680. Antazoline

Nomenclature

CAS number: 91-75-8
4,5-Dihydro-N-phenyl-N-(phenylmethyl)-1H-imidazole-2-methanamine; 2-(N-benzylanilinomethyl)-2-imidazoline; phenazoline; 2-(N-phenyl-N-benzylaminomethyl)imidazoline; imidamine; 5512-M.
C17H19N3; mol wt 265.35.
C 76.95%, H 7.22%, N 15.84%.

Description and references

Prepn: Miescher, Klarer, US 2449241 (1948 to Ciba). HPLC determn in ophthalmic solutions: S. C. Ruckmick et al., J. Pharm. Sci. 84, 502 (1995). Clinical trial in combination with naphazoline in allergic conjunctivitis: M. B. Abelson et al., Arch. Ophthalmol. 108, 520 (1990).

Chemical structure

Properties

Crystals, mp 120-122°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 2508-72-7
Antistine (Novartis); Antasten (Novartis).
C17H19N3.HCl; mol wt 301.81.
C 67.65%, H 6.68%, N 13.92%, Cl 11.75%.

Properties

Bitter crystals producing temporary numbness of the tongue. mp 237-241°. uv max: 242 nm (E1%1cm 495 to 515); min 222 nm. One gram dissolves in 40 ml water, in 25 ml alc. Practically insol in ether, benzene, chloroform. pH (1% aq soln): 6.3.

Derivative

Phosphate.

Nomenclature

CAS number: 154-68-7
C17H19N3.H3PO4; mol wt 363.35.
C 56.19%, H 6.10%, N 11.56%, P 8.52%, O 17.61%.

Properties

White crystalline powder. Bitter taste. mp 194-198°. Sol in water; sparingly sol in methanol. Practically insol in benzene, ether. pH (2% aq soln): 4.5.

Therapeutic Category

Antihistaminic.

Therapeutic Category (Veterinary)

Antihistaminic.

Keywords

Antihistaminic