Methoxsalen
(meth ox' a len).
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216.197H-Furo[3,2-g][1]benzopyran-7-one, 9-methoxy-.
9-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one
[298-81-7].» Methoxsalen contains not less than 98.0 percent and not more than 102.0 percent of C12H8O4, calculated on the anhydrous basis.
[Caution—Avoid contact with the skin.
]
Packaging and storage—
Preserve in well-closed, light-resistant containers.
USP Reference standards 
11
—
11—
USP Methoxsalen RS 
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Melting range, Class I 741:
between 143
and 148.
741:
between 143 and 148.
Water, Method I 921:
not more than 0.5%.
921:
not more than 0.5%.
Residue on ignition 281:
not more than 0.1%, a 1-g specimen being used.
281:
not more than 0.1%, a 1-g specimen being used.
Heavy metals, Method II 231:
0.002%.
231:
0.002%.
Chromatographic impurities—
Prepare a solution of it in chloroform containing about 20 mg per mL (Solution A). Dilute 1.0 mL of it with chloroform to 100.0 mL (Solution B). Apply 5-µL portions of both solutions at points along a line about 2.5 cm from one edge of a thin-layer chromatographic plate coated with a 0.25-mm layer of chromatographic silica gel mixture and previously dried at 105 for 30 minutes. Develop the plate in a suitable chamber, without previous equilibration, using a mixture of 9 volumes of benzene and 1 volume of ethyl acetate, until the solvent front has moved to about 15 cm above the line of application. Remove the plate from the chamber, air-dry, and observe under long-wavelength UV light: any spot in the chromatogram from Solution A, other than the principal spot, is not more intense than the spot from Solution B (1.0%).
for 30 minutes. Develop the plate in a suitable chamber, without previous equilibration, using a mixture of 9 volumes of benzene and 1 volume of ethyl acetate, until the solvent front has moved to about 15 cm above the line of application. Remove the plate from the chamber, air-dry, and observe under long-wavelength UV light: any spot in the chromatogram from Solution A, other than the principal spot, is not more intense than the spot from Solution B (1.0%).
Assay—
Mobile phase—
Prepare a solution of acetonitrile in water (35 in 100). Make adjustments if necessary (see System Suitability under Chromatography 621).
621).
Internal standard preparation—
Dissolve trioxsalen in alcohol to obtain a solution containing about 0.2 mg per mL.
Standard preparation—
Using an accurately weighed quantity of USP Methoxsalen RS, prepare a solution in alcohol having a known concentration of about 0.2 mg per mL. Transfer 2.0 mL of this solution to a 100-mL volumetric flask, add 2.0 mL of Internal standard preparation, dilute with Mobile phase to volume, and mix to obtain a Standard preparation having a known concentration of about 4 µg of USP Methoxsalen RS per mL. Pass through a 0.45-µm disk before using.
Assay preparation—
Using 20 mg of Methoxsalen, accurately weighed, proceed as directed for Standard preparation.
Chromatographic system
(see Chromatography 621)—The liquid chromatograph is equipped with a 254-nm detector and a 4-mm × 30-cm column that contains packing L1. The flow rate is about 1.5 mL per minute. Chromatograph the Standard preparation, and record the peak responses as directed for Procedure: the resolution, R, between the analyte and internal standard peaks is not less than 4.0, and the relative standard deviation for replicate injections is not more than 2.0%.
621)—The liquid chromatograph is equipped with a 254-nm detector and a 4-mm × 30-cm column that contains packing L1. The flow rate is about 1.5 mL per minute. Chromatograph the Standard preparation, and record the peak responses as directed for Procedure: the resolution, R, between the analyte and internal standard peaks is not less than 4.0, and the relative standard deviation for replicate injections is not more than 2.0%.
Procedure—
Separately inject equal volumes (about 20 µL) of the Standard preparation and the Assay preparation into the chromatograph, record the chromatograms, and measure the responses for the major peaks. The relative retention times are about 2.1 for trioxsalen and 1.0 for methoxsalen. Calculate the quantity, in mg, of C12H8O4, in the portion of Methoxsalen taken by the formula:
5C(RU / RS)
in which C is the concentration, in µg per mL, of USP Methoxsalen RS in the Standard preparation; and RU and RS are the ratios of the peak responses of methoxsalen to the internal standard obtained from the Assay preparation and the Standard preparation, respectively.
Auxiliary Information—
Please check for your question in the FAQs before contacting USP.
| Topic/Question | Contact | Expert Committee |
|---|---|---|
| Monograph | Feiwen Mao, M.S.
Senior Scientific Liaison 1-301-816-8320 |
(SM32010) Monographs - Small Molecules 3 |
| Reference Standards | RS Technical Services 1-301-816-8129 rstech@usp.org |
USP35–NF30 Page 3859