solution were dried over sodium sulfate and evaporated.The semi-solid residue was triturated with 100 ml. of 10% potassium hydroxide, filtered and washed with water. The combined filtrate and washings were extracted twice with chloroform and acidified with 25 ml. of hydrochloric acid. Extraction of the acid solution with five 125-ml. portions of chloroform gave a further 6.3 g. of crude a-mercaptobutyramide; total yield 7.5 g. (42%); m.p. 81-91°. It was not purified further in order to avoid partial oxidation to the disulfide.

Since Barger and Dale showed that possession of the skeleton of phenethylamine is the primary requirement for the manifestation of sympathomimetic properties,1 much work has been done to determine the effect of substituents attached either to the nucleus or to the side-chain of the parent molecule. In such study, alkyl groups have received their share of attention when attached to either carbon or nitrogen in the side-chain, but there are few references indeed to the effect of alkyl groups attached directly to the nucleus. The p-methyl, p-ethyl, and p-butyl derivatives of ephedrine have been prepared and were described as more toxic and having less circulatory effect than ephedrine.2 Likewise, the methyl group in either the meta5 or para4 position of phenylpropanolamine is said to lower the activity and increase the toxicity of the base. Simultaneous introduction of methyl and hydroxyl into the nucleus of phenylpropanolamine produced an interesting pair of compounds.6 The 3methyl-4-hydroxy derivative was found to be twice as active and about four times as toxic as the parent; the 4-methyl-3-hydroxy isomer was also twice as active but was somewhat less toxic than phenylpropanolamine.A few other nucleus-alkylated phenethylamines have been reported, but pharmacological data concerning them are lacking. Though the effect of methyl in the nucleus appears to be distinctly unfavorable to pressor activity, it seemed to the authors worth while to conduct a more comprehensive investigation along these lines, and to extend observations to * Presented before the Division of Medicinal Chemistry at the ninety-third

When hydrolyzed, both yielded isoergosterol, as plates melting at 137°with [c*]d of -32.6°. Bills and Cox1 give m. p. 140°, [o-]d (= [«W -r 1.27) = -31.2°for isoergosterol made by treatment with cinnamoyl chloride.Chloro-acetyl Derivatives.-An attempt was made to prepare ergosteryl chloroacetate by warming ergosterol with the acid chloride in pyridine, but this resulted in a halogen-free compound, due to a further condensing effect of the pyridine. The nature of this reaction will be reported in a later paper.Isoergosteryl chloro-acetate was readily obtained by warming 1.7 g. of ergosterol with 2 cc. of chloro-acetyl chloride on a steam-bath for three minutes. Crystallized from acetic acid and from ether it gave 1.2 g. of plates melting at 190°; [a]n was -45°.Anal. Caled, for C2SH43O2CI: Cl, 7.7. Found: Cl, 8.0. Hydrolysis gave the same isoergosterol described above. Summary Ergosteryl acid phthalate and its silver and copper salts, ergosteryl phenylurethan and m-and ^-nitrobenzoates have been prepared from the ergosterol of ergot, as well as the m-and ^-nitrobenzoates and chloroacetate of isoergosterol.