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PHENACETIN , C2H5O•CsH4,NHCOCH1 ( para-acetaminophenetol), aSee also: drug prepared by acetylating para-phenetidin, or by See also: heating para-acetylaminophenol and potassium See also: ethyl sulphate with alcoholic soda to 15o° C
.
Para-phenetidin is prepared by treating the 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•C6H4.OEt->2EtO•C6H4•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 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 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 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 cord, and a depressant action on the See also: 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 theSee also: 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 therapeutic use of phenacetin is as an antineuralgic, and it is of service in migraine, See also: rheumatism of the sub-acute type, intercostal neuralgia and locomotor ataxia
.
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