By ARTHUR HENRY SALWAY. THE constitution of physostigmine (eserine), Cl,H,102Ns, is a subject of considerable interest on account of the valuable them peutic properties which the alkaloid possesses. It has already been shown by Petit and Polonowsky (Bd2. SOC. chim., 1893, [iii], 9, 1008) that physostigmine is a monacidic tertiary base, and that it also contains a CO-NHMe complex, since carbon dioxide and methylamine are eliminated on heating with aqueous potassium hydroxide. Ehrenberg (Verh. Ges. deut. Naturforsch. A e r z t e , 1893, ii, 102) independently confirmed the conclusions of Petit and Polonowsky, and also obtained from the alkaloid by the action of potassium hydroxide in the absence of air a new base, CI3Hl80N2, to which the name of eseroline was given. Physostigmine was therefore stated by him to be a substituted carbamide, represented by the formula (C13Hl,0N)NH*CU*NHMe, and the action of alkalis on the alkaloid was represented by the equation: (C,3Hl,0N)NH*CO*NHMe + E,O = Eseraline is therefore, according to Ehrenberg, an amino-derivative of the complex CI3Hl60N, but it should be pointed out that the action of alkalis on physostigmine would be equally well expIained by assuming that the alkaloid is a urethane of the forrrrula NHMe*CO*O*C13H17N2, in which case eseroline would be an alcohol, Cl3Hl7N2*OH. It is well known that physostigmine absorbs oxygen rapidly in the presence of alkalis, and is converted into oxidation products known as rubreserine, eserine brown, and eserine blue respectively. Ehrenberg (Zoc. cat.) has already shown that rubreserine possesses the formula C,,Hl,O2N2, and that its formation from physostigmine depends on the primary conversion of the latter into eseroline according to the following scheme :

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The labiate plant Micromeria Chamissonis (Benth.) Greene (syn. iM. Douglassi Benth.), commonly known as "Yerba Buena," is a perennial, trailing or creeping, sweet-scented herb, which is indigenous to the Pacific coast of the United States. The generic name is stated t o be derived from the Greek milros, small, and mwos, part, on account of the small size of the flowers (compare Jepson's "Flora of Western Xiddle California," p. 463). A description of the anatomical characters of the plant, with illustrations, has been given by J. Moeller.2 The above-mentioned species of Micromeria is used t o some extent medicinally, but, so far as known to us, it has never been the subject of chemical investigation, and we have therefore availed ourselves of the opportunity of making a complete examination of its constituents. Experimental, The material employed in this investigation consisted of a bale of the entire, air-dried herb, which was kindly placed a t our disposal by Messrs. Burroughs, Wellcome & Co., of London. The genuineness of the material was assured by the fact that it had been specially collected for them in California under the supervision of a competent botanist, Mr.

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CLXII.-The Constituents of the Expressed Oil of Nutmeg. By FREDERICK BELDING POWER and ARTHUR HENRY SALWAY. HAVING undertaken a complete study of the constituents of the nutmeg, the essential oil of which has already been investigated by us (Trans., 1907, 91, 2037), it was necessary to obtain somewhat more precise information than is at present available respecting the composition of the expressed oil or fat. A n examination of the latter appeared the more important in view of the fact that the nutmeg is known to possess narcotic properties, and that the only known constituent to which it has been possible to attribute this action is myristicin, C,,H,,O, (3-methoxy-4 : 5-methylenedioxy-l-allylbenzene), which is a component of the essential oil, and therefore also contained in the expressed oil or fat. The deficiency of knowledge respecting the constituents of the expressed oil of nutmeg, commonly known as '(nutmeg butter," is indicated by the following statement recorded in Lewkowitsch's Chemical Technology and Analysis of Oils, E'ats, and Wkxes, Val. II., p. 718 : (' This fat varies considerably in its composition. It contains from 4 to 10 per cent. of an ethereal oil, and consists of about 45 per cent. of a solid fat-chiefly trimyristin-the rest being a liquid fat and free fatty acids." The only further information of importance regarding the composition of this fat appears to be the statement that the liquid portion consists chiefly of olein (compare Koller, Arch.