September i, 1882.] THE TROPICAL AGRICULTURIST. 



209 



PEELIMINARY NOTICE OP AN ALKALOID IN 



THE BAKK OF FRAXINUS AMERICANA 



(WHITE ASH).* 



BY PROFESSOR FKEDEIilCK B. POWER, VU. D. 



In the course of some experiments wbich were uniler- 

 takeu a few weeks ago by Mr. H. M. Edwards, under 

 my direction, in the chemical laboratory of the Philadel- 

 phia College of Pharmacy, our attention was directed 

 to the presence of an alkaloid in the bark under 

 notice. The body in question is apparently quite a 

 strong base, and is, witli a considerable degree of 

 probability, tlie principle upon which the therapeutical 

 virtues of the bark depend ; the preparation of the 

 bark which has been most successfully employed for 

 obtainiug its specific action beiu£( a wine, for which 

 a formula has been given by Mr. Thomas S. Wiegand. 



The object of tly's brief notice at this time is primarily 

 to make known the observation, which is attended with 

 special interest from the fact of no alkaloid having 

 as yet been observed in plants of the natural order 

 of Oleaeeic, and furthermore, as Mr. Edwards, a student 

 of the present class, will not have the opportunity 

 of pursuing the investigation to request that the 

 further chemical investigation, of the subject be reserved 

 for the writer. 



The researches herewith connected, embodying the 

 isolation of the aUaloid, its description, compositiou 

 and properties will be conijjleted and reported upon 

 at the earliest possible date, — PharmacetUicul Journal. 



INVESTIGATION OF THE ARGENTINE 



QUEBRACHO DRUGS, t 



by o. iiepse. 



Quebracho Colorado. 



The red quebracho occurs especially in the northern 

 portion of the Argentine Republic, where, besides being 

 called ''quebrocho Colorado," it is known under the 

 name of "cevil Colorado." The plant belongs to the 

 Terebinthacae, and Griisebach named it Loxopterijgium 

 Lorcnt;ii. The name Quchiaclua Lorent:ii, used for it 

 by Arata, would appear to be superfluous. 



The bark of this tree, in consequence of the con- 

 siderable amount of tauniu it contains, is used in its 

 native country for tanning purposes; whilst; the wood 

 only appears to be used in the preparation of an 

 extract which according to T. Stuckert, is manufact- 

 ured in Santiago del Estero. 



The wood, as its name implies, is of a red colour, 

 due essentially to a substance occurring also as a 

 solid cxud.ition in the cracks and fissures. Pedro N. 

 Arata, { who first observed thin exudation, named it 

 "gun)ml quebracho." This gum is of a ruby colour, 

 friable, and yields to ether a neutral crjstallizable 

 substance, also soluble in water, which is not coloured 

 with perchloride of iron. The residue, after treatment 

 with ether, is insoluble in chloroform and freely 

 soluble in cold alcohol. The alcohol solution, which 

 is inten.^ely brown-red, separ.ates brown-red flocks 

 upon an admixture with ether, but remains clear when 

 water is added. This polution is neutral and gives 

 with sugar of lead a briwn flocculent precipitate, 

 and with perchloi-iile of iron a dirty or en precipitate, 

 which becnmes violet upon the addition of a l.ttle 

 ammonia, or sudium carbonate or bicarbonate. Arata 

 is of opinion that this substance, is a puculiar tannic 

 acid, which he calls *'quel)rachot:ir.nic acid," but the 

 author's observations incline him to look upon it as 

 a catechio-like body. 



* From the Avicrican Journ. of Pharm,, March 1882. 

 t Aunalen tier Cliemic, vol. ccxi., p. 219. 

 } Phurm. Journ., [3], vol. ix., p. 531. 

 27 



The therapeutic action of red quebracho wood, first 

 observed by Penzoldt, which is siid to resemble that 

 of the bark of the white quebracho, naturally suggested 

 that in tliis case also the action was probably due 

 to an alkaloid, which was at first thought to be 

 aspidospermine. Although Volhard» failed to detect 

 any aspidospermine in the wood, Lutzt subsequently 

 separated, by means of ether, from au "extractum 

 ligni quebracho " purchased from Biidiugen, of Frankfort 

 on Maine, a substance that showed clearly the reactions 

 of aspidospermine. 



On the otiier hand Fraudef announced that Arata 

 had separated from quebracho Colorado an alkaloid 

 that had a compositiou and properties difi'ering from 

 those of aspidospermine. But this statemeut depended 

 upon amisundeisiandingof thepart of Fraude, against 

 which Arata put forward a protest. He wrote to 

 Fraude: — "Le Quebracho Colorado ne contient aucun 

 alcaloide. Je vous eupplie de rectifler, dans votre 

 prochaine communication, cette a,tiirniation, qui pourrait 

 faire contiuuer dans I'erreur plusieurs personnes sur 

 la nature de ces vt5gi5taux." 



It remained, therefore, only to test Lutz's state- 

 ment, the correctness of wjiich was the more doubtful 

 in that Volhard had found the red quebracho wocd 

 free from aspidospermine, aud the author could find 

 no alkaloid at all in it. An examination of the extract, 

 obtained from the same source, as might be expected, 

 gave not the least trace of an alkaloid. 



But although the presence of alkaloids in the 

 preparations at present made from quebracho Colorado 

 wood has been unanimously negatived, it cannot be 

 denied that the bark of the red quebracho, which 

 in this respect has been apparently overlooked, actually 

 contains two alkaloids, though scarcely in more than 

 traces. These two alkaloids are obtained by the same 

 process as given for the white quebracho. If the 

 ether residue be di.ssolved in dilute acetic acid the 

 yellow-brown solution gives with potassium sul- 

 phocyanide a precipitate of one alkaloid, whilst tho 

 other remains almost entirely dissolved aud can be 

 precipitatid with ammonia. 



Together with the flocculent sulphocyanide the greater 

 part of the yellow. bronn colouring matter goes down. 

 If the salt be decomposed with soda, the base extracted 

 with ether, a'ld this soultiou, after being treated with 

 animal charcoal, shaken with a few drops of very 

 dilute sulphuric acid, the acid acquires a miignificent 

 blue colour, and now gives all the reactions characteristic 

 of^ the alkaloid. As the acetic acid solution of the 

 original mixture is not blue, but yellow-brown, it 

 must be assumed that the blue-colouring alkaloid is 

 not present originally, but is subsequently formed 

 from another one. The correctness of this opinion may 

 be demonstrated by boiling the acetic acid solution 

 with some perchloric acid, when it at once becomes 

 greenislibliip, and not unfrequently, by longer boiling, 

 blue, like the sulphuric acid solution. It wnuld follow 

 that the blue-colouring alkaloid is an oxidation product. 

 The second alkaloid of the quebracho co orado bark 

 fortunately exhibits greater stability. By treatment 

 of it iu acetic acid solution with animal cJiarcoal and 

 then precipitating with ammonia, it is obtained per- 

 fectly pure. 



Loxopterijgine, as this new alkaloid has been named 

 bj' the autiior, is obtained in this way in white amorph- 

 ous flocks, freely soluble in ether, alcohol, chloroform, 

 benzine and acetone, and but slightly in cold water. 

 It is amorphous, has a strongly basic r. action and 

 tastes intensely bitter. Wilh perchloride of iron it 

 gives no coloration. It dissolves in concentrated nitric 



• Berliner kliit. Woelirnsclir, 1880, No. 10. 

 t Lutz, 'Ueber die therapeutisohen Wirknngen der 

 Quebracho- priiparate.' Dissertation, Bern, I8t0. 

 J Berichte, xii, p. 1560. 



