+)-α-methoxy-α-trifluoromethyl phenyl acetic acid were evaluated as chiral shift reagents (CSRs) for (1)H NMR spectroscopic resolution and determination of R and S enantiomers of modafinil (MDL) in bulk drugs and formulations. Effects of the nature of CSR and the weight ratio of substrate to shift reagent on enantiomeric discrimination were investigated. Intramolecular and intermolecular hydrogen bonding interactions between the drug and the CSR seem to be the driving force for desired resolution. A mechanism was proposed to explain the interactions between (R, S)-enantiomers of MDL and (R)-(-)-α-methoxy phenyl acetic acid. The method was validated and applied successfully to determine the enantiomeric purity of MDL in tablet formulations.
3.Dopamine D2High receptors stimulated by phencyclidines, lysergic acid diethylamide, salvinorin A, and modafinil.
Seeman P1, Guan HC, Hirbec H. Synapse. 2009 Aug;63(8):698-704. doi: 10.1002/syn.20647.
Although it is commonly stated that phencyclidine is an antagonist at ionotropic glutamate receptors, there has been little measure of its potency on other receptors in brain tissue. Although we previously reported that phencyclidine stimulated cloned-dopamine D2Long and D2Short receptors, others reported that phencyclidine did not stimulate D2 receptors in homogenates of rat brain striatum. This study, therefore, examined whether phencyclidine and other hallucinogens and psychostimulants could stimulate the incorporation of [(35)S]GTP-gamma-S into D2 receptors in homogenates of rat brain striatum, using the same conditions as previously used to study the cloned D2 receptors. Using 10 microM dopamine to define 100% stimulation, phencyclidine elicited a maximum incorporation of 46% in rat striata, with a half-maximum concentration of 70 nM for phencyclidine, when compared with 80 nM for dopamine, 89 nM for salvinorin A (48 nM for D2Long), 105 nM for lysergic acid diethylamide (LSD), 120 nM for R-modafinil, 710 nM for dizocilpine, 1030 nM for ketamine, and >10,000 nM for S-modafinil.
4.Enantioselective separation and determination of adrafinil and modafinil on Chiralcel OJ-H column in rat serum and urine using solid-phase extraction followed by HPLC.
Rao RN1, Shinde DD. Biomed Chromatogr. 2009 Aug;23(8):811-6. doi: 10.1002/bmc.1190.
A simple and rapid normal-phase HPLC method for enantiospecific separation of a psychostimulant, adrafinil (ADL), and its metabolite modafinil (MDL) in rat serum and urine was developed. The separation was accomplished on a normal-phase polysaccharide stationary phase Chiralcel OJ-H using n-hexane-ethanol (62:38 v/v) as a mobile phase at a flow rate of 1.0 mL/min. Detection was carried out at 225 nm using a photo diode array (PDA) detector. The elution order of the enantiomers was determined by a polarimeter connected in series with the PDA. ADL and its metabolite were recovered from rat serum and urine by solid phase extraction using Oasis HLB cartridges and the mean recoveries were >or=80%. The enantiomers were eluted within 15 min without any interference from endogenous substances. The calibration curves were linear (r(2) > 0.998) in the concentration range of 1.20-500 microg/mL for ADL and MDL. The assay was specific, accurate, precise and reproducible (intra- and inter-day precisions RSDs <7.
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CAS 112111-45-2 (R)-(-)-Modafinic acid

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