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Phenbenzamine, sold under the brand name Antergan and known by the former developmental code name RP-2339, is an antihistamine of the ethylenediamine class which also has anticholinergic properties.[1][2] It was introduced in 1941 or 1942 and was the first antihistamine to be introduced for medical use.[3][4][5] Soon following its introduction, phenbenzamine was replaced by another antihistamine of the same class known as mepyramine (pyrilamine; Neoantergan).[5][6] Following this, other antihistamines, such as diphenhydramine, promethazine, and tripelennamine, were developed and introduced.[5][7] Owing to their sedative effects, phenbenzamine and promethazine were assessed in the treatment of manic depression in France in the 1940s and were regarded as promising therapies for such purposes.[3] Whereas phenbenzamine was the first clinically useful antihistamine, piperoxan was the first compound with antihistamine properties to be discovered and was synthesized in the early 1930s.[7]
Chemistry
Synthesis
Phenbenzamine can be prepared by the reaction of N-benzylaniline with 2-chloroethyldimethylamine.[8][9]
^Maxwell RA, Eckhardt SB (6 December 2012). "Chloropromazine". Drug Discovery: A Casebook and Analysis. Springer Science & Business Media. pp. 113–. ISBN978-1-4612-0469-5.
^US 2634293, Kyrides LP, Zienty FB, "Process of preparing a monobasic salt of a secondary amine", issued 7 April 1953, assigned to Monsanto Chemicals
^Kaye IA, Parris CL, Weiner N (1953). "A Novel N-Alkylation Reaction". Journal of the American Chemical Society. 75 (3): 744–745. doi:10.1021/ja01099a508.
This page was last edited on 8 December 2023, at 19:34