Hydroxyamphetamine Hydrobromide
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This article is compiled based on the United States Pharmacopeia (USP) – 2025 Edition
Issued and maintained by the United States Pharmacopeial Convention (USP)
C9H13NO. HBr 232.12
Phenol, 4-(2-aminopropyl)-, hydrobromide.
(+)-p-(2-Aminopropyl)phenol hydrobromide CAS RN®: 306-21-8; UNII: 59IG47SZ0E.
Hydroxyamphetamine Hydrobromide contains not less than 98.0 percent and not more than 101.5 percent of C9H13NO. HBr, calculated on the dried basis.
Packaging and storage-Preserve in well-closed, light-resistant containers.
1 USP REFERENCE STANDARDS (11)
USP Hydroxyamphetamine Hydrobromide RS
2 Identification
Change to read:
A: Spectroscopic Identification Tests (197), Infrared Spectroscopy: 197K (CN 1-May-2020).
B: Dissolve about 500 mg of ammonium molybdate in 10 mL of sulfuric acid, and add to this solution about 2 mg of Hydroxyamphetamine Hydrobromide: an intense blue color is produced (distinction from similar amino compounds such as Amphetamine and methamphetamine, which, lacking a phenolic hydroxyl, do not undergo this reaction).
C: Dissolve about 200 mg in 2 mL of water, and add a solution of 500 mg of potassium carbonate in 2 mL of water. Extract with two 10-mL portions of ether, allow the clear ether solution to evaporate to dryness, and dry at about 80°: the hydroxyamphetamine so obtained melts between 124° and 127° (see Class I under Melting Range or Temperature (741)).
D: To a solution of about 10 mg of it in 10 mL of water add 1 mL of 2 N nitric acid, then add silver nitrate TS: a pale yellow precipitate is formed, and it is slightly soluble in 6 N ammonium hydroxide.
MELTING RANGE (741): between 189° and 192°.
LOSS ON DRYING (731)-Dry it at 105° for 2 hours: it loses not more than 0.5% of its weight.
RESIDUE ON IGNITION (281): not more than 0.1%.
Bromide content-Accurately weigh about 400 mg, and dissolve in 50 mL of water. Add 50 mL of methanol and 10 mL of glacial acetic acid, then add eosin Y TS, and titrate with 0.1 N silver nitrate VS. Each mL of 0.1 N silver nitrate is equivalent to 7.990 mg of Br: the content of Br, calculated on the dried basis, is between 33.6% and 35.2%.
ORDINARY IMPURITIES (466)
Test solution: methanol.
Standard solution: methanol.
Eluant: a mixture of toluene, methanol, and ammonium hydroxide (10:4:0.25).
Visualization: 1.
Assay-Dissolve about 400 mg of Hydroxyamphetamine Hydrobromide, accurately weighed, in a mixture of 10 mL of glacial acetic acid and 10 mL of mercuric acetate TS, warming slightly, if necessary, to effect solution. Add crystal violet TS, and titrate with 0.1 N perchloric acid VS. Perform a blank determination, and make any necessary correction. Each mL of 0.1 N perchloric acid is equivalent to 23.21 mg of C9H13NO. HBr.
