Codeine Derivatives Research Articles

Hydroxylated Codeine Derivatives

Hydroxylated Codeine Derivatives

Dihydrocodeine; further development in measurement of analgesic power and appraisal of psychologic side effects of analgesic agents.

DIHYDROCODEINE and dihydroisocodeine are hydrogenated derivatives of codeine and isocodeine. Eddy and Small1 investigated the toxicity and analgesic potency of the two isomers in animals. As with codeine, both drugs in mice and rabbits produced initial Central-nervous-system depression. The doses required were smaller than those for codeine. A further increase in the dosage of dihydrocodeine resulted in convulsions. Dihydroisocodeine in large dosage did not produce convulsions at all. Analgesic potency was measured in cats by the tail-pressure method. Both dihydroisocodeine and dihydrocodeine produced greater analgesia than codeine, milligram for milligram. These agents were thus candidates for clinical trial.In the . . .

2-Anthraquinone Sulfonate Derivatives of Morphine and Codeine

2-Anthraquinone Sulfonate Derivatives of Morphine and Codeine

CONTACT DERMATITIS FROM OPIUM DERIVATIVES

Drug eruptions from the ingestion of or parenteral use of morphine, codeine and other opium derivatives are well known to dermatologists. Most American authors of textbooks on dermatology include opium and its derivatives as a cause of drug eruptions. Scheer and Keil 1 in 1934 called attention to codeine as a cause of dermatitis medicamentosa. Touraine 2 in 1936 exhaustively described drug eruptions from opium compounds. Many morphologic types of eruption have been produced by the ingestion of or parenteral use of opium compounds. The most common are urticarial, morbilliform or scarlatiniform, but eczematous eruptions in which the chief allergic response is at the same site as in contact dermatitis have been described. Thus opium compounds are capable of producing not only an urticarial and scarlatiniform eruption but also an eczematous response when taken internally by ingestion or injection. Eczematous dermatitis from opium compounds used externally in the form of

3. The Formula of Morphine

As the alkaloid morphine, discovered in 1804, was the first substance of the kind known, it naturally received a good deal of attention. Some years later the new base was analysed by several distinguished chemists, but their results did not lead them to a formula accurately indicating the composition of the alkaloid. To Laurent belongs the honour of having given the formula C17H19NO3 (using the modern notation), the accuracy of which formula has been confirmed by subsequent analyses, particularly by those of Matthiessen and Wright. Nothing was ever observed to suggest that the formula is a multiple of these members until Wright, after an elaborate investigation of the derivatives of morphine and codeine, came to the conclusion that the true formula must be at least double the empirical, and that we ought therefore to write C34H38N2O6.

Scientific Serials

THE Journal of the Chemical Society, April and May.—The April number contains the following papers:—Researches on the paraffins existing in Pennsylvanian petroleum, by Thos. M. Morgan. This paper is followed by some remarks on the same subject by Prof. C. Schorlemmer.—On Groves' method of preparing chlorides, by the same.—A note on aricine, by David Howard.—On the precipitation of metals by zinc, by J. L. Davies. The author failed to precipitate to any large extent many of the metals which, according to some metallurgical books, are precipitated by zinc from acid solutions. Copper and the other well-known metals reduced by zinc precipitate well enough, but nickel, cobalt, iron, &c., do not. If, however, ammonia was added to their solutions the precipitating power of the zinc was rendered as efficient as under ordinary circumstances it is with copper, &c. The zinc was used in the shape of filings, and the author remarks that the metals precipitated by it under the above circumstances present a beautiful metallic appearance, and are in a weighable form.—On the action of the organic acids and their anhydrides on the natural alkaloids (Part III.), by G. H. Beckett and C. R. Alder Wright. The authors in this paper treat first of the action of acetic anhydride on the polymerides of codeine and morphine (dicodeine, tetracodeine, and tetramorphine being considered, further also the action of ethyl iodide on tetracodeine and octacetyl-tetracodeine); they then speak of isomeric diacetyl morphines, and of the action of ethyl iodide on acetylated morphine, codeine derivatives,;and analogous products. The compounds treated of in the latter division are diacetyl-codeine ethiodide, tetracetyl-morphine ethiodide, α-, β-, and γ-diacetyl-morphine ethiodide dibutyryl-codeine ethiodide, tetrabutyryl-morphine ethiodide, dibutyryl-morphine ethiodide, dibenzoyl-codeine ethiodide, tetrabenzoyl-morphine ethiodide, and α diacetyl-dibenzoyl-morphine ethiodide. Finally, there is an account of the action of ethylate of sodium on acetylated codeine and morphine.—The Journal, as usual, contains numerous abstracts from other serials.—The May number contains the following papers:—Further researches on bilirubin and its compounds, by Dr. J. L. W. Thudichum. This is a most elaborate paper, and we must refrain from entering on its details, confining ourselves to a mere outline of its contents. First, the author gives an account of the behaviour of bilirubin with the halogens, and in turn speaks of mono- and dibromo-bilirubin, the tri- and tetrachloro-bilirubin (with iodine there is no reaction at 80° to 100°). Then Dr. Thudichum proceeds to consider the operations made by chemists on bilirubin, prior to his own. He then describes some experiments bearing upon the alleged transformation of bilirubin into the colouring matter of urine, and treats of Maly's hydrobilirubin, urochrome spectra, and the spectra of the chemolytic products of bilirubin. We then have an account of experiments made with Jaffé's product, with which Maly compared his biliary product more particularly. Jaffé's product was obtained from febrile persons, and Dr. Thudichum points out that a source of error must here be eliminated, namely, the abnormal product urerythrin. He gives the spectrum and a new reaction of this compound; finally, there is a note on Jaffé's urobilin. The paper ends with a summary of conclusions against the alleged metamorphosis, and with some remarks on the author's theory of bilirubin and bilirubates, and on Städeler's hypothesis regarding the same.—On calcic hypochlorite from bleaching powder, by Charles T. Kingzett. This treatise turns on the chemical constitution of bleaching powder, on which subject the opinions of eminent chemists are at variance. The author describes four experiments which he made with a view to bring light into the matter, but he was not completely successful. Although his experiments may be regarded as a perfect proof of the body being in mass hypochlorite of calcium, yet he is nevertheless reluctant in being too positive on the subject, and recommends further investigation.—On a simple method of assaying iron, by Walter Noel Hartley. The principles on which this method depends are (1) The abolition of weights by exactly balancing a quantity of the ore to be examined against pure iron wire. (2) The reduction of inaccuracies in weighing by making the solutions of the iron and the ore up to the same volume, and taking a fraction (about 1/10) of the liquid for experiment, whereby the error of the balance is diminished 1/50. (3) The reduction of all other experimental errors to a minimum by putting comparable quantities of both ore and pure iron under precisely the same conditions. There is the usual number of abstracts in this part.

IV.—Action of the organic acids and their anhydrides on the natural alkaloids. Part II. Butyryl and benzoyl derivatives of morphine and codeine

IV.—Action of the organic acids and their anhydrides on the natural alkaloids. Part II. Butyryl and benzoyl derivatives of morphine and codeine