The CuSO4-NaOH test was applied to a series of 27 aromatic amines, of which 6 were optical isomers of ephedrine. Twenty-two of them showed positive results (development of a purplish or deep blue color). All those that give positive readings contain an OH group which is attached to the β-C-atom from the amine N. The Cu-complexes formed by 16 amines are insoluble in alkaline solution. Thirteen amines yield Cu-complexes that are soluble in ether. The same test can serve as a means to distinguish the three ephedrines from the three pseudoephedrines, and also the optical isomers of ephedrine and pseudoephedrine from the racemic isomers.
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K.K. Chen (1929) studied this question.