Propoxyphene Napsylate
(proe pox' i feen nap' si late).
C22H29NO2·C10H8O3S·H2O
565.72
Benzeneethanol,
-[2-(dimethylamino)-1-methylethyl]--phenyl-, propanoate (ester), [S-(R*,S*)]-, compd. with 2- naphthalenesulfonic acid (1:1), monohydrate.
(S,1R)--[2-(Dimethylamino)-1-methylethyl]--phenylphenethyl propionate compound with 2-naphthalenesulfonic acid (1:1) monohydrate
[26570-10-5].
565.72Benzeneethanol,
-[2-(dimethylamino)-1-methylethyl]--phenyl-, propanoate (ester), [S-(R*,S*)]-, compd. with 2- naphthalenesulfonic acid (1:1), monohydrate.
(
S,1R)--[2-(Dimethylamino)-1-methylethyl]--phenylphenethyl propionate compound with 2-naphthalenesulfonic acid (1:1) monohydrate
[26570-10-5].Anhydrous 547.72
[17140-78-2].» Propoxyphene Napsylate contains not less than 97.0 percent and not more than 103.0 percent of C22H29NO2·C10H8O3S, calculated on the anhydrous basis.
Packaging and storage—
Preserve in tight containers.
USP Reference standards 
11
—
11—
USP Propoxyphene Napsylate RS 
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USP Propoxyphene Related Compound A RS
a-d-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol hydrochloride.
C19H25NO·HCl 319.87
a-d-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol hydrochloride.
C19H25NO·HCl 319.87
USP Propoxyphene Related Compound B RS
-d-2-Acetoxy-4-dimethylamino-1,2-diphenyl-3-methylbutane.
C21H27NO2 325.45
-d-2-Acetoxy-4-dimethylamino-1,2-diphenyl-3-methylbutane.
C21H27NO2 325.45
Identification—
A:
Infrared Absorption 197K: previously dried at 105
for 3 hours.
197K: previously dried at 105 for 3 hours.
B:
Ultraviolet Absorption 197U—
197U—
Solution:
40 µg per mL.
Medium:
methanol.
Absorptivities at 275 nm, calculated on the anhydrous basis, do not differ by more than 3.0%.
Melting range, Class I 741:
between 158 and 165, but the range between beginning and end of melting does not exceed 4, determined after drying at 105 for 3 hours.
741:
between 158 and 165, but the range between beginning and end of melting does not exceed 4, determined after drying at 105 for 3 hours.
Water, Method I 921:
between 2.5% and 5.0%.
921:
between 2.5% and 5.0%.
Residue on ignition 281:
not more than 0.5%.
281:
not more than 0.5%.
Heavy metals, Method II 231:
0.003%.
231:
0.003%.
Related compounds—
Mobile phase and Chromatographic system—
Proceed as directed in the Assay.
Standard stock solution—
Accurately weigh about 10 mg each of USP Propoxyphene Related Compound A RS and USP Propoxyphene Related Compound B RS into a 50-mL volumetric flask, dissolve using 2 mL of methanol, dilute with Mobile phase to volume, and mix.
Standard solution—
Transfer 5.0 mL of the Standard stock solution to a 50-mL volumetric flask, dilute with Mobile phase to volume, and mix.
System suitability solution—
Dissolve an accurately weighed quantity of USP Propoxyphene Napsylate RS in Standard solution, and dilute quantitatively, and stepwise if necessary, to obtain a solution having known concentrations of about 4.5 mg per mL of USP Propoxyphene Napsylate RS, about 0.02 mg per mL of USP Propoxyphene Related Compound A RS, and about 0.02 mg per mL of USP Propoxyphene Related Compound B RS.
Test solution—
Use the Assay preparation.
Chromatographic system—
Chromatograph the System suitability solution, and record the peak responses as directed for Procedure: the relative retention times are about 0.63 for propoxyphene related compound A, 0.78 for propoxyphene related compound B, and 1.0 for propoxyphene napsylate; the resolution, R, between propoxyphene related compound B and propoxyphene related compound A is not less than 2.0; and the relative standard deviation for replicate injections is not more than 2.0%.
Procedure—
Separately inject equal volumes (about 50 µL) of the Standard solution and the Test solution into the chromatograph, record the chromatograms, and measure the peak responses. Calculate the quantity, in mg, of propoxyphene related compound A in the portion of Propoxyphene Napsylate taken by the formula:
50C(491.67/319.88)(rU / rS)
in which C is the concentration, in mg per mL, of USP Propoxyphene Related Compound A RS in the Standard solution; 491.67 and 319.88 are the molecular weights of propoxyphene related compound A napsylate and propoxyphene related compound A, respectively; and rU and rS are the propoxyphene related compound A peak responses obtained from the Test solution and the Standard solution, respectively: not more than 0.5% of propoxyphene related compound A napsylate is found. Calculate the quantity, in mg, of propoxyphene related compound B napsylate in the portion of Propoxyphene Napsylate taken by the formula:
50C(533.71/325.45)(rU / rS)
in which C is the concentration, in mg per mL, of USP Propoxyphene Related Compound B RS in the Standard solution; 533.71 and 325.45 are the molecular weights of propoxyphene related compound B napsylate and propoxyphene related compound B, respectively; and rU and rS are the propoxyphene related compound B peak responses obtained from the Test solution and the Standard solution, respectively. Not more than 0.6% of propoxyphene related compound B napsylate is found.
Assay—
0.1 M Monobasic ammonium phosphate buffer, pH 6.3—
Dissolve 11.5 g of monobasic ammonium phosphate and 1.0 mL of triethylamine in 1000 mL of water, adjust with 10% sodium hydroxide to a pH of 6.3 ± 0.05, and mix.
Mobile phase—
Prepare a filtered and degassed mixture of methanol and 0.1 M Monobasic ammonium phosphate buffer, pH 6.3 (67:33). Make adjustments if necessary (see System Suitability under Chromatography 621).
621).
Standard preparation—
Dissolve an accurately weighed quantity of USP Propoxyphene Napsylate RS in Mobile phase to obtain a solution having a known concentration of about 5.0 mg per mL.
Assay preparation—
Transfer about 250 mg of Propoxyphene Napsylate, accurately weighed, to a 50-mL volumetric flask, dissolve in and dilute with Mobile phase to volume, and mix.
Chromatographic system (see Chromatography 621)—
The liquid chromatograph is equipped with a 254-nm detector and a 3.9-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 retention time of propoxyphene napsylate is about 9 minutes; the tailing factor for the propoxyphene napsylate peak is not more than 3.5; 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 3.9-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 retention time of propoxyphene napsylate is about 9 minutes; the tailing factor for the propoxyphene napsylate peak is not more than 3.5; and the relative standard deviation for replicate injections is not more than 2.0%.
Procedure—
Separately inject equal volumes (about 50 µL) of the Standard preparation and the Assay preparation into the chromatograph, record the chromatograms, and measure the responses for the major peaks. Calculate the quantity, in mg, of C22H29NO2 ·C10H8O3S in the portion of Propoxyphene Napsylate taken by the formula:
50C(rU / rS)
in which C is the concentration, in mg per mL, of USP Propoxyphene Napsylate RS in the Standard preparation; and rU and rS are the peak responses 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 | Clydewyn M. Anthony, Ph.D.
Senior Scientific Liaison 1-301-816-8139 |
(SM22010) Monographs - Small Molecules 2 |
| Reference Standards | RS Technical Services 1-301-816-8129 rstech@usp.org |
USP35–NF30 Page 4457
Pharmacopeial Forum: Volume No. 30(3) Page 927