2808. Damascenine

Nomenclature

CAS number: 483-64-7
3-Methoxy-2-(methylamino)benzoic acid methyl ester; 2-(methylamino)-m-anisic acid methyl ester; methyl 2-(methylamino)-3-methoxybenzoate; methyldamascenine; nigelline.
C10H13NO3; mol wt 195.22.
C 61.52%, H 6.71%, N 7.17%, O 24.59%.

Description and references

Odoriferous principle of oil of Nigella from seeds of Nigella damascena L. and Nigella arvensis L., Ranunculaceae. Early syntheses: Ewins, J. Chem. Soc. 101, 544 (1912); Kaufman, Rothlin, Ber. 49, 578 (1916); Sornet, Manuf. Chem. 5, 87 (1924); Keller, Schulze, Arch. Pharm. 263, 481 (1925). Improved synthesis: Mutschler, ibid. 298, 861 (1965); M. Thoinet et al., Ann. Pharm. Fr. 36, 337 (1978). Toxicity study: Bekemeier et al., Arch. Int. Pharmacodyn. Ther. 168, 199 (1967).

Chemical structure

Properties

Prisms from abs. alc. Nutmeg-like odor, mp 27-29°. bp 270° (slight dec), bp10 147°. Volatile with steam. Insol in water. Freely sol in alc, ether, chloroform, petr ether, oils.

Derivative

Hydrochloride.

Properties

Deliquesc prisms, mp 156°. (Hydrate, mp 122°). LD50 orally in mice: 1800 mg/kg (Bekemeier).