NOMENCLATURE AND TERMINOLOGY OE AL- KALOIDAL SALTS A SYMPOSIUM OF AUTHORITIES Nkw Y4k Merck’s Report 1897 NOMENCLATURE AND TERMINOL- OGY OF ALKALOIDAL SALTS A SYMPOSIUM OF AUTHORITIES Page E. H. BARTLEY B S., M.D., Phar.D 27 29 CHARLES CASPARI, Jr., Ph.G 14 18 A. R. L. DOHME, Ph.D 9 12 W. H. GREENE, M.D, F.C.S 26,27 WILLIAM MARTINDALE, F.C.S 8 T. H. NORTON, Ph.D., F.C.S 13, 14 OSCAR OLDBERG, Phar.D 25 A. B. PRESCOTT, M D., Ph D., F.C S 12,13 IRA REMSEN, Ph.D 14 J P. REMINGTON, Ph.M., F.C.S 7,8 CHARLES RICE, Ph D , Ph.M 3 5 H. H. RUSBY, M 0..., 18 22 L. E. SAYRE, B.S , Ph.M 27 D. K. SHUTE. M.D 23, 24 WILLIAM SIMON, Ph D 22, 23 ALONZO B. STEVENS, Ph.C 24, 25 T. E. THORPE, Ph D., D.Sc., LL.D., F.R.S 7 WITH TABULAR SUMM ARY BY if. \V, W.UMS KKl'lll.NT '*rs6»J - w' Merck’s Report, Vol. yi No«. 12, 13, 14 ami lfr L NOMENCLATURE OF ALKALOIDAL SALTS A SYMPOSIUM OF AUTHORITIES INVITED BY S. W. Williams, Ph.C.,F.C.S. ON the eve of a new. British Pharma- copoeia and nearing a revision of our own, it seemed to the writer a proper time for a careful consideration of the conflicting usages of Chemistry, Pharmacy, Medicine, and Commerce in regard to the naming of alkaloidal salts. He, therefore, sought the views of a number of the best authorities, and takes pleasure in submitting herewith the kind replies received. ONTHE PROPOSED CHANGE OF NOMEN- CLATURE OF ALKALOIDAL SALTS [Charles Rice, Ph.D.—Chairman U. S. P. Com- mittee of Revision] The question of what ought to be the titles, in the Pharmacopoeia, of certain chemicals that are used in medicine and that now bear names not entirely agreeing with modern chemical views, is still a sub- ject of discussion and is liable to remain so until the appearance of the next Pharmaco- poeia* at which time it will be seen whether the next Committee of Revision will have become converted to the modern views or not. Among these chemicals there is one 3 group which is more especially under dis- cussion, namely, the salts of alkaloids with hydrogen acids (hydracids), which, accord- ing to the old nomenclature, bear such names as “hydrochlorate,” “hydrobro- mate,” etc., while the disciples of modern chemistry claim that they should be called “hydrochloride,” “hydrobromide,” etc. It is proper and useful to keep this question alive, at least until its settlement by the next Committee of Revision. While the under- signed has already put himself on record regarding this question at a former occa- sion, he now recurs to it, feeling justified in making some concessions to the arguments since then advanced in favor of the change. A series of interesting articles recently' published by Seward W. Williams in Merck’s Report (Jan. i, Jan. 15, and Feb. 1, 1897), bears the title: “Should Pharmacy and Chemistry Speak the Same Lan- guage?” To this question, regarded in the abstract, an affirmative answer may be given without hesitation. The intelligent and educated pharmacist at the present time, particularly if he has had a college and laboratory training, will prefer to speak in terms identical with those used by the chemist. In his intercourse with the latter he will also write in such terms, in short, he will gladly use, in general, the same terms as the chemist, except where habit or some official injunction prevent him. If this question of uniformity of terms were one 4 to be settled only between the pharmacist and the chemist, an agreement could easily be reached. But it must be remembered that there is a third party to the action, with whom at least the pharmacist must reckon, and who has a voice in the matter. This third party is the physician, or, to de- fine him for our present purpose more closely, the medical prescriber, who, as a rule, cares nothing for changes in official names, but keeps on writing his prescrip- tions in the terms which became familiar to him at the beginning of his practice. The wishes, preferences, or claims of this third party must not be entirely overlooked or overridden. Whatever agreements may be come to between the pharmacist and the chemist regarding the names of the medi- cines which the physician habitually pre- scribes, more particularly the names of those of long standing, they should not go so far as to create the risk of the prescribed in- tentions being misunderstood. It is quite well for the pharmacist and the chemist to keep on moving ahead, but they should never so outstrip tne physician, whose chief interests lie in other directions, as to disap- pear from his horizon altogether. When a physician in our days wants to prescribe the “hydrochloride of quinine,” he will, in nine cases out of ten probably, write: “Quin. Mur.,” which is so much shorter than “Quin. Hydrochlor.,” for the abbreviated form of the word “Hydro- 5 chloride” could not well be less than “Hy- drochlor.” without causing confusion. But, in view of the fact that probably no pre- server ever writes out such terms in full, and therefore never gets as far, with his pen, as the disputed end of the word, may this now be either “Hydrochloratis” or “Hydrochloridi” (gen.), and, further, since the proposed change in this particular group of compounds cannot well cause any confusion or danger, the undersigned is willing to accept them. But he cannot ac- cept the dropping of the prefix “hydro” (which has been recommended by some), either in the Latin or the English official title, because “Morphinae Bromidum” and “Morphine Bromide” would need as much and probably more apology ior their an- omalous existence, as the term “Hydro- chlorate” does now. As to the proposition to place an apostrophe before the word “Bromide” (thus: Morphine ’bromide), the undersigned appreciates the ingenuity of the device, but fails to see how this would save either time or trouble. For surely such an important sign, made visible to the eye (and meaning something), should also be made audible to the ear. And the un- dersigned cannot see how else the term could be pronounced than “Morphine apos- trophe bromide.” Charles Rice. 6 EFFORT TO BRING THE NOMENCLATURE OF THE BRITISH PH ARM ACOPCEIA INTO CONFORMITY WITH THAT OF THE CHEM- ICAL SOCIETY [T. E. Thori-k, LL.D., F.R.S.] * * * In the forthcoming edition of the British Pharmacopeia, a committee consisting of Professors Tilden, Emer- son Reynolds, and myself, who were charged by the Medical Council to revise the chemical portion of the work, have strongly recommended—to use your own phrase—that Pharmacy and Chemistry should speak the same language; and with this view and to avoid confusion, we have sought to bring the nomenclature of the British Pharmacopoeia into conformity with the system of the Chemical Society of Lon- don, which is being rapidly introduced into all modern English text-books on chem- istry. We have consistently used “hydrochlor- ide” for “hydrochlorate.” T. E. Thorpe. •THE COMMA CONTRACTION APPROVED [Prof. J. P. Remington, Ph.M., F.C.S.—Vice- Chairman U.S.P. Committee of Revision] I think very well of your proposition to indicate hydracid salts of the alkaloids, * The words “comma” and “apostrophe” are used throughout the discussion in the same sense. Nuttalls’s definition of apostrophe is: “ The contraction of a word by the omission of a letter or letters, which omission is marked by a comma. The comma so used is also called an apostrophe.” 7 when it is necessary to contract them, by replacing the prefix hydro with a comma. My position has not changed, and I very much prefer “hydrochloride” and “hydro- bromide” to “hydrochlorate” and “hvdro- bromate;” but ‘“hydrosulphate” is, unfor- tunately, suggestive. The comma obliter- ates this objection, and if adopted would soon cease to excite comment. Joseph P. Remington. SAFETY, CLEARNESS, BREVITY, AND ACCURACY [William Martindai.e, F.C.S.—Author of “The Extra Pharmacopoeia”] The nomenclature of a pharmacopoeia should be consistent with safety, clearness, brevity, and accuracy—it should not change otherwise. In English chemical language the term “hydrochloride” as applied to the well-known alkaloidal salts, morphine hy- drochloride and cocaine hydrochloride, has now for a long time correctly replaced that of “hydrochlora/e;” and pharmacopoeias in English should now adopt the term hydro- chloride for these salts. Your idea of decapitating the prefix hydro and writing ’chloride is ingenious, and might be useful as a contraction. There is no reason why affixes only should be deleted for contractions, so long as safety is guarded. William Martiivdale. 8 HYDROCHLORIDE AND HYDROSUL- PHATE [Alfrkd R. L. Do HITE, Ph.D.— A.Ph. A. Com- mittee of Revision] * * * It is unfortunate that our chem- ical nomenclature is unsatisfactory in the matter of the halogen acids and oxyhalogen acids, the only distinction between HC1 and HCIO,, etc., being the prefix hydro, where- as an entirely different name should have been adopted. However, we must endeavor to make the best of what we have, and under the circumstances it is best to use the no- menclature that is least misleading, and this is “hydrochloride” for R. HC1, and “hydro- chlorate,” for R. HC10a (“R.” representing the alkaloid molecule). To be consistent it is then, of course, necessary to adopt “hy- drosulphate” for R. H2S04, “hydronitrate” for R. HN03; and I believe it not a bad idea to do so, as the oddity of the nomen- clature will point out per se the fact that the salts arc addition and not substitution salts. Personally, I believe that all alka- loidal salts are merely the result of the satu- ration of the trivalent nitrogen atom, the same becoming pentavalent. This process is, of course, different from the ordinary formation of salts, which is plainly a double decomposition, due to the more stable re- arrangement of the chemical affinities. ()nly four possibilities present themselves as solutions of the problem, and these are: (i) Alkaloid hydrochloride—i. e., giving the 9 entire name of the acid, with prefix “hydro” in all cases, to point out the fact that the salt is an addition salt; (2) Alkaloid chloride— merely giving the acid radical portion of the acid as the name of the acid; (3) Alkaloidonium chloride—which says that in the process of its nitrogen assuming pen- tavalency the alkaloid has altered its char- acter and become of the nature of a metal; and (4) Hydro-alkaloid chloride—which points out that the salt formation has result- ed in the hydration of the alkaloid, and the formation at the same time of the chloride of this hydrated alkaloid. Nos. 1 and 4 are tenable and uncontrovertible; but Nos. 2 and 3 are untenable, because the salt is not the chloride of' the alkaloid, but of the hy- drated alkaloid (H. R. Cl.) in case of No. 2, and because it is not a fact that mono- hydrated alkaloids act like metals and are liberated as such if set free, in the case of No. 3. It hence remains to select between Nos. 1 and 4, both of which are, chemically speaking, correct; but, as they are practi- cally identical, we naturally select the more euphonious and least grating of the two and adopt as the most correct and hence prefer- able, No. 1, “alkaloid hydrochloride.” When I suggested the change from “hy- drochlorate” to “ide” I had in mind only the fact that the former was certainly incorrect, while the latter was correct. Whether the latter was the most suitable did not enter my mind at the time, or whether other pos- 10 sibly also correct nomenclatures were per- haps better. I do not approve of your suggestion of adopting the apostrophe to replace the pre- fix “hydro,” because it may lead to confu- sion, as it is easily omitted and overlooked and there may arise an instance where the chloride of the alkaloid, as well as the hy- drochloride, arc known, in which case con- fusion would surely result. l>v the chloride of the alkaloid I mean the alkaloid plus one or two chlorine atoms, which may be added to the other portion of the pyridine or ben- zene or other nucleus, and not to the nitro- gen atom, thus: A _T5 ill ITH* HC CH C-0 \V II k-n-ci o H C.H.Cl cHi \/\ I 4« iT5)j HC CH C-0 V II _ NO-* This is, of course, a forced example, since tin's latter compound does not exist; but it might be formed, and, if so, would not be a substitution product, and would not be called dichlor-pilocarpine. I hence maintain that “cocaine hydro- chloride” is correct and the best nomencla- ture for the salt; and, further, that “mor- phine sulphate” is incorrect, chemically speaking, and should be “morphine hydro- sulphate,” for morphine sulphate is (CltH1#NOt)a S04, while our salt, as we know, is (C17II1UN03)2H2S04. 11 I have given you all that I have to say in reference to the subject, and I place the same at your disposal. Pharmacy should, of course, speak the language of chemistry; and the sooner she adopts it in toto, the bet- ter for pharmacy. I am pleased at the in- terest you have taken in the matter, and wish you success. Alfred R. L. Dohme, RASH TO PREDICT ADOPTION OF THE “-IUM” TERMINATION [Prof. A. B. Prescott, M. D., P11. D.—Dean School of Pharmacy, University of Michigan] As compared with other sciences, chem- istry has been fortunate in the adoption of systematic nomenclature. But we have not by any means reached a regular nomen- clature for all classes of organic compounds. The most ambitious attempt to do tnis by agreement was made at the International Conference of Chemists, at Geneva, in 1892. tfbat Conference does not appear to have dealt specially with the naming of the salts of the organic bases. The recommendations of the Conference have had some effect, but scientific nomenclature is a matterof growth more than of convention. It is only the quarternary bases formed of univalent alkyls that have entirely rational names for their salts and their hydroxides. We say “tetramethyl-ammonium iodide,” or, with Beilstein,“tetramethylium iodide,” and always “tetramethylphosphonium iodide,” etc., etc. Chemists commonly say “tri- methyl-ammonium iodide.” 12 Nevertheless, the quarternary organic bases, having stable hydroxides, are termed ammonium bases, in contrast with the pri- mary, secondary, and tertiary bases. The latter form salts as stable as does ammonium itself. It is quite true that the valency of nitrogen in all ammonium compounds and amine salts remains an open question, but at any rate all these compounds have enough common character to be named in unison. AVe must wait for systematic nomenclature of the salts of pyridine derivatives. In salts of quarternary bases the name “pyri- dinium,” or “quinolinium,” has been ven- tured upon here and there by chemical writers, but without present advantage. It would be rash to predict that the “-ium” termination will come into use for the alka- loidal salts. It is safe to say “pyridine- methyl nitrate.” It would be in one sense correct to say “pyridine-hydrogen nitrate,” or “cocaine-hydrogen chloride,” but the longer name is not, upon the whole, as pre- cise as the shorter one. Albert B. Prescott. 'CHLORID, 'IODID. ’NITRATE, ETC. [Prok. T. H, Norton, University of Cincinnati; Chairman Committee on Nomenclature of the Am. Ass’n for Adv. of Science] I have read with great interest your valuable pamphlet on the nomenclature of our alkaloidal salts, and I am heartily in favor of the adoption of your proposed method, i. e., the use of ’chlorid, ’iodid, ’ni- 13 trate, etc., as the nearest approach to uni- formity in nomenclature which we can at present in any simple way attain. A nomenclature based upon that of the ammonium compounds is logically the cor- rect outcome, and I hope that we may see it introduced in the near future. It will, how- ever, involve much discussion and delibera- tion. Your proposal is simple, feasible, and un- derstandable. T. H. Norton. THE“-IUM"TERMI NATION NOT ADVISED [Prof. Ira Remsen, Ph.D. ; Editor American Chemical Journal] I do not think I can state my opinion on the subject of the nomenclature of the salts of the alkaloids more clearly than I did in my letter to the Drug News twelve years ago. So far as chemistry is concerned, the situation has not changed since then. “Hy- drochloride” and "hydrochlorate” will both continue to be used. Such terms as “hy- drococaine chloride” will not be used, be- cause they are misleading; and such as “co- cainium chloride” are also objectionable. They are based upon a theory that has to be extended to meet the case of every alkaloid. I. Remsen. RESTRICT “HYDRO” PREFIX TO HY- DRACID SALTS [Prof. Charles Casparf, Jr., Permanent Secretary A.Pn.A., Professor of Phar- macy Baltimore College of Pharmacy] * * * For the past few years I have 14 used the terms “hydrochloride,” “hydrobro- mide, ” and “hydroiodide” exclusively, when speaking of the salts of alkaloids with hy- dracids, and have endeavored to impress uj)on my students that such terms are alone correct. I can see no necessity for using such terms as “hydrosulphate,” “hydroni- trate,” “hydrocitrate,” “hydrosalicylate,” etc., since we do not use the prefix “hydro” when speaking of the respective acids. It does not seem to me that consistency re- quires us to add the prefix “hydro” in the case of salts of the oxyacids simply to show that the 11 of the acid is not displaced when these acids are neutralized by alkaloids. I take it that in the case of hydracid salts the prefix “hydro” at once* indicates the differ- ence between halides and hydracid salts, and students can easily be taught that the terms “iodide,” “bromide,” and “chloride” are not applicable to alkaloidal salts. The dif- ference between alkaloidal hydrobromides, hydroiodides, etc., and alkaloidal bromides and iodides in the form of perbromides and periodides can Easily be explained. No II being split off (at least to the best of our present knowledge) in the union of alka- loids and hydraeids, we should indicate this fact by retaining the full name of the acid and simply change the ending “ic” into “ide” for the salt, the ending “ide” having been universally adopted (recently changed to “id") for compounds of the halides. The terms “hydrochlorate,” “hydrobromate,” 15 and “hydroiodate” might be mistaken by some to indicate salts of oxyacids of Cl, Br, and I, although we do not use the prefix “hydro” for these acids. For ammonium salts the terms “chloride,” “bromide,” and “iodide” are undoubtedly correct, and the use of the prefix “hydro” would be im- proper, for H is split off and halides are formed. Whether we consider ammonia as NH3 or NH4OH, the H of our hydracids separates, as is clearly shown in the follow- in equation: NH3+HBr=NH4Br; NH40H + HBr=NH4Br+H20 As I can see no reason whatever for speaking of “hydronitrates,” “hydrotar- trates,” etc., the use#of a comma (’) in “ni- trate,” “tartrate,” etc., also appears quite un- necessary and even confusing. Let phar- macists understand clearly that in all alka- loidal salfs the H of the acid remains, and that in the case of the salts of hydracids the prefix “hydro” is retained as part of the name of the acid, and that the ending “ide” is used to indicate the difference between salts of hydracids and oxyacids. I think the confusion will then rapidly disappear. That the ending “ate” is used for salts of all oxyacids, is known to every one who has studied pharmacy or chemistry. The study of alkaloidal salts has shown thus far that the alkaloids differ from other substances in their behavior toward all acids', the hydrogen of the acid not being split off or displaced and the salts apparently i6 forming by simple addition of the base and acid. The names of alkaloidal salts are de- rived from the names of the respective acids, and the same endings should be employed to indicate the difference between hvdracid and oxyacid combinations, as in the case of all other salts; but in order to distinguish between alkaloidal salts of hydracids, as re- taining the acid hydrogen, and other salts of the same acids in which the acid hydrogen is displaced, it is desirable to use the prefix “hydro,” a part of the name of the acid, in connection with the name indicating the par- ticular hydracid compound of the alkaloid, thus: “hydrochloride,” “hydrobromide,” etc. The use of the prefix “hydro” in connection with oxyacid salts of the alkaloids appears unnecessary and confusing, since it is not a part of the name of the respective acids; the terms “sulphate,” “citrate,” “phosphate,” “nitrate,” etc., are therefore perfectly proper as applied to alkaloidal salts, in spite of the fact already stated that oxyacids also retain their acid hydrogen when forming salts with alkaloids. The ending “ide” (or “id,” as now pre- ferred by many) should be retained as .dis- tinctive for all simple combinations of two elements, or of elements with groups acting as elements. The salts of the hydracids surely belong in this category, as in every combination with metals a simple union of the haloid and the metal results; and the use of the ending “ate” employed for salts of 17 acids ending in “ic” does not therefore ap- pear warranted in the case of hydracid salts. The fact that the alkaloids do not combine directly with the haloid elements, is simply an exception to the general rule in the for- mation of hydracid salts, and should not in- terfere with long-established nomenclature. Chas. Caspari, Jr. RELATIONS OF CHEMICAL TO GENERAL NOMENCLATURE [Prof. H. H. Rusby, M.D., New York College of Pharmacy, Member U. S. P. Committee of Revision] Discussions of the nomenclature of special subjects do not always keep sight of the principles that have already been estab- lished for nomenclature in general. The nomenclature of chemistry is one of the last to be recognized, and it should derive great assistance from a study of the conclusions already reached in other departments of science. In the biological sciences it has been found necessary—or, at least up to the present, highly desirable—to follow different rules in treating scientific terms from those followed in treating the names of the objects studied. The former subject has been called “terminology,” the latter “nomenclature.” It has been found almost—if not quite—a matter of necessity to change scientific terms as the ideas which they represent are modified through discovery; but it has been found equally desirable to change as little as possible the- scientific names of things, and here priority, in both botany and zoology, 18 has been accorded the highest importance in deciding between names. Indeed, the first name given must always remain the name, whether it be used or not. When for any reason it is proposed to change names, two classes of cases are rec- ognized. In the first case, a new name is to be applied to a known thing, and this is not a very serious clrange. By it the thing merely comes to have two names instead of one, and the only evil is an addition to synonomy. In the other case, a previously recognized name is given to a different thing; a much more serious matter, as it at once involves doubt as to which thing is re- ferred to when the name is seen in use. This action has always been regarded as highly objectionable. It is opposed to the chief object of the existence of a scientific, as op- posed to a vulgar, nomenclature, that of pre- cision of meaning. If only uniformity in the different departments of science were concerned, we might well doubt whether any special nomenclature can permanently exist on a basis opposed to that generally adopted. There are, however, several reasons why such a procedure would be more objectionable in chemistry than else- where. The names of organic beings are commonly followed by the names of their authors, so that if the same name has been applied by different authors to different things, we can always ascertain from the records which thing is to be understood. 19 This practice does not prevail in chemistry. Although it has been found necessary in the case of some alkaloids and other substances to append the name of the discoverer, the cases are exceptional and the practice would not be applicable to numerous series of salts. Again, we have before us the very impor- tant practical results that would be effected by introducing confusion into the nomen- clature of potent medicinal agents, by hav- ing two things called by the same name. If a general agreement could be reached in advance, it would be only less bad, but fail- ing this, it would appear altogether inde- fensible and its ultimate rejection would be pretty certain. So far as the Pharmacopoeia is concerned, there is a long line of precedents establish- ing this custom, and there is also a direct enunciation of the principle that, “In the choice of titles of official articles it is rec- ommended that convenience, established custom, and considerations of safety against mistakes through similarity or changes in names, should outweigh purely theoretical consideration or scientific preciseness” (U. S. P., 7th Revision, p. xxv). This principle is illustrated in such titles as “Prunus Virginiana,” followed by a defi- nition that carefully excludes the bark of the plant Prunus Virginiana, and “Rhus Toxi- codendron,” defined, as the leaves of Rhus Radicans. The Pharmacopoeia has no choice as to the names used in the definition. It can 20 not pose as a botanical authority, but must itself follow such authority in the use of plant names. Its titles, however, are its own property, and it has decided on what lines to form them. In the case of chemicals there is no such stAte of affairs, there bein£ no definition in which to specify the name indorsed by chem- ical authority for the substance named by the title. The formula, in a certain way, constitutes such a specification, but it does not mention the chemical name. It would seem to be a wise procedure to introduce chemical definitions, in which the chemical name is specified, in those cases where the form of the title does not agree with chem- ical authority. In any case the essential point is that the title itself is not the place for introducing a chemical name, when the form of that name violates the principles on which the work is compiled. I perhaps have no special authority to dis- cuss chemical nomenclature, but I have given special study to the general subject and to the position of the Pharmacopoeia re- garding it, and 1 should not like to see any inconsistency introduced. As regards the use of the termination “ide” in the names, where appropriate, it does not appear that it would violate any es- sential principle of the work, and I should prefer to sec this termination introduced; but the introduction of a new and dangerous application of the prefix “hydro” would 21 seem very objectionable until after it had been pretty generally accepted in chemistry, in popular usage as well as by authority. This is written in spite of the fact that every effort to make names accurately expressive is heartily appreciated by the writer. H. H. Rushy. PREFERENCE FOR “IA” AND “IUM” TER- MINATIONS [Dr. W. Simon, Professor of Chemistry Mary- land College of Pharmacy] I have placed myself on record for many years past as being decidedly opposed to the terms hydrochlorate, etc., adopted by the U. S. P. . In my opinion, the best solution of the problem would have been to use the end- ings “ia” and “ium” for the free alkaloids and their salts, respectively, as we have done and do now for ammonia and ammonium compounds. This would give us “morphia,” “strychnia,” etc.; but “morphiwm acetate,” “strychniwm chloride,” etc. If the above method is not adopted, the terms “hydro- chloride” and “hydrobromide” are vastly superior to the terms “hydrochlorate” and “hydrobromate.” You are right in saying that for the sake of consistency the terms “hydronitrate,” etc., had better be used; but, as the highest chemical authorities, both in this country and in Europe, use simply “sulphate,” “nitrate,” etc., I think the phar- macists might leave this nomenclature as it stands, at least for the present. 22 Whether apostrophizing the long terms to “’bromide,” “’phosphate,” etc., is of prac- tical value, I am not prepared to say; in fact, I somewhat doubt it. W. Simon. [Dr. D. K. Shutk; Dean Medical Dept. Columbian University] A PHYSICIAN’S OPINION * * * In my judgment, it is most de- sirable that Pharmacy and Chemistry should speak the same language. In giving my opinion I speak, of course, only as an amateur in chemistry; although, as a physician, I have always been much in- terested in the study of chemistry. I am always in favor of amending no- menclature where the amendment leads to greater clearness and consistency. For in- stance, it seems to me a great barbarity that pharmacists should say that the antidote to arsenic is the freshly prepared “hydrated sesqui oxide of iron,” instead of “ferric hy- drate.”* It also seems a puzzling incon- sistency that under theoretical chemistry we should be told that an ortho acid is one in which we find as many molecules of hy- droxyl as the negative element has bonds, that is, as many hydrogen as oxygen atoms, and then under practical chemistry be told that IIgP04 (phosphoric acid) is an ortho acid.f *Fe,(OH)#is variable to Fe,0,(0H)r fThe following definition of an ortho acid seems preferable: “Theone of several acids of the same element, which actually occurs with the greatest number hydroxyl groups; as 23 It seems to me the climax of inconsis- tency to say “chloride of ammonium” and “hydrochlorate of cocaine.” It would appear that contractions like “ ’chloride” and “ ’sulphate” are preferable to the other expressions that are constantly used; the “coma” before the contractions will die a natural death. What you say of the physician’s training in “incompatibles” is very important, and such terms as “hydrochlorate” are. very con- fusing to medical students and practitioners alike. D. K. Shute. HYDROCHLORIDE AND HYDROSUL- PHATE, OR CHLORIDE AND SULPHATE [Prof. A. B. Stevens, Ph.C. ; Member A. Ph. A. Committee of Revision] I am pleased to learn that you are agi- tating the question of nomenclature. The ending “ate” for salts formed by combina- tion of alkaloids with the acids hydrochloric, hydrobromic, and hydroiodic, is certainly wrong and should no longer be fostered. However, the question of “chloride” or “hy- drochloride” is not so easily dismissed. If we are to retain the prefix “hydro” for alka- loidal salts of hydrochloric, hydrobromic, and hydroiodic acids, then let us be consist- ent and extepd its use to all corresponding salts of the alkaloids, as quinine “hydrosul- phate,” “hydronitrate,” etc. I decidedly prefer quinine “chloride,” “iodide,” and “bromide,” especially if the 24 names quinine “sulphate” and morphine “sulphate” are to be retained. A. B. Stevens. “CHLORIDE,” “NITRATE,” ETC., FOR CONSISTENCY [Prof. Oscar Oldberg, Phar. D.; Dean North- western University School of Pharmacy; Member U.S.P. Committee of Revision] * * * The views you express coin- cide entirely with those I have always held. I am heartily in favor of such terms as “strychnine nitrate,” “strychnine chloride,” etc. Such terms are consistent with each other and are not ambiguous. Oscar Oldberg. [The writer did not go quite so far as Dr. Oldberg, but favored a position like that taken by Dr. Dohme, involving such terms as “hydrochloride” and “hydrosulphate,” which are both accurate and consistent; and, then, to make the change practical, apos- trophizing these terms to “’chloride” and “’sulphate.” The position was designed to be a happy medium between the very prac- tical idea of Dr. Oldberg and the very ac- curate view of Dr. Dohme. The full and correct name for C20H24N2O2.HClO3 would naturally be' quinine hydrogen chlorate, which would be contracted to quinine hydrochlorate just as quinine hydrogen chloride is abbreviated to quinine hydrochloride. But as quinine hydro- chlorate has so long been used as the name for the salt formed by quinine with hy- 25 drogen chloric?*?, we cannot apply the term to another salt without incurring the dangers which Dr. Rusby cautions against. As it was inaccurate to call an addition product with hydrogen chlorate (HC103) a chlorate, and as it was unsafe to give it its correct name hydrochlorate, the writer suggested ’chlorate as being as accurate as was consistent with safety and as practical as was consistent with accuracy. He ad- mits, however, that expediency points to accepting Professor Caspari’s view of the case.—S. W. W.] CHLORIDE, BROMIDE, ETC., FOR SIM- PLICITY [Prof. Wm. H. Greene, Philadelphia] * * * There can be no valid reason why Pharmacy and Chemistry should not speak the same language when dealing with same matters. The rules for abstractors for the Journal of the Chemical Society of London still sanc- tion the use of “hydrochloride,” etc., for salts of alkaloids and prohibit the use of “hydrochlorate.” Since it is quite understood by chemists and pharmacists that alkaloids do not unite directly with acid radicals; since, also, chem- ists and pharmacists agree that it is exceed- ingly probable that the alkaloids do not unite with acids per se, but rather with the acid ion and the hydrogen, is it not prefer- able to sacrifice absolute accuracy of de- scriptive nomenclature, as suggested by Dr. 26 Remsen and Dr. Barker, to obtain a sim- plicity of form that can involve no error of conception? With all due respect to committees, the continued use of words like “hydrochlo- rate” and “muriate” appears unpardonable. “Chloride,” “bromide,” “sulphate,” etc., for salts of the alkaloids could hardly be unin- telligible to a chemist or a pharmacist. William H. Greene. [Prof. L. E. Sayre, Pu.G., Ph.M. ; Professor of Pharmacy University of Kansas; Mem- ber U.S.P. Committee of Revision] THE VALUE OF THE APOSTROPHE RECOGNIZED * * * I would say that at first thought I did not like the novel idea of using the apostrophe, as you have suggested. But, on further study, I have concluded that the use of the apostrophe would be helpful in economizing space; and when the prefix “hydro” is omitted, it will prevent am- biguity.' It will at once show that the sub- stance thus designated is the product of a different reaction from that between a metal and an acid. I should be very sorry, however, to see the pharmacist take the ini- tiative in abbreviating the names of alka- loidal salts in this way; he may well sug- gest it. L. E. Sayre. RETAIN THE “HYDRO- “PREFIX [I)k. E. H. Barti.ey; I)can of the Brooklyn Col- lege of Pharmacy; Member ofA.Ph.A. Committee of Revision] In reply to your query as to my idea of 27 the proper nomenclature of the alkaloidal salts, I must say that I am not satisfied with the nomenclature of the last U. S. P. The only object of entering into such a discussion is to try to secure uniformity. The first thing we should do, very nat- urally, is to learn what the custom is in other countries, speaking the same lan- guage, and then the custom in other lan- guages. We find that the custom in Eng- land, in regard to the salts of the alkaloids with the halogen acids, is to use the names “hydrochloride,” “hydrobromide,” “hydro- iodide,” etc. This is also the custom in the Colonies, where the English language is used. These seem to be the proper terms. All inorganic salts derived from HC1 are always called chlorides, while the term chlo- rate is reserved for the salts of chloric acid. If an alkaloid should be found that combines with the Cl alone, there could be no ques- tion that it must receive the name of chlor- ide. When the alkaloid takes up the hydro- gen, as well as the chlorine, I cannot see why it should receive a name that indicates that the acid is a ternary acid. The ter- mination “ate” has a definite meaning in chemical nomenclature, which is entirely at variance with this use. I suppose this ground has been gone over very fully, and all the arguments have been ably presented, but I cannot see any reason in the use of cocaine “hydrochlorate” for “hydrochlor- ide,” any more than the use of antimony 28 “oxychlorate” for “oxychloride.” I do not favor the contraction of the names of these alkaloidal salts into “chlor- ide,” “bromide,” “iodide,” etc., for that would interfere with the differentiation of two groups of very differently constituted compounds. The prefix “hydro” has a well- known place in the nomenclature of organic bodies, and must be retained for the desig- nation of the hydro substitution compounds and the addition compounds such as those under discussion. E. H. Bartley. D) as affording the easiest and most prac- unable to prove either the existence of a tical way of avoiding the difficulty. true ammonium hydroxide (hvdrate) or am- Colunin A of the table herewitl Some authorities regard any recognition monium amalgam; but it is nevertheless gives the notation of representative alka of the unreplaced hydrogen of the combin- simply a theory, and it would hardly seem loidal salts as accepted by both Chemistry ing acid as unimportant and would adopt advisable to change both notation and no- and Pharmacy. Accuracy and consistency column D without the apostrophe. A care- menclature until actual determinations of would give these salts, as "addition prod ful comparison of columns C and G will the constitution of alkaloidal salts prove the nets,” the names appearing in columns B, show how impractical it is to adopt both theory correct. C, or D. accurate and consistent terms. A perusal The most expedient and least confusing In arguing for the adoption by Phar- of the letters from Drs. Prescott, Remsen, change will be to accept E, imperfect as it macy of the nomenclature of modern chem(- Norton, and Simon shows that the best is. Pharmacy will then agree with chem- istry, the writer was met by the objection authorities are divided on the advisability istry, and we may look for uniformity in that such terms as "hydrochloride” required of applying the ammonium theory to the labels. This will require a change of only for consistency such objectionable names nomenclature of alkaloidal salts. The two letters in present pharmacopoeial terms as . He therefore pro- theory is admittedly a good one, even for hydracid alkaloidal salts and no change posed the use of the apostrophe (column ’though in trying to support it we may be in the case of the oxyacid salts. TABULAR SUMMARY A B c D E F G H 1 J Accepted Notation of l.Vpivsentath e Salts. Full Designation — Name of Al- kaloid -|- Name of Acid. Consistent Nat- ural Contrat- tions. Consistent Prac- tical Contrac- tions. Usage of Modern Chemistry. Terms largely Ob- taining in Com- merce. Names Agreeing with Pliarina- copoeial Nom- enclature. Notation Agreeing with the Ammonium Theory. Nomen clature Agreeing with the Ammonium Theory. Names of the Free Alkaloids Ac- cording to Am- monium Theory. Cl, Hn N 04. HC1 Cocaine hydro- gen chloride. Cocaine hydro- chloride. Cocaine ’clioride. Cocaine hydro- chloride. Cocaine muriate. Cocaine hydro- chlorate. C17 H22 O4 Cl Cocainlom chlo- ride. Cocainia. C„ Hu N O,. 11 Br Morphine hydro- gen bromide. Morphine hydro- bromide. Morphine ’bro- mide. Morphine hydro- bromide. Morphine bro- mide. Morphine hydro- bromate. C„ HjoN Oj Br Morpliium bro- mide. Morphia. C11 H*j Nt Oj. HI Strychnine hy- drogen iodide. Strychnine hy- droiodide. Strychnine ’io- dide. Strychnine hy- droiodide. Strychnine io- dide. Strychnine liy- droiodate. C„ H„ Ns Os I Strychnium io- dide. Strychnia. Cjt Hn N 04. HCIO* Cocaine hydro- gen chlorate. Cocaine hydro- chlorate. Cocaine ’chlo- rate. Cocaine chlorate. Cocaine chlorate Cocaine chlorate. C17 H22 N O4 Cl O3 Cocainium chlo- rate. Cocainia. C17 H„ N 0,. HBr O, Morphine hydro- gen bromate. Morphine hydro- bromate. Morphine ’bro- mate. Morphine bro- mate. Morphine bro- mate. Morphine bro- • mate. C17 H20 N O3 Br O3 Morpliium bro- mate. Morphia. Cn Hj, N, Oj. HI Of Strychnine hy- drogen iodate. Strychnine hy- droiodato. Strychn'ne ’io- date. Strychnine io- date Strychnine io- date. Strychnine io- date. Cji Hjj Ns Oj IO3 Strychnium io- date. Strychnia. (C*u lf|4 N, 0,)j. Hj so4 (Quinine hydro- gen sulphate. Quinine hydro- sulphate. Quinine ’sul- phate Quinine sul- phate. Quinine sul- phate. Quinine sul- phate. (Cjo H25 N* Oj)* SO4 Quinium sul- phate. Quinia. Cu H„ N, Oj. HOj Hs0, Physosti g m i n e hydrogen sal- icylate. Phvsostiginine hydrosalicylate. Physostigmine ’salicylate. Physostigmine salicylate. Physostigmine salicylate. Physostigmine salicylate. C15 H22 N3 Oj C7 H5 O3 Pliysostigmium salicylate. Pliysostigmia.