Properties and Uses. - Antiseptic, antifermentative, deodorizer, stimulant, typhoid fever, ozaena, eczema, prurigo, herpes, favus, conjunctivitis, chronic laryngitis, otitis, ringworm, psoriasis, scabies, abscesses, acne, diarrhoea, dysentery. Apply in alcoholic solution, 1-2 p. c, or ointment, 10-15 p. c.
1. Naphthalenum. Naphthalene, C10H8, official 1890-1910. - Obtained from coal-tar and purified by crystallization, being formed by the union of 2 benzene groups, so as to have 2 carbon atoms in common; when coal-tar is distilled between 180-250° C. (356-482° F.) and the distillate has deposited gradually a dark crystalline substance, chiefly impure naphthalene, it is treated successively with NaOH and H2SO4 (to remove acid and basic by-products - phenols, aniline, etc.), then purified by distillation in the presence of steam, further heating with H2SO4 and distilling. It is in colorless, shining, transparent laminae, strong characteristic odor of coal-tar, burning, aromatic taste, slowly volatilized and brownish by exposure, insoluble in water, soluble in alcohol (13), freely in ether, chloroform, carbon disul-phide, fixed and volatile oils. Test: 1. On shaking with sulphuric acid should remain colorless, and if heated 5 minutes should not acquire more than a pale reddish tint (abs. of impurities derived from coal-tar). Antiseptic, expectorant, parasiticide, vermifuge; intestinal catarrh, inflammation, typhoid fever, diarrhoea, whooping-cough, chronic bronchitis, bronchorrhoea, wounds, ulcers, scabies, dysentery, prurigo. Dissolved in alcohol and used like spirit of camphor, for sprains, contusions. Should be kept in well-stoppered, amber-colored bottles. Dose, gr. 2-15 (.13-1 Gm.).
6. Benzene Derivatives containing Nitrogen.
By analysis the exact molecular composition of many vegetable alka- . loids has been determined, and inasmuch as many of these are troublesome to extract, hence expensive to the consumer, experimenters have interested themselves in trying to reproduce artificially such substances by joining their elements synthetically in the proper proportions. While this has often been found impracticable, yet the building, substitution, and replacement of elements with such an end in view have been remarkably successful. The greatest satisfaction has resulted from starting with basal products which contain the necessary elements in a condition or form susceptible of ready displacement. The cheapest and most acceptable base so far discovered is coal-tar, of which mention has been made in several connections. In experimenting with coal-tar, myriads of approximate principles or alkaloids have been formed, many of which, although not having the exact formulae, are identical in most respects with its vegetable prototype. Beginning with coal-tar - in the first place it is distilled to obtain benzene, which is converted by nitric acid into nitrobenzene, and into this nascent hydrogen is passed, producing aniline or phenylamine, C6H5NH2:
(1) C6H6+HNO3 + C6H6NO2 + H2O. (2) C6H6NO2 + 6H = C6H5NH2 + 2H20.
Aniline (Ar. anil, indigo - i. e., its brilliant violet and indigo dyes) is therefore the assumed basal product, which is a colorless, oily, alkaline liquid, peculiar aromatic odor, bitter taste, boiling at 181° C.
(359° F.), insoluble in water, poisonous; it is an amine acting like a base, hence combines with acids, forming well-defined salts.
Acetanilidum. Acetanilid. - (Fr.acet(ic) + anil(ine) + id(e) - i. e. referring to its components.) (Syn., Acetanil., Acetanilide, Anti-febrin(um), Phenylacetamide, Antifebrinum, Antifebrin, Acetyl-amidobenzene; Fr. Acetanilide; Ger. Antifebrin.)
Manufacture: This monoacetyl derivative of aniline is obtained from the latter by replacing its hydrogen by the acetic radical - acetyl, C2H3O - by boiling together aniline and glacial acetic acid for 1-2 days; now distil, collect portion passing over at 295° C. (563° F.), and when cool acetanilid congeals - C6H5NH2 + HC2H3O2 = C6H5-NHC2H3O + H2O; purify by repeated crystallization from water. It is in colorless, shining, micaceous, crystalline laminae or powder; odorless; slightly burning taste; permanent, melts at 112° C. (234° F.); soluble in water (190), boiling water (20), alcohol (3.4), boiling alcohol (.6), chloroform (3.7), ether (17), benzene (47), glycerin (5); aqueous solution neutral. Tests: 1. Boil .1 Gm. with potassium hydroxide T. S. (5) - characteristic aniline odor, + chloroform (1), heat - disagreeable odor of poisonous phenylisocyanide. 2. Boil .1 Gm. with hydrochloric acid (2) - clear solution, + aqueous solution of phenol, 1 in 20, (3), + filtered, saturated solution of chlorinated lime (5) - brownish-red, turning deep blue with ammonia water. 3. Aqueous solution + bromine T. S. - white crystalline precipitate; incinerate 2 Gm. - ash .05 p. c. Impurities: Aniline salts, allied, and readily carbonizable substances. Dose, antipyretic, gr. 5 (.3 Gm.), anodyne, gr. 1-2 (.06-.13 Gm.), in pill, tablet, capsule, or in alcohol, then diluted in water; may repeat every 4 hours.
Preparation. - (Unoff.): Pulvis Acetanilidi Compositus: acetanilid 70 Gm., caffeine 10, sodium bicarbonate 20, dose, gr. 5-10 (.3-.6 Gm.).
Properties. - Antipyretic, analgesic, antispasmodic, diuretic (increases excretion of urea and uric acid), diaphoretic. Small doses cause quietness; if large have headache, weakness, ringing in ears, a peculiar cyanosis, somnolence, mydriasis, temperature falls, slow respiration, feeble, irregular pulse, vomiting, profuse sweat, coma, collapse, general paralysis, dark urine, oxygen-carrying power of the blood is diminished, and corpuscles may be destroyed; blue color due to reduction of haemoglobin to methsemoglobin in the blood. In the system acetanilid breaks up into acetic acid and aniline, and this latter oxidizes into paramidophenol. Action is chiefly on heart, liver, and kidneys, causing fatty degeneration; continued use is highly injurious.