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Antipyrine structural formula. The meaning of the word antipyrine in the reference book of medicines

AntipyrineAntipyrinum

1- Phenyl-2,3-dimethylpyrazolan-5,

The starting product for the synthesis of antipyrine is acetoacetic ester and phenylhydrazine.

Acetoacetic ester is obtained by condensation of two molecules of ethyl acetate in the presence of sodium ethylate.

Antipyrine

Antipyrine is colorless crystals of silt, white crystalline powder, slightly bitter taste, odorless. Very easily soluble in water, easily in alcohol, chloroform, difficultly soluble in ether.

The authenticity of the drug is determined by: a) the reaction of the formation of nitrozoantipyrine (emerald green color) when the drug interacts with a solution of sodium nitrite in an acidic environment.

pitrosoantipyrine

b) reaction with a solution of ferric oxide chloride; is formed; intense red coloration due to formation! complex salt - ferripyrine.

The quantitative content of antipyrine is determined by the iodometric method, which is based on the ability of antipyrine to react with halogens due to the mobile hydrogen in position 4 of the molecule.

Titration of a sample of the drug with iodine is carried out in the presence of sodium acetate, which binds the released hydroiodic acid and thereby prevents the reversibility of the reaction.

The iodopyrine formed during the reaction can absorb a certain amount of iodine on its surface, so alcohol or chloroform is added, which dissolve the resulting iodopyrine.

Antipyrine is used as an antipyretic, analgesic and sedative. Use for headaches, neuralgia, rheumatism.

Available in powder and tablets of 0.25 g.

Antipyrine can easily react with acids, phenols, aldehydes, and mercury salts. Reacting with some of these substances, antipyrine turns into a liquid state, which must be taken into account when prescribing prescriptions. List B.

Antipyrine

ANTIPYRIN (Antipyrinum). 1-Phenyl-2, 3-dimethylpyrazolone-5.

Synonyms: Analgesin, Anodynin, Azophen, Methozin, Parodyne, Phenazonum, Phenazone, Phenylon, Pyrazoline, Pyrodin, Sedatin, etc.

Colorless crystals or white crystalline powder, odorless, slightly bitter taste. Very easily soluble in water (1:1), easily soluble in alcohol. Solutions (pH 6.0 - 7.5) are sterilized at + 120 C for 20 minutes.

Antipyrine was one of the first synthetic analgesics, pyrazolone derivatives, to find use in medicine (1884). With the introduction of other analgesics, they began to be used relatively rarely. It is not widely used at present. However, it did not completely lose its meaning and remained in the nomenclature of medicines.

Like other pyrazolone derivatives, antipyrine has an analgesic, antipyretic and, to varying degrees, anti-inflammatory effect. In terms of analgesic and antipyretic activity, drugs in this group are close to salicylic acid derivatives. Pyrazolone derivatives reduce capillary permeability and prevent the development of an inflammatory reaction. The mechanism of this action is not clear. These compounds do not have an effect on the pituitary-adrenal system.

The most active anti-inflammatory drug in this group, butadione, relatively strongly inhibits the biosynthesis of prostaglandins. It belongs to the group of non-steroidal anti-inflammatory drugs.

Antipyrine has moderate analgesic, antipyretic and anti-inflammatory effects. When applied topically, some hemostatic effect is noted.

Antipyrine is used for neuralgia and colds.

Give adults 0.25 - 0.5 g orally; children over 6 months - 0.025 - 0.15 g per dose, depending on age. Take 2 - 3 times a day.

Higher doses for adults orally: single dose 1 g, daily dose 3 g.

As a hemostatic agent, antipyrine is sometimes used (10 - 20% solution) to wet tampons and napkins for nasal and parenchymal bleeding.

When prescribing antipyrine, the possibility of increased sensitivity of patients to the drug with the appearance of urticaria and a fixed rash should be taken into account; Possible inhibition of hematopoiesis (see Amidopyrine).

Release forms: powder and tablets of 0.25 g.

For use in pediatric practice, tablets of 0.05 are produced; 0.075; 0.1 and 0.15 g.

Storage: List B. In a well-closed container, protected from light.

Rр.: Tab. Antipyrini 0, 25 N. 10

D.S. 1 tablet 2 - 3 times a day

Rp.: Sol. Antipyrini 10% 30 ml

D.S. For moistening tampons in cases of nosebleeds

Tablets > (Tabulettae >).

Composition: antipyrine and phenacetin 0.25 g each, caffeine-sodium benzoate 0.05 g. Analgesic and antipyretic. Prescribe 1 tablet 1 - 2 - 3 times a day.

Storage: list B.

Directory of medicines. 2012

See what "ANTIPYRIN" is in other dictionaries:

Antipyrine... Spelling dictionary-reference book

- (Antipyrinum). 1 Phenyl 2,3 dimethylpyrazolone 5. Synonyms: Analgesin, Anodynin, Azophen, Methozin, Parodyne, Phenazonum, Phenazone, Phenylon, Pyrazoline, Pyrodin, Sedatin, etc. Colorless crystals or odorless white crystalline powder,... ... Dictionary of medicines

antipyrine- a, m. antipyrine f. honey. White powder with a slightly bitter taste; antipyretic agent. Pavlenkov 1911. Antipyretic and analgesic. SIS 1954. Medicine is enriched by the discovery of new fever-reducing drugs. To replace salicylic acid... ... Historical Dictionary of Gallicisms of the Russian Language

ANTIPYRINE- Antipyrinum. Synonyms: analgesia, azophen, metozin, pyrazoline, sedatin, phenazone. Properties. Colorless crystals or white crystalline powder, odorless, slightly bitter taste. Very easily soluble in water (1:1) and alcohol. Solutions have a weak... Domestic veterinary drugs

ANTIpyRINE, a chemical solution containing boric acid and borax. Flammable substances are impregnated with the solution to slow down the combustion process. During construction, the risk of fire is reduced by using... ... Scientific and technical encyclopedic dictionary

ANTIpyRINE, antipyrine, many others. no, husband (from Greek anti against and pyr fire, heat) (apt.). Antipyretic and analgesic. Ushakov's explanatory dictionary. D.N. Ushakov. 1935 1940 ... Ushakov's Explanatory Dictionary

ANTIPYRINE

ANTIPYRIN (Antipyrinum). 1-Phenyl-2,3-dimethylpyrazolone-5. Synonyms: Analgesin, Anodynin, Azophen, Methozin, Parodyne, Phenazonum, Phenazone, Phenylon, Pyrazoline, Pyrodin, Sedatin, etc. Colorless crystals or white crystalline powder, odorless, slightly bitter taste. Very easily soluble in water (1:1), easily soluble in alcohol. Solutions (pH 6.0 - 7.5) are sterilized at + 120 C for 20 minutes. Antipyrine was one of the first synthetic analgesics, pyrazolone derivatives, to find use in medicine (1884). With the introduction of other analgesics, they began to be used relatively rarely. It is not widely used at present. However, it did not completely lose its meaning and remained in the nomenclature of medicines. Like other pyrazolone derivatives, antipyrine has analgesic, antipyretic and, to varying degrees, anti-inflammatory effects. In terms of analgesic and antipyretic activity, drugs in this group are close to salicylic acid derivatives. Pyrazolone derivatives reduce capillary permeability and prevent the development of an inflammatory reaction. The mechanism of this action is not clear. These compounds do not have an effect on the pituitary-adrenal system. The most active anti-inflammatory drug in this group, butadione, relatively strongly inhibits the biosynthesis of prostaglandins. It belongs to the group of non-steroidal anti-inflammatory drugs. Antipyrine has moderate analgesic, antipyretic and anti-inflammatory effects. When applied topically, some hemostatic effect is observed. Antipyrine is used for neuralgia and colds. Give adults 0.25 - 0.5 g orally; children over 6 months - 0.025 - 0.15 g per dose, depending on age. Take 2 - 3 times a day. Higher doses for adults orally: single 1 g, daily 3 g. As a hemostatic agent, antipyrine is sometimes used (10 - 20% solution) for wetting tampons and napkins for nasal and parenchymal bleeding. When prescribing antipyrine, the possibility of increased sensitivity of patients to the drug with the appearance of urticaria and a fixed rash should be taken into account; Possible inhibition of hematopoiesis (see Amidopyrine).

Available: powder and tablets of 0.25 g. For use in pediatric practice, tablets of 0.05 are produced; 0.075; 0.1 and 0.15 g.

Store: List B. In a well-closed container, protected from light. Rр.: Tab. Antipyrini 0.25 N. 10 D.S. 1 tablet 2 - 3 times a day Rp.: Sol. Antipyrini 10% 30 ml D.S. For wetting tampons during nosebleeds Tablets "Ankofen" (Tabulettae "Ancophenum"). Ingredients: antipyrine and

Chemical properties

The characteristic properties of Schiff bases are associated with the polarity of the -C=N- group, the structure of which can be described by the resonance of the structures, this indicates that the -C=N- group has two centers: nucleophilic and electrophilic:

Electrophilic reagents react with Schiff bases at the nitrogen atom. Iminium salts are formed with strong acids and alkyl halides (the reaction is carried out in an anhydrous environment due to the rapid hydrolysis of the latter); with acid chlorides and acid anhydrides - addition products that, in the presence of triethylamine, are converted into azetidinones:

Reactions with nucleophiles occur at the carbon atom. In the presence of dilute acids, Schiff bases hydrolyze to amines and ketones; in an alkaline environment, most are stable; add amines; react with Grignard reagents and organolithium compounds in a similar way to carbonyl compounds:

Schiff bases are characterized by cycloaddition reactions. Thus, aziridines are formed with carbenes (reaction 1), with ketenes - lactams (2), with phosphorus ylides (the reaction proceeds according to the Wittig reaction type) - alkenes and iminophosphoranes (3), with 1,3-dipolar compounds - five-membered cycloproducts ( 4, 5):

Oxidation of Schiff bases leads to the formation of carbonyl compounds; at low temperatures, oxaziridines can be obtained:

Schiff bases are also reduced to the corresponding amines by the action of formic acid. This type of reduction of azomethines is believed to be a key step in the synthetically important reductive alkylation of ammonia and amines with aldehydes and ketones in the presence of formic acid (Leuckart reaction) or formic acid in combination with formaldehyde (Eschweiler-Clark reaction).

Application

Schiff bases are used in organic synthesis, mainly for the preparation of heterocyclic compounds and secondary amines; to protect the aldehyde group, for example, during the cyclization of terpenes; in analytical chemistry - for the identification of aldehydes and primary amines. Schiff's bases, known as azomethine dyes, are used to dye acetate and synthetic fibers and are also used in color photography to reduce the light sensitivity of photographic emulsions.

Antipyrine, concept, properties, application

Antipyrine (phenazone; 2,3-dimethyl-1-phenyl-3-pyrazolin-5-one), molecular weight - 188.23; bitter-tasting crystals; melting point = 113°C, boiling point 319°C. It is highly soluble in water, ethanol, chloroform, acetone, and poorly soluble in diethyl ether and toluene.

Weak one-acid base, pK a 1.5. Antipyrine is capable of electrophilic substitution; easily condenses with aldehydes to form diantipyrylmethanes; with ketones containing electron-donating substituents, it produces so-called antipyrine dyes such as chromium pyrazoles; combines with diazo compounds to form azo dyes. Forms complex compounds with rare earth elements, transition metals and other elements.

Antipyrine, used as an antipyretic, anti-inflammatory and analgesic; to obtain amidopyrine, analgin; in the synthesis of analytical reagents; reagent for gravimetric determination of Cd, Sc, W, nephelometric determination - Hg, Cd, Bi, Sb, P, photometric determination - K, Ca, Co, Fe, NO 2, for extraction separation of Co, Pd, Au, In, Zr, Th. Especially widely used for the photometric determination of Mo(VI), Ge(IV), W(VI).

It was first obtained by Knorr in 1883 as a result of the search for antipyretics to replace quinine.