328. Hexamethylentetraminum

Hexamethylenetetramine

Urotropinum Urotropin Methenaminum *

C 6 H 12 N 4 M. c. 140.19

Description. Colorless crystals or white crystalline powder, odorless, burning and sweet, and then bitter taste. When heated, it evaporates without melting.

Solubility. Easily soluble in water and alcohol, soluble in chloroform, very slightly soluble in ether.

Authenticity. 2 ml solution of the drug (1: 10) is heated with 2 ml diluted sulfuric acid; there is a smell of formaldehyde. Then add 2 ml 30% sodium hydroxide solution and heated again; there is a smell of ammonia.

acidity or alkalinity. Solution 4 G drug at 10 ml water should be alkaline to litmus and not alkaline to phenolphthalein.

Ammonium salts and paraforms. K 10 ml 5 drops of Nessler's reagent are added to a freshly prepared solution of the drug (1: 20) and heated in a water bath at 50 ° for 5 minutes. Yellow coloring and turbidity of the solution should not appear.

Note. To prepare a solution of the drug (1:20), distilled water that meets the requirements of the State Pharmacopoeia is additionally boiled (up to approximately 1/3 of the volume) until a negative reaction with Nessler's reagent is obtained. The test is carried out as follows: 10 ml water is heated with 5 drops of Nessler's reagent in a water bath at 50 ° for 10 minutes. Yellow discoloration and cloudiness should not appear.

Nessler's reagent is used with a shelf life of not more than one month. organic impurities. In a test tube previously rinsed with concentrated sulfuric acid, pour 2 ml concentrated sulfuric acid, gradually pour 0.1 G drug and shake. The solution should not be colored.

Chlorides. 1.5 G the drug is dissolved in 30 ml water. ten ml the resulting solution must withstand the test for chlorides (not more than 0.004% in the preparation).

sulfates. ten ml of the same solution must pass the sulfate test (no more than 0.02% in the preparation).

Heavy metals. Solution 2 G drug at 10 ml water must withstand the test for heavy metals (no more than 0.00025% in the preparation).

sulfate ash. 0.5 G the drug is placed in a weighed crucible and carefully burned. After cooling the crucible, the residue is moistened with 0.5 ml concentrated sulfuric acid, heated and calcined to constant weight. Sulphated ash should be weightless.

Quantitation. About 0.12 g of the drug (accurately weighed) is dissolved in a conical flask in 10 ml water, pour 50 ml 0.1 N sulfuric acid solution, the mixture is boiled over low heat for 30 minutes and cooled. 2 drops of methyl red solution are added to the cooled liquid and the excess sulfuric acid is titrated with 0.1 N. sodium hydroxide solution until yellow.

In parallel, conduct a control experiment.

1 ml 0.1 n. sulfuric acid solution corresponds to 0.003505 G C 6 H 12 N 4 , which should be at least 99.0% in the preparation.

Storage. In a well sealed container.

Antiseptic, used inside and intravenously.

Note. Hexamethylenetetramine for injection must additionally pass the following tests.

Amines. 2 G the drug is dissolved in 5 ml water, add 0.5 ml acetone and 10 drops of freshly prepared sodium nitroprusside; no pink-violet coloration should appear after 10 minutes.

Ammonium salts and paraforms. Solution 2 G drug at 10 ml water must pass the test for ammonium salts and paraforms.

Urotropin (Hexamine, Hexamethylenetetramine, Methenamine, food additive E239, dry fuel, dry alcohol)- a synthetic drug, an antibacterial drug, a component in the production of plastics and synthetic rubber.

Physiochemical properties.

Chemical formula: C 6 H 12 N 4 . Appearance - colorless rhombic crystals, odorless. Density: 1.27 g/cm3. Melting point 263°C. Decomposition temperature 280°C. When heated, it evaporates without melting. It burns with a pale flame. Aqueous solutions are alkaline. In an acidic environment, it breaks down, releasing formaldehyde.

Solubility of urotropine in various solvents

Solvent	Temperature, °C	Solubility, g/100g solvent
ethanol	12	3,2
	20	2,89
methanol	20	7,25
Acetone	20	0,65
Benzene	20	0,23
Amyl alcohol	20	1,84
liquid ammonia	20	1,3
Glycerol	20	20,5
diethyl ether	20	0,06
xylene	20	0,14
Petroleum ether		Not soluble
carbon disulfide	20	0,17
Carbon tetrachloride	20	0,85
Trichlorethylene	20	0,11
Chloroform	20	13,4
Water	12	81,3
	20	167

Application.

Urotropin is used to grow uterine cultures of yeast. In ready-made yeast, its residue should not be.
Urotropin technical is used in the production of plastics, synthetic rubber, varnish films; in analytical chemistry for the preparation of buffer solutions, for microcrystalloscopic discovery of a number of ions; in the production of explosives (raw material for the production of hexogen) and hexamethylene triperoxide diamine; as a corrosion inhibitor.
It is used in medicine as a drug (antiseptic) for the treatment of the urinary tract and anti-influenza agent.
In the food industry, hexamethylenetetramine is used as an E239 preservative additive. It is used in cheese making, as well as for the preservation of red caviar.
In everyday life, it is used as a dry fuel (“dry alcohol”) for cooking (heating) food, for kindling and calcining stoves, heating cellars, garages, etc. The calorific value is 30.045 MJ / kg.

The use of urotropine as a corrosion inhibitor in the cleaning of thermal power equipment.

For the chemical removal of iron oxide deposits of carbon steels in heat exchangers, various complex inhibitors are used, which include urotropine.

Simultaneous cleaning of the inner surface from iron oxides and degreasing are carried out with an aqueous solution: 0.5% urotropine; 0.5% PB-5 inhibitor; 0.3% OP-7. This solution protects steel at temperatures above 60 °C. The dissolution rate of steel under scale (at 80 °C) is 15 g/m 2 *h.

For Steel 20 and static tensile stresses up to 220 MPa, a washing solution of 4% hydrochloric acid with the addition of 0.5% urotropine and 0.5% PB-5 is used.

To clean the scale of high-temperature boilers with a significant reduction in the hydrogenation of boiler steel, a solution can be used: 3% hydrochloric acid; 1% sulfuric acid; 0.3% catapine; 0.5% urotropin. The temperature of the working solution is 80°C.

The surface of heat exchange equipment made of L-62 brass is cleaned from iron-copper deposits by washing with a 3% hydrochloric acid solution containing 0.05% Fe 3+ and Cu 2+ (temperature 60-80 ° C, solution velocity 1 m / s ) with the addition of inhibitors: 0.5% PB-5; 0.15% urotropine; 0.96% sodium thiosulfate. The dissolution rate of brass under deposits at 80°C is 13.8 g/m 2 *h, and at 60°C it is 6 g/m 2 *h.

Etching of metals is a preparatory operation before applying paints, protective and decorative films to metal surfaces, as well as before coating them with other metals. The final result of all work depends on the quality of etching.

Etching allows you to remove contaminants firmly adhered to their surface (rust, scale and other corrosion products) from metal parts. The main purpose of etching is the removal of corrosion products; while the base metal should not be etched.

In recipes for etching, solutions of acids are used: nitric, sulfuric, hydrochloric, orthophosphoric, acetic. To prevent metal etching, special additives are introduced into the solutions. Urotropin refers to such additives. Urotropin is characterized by versatility of application for all the above solutions of acids and their combinations. 0.5 g of urotropine per 1 liter of acid solution is added to all etching solutions.

Urotropin is used to preserve a limited number of food products (non-mass consumption products). This is due to the danger of urotropin for human health. In particular, for the preservation of fish eggs, urotropine is used at a concentration of up to 1000 mg/kg of the product.

Urotropin contains formaldehyde, which is its active principle. When urotropin is reformed, formaldehyde is cleaved off. Formaldehyde is a strong disinfectant. It is not recommended as a food additive by the Joint FAO/WHO Committee on Food Additives. Formaldehyde actively interacts with proteins and forms difficult-to-cleave protease complexes with them. In this case, the hardening of proteins occurs. This phenomenon is used in the storage of histological preparations.

Receipt.

Urizol is produced by the contact conversion of methanol to formaldehyde, which reacts with ammonia in the liquid phase to form urotropin crystals, followed by its isolation by precipitation and centrifugation, drying and stabilization with silicon dioxide.

General
Systematic Name	1,3,5,7-tetraazotricyclodecane
Traditional names	Urotropin, methenamine
Chem. formula	C 6 H 12 N 4
Physical properties
Molar mass	140.2 g/mol
Classification
Reg. CAS number	100-97-0
PubChem
Reg. EINECS number	202-905-8
SMILES
InChI
Codex Alimentarius	E239
CHEBI
ChemSpider
Data is based on standard conditions (25 °C, 100 kPa) unless otherwise noted.

Getting and properties

First obtained by the Russian chemist A. M. Butlerov in 1859. It is formed by the interaction of ammonia (4 mol) with formaldehyde (6 mol). Structurally similar to adamantane.

White crystalline substance with the smell of rotten fish, sweet in taste, sublimes at 270 °C. Hygroscopic, easily soluble in water, alcohol, soluble in chloroform and carbon disulfide, sparingly soluble in diethyl ether. A solution of urotropine in water has an alkaline reaction. Urotropine crystallizes from ethanol in the form of colorless shiny rhombohedrons, sublimes in vacuum almost without decomposition, and dissolves in water with the release of heat and with the formation of a hexahydrate. In warm water, urotropin is less soluble than in cold water, and in ethyl alcohol, on the contrary, urotropin is more soluble in hot water than in cold water.

When interacting with alkali, urotropin releases ammonia, which is easily detected. With acids, it forms crystalline compounds that are soluble in water. Reacts with hydrogen peroxide in the presence of organic acids or nitric acid to form hexamethylene triperoxide diamine. It has a very high reactivity and forms many salts, with phenols gives addition products. When set on fire, it burns with a calm, non-smoking flame; flammable but not explosive. The heat of combustion is 30.045 MJ/kg.

The largest producer of urotropine in Russia is Gubakhinsky OAO Metafrax.

Application

Polymer production

It is used in the production of phenol-formaldehyde resins. Urotropin is also used in the production of protein and other plastics as a substitute for formaldehyde.

The medicine

Hexamethylenetetramine is one of the few synthetic drugs currently in use with more than 100 years of history: it began to be used at the turn of the 19th-20th centuries. The drug has an antiseptic effect, mainly in the urinary tract. It is used in pure form and as part of combined medicines (for example, calcex). In its pure form, hexamethylenetetramine is administered orally or intravenously, in the form of salts: hippurate, indigo carminate or camphorate. The mechanism of action is based on the release of free

Hexamethylenetetramine. Urotropine Hexamethylentetraminum

Hexamethylenetetramine is a product of the interaction of a formaldehyde solution with ammonia. It was first obtained by A. M. Butlerov (1860), but only 35 years after the discovery it began to be used in medicine. Raw material for semi-

Hexamethylenetetramine is treated with a 40% solution of formaldehyde in water and ammonia water. 25% ammonia water is added to the formaldehyde solution, the mixture is stirred and the temperature is maintained within 40-50 °C.

After completion of the reaction, the medium of the reaction mixture should “be alkaline and smell of ammonia. Activated carbon is added to the mixture, it is filtered, the filtrate is evaporated in vacuum to a mushy mass. Upon cooling, crystals of hexamethylenetetramine crystallize. They are sucked off, washed and dried at a temperature of 30-35 °C. The resulting hexamethylenetetramine is recrystallized from alcohol.

Hexamethylenetetramine is a white crystalline powder, highly hygroscopic. Has no smell. The taste is burning, at first sweet, then bitter. The drug is readily soluble in water and alcohol, soluble in chloroform, almost insoluble in ether. Aqueous solutions of hexamethylenetetramine have a slightly alkaline reaction. When heated, they evaporate without melting. When heated aqueous solutions of hexamethylenetetramine, it hydrolyzes with the formation of formaldehyde and ammonia.

In an acidic environment, hexamethylenetetramine decomposes with the release of formaldehyde. When an alkali solution is added to the reaction mixture, the smell of ammonia is felt.

This reaction is given by GF X as a reaction of authenticity to .hexamethylenetetramine.

When heated with salicylic acid in the presence of concentrated sulfuric acid, a violet-red color is formed.

The reaction is based on the release of formaldehyde, which, with salicylic acid in the presence of sulfuric acid, forms an aurine dye (see Authenticity reactions Solutio Forma ldehydi)

Hexamethylenetetramine is a single acid base,

tertiary nitrogen gives it its basic properties, therefore it forms double salts with acids, for example, hexamethylenetetramine hydrochloride (CHL^-HC!. The presence of tertiary nitrogen, like in alkaloids, also causes the formation of picrates (yellow precipitate), tetraiodides (CH 2) in ^-14 and other reaction products.Hexamethylenetetramine has the ability to give complex compounds with salts of silver, calcium and phosgene.

With regard to the good quality of the drug, GF X requires the absence of organic impurities and impurities of ammonium salts (yellow staining should not appear from adding the drug to the solution when Nessler's reagent is heated), paraform impurities (clouding of the solution from adding Nessler's reagent when heated). Impurities of chlorides, sulfates, heavy metals are allowed within the limits of the corresponding standards.

The quantitative content of the drug can be determined by the method of neutralization. A sample of the drug is heated with a certain amount of titrated sulfuric acid solution, after cooling the mixture, the excess acid is titrated with alkali over methyl red. In parallel, under the same conditions, a control experiment is carried out (pharmacopoeial method).

Hexamethylenetetramine as a base can be titrated with acid against a mixed indicator (methylene blue and methyl orange) until the color changes from green to blue-violet.

This method is less accurate than the first one, but it is widely used in express analysis of drug mixtures.

Hexamethylenetetramine is used as a disinfectant. Its action is based on the formation of formaldehyde in an acidic environment, which has a disinfecting effect. Used for urinary tract infections. It should be borne in mind that if the urine does not have an acidic reaction, the drug is ineffective, since it will not split into formaldehyde. Along with the antiseptic effect, hexamethylenetetramine also exhibits to some extent an anti-odagra effect, therefore it is also used for rheumatism.

Hexamethylenetetramine is also widely used as an anti-influenza agent. The drug is administered orally in powders and tablets and intravenously as a 40% solution.

Available in powder and tablets of 0.25 and 0.5 g, as well as in 5-10 ml ampoules of a 40% solution. Store in well-closed jars.

In the modern world, absolutely every person at least once had some kind of infectious disease caused by a certain pathogenic microorganism. One of the most common localizations of bacteria in the human body is the urinary system. When these organs are affected, unpleasant symptoms occur, such as:

If one or more of these signs occur, you should immediately contact a urologist who will prescribe the appropriate tests and carry out the necessary treatment.

So, for example, Urotropin is often used in such cases. What kind of drug is it, what is its formula, and what is part of "Urotropin" will be discussed in detail below.

Description

The drug, which is produced by the Russian plant OJSC Metafrax, located in the Perm Territory, the city of Gubakha, has a substance called methenamine as the main active ingredient.

Outwardly, it is a powder, consisting of white rhombic crystals, and also having a slight specific smell and sweet taste.

A characteristic feature of the drug is its rich history of use in medicine. It has about a hundred years, that is, for about a century the drug has been helping to effectively cope with certain ailments.

Formula

"Urotropin" by its chemical nature belongs to the class of polycyclic amines. These are organic substances, which contain several benzene rings, as well as nitrogen atoms.

The full name of the chemical formula "Urotropin" is 1,3,5,7-tetraazotricyclo-decane.

If we talk about how the atoms of nitrogen, which is part of the drug molecule, are located, then their location is as follows.

This is called the structural formula "Urotropin", looking at which you can clearly see how the nitrogen atoms are connected to each other by carbon bonds.

However, it often happens that such spellings of a substance are not always convenient. Therefore, the short formula "Urotropin" is often used - C 6 H 12 N 4.

Thus, methenamine consists of carbon and hydrogen atoms. In addition, the formula "Urotropin" includes four more nitrogen atoms.

Components of the drug

Most often in medical and veterinary practice, a solution for injection is used. Next, we will analyze in more detail the composition of "Urotropin".

Instructions for use indicate that it includes:

• Methenamine is the active ingredient.
• Water for injection - as a solvent.

Release form

On the pharmaceutical market, the drug is presented in several forms:

1. Injection solution for intravenous administration, having a concentration of 40%.
2. Powder, which is packaged in bags.
3. Tablets of 0.25 and 0.5 gr.

Indications for use

"Urotropin" is a universal drug. In addition, it has a rather diverse list of conditions in which its use is relevant. These include:

• Infectious diseases of the urinary system (cystitis, pyelitis, pyelonephritis).
• Hyperhidrosis. The drug is effectively used to eliminate sweating of the armpits, palms and feet.
• "Urotropin" is widely used in veterinary medicine. Possessing an anti-inflammatory effect, it is able to quickly eliminate diseases of the kidneys, bladder, and mammary glands in cattle.

Contraindications for use

Like any other drug, "Urotropin" has a number of contraindications, namely:

• Children's age up to 6 years.
• Individual intolerance to the drug.
• Renal or liver failure.
• Dehydrated state of the body.

Use during pregnancy and during breastfeeding

There are no scientifically proven data on the safety of women during this period, so it is better for this group of people to refrain from treatment with Urotropin.

Side effects

In some cases, Urotropin can have a negative effect on the body, especially on the function of the kidneys and bladder.

The main unwanted side reactions are as follows:

• An allergic reaction in the form of an itchy rash on the skin. This symptom quickly and without a trace disappears after discontinuation of the drug.
• Hematuria is the appearance of blood in the urine.
• Proteinuria is the appearance of protein in the urine.
• Frequent urination.

If such negative reactions occur, you should immediately consult a doctor in order to resolve the issue of stopping treatment with Urotropin or adjusting its dosage.

Storage conditions

The drug should be stored in a dry place, at a temperature not exceeding 25 degrees, away from sunlight and out of reach for children.

Terms of dispensing from pharmacies

"Urotropin" is a prescription drug, so it cannot be found in the public domain. When selling it, the pharmacist (or pharmacist) will definitely ask for a prescription form, which the attending physician must write out.

Medication cost

"Urotropin" (formula C 6 H 12 N 4) is a cheap drug. Its cost does not exceed 100 rubles per package.

Conclusion

"Urotropin" is a unique drug with a wide spectrum of action.

The main advantages of the drug are its low cost, as well as high efficiency, time-tested.

The disadvantage is the presence of a whole list of side effects, due to the occurrence of which some patients have to stop the course of treatment with Urotropin and go to the doctor again to replace the medication.

It should be remembered that the remedy can negatively affect the body, therefore it is unacceptable to use it independently without a prescription from a doctor.