921. Azomycin

Nomenclature

CAS number: 527-73-1
2-Nitro-1H-imidazole.
C3H3N3O2; mol wt 113.07.
C 31.87%, H 2.67%, N 37.16%, O 28.30%.

Description and references

Antibiotic substance produced by an unidentified Streptomyces sp. (resembling Nocardia mesenterica in some aspects) from soil collected at Shiba Shirokane Daimachi (Japan): Maeda et al., J. Antibiot. 6A, 182 (1953); Okami et al., ibid. 7A, 53 (1954); Nakamura, Umezawa, ibid. 8A, 66 (1955). Structure: Nakamura, Pharm. Bull. 3, 379 (1955). Synthesis: Beaman et al., J. Am. Chem. Soc. 87, 389 (1965); Lancini, Lazzari, Experientia 21, 83 (1965).

Chemical structure

Properties

Crystals from methanol, dec 283°. uv max (ethanol): 313 nm (E1%1cm 915); in 0.1N NaOH: 374 nm (ε 12750). Soluble in methanol, ethanol, acetone, ethyl acetate, butyl acetate, alkaline water. Practically insol in ether, petr ether, chloroform, acidic water. LD50 i.v. in mice: 80 mg/kg (Maeda).

Caution

Irritating to skin.