Hydroxylamine - Not organic compound with the formula NH2OH. It is a derivative of ammonia (NH3), in which one hydrogen atom is replaced by a hydroxyl group –OH. The name also indicates that the reagent is similar to amines, which are also derivatives of ammonia, but with a hydrocarbon radical instead of one hydrogen atom or atoms.

Hydroxylamine is obtained by chemical synthesis from hydrogen and nitric oxide NO.

Properties

Crystalline powder with colorless, very hygroscopic crystals. Water soluble, from aqueous solution crystallizes out as a crystalline hydrate. Mixes with ethyl and methyl alcohol in any ratio. Insoluble in benzene, chloroform, carbon disulfide and ethers. Easily decomposes when heated into water, nitrogen and ammonia; explodes when heated quickly. In air at normal conditions unstable and gradually decomposes. Melt is a good solvent. Hydroxide, nitrate, sodium chloride dissolve in it; ammonia; iodite and potassium cyanide; many other salts.

From a chemical point of view, hydroxylamine is a weak base, but in reactions it exhibits both acidic and basic properties. It interacts with strong and weak acids, is oxidized by oxygen, and reacts with ketones and aldehydes. Liquid hydroxylamine reacts violently and ignites when interacting with strong oxidizing agents, such as potassium permanganate, barium oxide, chlorine, etc. Reactions with bromine, chlorates, and silver nitrite proceed more calmly. Capable of forming complex compounds and react with alkalis. With sulfuric, hydrochloric and perchloric acid it forms industrially important salts: hydroxylamine hydrochloric acid, hydroxylamine sulfate, hydroxylamine perchlorate.


Precautions

The reagent, as well as its derivatives, is toxic. In addition, hydroxylamine is a carcinogen that can cause cellular mutations. Can be absorbed into the blood through the skin. Contact with skin leads to irritation, skin diseases and suppuration. Ingestion and entry into the blood are dangerous for the nervous system and blood composition (translates hemoglobin into passive methemoglobin and causes the breakdown of red blood cells). Has an inhibitory effect on nervous system. Poisoning with a large dose can lead to convulsions, paralysis, respiratory arrest and, as a result, death.

The victim of poisoning should be given to drink 2-3 glasses of water with table salt dissolved in it (1 tablespoon per glass of water) to induce vomiting. At the first sign of suffocation, give oxygen and methylene blue as an antidote.

If the reagent comes into contact with the skin or eyes, rinse them thoroughly with water.

Hydroxylamine is fire and explosive, melts at t +32 °C, is capable of self-ignition and explosion during long-term storage, increased air temperature, or contact with air. Therefore, it is stored in sealed packaging in temperature-controlled warehouses, away from heat sources and strong oxidizing agents. The room should be cool and well ventilated.

In production, workers must use special clothing: respirators (type Lepestok and Astra-2), goggles, rubber gloves. Workplace and the entire room must be equipped with exhaust ventilation. If possible, operations with the reagent should be carried out automatically, without the presence of people. The air in the work area must be constantly monitored for hydroxylamine concentrations.

For greater safety, it is often not pure hydroxylamine that is transported and used in production, but its salts.

Application

  • In organic synthesis to obtain important connections- such as hydroxylamine sulfate, chloride and perchlorate. In the production of caprolactam.
  • Derivatives of ketones and aldehydes (oximes), hydroxamic acids are used in the manufacture of a large class of compounds used in pharmaceuticals and perfumes, as well as in the production of dyes.
  • When conducting tests inorganic substances; in titrometry of carbonyl compounds.
  • In the quantitative analysis of glucose, camphor, furfural, formaldehyde.
  • In photography, it is added to developers for color films and photographs.
  • In the electronics industry, it is used as a wash in the production of photoresists using lithography.
  • Hydroxylamine nitrate and perchlorate are used in rocket fuel.

if we are talking about medications, for example
10/08/2006 21:59

A hydrochloride of something is most often called a compound of the main
organic matter with hydrogen chloride (hydrochloric acid) HCl.

Most often, the structure of that same organic substance contains
nitrogen (N) in some form (entirely bound to carbon atoms in
heterocycles, for example, or in the form of an amino group Nh3). When conducting
reactions hydrogen (H) from hydrogen chloride “adds” to nitrogen with
the formation of positively charged NH+ (in the case of a heterocycle) or
Nh4+ (in the case of an amino group). And Cl “remains” in the form of Cl-.
In this way, the organic compound is “translated” into the form of a salt, which
usually improves its solubility in polar solvents (water) and,
accordingly, increases bioavailability.

www.ljpoisk.ru

sodium p-guanidinosalicylate hydrochloride – RF patent 2237658

The invention relates to the field of medicine and veterinary medicine and concerns a new compound that has anti-tuberculosis activity and is sodium p-guanidinosalicylate of formula 1. The compound has increased efficacy and reduced toxicity in the treatment of tuberculosis. 1 table

The invention relates to medicine, namely to drugs for the treatment of tuberculosis, as well as veterinary medicine.

The known anti-tuberculosis drug p-aminosalicylic acid (PAS) and its sodium salt(Encyclopedia of Medicines. - 8th ed. edited by Yu.F. Krylov. - M.: “RLS”, 2001, p. 76).

The disadvantages of this drug are its fairly high toxicity and the relatively rapid addiction of Mycobacterium tuberculosis to it.

The anti-tuberculosis drug streptomycin, a derivative of guanidine base, is also known (Encyclopedia of Medicines. - 8th ed. edited by Yu.F. Krylov. - M.: "RLS", 2001, p. 813).

Its disadvantages are its relatively low activity (10-fold doses compared to PAS), as well as harmful effects on the body (damage to the auditory nerve).

The technical objective of the invention is to reduce the toxicity and increase the effectiveness of the drug in the fight against tuberculosis infection.

To solve a technical problem, a new anti-tuberculosis drug was synthesized, which is sodium p-guanidinosalicylate hydrochloride, having the following structural formula:

The essence of the invention is explained as follows.

The new compound retains the physiologically active structure of p-substituted salicylic acid and, in addition, contains a guanidine group in a more stable and less dangerous hydrochloride form, which is also effective against Mycobacterium tuberculosis. The absence of an aniline-type amino group in the guanidino salicylate molecule increases its resistance to oxidation by air and reduces toxicity. As a result, the new drug is a stable crystalline substance white in color, which is easily cleaned by recrystallization from alcohol and washing with acetone.

The molecular weight of the drug is almost twice the molecular weight of the original PAS.

Sodium p-guanidinosalicylate hydrochloride purified in this way is a white crystalline powder with a melting point of 130C.

The salt form provides an additional reduction in toxicity and increased stability of the drug.

The synthesis of sodium p-guanidinosalicylate hydrochloride is carried out in the following way.

A portion of PAS is dissolved in an equimolar amount of strong sodium hydroxide solution. An equimolar amount of ammonium chloride is added to the resulting solution, and the resulting solution is dehydrated to dryness. At the same time, ammonia gas is removed

The resulting hydrochloride salt of sodium p-aminosalicylate is crushed and mixed with a half-molar amount of dicyandiamide. The mixture is heated to a temperature of 150C in an oil bath until completely melted and sodium p-guanidinosalicylate hydrochloride is obtained. The dark-colored reaction product is cooled and dissolved in a small amount of alcohol when heated (50-60C).

The solution is filtered and cooled. In this case, a precipitate of sodium 4-guanidinosalicylate hydrochloride crystallizes from the solution. The crystalline precipitate is filtered and washed several times with acetone, in which it is insoluble, until the colored PAS impurity with its oxidation products is completely removed, dried and analyzed. If necessary, the recrystallization process can be repeated. The minimum retention concentration of the drug for Mycobacterium tuberculosis and oral toxicity for rats are determined. The obtained data are shown in the table.

Example of concrete implementation

A 13.9 g (0.1 mol) portion of p-aminosalicylic acid is dissolved in 10 ml of water along with 4 g of sodium hydroxide, then 5.5 g of ammonium chloride is added to the resulting solution, and the resulting reaction mixture is dried, ground into powder and mixed with 4.2 g (0.05 mol) dicyandiamide. The resulting mixture is heated in a glass in an oil bath at a temperature of 120C. In this case, the mixture melts and turns dark red.

After cooling the melt of the reaction mixture, it is crushed and dissolved when heated to a temperature of 50C in 100 ml of alcohol. The filtered alcohol solution of the reaction mixture is cooled to room temperature. In this case, the formation of a dark-colored precipitate was observed. The precipitate is filtered off and washed 4 times with 20 ml portions of acetone. The result was 18 g of light pink sodium p-guanidinosalicylate hydrochloride with a melting point of 130C and elemental analysis C 8 H 9 N 3 O 3 ClNa.

Calculated, %: C 38.0; N 16.6; Cl 14.0.

Found, %: C 37.7; N 15.9; Cl 14.1.

Sodium p-guanidinosalicylate hydrochloride has been obtained, having the following structural formula:

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Hydrochloride

hydrochloride, -a


Russian spelling dictionary. / Russian Academy Sci. Institute of Russian language them. V. V. Vinogradova. - M.: "Azbukovnik". V. V. Lopatin (executive editor), B. Z. Bukchina, N. A. Eskova and others.. 1999 .

See what “hydrochloride” is in other dictionaries:

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    LINCOMYCIN HYDROCHLORIDE- (Lyncomycini hydrochloridum). Lincomycin is an antibiotic produced by Streptomyces lincolniensis or other related actinomycetes. Synonyms: Neloren, Albiotic, Cillimycin, Lincocin, Lincolnensin, Liocin, Mycivin, Neloren, etc. Available in ... Dictionary of medicines

    Loperamide hydrochloride- Loperamide Chemical compound IUPAC 4 (4 Chlorophenyl) 4 hydroxy N,N dimethyl aa diphenyl 1 piperidine butanamide hydrochloride Gross formula ... Wikipedia

    TETRACYCLINE HYDROCHLORIDE- Tetracyclini hydrochloridum. Synonym: aureomycin. Properties. Crystalline powder yellow, bitter taste, soluble in water up to 1%, poorly soluble in chloroform and acetone. 1 mg of pure drug contains 930 units. Release form. Release... Domestic veterinary drugs

    LEVAMISOL HYDROCHLORIDE 7.5% FOR INJECTION- Action. Anthelmintic from the tetramizole group. Active against nematodes. Application. Deworming of large and small ruminants, as well as pigs. Doses. Levamisole hydrochloride 7.5% for injection is administered in the following doses: cattle... ... Imported veterinary drugs

    ANABAZINE HYDROCHLORIDE- (Anabasinum hydrochloridum). Anabasine is an alkaloid found in the plant Anabasis aphylla L. (barnyard grass), fam. goosefoot (Chenopodiaceae). Chemically it is 3 (piperidyl 2) pyridine. Pharmacological properties are close to... ... Dictionary of medicines

GENERAL INFORMATION

Empirical formula. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . HCl

Molecular weight, kg/kmol. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 36.46

Aggregate state. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . gaseous

Appearance: colorless gas, when released into the atmosphere with moist air, it smokes strongly, forming tiny droplets.

Smell. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . specific, acute

Application: used as a raw material in the production of vinyl chloride and acetylene, synthetic rubber - nairit, ethyl chloride from ethylene, methyl chloride from methyl alcohol and a number of other hydrochloride products

Rumination of organic compounds.

PHYSICAL AND CHEMICAL PROPERTIES

Gas density at 0 °C and 101.3 kPa, kg/m3. . . . . . . . . . . . . . . . . . . . . . . . . . . 1.639

Relative density in air. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .1.268

Boiling point at pressure 101.3 kPa, °C. . . . . . . . . . . . .minus 85.1

Melting point at pressure 101.3 kPa, °C. . . . . . . . . . minus 114.2

Critical temperature, °C. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 51.4

Critical pressure, MPa. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8.26

Specific heat capacity of gas, cal/(g? deg). . . . . . . . . . . . . . . . . . . . . . . . . . . 0.194

Constants of Antoine's equation, in the temperature range minus 136 - minus 73 ° C

A. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 16.5040

IN. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1714.25

WITH. . . . . . . . . . . . . . . . . . . . . . . . . . minus 14.45

:

*T - solid.

Solubility in water under standard conditions, g / 100 g of water:

At 0 °C. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 82.3

At 30 °C. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 67.3

At 40 °C. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 63.3

At 50 °C. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59.6

At 60 °C. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 56.1

It is highly soluble with the release of heat and the formation of hydrochloric acid. Forms a series of liquid hydrates.

Reactivity: soluble in alcohols, diethyl ether, benzene. Strong oxidizing agents oxidize hydrogen chloride to chlorine.

SANITARY AND HYGIENIC CHARACTERISTICS

CAS registration number. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .7647-01-0

Hazard class in the air of the working area. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2

MPCm.r. in the air of the working area, mg/m3. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5.0

Air pollutant code: . . . . . . . . . . . . . . . . .0316

Hazard class in atmospheric air. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 2

MPCm.r./s.s. in atmospheric air, mg/m3. . . . . . . . . . . . . . . . . . . . . . . . . . . 0.2/0.1

Effect on people: toxic. At high concentrations - irritation of mucous membranes, especially the nose; conjunctivitis; corneal clouding. Hoarseness, feeling of suffocation, tingling in the chest, runny nose, cough.

First aid measures for victims of exposure to the substance: immediately take the victim to fresh air, free from clothing that restricts breathing. Oxygen inhalation. Rinse eyes, nose, rinse with 2% solution of baking soda (NaHCO3). Drink warm milk with soda and Borjom, butter or honey.

Precautionary measures: seal containers for storage and transportation. Ventilation of industrial premises in which hydrogen chloride circulates.

FIRE AND EXPLOSION PROPERTIES

Flammability group: . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .non-flammable gas.