Nitroso- -ephedrine

The base forms white rhombic crystals, m.p. 118° (from water) [ 1d + 512° (alcohol) and is much less soluble in water than ephedrine. Hydrochloride, colorless needles, m.p. 181-182° [a] + 62.5 (water) the salt is soluble in chloroform. Hydriodide, rhombic crystals, m.p. 172° [a]n + 43.0° (43). Oxalate, needles, m.p. 219° (165), readily soluble in water. Nitroso- -ephedrine, m.p. 86°. 

Several other 8-hydroxynitrosamines have been or are likely to be found in environmental samples. Among these are N-nitroso-3-hydroxypyrrolidine X (l ) (found in bacon), N-nitrosobis(2-hy-droxypropyl)amine XI (a potent pancreatic carcinogen in hamsters, the amino progenitor of which is used in many of the same applications as diethanolamine) (16), and the N-nitroso derivatives of the common drugs ephedrine XII (17) and ethambutol XIII (18), both of which have been shown to be carcinogenic. 

The /i-amino nitrates are generally unstable, hence the crude reaction mixture is usually converted to //-hydroxy amines with moderate yield and low diastereoselectivity (Table 5). The oxidative photoaddition of A-nitroso amines was applied to the preparation of ephedrine-like compounds98, however, a mixture of diastereomers was produced which can be separated. 

Efdiedrine, CnHjsON, crystallises from ether in rhombs, m.p. 118-9 , Md + 51 2 (EtOH), and, unlike ephedrine, is sparingly soluble in water. The hydrochloride, B. HCl, crystallises in colourless, slender needles, m.p. 181-2 , [a] -f- 62-05 (HjO), and, unlike the ephesulphate forms prisms, [a]i> + 52-5 the oxalate, m.p. 218 (dee.), unlike that of ephedrine, is readily soluble in water the aurichloride has m.p. 126-5-127-5 . Nitroso-0-ephedrine has m.p. 86 , and dibenzoyl- -ephedrine melts at 119-120 . By Mitchell s process d- -ephedrine yields an acetyl derivative, m.p. 103-5-104 ,... 

---