PHENACETIN

This article appears in Volume V21, Page 364 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: PER-PIG

PHENACETIN , C2H5OCsH4,NHCOCH1 (para-acetaminophenetol), a drug prepared by acetylating para-phenetidin, or by

heating

HEATING

para-acetylaminophenol and potassium

ethyl

ETHYL

sulphate with alcoholic soda to 15o C. Para-phenetidin is prepared by treating the sodium

salt

of para-nitrophenol with

ethyl

ETHYL

iodide, and reducing the nitrophenetol to para-phenetidin or aminophenetol. The yield may be doubled by diazotizing para-phenetidin, coupling with phenol, ethylating and reducing:
EtOCEHeNH2-->EtOCsH4N20H-->EtOCsH4.N2.CEHOH-
EtO C6144N2C6H4.OEt->2EtOC6H4NH2.
It crystallizes from water in colourless plates, melting at 135 C. It is. soluble in about 70 parts of hot and in about 1400 parts of cold water.
Several compounds related to phenacetin have been introduced into

medicine

MEDICINE

. Triphenin is propylphenetidin; lactophenin is lactylphenetidin; pyrantin is para-ethoxyphenyl succinimide, EtOC6H4N[COC112]2; salophen or saliphenin is salicylphenetidin; amygdophenin is mandelylphenetidin. In addition, several other derivatives have been suggested which have a greater solubility than phenacetin, e.g. phesin, which is the sodium

salt

SALT (a common Teutonic word, cf. Dutch zout, Ger. Salz, Scand. salt; cognate with Gr. &Xs, Lat. sal)
BART
- BART, JEAN (1651-1702)
.html">SALT, SIR TITUS, BART

of phenacetin sulphonic acid, apolysin and citrophen (citrophenin), which are citric acid derivatives of para-phenetidin, &c.
Phenacetin is contained in both the British and United States pharmacopoeia, in the latter under the name of acetphenetidin. The dose is 5 to to grs. given in cachets or in suspension. When the drug is carelessly made it may contain impurities, producing considerable irritation of the kidneys. The physiological action of phenacetin consists in a sedative action on the sensory tracts of the spinal cord, and a depressant action on the heart, where it
tends to paralyse the action of the cardiac muscle. Upon the bodily heat it exercises a marked effect, decreasing the action of the heat-producing centre as well as increasing the dissipation of heat, and thus causing a marked fall in temperature. In toxic doses the blood becomes dark and blackish from the formation of methaemoglobin, and the urine is changed in colour from the passage of altered blood. The

chief

CHIEF (from Fr. chef, head, Lat. caput)

therapeutic use of phenacetin is as an antineuralgic, and it is of service in migraine,

rheumatism

RHEUMATISM (from Gr. /56琦, flux)

of the sub-acute type, intercostal

neuralgia

NEURALGIA (Gr. veiipov, nerve, and iXyos, pain)

and locomotor ataxia.

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