2209. Choline Salicylate

Nomenclature

CAS number: 2016-36-6
2-Hydroxy-N,N,N-trimethylethanaminium salt with 2-hydroxybenzoic acid (1:1); (2-hydroxyethyl)trimethylammonium salicylate; choline salicylic acid salt; salicylic acid choline salt; Actasal (Purdue Frederick); Arthropan (Purdue Frederick); Artrobione; Audax (Napp); Mundisal (Purdue Frederick).
C12H19NO4; mol wt 241.28.
C 59.73%, H 7.94%, N 5.81%, O 26.52%.

Description and references

Prepn from choline chloride and sodium salicylate: Broh-Kahn, Int. Rec. Med. 173, 219 (Apr. 1960); cf. Johnson, GB 8031 (1919); Broh-Kahn et al., US 3069321 (1962 to Labs. for Pharmaceut. Dev.). Variations of process: BE 583513 (1960 to Mundipharma, AG).

Properties

Extremely hygroscopic solid, mp 49.5-50.0°. Very freely sol in water. Also sol in alcohol, acetone, other hydrophilic solvents. Practically insol in ether, petr ether, benzene, oils. Aq solns are stable, they contain the compd in the form of its dissociated choline and salicylate ions. pH of 10% aq soln 6.5. Aq solns are easily discolored by minute traces of iron. The addition of acid to aq solns immediately precipitates free salicylic acid, while choline base, readily recognized by its fishy odor, is liberated upon the addition of alkali.

Therapeutic Category

Analgesic; antipyretic.

Keywords

Antipyretic; Analgesic; Non-opioids; Salicylic Acid Derivatives