AMINES — a class of the nitrogen-containing organic compounds which are substitution products of one or several hydrogen atoms in molecules of ammonia (NH 3 ) or volatile caustics (NH 4 OH) on organic radicals.
Many And. have high biological activity (tyramine, serotonin, a histamine, etc.). In a molecule ammonia (see) it is possible to replace with a radical (R) one, two or three of hydrogen atom, and in volatile caustic — four hydrogen atoms and to receive amines of the following four types:
On character of the radicals connected with a nitrogen atom, And. subdivide on And. fat (e.g., methylamine), alicyclic (e.g., cyclohexylamine), aromatic (e.g., aniline) and heterocyclic row (e.g., amine pyridine). Diamines support two, and polyamines — several amine groups at various carbon atoms. One of the most widespread methods of synthesis And. a fatty series it is based on use of interaction of ammonia with halide derivative:
And. an aromatic series receive almost only by N. N. Zinin's method — recovery of nitro compounds:
Methylamine, dimethylamine and trimethylamine — gases, the highest And. — the substances deprived of a smell. Solubility And. in water decreases in process of increase in molecular weight. In total And. have properties of the bases and are capable to formation of salts with acids.
In the course of a biological pnaktivirovaniye And. the important role belongs to reaction of oxidizing deaminations (see). This reaction is catalyzed monoamine oxidase (see), oxidizing monoamines, and diaminoxidase, or the histaminase oxidizing a histamine and other diamines. At effect of these enzymes A. (see. Aminoxidases ) turn into aldehydes:
Formed at deamination And. aldehydes quickly are exposed to oxidation in the corresponding acids which have no pharmacological activity.
In a human body and animals by decarboxylation of some amino acids the connections called by biogenic amines are formed:
This process is catalyzed decarboxylases (see) under the influence of which of pharmacological rather inert amino acids (a histidine, tyrosine, etc.) are formed And., the making strong impacts on an organism, e.g. tyramine (see), histamine (see), and also participating in the transformations leading to formation of biologically active compounds: serotonin (see), adrenaline (see), sincaline (see), etc. From glutaminic to - you in an organism are formed γ-aminobutyric to - that to - that to - that, playing an important role in activity of c. N of page. Consider that γ-aminobutyric to - that to - that to - that is a natural inhibitive factor in nervous cells.
All connections stated above play extremely important role as stimulators or as inhibitors (see) various aspects of activity of an organism. In normal conditions biogenic And. are oxidized monoaminoxidases, turning into aldehydes which are removed then with urine.
Amines of an aliphatic (fat) series — the gaseous, liquid or solid matters possessing a pungent ammoniac smell. Are applied in production of vulcanization accelerators, pharmaceuticals, dyes. The lowest And. malotoksichna; with increase a pier. weight toxic action, first of all on c. the N of page, increases. Besides, under influence And. there are changes in blood (reduction of amount of hemoglobin and erythrocytes, a reticulocytosis) and functions of a liver and kidneys. And. irritate skin p mucous membranes of respiratory tracts and eyes. Threshold of irritant action gaseous And. and their vapors on mucous membranes of the person makes: for methylamine — 10 mg, dimethylamine — 50 mg on 1 m 3 air. The highest And. get through the unimpaired skin. Ethylene diamine and the highest And. possess allergenic action. Under production conditions at concentration in air of diisopropyl amine of 200 — 500 mg/m 3 working had a headache, nausea, «foggy sight». At contact with And. working have dermatitis.
Amines of an alicyclic (polymethylene) row — gaseous or liquid substances; are applied at organic synthesis, in production of insecticides p inhibitors of corrosion. Have the expressed toxicity, sharp irritant action on skin. The cases of serious production poisoning cyclohexylamine which are followed by vomiting, a diarrhea, block of reactions, expansion of pupils are described. The same changes of blood are found in an experiment on animals, as at action aliphatic And., with formation of a methemoglobin.
Arylamines — the liquid and solid matters which are applied in anilinocolourful, chemical pharmaceutical industry, production of rubbers, plastic, insecticides in the perfumery, soap-producing and textile industry. They are much more toxic, than aliphatic A. Sposobna to cause acute, subacute and hron. poisonings. Poisonings at penetration through the unimpaired skin — idiosyncrasy aromatic And. In operation And. on an organism are most typical formation of a methemoglobin (see. Methemoglobinemia ) and degenerative changes of erythrocytes (Heinz's little body).
At acute poisoning And. the symptomatology testimonial of defeat of a nervous system and disturbances of mentality is characteristic: increase in tendon jerks, expansion of pupils, hyperphrenia (aniline), tremor (dimethyl aniline), nystagmus, fibrillar twitching of language (phenylhydrazine), disturbances of mentality (hexil), etc.
At hron. poisoning And. the increased nervous irritability, emotional instability, vegetative dystonia is noted.
For action of the majority And. professional dermatitis and eczemas are very characteristic. At workers of the anilinocolourful industry the professional tumors of a bladder connected with impact on an organism of β-naphthylamine were observed ((((((((((see. Beta naphthylamine ), α-naphthylamine, benzidine (see) and dianizidinsulfat. In the USSR production of such carcinogenic substances as β-naphthylamine, 4 dimethylaminoazobenzene, ο-aminoazotoluene, dark red and yellow fat colors — are stopped (see. Azoic dyes , Dyes ). Use And., suspicious in the cancerogenic relation (see. Oncogenous substances ), it is allowed on condition of the maximum automation of technological processes, sealing of the equipment, use of protective clothes (see. Clothes protective ), gloves or mittens, impenetrable for liquids and dust, gas masks or respirators (see. Gas masks ).
Treatment-and-prophylactic actions include preliminary and periodic medical examinations working (see. Medical examination ), additional preventive foods, sanatorium treatment, temporary or constant transfer for other work of the persons who got occupational disease, etc.
Work of women by production and use aromatic And. in the USSR it is prohibited.
For diagnosis of poisonings And. clinical laboratory methods of a research are used: determination of content in blood of hemoglobin, erythrocytes, methemoglobin and Heinz's little bodies. At poisoning aniline (see) diagnostic value has detection in biosubstrates of its metabolite — p-aminophenol. At medical examinations at working with And. define amount of hemoglobin, leukocytes and ROE, during the work with aniline, besides, bilirubin in blood (see, e.g., Wang - den - Berg reaction ) also carry out sedimentary tests; working with aromatic And. are exposed tsistoskopiya (see).
First aid at poisoning with amines — removal from the workshop, release from the contaminated clothes, washing of the contaminated site of skin alcohol or in 1 — 2% solution acetic to - you, then warm water with soap (the hot shower is contraindicated). Inhalation of oxygen and Carbogenum. According to indications — bloodletting, intravenous administration of 40% of solution of glucose, 20% of solution of sodium hyposulphite, cardiacs.
Maximum allowable concentration in air of a working zone, (CH 245 — 71) specified in «Sanitary standards of design of the industrial enterprises» for more than 30 A. and their derivatives, are various depending on degree of their danger: from 0,1 mg/m 3 (aniline) to 100 mg/m 3 (triftor ethyl amine).
Chemical definition of the lowest aliphatic And. in air it is based on reaction with p-nitrobenzene diazonium, 2,4 dinitrobenzene chloride; definition of the highest And. — on reaction with methyl orange. Methods of definition aromatic And. (aniline, benzidine, α-and β-naphthylamines, etc.) are based on reactions of formation of azoic dyes.
Bibliography: Zbarsky B. I., Ivanov I. I. and Mardashev S. R. Biological chemistry, L., 1972; Nenitsesku K. D. Organic chemistry, the lane from Romanians., t. 1, M., 1963; Filippevich Yu. B. Fundamentals of biochemistry, M., 1969.
And. — professional harm — Bykhovskaya M. S., Ginzburg S. L. and Halizova O. D. Methods of definition of harmful substances in air, page 329, M., 1966; Harmful substances in the industry, under the editorship of N. V. Lazarev of t of 1 page 521, 537, L., 1971; Gadaskina I. D. and Filov V. A. Transformations and definition of industrial organic poisons in an organism, page 241, 268, L., 1971; Slyusar M. P. Aromatic amine and nitro compounds, the Guide to occupational health, under the editorship of F. G. Krotkov, t. 2, page 250, M., 1963; Encyclopaedia of occupational health and safeti, International labor office, v. 1, p. 91, 93, Geneva, 1971.
P. S. Krivchenkova; Yu. L. Egorov (prof).