crystals, melting at 90° with decomposition; when heated at 200°, a new dibromoquinoline is formed, which sublimes in colourless, lustrous needles melting at 90° (uncorr.).

Metabromaniline yields a mixture of two isomeric metabromoquinolines which are best separated by means of the nitrates.

Metabromoquinoline, C,NH,Br, is an almost colourless oil, which boils at 280° (uncorr.), and does not solidify at -4°. The hydrochloride (with 1 mol. H2O) is readily soluble in water, and melts at 225° with decomposition; the platinochloride is a yellow, very sparingly soluble substance; the nitrate is readily soluble in water, and melts at 165° (uncorr.); the dichromate forms reddish-yellow needles, melting at 190° with previous decomposition; the ethobromide melts at 290 (uncorr.). Metabromoquinoline dibromide hydrobromide is an orange-red crystalline substance, melting at 107° (uncorr.); when heated at 200°, it yields a dibromoquinoline which crystallises in prisms melting at 119° (uncorr.).

Anabromoquinoline is crystalline, melts at 32° and boils at 290° (uncorr.). The hydrochloride (with 1 mol. H2O) forms small branched crystals, very readily soluble in water; it melts at 213°. The nitrate is much more sparingly soluble in water than its isomeride, and separates in concentrically-grouped needles melting at 199° (uncorr.). The ethobromide crystallises from alcohol in colourless, lustrous needles melting at 214°. Anabromoquinoline dibromide hydrobromide forms light yellow crystals, which melt at 106-107° (uncorr.) with decomposition; when heated at 200°, dibromoquinoline, melting at 108° (uncorr.), is obtained. This crystallises in small, colourless needles, N. H. M.

Ethyl Hydroxyquinoline Carbonate, By E. LIPPMANN (Monatsh., 8, 439-441).-When ethyl chloroformate and hydroxyquinoline are heated together, ethyl hydroxyquinoline carbonate, C,NH, O'COOEt, is formed. This crystallises in prisms, is soluble in boiling alcohol, chloroform, and ether, melts at 105°, and gives no coloration with ferrous sulphate or ferric chloride. The platinochloride,

(C12H1NO3)2, H2PtCl,

crystallises in orange needles,

This ethyl salt when heated with caustic soda yields alcohol, hydroxyquinoline, and sodium carbonate; with strong hydrochloric acid at 140°, it yields ethyl chloride, carbonic anhydride, and hydroxyquinoline. It is thus a carbonate and not a carboxylic acid, and is not converted into the latter even by heating at 200°.

L. T. T.

Pyrenoline. By R. JAHODA (Monatsh., 8, 442-448).-Amidopyrene hydrochloride (Abstr., 1881, 206) was treated by Skranp's reaction with glycerol and sulphuric acid, when pyrenoline, C1NH, was formed. This substance forms yellow scales soluble in boiling alcohol, and a dilute solution shows a strong green fluorescence. It is also soluble in benzene, ether, and chloroform. It melts at 152-153°. The hydrochloride forms orange, microscopic needles melting at 270°; the sulphate pale red, hygroscopic needles melting at 246°; the

platinochloride a red precipitate, still solid at 290°; the methiodide dark red, microscopic needles melting at 212°, and soluble in alcohol; and the picrate yellow, microscopic needles, which decompose at 260°. The latter compound is well suited for the purification of the base. When oxidised with permanganate, an acid is formed, but has not yet been isolated. L. T. T.

Action of Sulphuric Acid on Morphine and Bibasic Acids. By P. CHASTAING and E. BARILLOT (Compt. rend., 105, 941-943, 1012-1014). When morphine is dissolved in excess of dilute sulphuric acid, and the solution evaporated until white fumes are given off, sulphomorphide, a substance of variable composition which gives brown products with alkalis, is formed. If, however, morphine is heated with concentrated sulphuric acid at 120°, diluted with water, treated with alkalis for a very short time and then neutralised, it yields a slightly soluble compound of the composition CH,NO. It always contains some sulphur in the form of sulphuryl, which is removed by strong alkalis, the compound being decomposed at the same time.

If morphine, 1 part, oxalic acid, 2 parts, and sulphuric acid, 1.5 part, are heated together at 115-120° for some hours, cooled and mixed with a large excess of water, a yellowish-white compound of the composition Č1HNO, or CHN2O, is obtained. Malonic acid under similar conditions yields the compound C30H3N2O16, and succinic acid the compound C2H2N2012. These compounds differ by 2CH2O. They are white, non-crystallisable substances which become greenish when exposed to air and light. They are insoluble in most neutral solvents, but are slightly soluble in cold water, more soluble in hot water. They behave like polyhydric phenols, and when mixed with alkalis oxidise on exposure to the air, forming red solutions. When these solutions are acidified, they deposit a deep blue flocculent precipitate soluble in ether, forming a violet-red solution, and in chloroform forming a blue solution, both of which deposit blue crystals of the composition C2H22N2O, on evaporation.

The same compound, morphine-blue, is obtained with all three of the acids above-mentioned. At 100°, it contains 1 mol. H2O, which is expelled at 120-125°. Each of the products from the bibasic acids absorbs 2 mols. of oxygen in alkaline solution, and forms 1 mol. of morphine-blue. This compound crystallises in slightly oblique prisms with a square base, which are red by transmitted light and blue by reflected light. They have no action on polarised light and melt to a blue liquid at a very high temperature. They are insoluble in water, slightly soluble in alcohol, and very soluble in ether, forming a solution which is red by transmitted light, and violet-red by reflected light. It also dissolves in chloroform, and alkalis remove the compound from both the ethereal and the chloroform solution, forming blue solutions. The compound in fact combines with alkalis to form salts which are somewhat stable when exposed to air. C. H. B.

Cinchonamine. By C. FRIEDEL (Compt. rend., 105, 985-987). -The crystals examined were obtained by Arnaud by gradually cool

ing an alcoholic solution. They formed hexagonal prisms terminated by rhombohedral faces, the faces of the prisms being tangent to the edges of the rhombohedron. Sometimes the latter is modified by other faces. Optical examination shows, however, that the rhombo. hedral form is only apparent, and the crystals really consist of three rhombic sections macled along the faces m, and the faces which seem to be those of the fundamental rhombohedron are really the faces a'. The fundamental form is a rhombic prism, in which mm = 60°, and bh=16157. The other angles were found to be a'm = 47° 39′; a'p 51° 4' (calc.), e,a' = 42° 21′ (calc.), p = 31° 45′ (calc.), a'a 53° 29′ (calc. 53° 25') xp = 68° 10′ (calc.); xm = 36° 42'.

In two adjacent sections of the macle, a'a' = 84° 42'. There is no outward sign of the structure, the faces e and a being perfectly united, but the macles are not always regular, especially in the larger crystals. The crystals do not become unaxial at a higher temperaC. H. P.

ture

Alkaloïd from Solanum Grandiflora. By D. FREIRE (Compt. rend., 105, 1074-1076).—The so-called "Wolf Fruit " of Brazil is the fruit of Solanum grandiflora, var. pulverulentem. Externally it is green, but the sarcocarp is white, somewhat thick, and has a bitter and disagreeable taste. It was treated with water and calcium hydroxide, evaporated to dryness on the water-bath, and the residue extracted with absolute alcohol and the solution filtered. The liquid was then concentrated to a small bulk, resinous matter being removed as it separated. After cooling, the semi-solid residue was treated with dilute hydrochloric acid, which dissolved the alkaloïd but left the resinous matter undissolved. The acid solution was decolorised by animal charcoal, precipitated with ammonia, and the precipitate washed with water and dried over sulphuric acid.

The alkaloïd thus obtained is a white substance with a very bitter taste, insoluble in water but soluble in alkalis and dilute acids. When heated with potassium hydroxide, it gives off ammonia, and its solution gives the usual reactions for alkaloïds. With platinum tetrachloride, it gives a yellow precipitate; mercuric potassium iodide, a yellow precipitate; tannin, a turbidity; ammonia, a white precipitate; concentrated sulphuric acid, an egg-yellow colour changing to red; with sulphuric acid and manganese dioxide, a yellow colour becoming first green and then violet; concentrated nitric acid, a purplish-red colour. The molecular weight as determined by means of the platinum compound is 236-4.

It is an

The author proposes to call this alkaloïd grandiflorine. energetic poison, and the fruit itself kills sheep which eat it, hence its name.

C. H. B.

Trigonelline. By E. JAHNS (Ber., 20, 2840-2843).-Trigonelline (Abstr., 1886, 85), when heated at 120° with an aqueous solution of barium hydroxide saturated at the boiling point, yields the whole of its nitrogen as methylamine, and when heated with excess of hydrochloric acid (sp. gr. = · 1·2) at 260-270° is converted into nicotinic acid and a combustible gas burning with a green flame, probably

methyl chloride. On these grounds, trigonelline is regarded as identical with the methylbetaïne of nicotinic acid, and a comparison of the properties of the two substances shows this to be the case.

W. P. W. Alkaloïds extracted from the Bark of the Xanthoxylon Senegalense. By GIACOSA and MONARI (Gazzetta, 17, 362-367).— On extracting the bark of the Xanthoxylon senegalense (artar-root) with petroleum, an oil is obtained, from which a crystalline substance separates; this contains no nitrogen, and when purified has a white micaceous appearance, melts at 120-125°, and gives a purple-red coloration with chloroform and sulphuric acid. It is probably a pseudocholesterin, but sufficient material was not at hand for a more complete investigation. The bark, after treatment with petroleum, gives on prolonged boiling with alcohol a brownish extract, from which, on addition of alkali, a yellowish solid is obtained. This consists of two alkaloïds, one of which is amorphous and insoluble in hot water, the other crystalline and soluble. The former was not further examined; the latter forms a hydrochloride, crystallising in minute needles or prisms, soluble in cold water, and of intensely bitter taste. The nitrate crystallises in needles melting at 215-220°; the platinochloride forms sparingly soluble yellowish prisms. The insoluble alkaloïd produces muscular irritation with coagulation of myosin, and physiological disturbances analogous to those observed with veratrine. The compounds were not analysed. V. H. V.

Formation of Peptone. By A. CLERMONT (Compt. rend., 105, 1022-1023).—20 grams of chopped meat is mixed with 30 grams of water and 0.5 gram of sulphuric acid, and heated in sealed tubes at 180° for six hours. The products are gases and a slightly brown liquid, which is easily filtered. When evaporated to dryness, ammoniacal vapours are given off, and the residue dissolves readily in water. The solution is not affected by boiling, nor by hydrochloric, nitric, or acetic acids, but it is precipitated by 4 vols. alcohol of 90°, or by tannin, mercuric chloride, or platinic chloride. 4 grams of peptone are obtained from 20 grams of fresh meat. When heated with water without any acid, the meat is converted into syntonin, which is readily converted into peptone by pepsin at 35° in a slightly acid solution. C. H. B.

Mucin of the Submaxillary Gland. By O. HAMMARSTEN (Zeit. physiol. Chem. 12, 163-195).-Obolensky (Pflüger's Archiv, 4, 336) and Landwehr (Zeit. physiol. Chem., 5, 371) have both made analyses of submaxillary mucin, but their method of preparing the mucin was faulty. In the present research, the following method was first employed: the glands were extracted with water, the extract filtered, and freed from microscopic elements by centrifugalising; acetic acid was used to precipitate the mucin from this solution; the precipitate had a stringy character. Attempts were then made to wash this precipitate free from proteïds by water acidified with acetic acid, "the precipitate being repeatedly well kneaded with the acidified water; this was found to be exceedingly difficult. The mucin was redis

solved in faintly alkaline water, and reprecipitated by acetic acid several times, but there was always the same difficulty in freeing it from proteïds. This was found to be due to the presence in the gland extract of a proteïd which is precipitable by acetic acid, and which is with difficulty soluble in excess of that reagent. It belongs to the class of proteïds to which the name nucleo-albumin has been given. The older method of extracting the mucin from the glands with a weak alkali was not used, because it was found that submaxillary mucin is readily decomposed by this treatment. The nucleoalbumin contains 17 per cent. of nitrogen; and it was admixture with this substance that gave in Landwehr's analyses the somewhat higher percentage of nitrogen than was found subsequently in the present research. The new method ultimately adopted for the preparation of the mucin was as follows: the clear watery extract was acidified with hydrochloric acid until the percentage of the latter reached 0·1— 015; the mucin which was first precipitated was redissolved when the acid present reached the percentage mentioned. The mixture was then diluted with three to five times its bulk of distilled water; by this means the mucin was precipitated, and the nucleo-albumin remained in solution. This process was repeated several times, until ultimately the mucin was obtained pure. Repeated precipitation and re-solution by this method does not alter the physical properties of the precipitate, which occurs in sticky, yellowish strings, nor does it alter its chemical properties or its elementary composition. This is in contrast with what occurs with dilute alkalis; a 0.1 per cent. solution of sodium hydroxide, or saturated or half saturated lime-water dissolves the mucin; but when precipitated by acetic acid its stringy character is lost, and the precipitate is flocculent; ammonia is given off in small quantities, and the percentage of nitrogen in the precipitate increases, the precipitate probably consisting of acid albu

min.

The mucin prepared in the manner described was washed with water by decantation; when free from acid, it becomes white in colour, but becomes again brownish-yellow on the addition of acetic acid; it was then washed with alcohol and ether, and dried. Elementary analysis of seven preparations gave the following average results in percentages:-C, 48-84; H, 6·8; N, 12·32; S, 0·843; ash, 0:35. Previous statements as to the absence of sulphur in mucin appear to be incorrect. The extremely small quantity of phosphorus found might have been contained in the ash. The percentage composition corresponds closely with that obtained by Loebisch (Abstr., 1886, 166), for tendon mucin. Mucin prepared in this way was found to be acid in reaction; this cannot be from union with the acid during its preparation, as the quantity of chlorine found by analysis was so excessively small; but mucin is probably itself of the nature of an acid. A neutral solution of mucin in 8 per cent. sodium chloride solution does not coagulate on heating, and even after adding acetic acid it only becomes slightly cloudy.

Alcohol precipitates mucin from a neutral solution; the precipitate is soluble in water, unless sodium chloride is present, in which case the precipitate is very insoluble. Mineral acids in small quantities pre