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PHENACETIN

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Originally appearing in Volume V21, Page 364 of the 1911 Encyclopedia Britannica.
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PHENACETIN , C2H5O•CsH4,NHCOCH1 (See also:

para-acetaminophenetol), a See also:drug prepared by acetylating para-phenetidin, or by See also:heating para-acetylaminophenol and See also:potassium See also:ethyl sulphate with alcoholic soda to 15o° C. Para-phenetidin is prepared by treating the See also:sodium See also:salt of para-nitrophenol with 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: EtO•CEHeNH2-->EtO•CsH4•N20H-->EtO•CsH4.N2.CEH•OH- EtO• C6144•N2•See also:C6H4.OEt->2EtO•C6H4•See also:NH2. It crystallizes from See also:water in colourless plates, melting at 135° C. It is. soluble in about 70 parts of hot and in about 1400 parts of See also:cold water. Several compounds related to phenacetin have been introduced into See also:medicine. Triphenin is propylphenetidin; lactophenin is lactylphenetidin; pyrantin is para-ethoxyphenyl succinimide, EtO•C6H4•N[CO•C112]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 of phenacetin sulphonic See also:acid, apolysin and citrophen (citrophenin), which are citric acid derivatives of para-phenetidin, &c. Phenacetin is contained in both the See also:British and See also:United States See also: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 See also:action of phenacetin consists in a sedative action on the sensory tracts of the See also:spinal See also:cord, and a depressant action on the See also:heart, where it tends to paralyse the action of the cardiac muscle.

Upon the bodily See also:

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 See also:blood becomes dark and blackish from the formation of methaemoglobin, and the urine is changed in See also:colour from the passage of altered blood. The See also:chief therapeutic use of phenacetin is as an antineuralgic, and it is of service in migraine, See also:rheumatism of the sub-acute type, intercostal See also:neuralgia and locomotor ataxia.

End of Article: PHENACETIN

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