Cholic acid structural formula. What is the function of bile acids and what is their structure? Functions of bile acids
Update: February 2019
The Federal Polytechnic School of Lausanne (EPFL) has been distinguished by the sensational results of a new study led by Dr. Laura Velázquez. Bile acids can help overweight people burn fat.
Obesity in most cases is due to a mismatch between the intake and expenditure of calories in our body. It is widespread among the population and is associated with many endocrine and cardiovascular diseases. This makes it the most important goal of modern medicine, however, so far it has been difficult to achieve.
- The best “cure” for excess weight is a regular low-calorie diet combined with metered physical activity (see). Patients do not always agree to adhere to such a lifestyle, especially older people.
- Another option is taking medications that slow down the absorption of fats in the intestinal lumen (ezetimibe). But this method is not always approved among obese patients.
- Increasingly, people are resorting to surgical methods of body weight correction, which is not always safe and much more expensive than standard methods.
A new study has shown that bile (cholic) acids are a potentially effective treatment for obesity. As you know, bile "breaks" the fat coming from food into many tiny spherical particles so that they become available for processing by pancreatic enzymes. Cholic acids, as scientists have found, can also repurpose adipocytes (fat cells) into so-called "fat-burning cells."
When the specialized receptor "TGR5" is activated on the surface of adipocytes with the help of bile acids, the process of transition of the original cell into a fat burner is started. In the renewed cells, the number of mitochondria and energy exchange towards the breakdown of fats are increased. Now fat reserves become the main energy source for the functioning of the whole organism.
It is on this effect of bile acids that the conclusions of Laura Velazquez are based. Enough to start fat burning processes even small concentrations of cholic acids. This circumstance will allow you to control the rate of weight loss by increasing or decreasing the dose of the drug. Today, cholic acid preparations are:
- primarily ursodeoxycholic (Ursodez, Ursofalk)
- and chenodeoxycholic acid (Henochol, Henofalk).
These drugs have a number of contraindications (for example, X-ray-positive gallstones, inflammation of the gallbladder, intestines, dysfunction of the pancreas, liver, kidneys), so they should be prescribed only by a doctor according to indications.
At the moment, studies have not been completed and it is not known when the newly discovered drug with small doses of cholic acids will be included in the world clinical guidelines for the treatment of obesity.
According to its structure and chemical and physical parameters, food supplement E1000 Cholic acid is a monocarboxylic acid, which belongs to the group of bile acids. The main feature of these compounds can be considered that some bile monocarboxylic acids are found in the human body. It is worth noting that the food supplement E1000 Cholic acid belongs to the category of these acids. Cholic acid is nothing more than the primary secret that the human liver produces.
We can say that the food supplement E1000 Cholic acid belongs to the group of organic compounds of natural origin. The active acidic compound is formed as a result of the interaction and decomposition of acids such as glycocholic and taurocholic. Cholic acid is not only a breakdown product, but also the result of the crystallization of alcohols. It should be noted that according to its chemical structure, food additive E1000 Cholic acid belongs to the so-called monobasic acids.
Food additive E1000 begins to melt at a temperature of 195C, and also forms an ester when exposed to temperature on acetic anhydride. In addition, food additive E1000 Cholic acid enters into various reactions with other chemical reagents. This ability of the compound is actively used in the chemical industry, where the food additive E1000 is used to obtain other organically active compounds.
It is worth emphasizing that cholic acid is considered one of the most important bile monocarboxylic acids for the human body. In the human body, cholic acid occurs when cholesterol is oxidized by the liver. In the chemical industry, cholic acid is produced in the form of a white crystalline powder or peculiar plates, which are distinguished by a bitter taste, which gradually turns into sweet.
In the food industry, the food additive E1000 has found enough applications. This is primarily due to the chemical properties of the food additive, which can act as an emulsifier, antifoaming or glazing agent, as well as a sugar substitute or sweetener. In the food industry, it is allowed to use the food additive E1000 Cholic acid to stabilize the dispersed states of finished food products.
As a rule, food additive E1000 helps food manufacturers to form the necessary consistency of food products. Food additive E1000 Cholic acid can give products a certain level of viscosity and maintain it for a long period of storage. Usually E1000 can be found in the composition of bakery and confectionery products, as well as fruit and fruit juices.
The liver not only performs the function of detoxifying the body, but also produces bile. This component is necessary for the implementation of the digestion process, but not everyone knows exactly how it affects it, what its composition is.
What is bile
The word bilious is usually used in relation to a person who is gloomy, irritable, prone to aggression. Such people usually have a stale complexion, and this is no coincidence. Most often, they have impaired functions of the outflow of bile, as a result of which it enters the bloodstream, and the presence of bilirubin in it provides the skin and mucous membranes with a characteristic yellow tint. The cause of this pathology is usually liver disease or gallstone disease.
Bile is produced in the liver cells and stored in the gallbladder. It has a complex composition, including proteins, bile acids, amino acids, some hormones, inorganic salts, and bile pigments. At each meal, it is released into the intestines to grind or emulsify fats and further transport them and bilirubin to the intestines. In the intestines, bile promotes the absorption of fatty acids, calcium salts and fat-soluble vitamins, and is involved in the decomposition of triglycerides. In addition, it is the small intestine, as well as the production of pancreatic secretions and gastric mucus.
Having fulfilled its functions, bile is not completely utilized by the body, part of its components are absorbed into the blood and returned to the liver through the portal vein. These components include bile acids, thyroid hormones, and some pigments.
Cholic acid
Cholic acid is one of the two primary bile acids and is one of the most important constituents of bile. Its chemical formula is C24H40O5, it belongs to the group of monocarboxylic acids. In the liver, it is synthesized from cholesterol, but not directly, but through several intermediate reactions. The adult liver produces approximately 250 mg of this substance per day. It enters the gallbladder not in its pure form, but in compounds with taurine (taurocholic acid) and glycine (glycocholic acid). In the small intestine, under the influence of microflora, they turn into deoxycholic acid, most of which (up to 90%) is absorbed through the blood and again enters the liver (about 5-6 such turnovers occur per day). The rest of the bile acids are excreted through, and its loss is replenished by the synthesis of new bile acids, including cholic acids, by liver hepatocytes. This acid, along with other bile acids, performs the following functions:
- grinding, emulsification and solubilization of fats in the intestine;
- participation in the regulation of cholesterol synthesis in the liver;
- regulation of bile formation;
- has a bactericidal effect;
- transport to the intestines of the end product of metabolic processes associated with hemoglobin (bilirubin);
- stimulates intestinal motility;
- activates pancreatic lipase;
- surface-active effect on cell membranes;
- participation in the absorption of fats;
- the formation of some steroid hormones;
- influence on the nervous system.
With insufficient formation of cholic acid or its complete absence, fats cease to be absorbed and are completely excreted along with feces, which in this case becomes light. Bile with a low content of cholic and other bile acids is usually produced by the body of a person who abuses alcohol. As a result, a person does not receive many substances necessary for normal functioning, including fat-soluble vitamins, he may develop diseases of the lower intestine, which is not designed for such secretions. Cholic acid is part of the Panzinorm forte preparation, designed to facilitate the digestion of fatty foods.
Food supplement
Food supplement E - 1000, sometimes also called cholic acid, bile acid, Cholic Acid, is excluded from the list of approved for use in the Russian Federation, since its effect on human health has not been studied enough. There are supplements that are scientifically proven to be harmful, but cholic acid is not one of them. North America, EU countries, Australia and New Zealand also ban its use in the food industry. However, its use in the preparation of animal feed is permitted.
Previously, it was used as an emulsifier, i.e. a substance that improves the miscibility of products of different origin, stabilizes the dispersed state, maintains a certain consistency and viscosity of finished products, such as juices, confectionery and bakery products. This nutritional supplement is obtained by hydrolysis of the solid bile of mammals.
Video about the chemical structure of bile acids
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Ursodeoxycholic acid - or why bears don't get sick...
CHOLIC ACID
C 24 H 40 O 5 ? is a breakdown product of glycocholic (see) and taurocholic (see) acids; crystallizes from alcohol, with one particle of crystallization alcohol, in the form of colorless shiny octahedrons, easily weathered in air, almost insoluble in water and easily soluble in alcohol and ether. Solutions of X. acid and its salts rotate the plane of polarization to the right. X. acid? monobasic acid and, apparently, tetrahydric. Melts at 195¦. When boiled with acetic anhydride, it forms diacetic ester. Upon careful oxidation with chromic acid in acetic solution, it transforms into dehydrocholic acid N 24 H 34 O 5 , melting at 231?232¦. When oxidized with nitric acid or a chameleon, it forms cholanic acid C 24 H 36 O 7 (melting at 285 ¦), bilianic acid C 24 H 34 O 8 (melting at 269 ¦) and isomeric with it isobilianoic acid. When oxidized with a chameleon in an alkaline solution, it forms cyanic acid C 20 H 30 O 10 (melts at 242¦), and with stronger oxidation it turns into orthophthalic acid C 6 H 4 (COOH) 2. With iodine X. acid forms, like starch, a blue compound. With sugar and sulfuric acid X. acid gives the so-called. Pettenkofer bile reaction (see Bile).
Brockhaus and Efron. Encyclopedia of Brockhaus and Efron. 2012
See also interpretations, synonyms, meanings of the word and what is CHOLIC ACID in Russian in dictionaries, encyclopedias and reference books:
- CHOLIC ACID in Medical terms:
bile acid, which is a monocarboxylic trihydroxy acid; in bile is in the form of sodium salts of glycocholic and taurocholic ... - CHOLIC ACID
acid (from the Greek. chole - bile), monocarboxylic steroid acid from the group of bile acids. Sodium salts of its compounds with amino acids ... - CHOLIC ACID
C24H40O5 - is a breakdown product of glycocholic (see) and taurocholic (see) acids; crystallizes from alcohol, with one particle of crystallization alcohol, in ... - ACID in Miller's Dream Book, dream book and interpretation of dreams:
Drinking some kind of acid is an unfavorable dream that brings you a lot of anxiety. For a woman, drinking acidic liquids means that she can ... - ACID in the Encyclopedic Dictionary:
, -s, pl. -dm, -dr, f. A chemical compound containing hydrogen, which, when reacted with bases (in 8 values), gives salts and ... - ACID in the Full accentuated paradigm according to Zaliznyak:
acid, sour "you, acids", sour "t, acid", sour "there, acid", sour "you, acid", acid "yu, sour" tami, acid "... - ACID in the dictionary of Synonyms of the Russian language:
aqua acid, alacreatine, alkylbenzenesulfonic acid, alkoxy acid, aldehyde acid, amide, anthrax, aurin, barbital, benzene sulfonic acid, benzene sulfonic acid, bilitrast, butanedic acid, halo, halogen acid, hexafluorosilicic acid, hexafluorosilic acid, hexachloroplatinic acid, heteropoly acid, ... - ACID in the New explanatory and derivational dictionary of the Russian language Efremova:
and. 1) Distract. noun by value adj.: sour. 2) A chemical compound containing hydrogen that can be replaced by a metal when a salt is formed. 3) ... - ACID in the Dictionary of the Russian Language Lopatin:
acids`a, -`s, pl. -`ot, ... - ACID in the Complete Spelling Dictionary of the Russian Language:
acid, -s, pl. -ot, ... - ACID in the Spelling Dictionary:
acids`a, -`s, pl. -`ot, ... - ACID in the Dictionary of the Russian Language Ozhegov:
1 chemical compound containing hydrogen, which, when reacted with N8 bases, gives salts and turns litmus paper red Nitric, ... - ACID in the Explanatory Dictionary of the Russian Language Ushakov:
acids, pl. acids, g. 1. Only units. Distraction noun to sour, sth. sour (colloquial). I tried, I feel: some kind of acid. 2. … - ACID in the Explanatory Dictionary of Efremova:
acid 1) Distract. noun by value adj.: sour. 2) A chemical compound containing hydrogen that can be replaced by a metal when a salt is formed. … - ACID in the New Dictionary of the Russian Language Efremova:
and. 1. distraction noun according to adj. acidic 2. A chemical compound containing hydrogen that can be replaced by a metal in the formation of a salt. 3. Anything... - ACID in the Big Modern Explanatory Dictionary of the Russian Language:
and. 1. A chemical compound containing hydrogen that can be replaced by a metal when a salt is formed. 2. The fact that with its properties - color, smell, ... - Hydrochloric-hydrochloric, or hydrochloric, acid
- FUMAric ACID in the Encyclopedic Dictionary of Brockhaus and Euphron:
(chemical), butenedic acid C4H4O4 = C2H2 (CO2H) 2 - stereoisomer (monotropic isomer? - cf. Phosphorus, allotropy) of maleic acid (see). It is located ready in the vegetable kingdom, and ... - URIC ACID in the Encyclopedic Dictionary of Brockhaus and Euphron.
- LACTIC ACID in the Encyclopedic Dictionary of Brockhaus and Euphron:
(ac. lactique, lactic ac., Milchs?ure, chem.), otherwise?-hydroxypropionic or ethylidene-lactic acid - C3H6O3 \u003d CH3 -CH (OH) -COOH (cf. Hydracrylic acid); known three... - Tartaric or tartaric acid in the Encyclopedic Dictionary of Brockhaus and Euphron:
(acide tartarique, tartaric acid, Weinsteins?ure) - C4H6C6, otherwise dioxysuccinic - is significantly common in the plant kingdom, where it is found free or ... - FUMAric ACID
(chem.), butenedic acid C 4 H 4 O 4 \u003d C 2 H 2 (CO 2 H) 2? stereoisomer (monotropic isomer? ... - URIC ACID* in the Encyclopedia of Brockhaus and Efron.
- LACTIC ACID in the Encyclopedia of Brockhaus and Efron:
(ac. lactique, lactic ac., Milchs a ure, chem.), otherwise? -oxypropionic or ethylidene lactic acid? C 3 H 6 O 3 ... - WINE ACID* in the Encyclopedia of Brockhaus and Efron:
or tartaric (acide tartarique, tartaric acid, Weinsteinsaure)? C 4 H 6 C 6, otherwise dioxysuccinic? widely spread... - CHOLALEMIA in Medical terms:
(outdated; cholalaemia; lat. acidum cholalicum cholic acid + Greek haima blood) see Cholemia ... - BILE ACIDS in the Great Soviet Encyclopedia, TSB:
acids, steroidal monocarboxylic acids, cholanic acid derivatives, formed in the liver of humans and animals and excreted with bile into the duodenum. … - CYLIANIC ACID in the Encyclopedic Dictionary of Brockhaus and Euphron:
see Holevaya ... - CYCLIC ACIDS in the Encyclopedic Dictionary of Brockhaus and Euphron:
are carboxylated (see Carboxyl) derivatives of cyclic hydrocarbons. In this article, acids of the formula Сn?2n - x(C?2?)x or CmH2(m ... - CHOLANIC ACID in the Encyclopedic Dictionary of Brockhaus and Euphron:
see Holevaya ... - CHOLALIC ACID in the Encyclopedic Dictionary of Brockhaus and Euphron:
= Cholic acid … - PHTHALIC ACID in the Encyclopedic Dictionary of Brockhaus and Euphron:
This name refers to the simplest aromatic dicarboxylic or dibasic acids of the composition C6H4 (CO2H) 2. F. acids, as disubstituted derivatives of benzene (see Aromatic hydrocarbons), ... - UREIDS in the Encyclopedic Dictionary of Brockhaus and Euphron:
(chemical) an extensive class of nitrogenous organic substances representing urea derivatives NH2.CO.NH2, formed through the replacement of one or more hydrogen atoms in it with acidic ... - TAURINE in the Encyclopedic Dictionary of Brockhaus and Euphron:
or amidoethylenesulfonic acid C2H7NSO3 \u003d NH2-CH2-CH2-SO2OH was discovered by Gmelin in 1826 as a decomposition product of taurocholic acid in bile ...
Bile acids are cholan derivatives containing a COOH group in the side chain. Bile acids are formed in the liver from cholesterol.
Cholic acid:
Glycocholic acid, taurocholic acid 
Cholic acid - cholic acid (C 24 H 40 O 5), is a breakdown product of glycocholic and taurocholic acids; crystallizes from alcohol, with one particle of crystallization alcohol, in the form of colorless shiny octahedrons, easily weathered in air, almost insoluble in water and easily soluble in alcohol and ether. Solutions of cholic acid and its salts rotate the plane of polarization to the right. Cholic acid is a monobasic acid.
Glycocholic acid is a crystalline substance that melts at 132-134 °C. Empirical formula C 26 H 43 NO 6 . Refers to bile acids. It is found as sodium salt in bile, especially bovine bile. Like hippuric acid, it decomposes with alkalis, forming glycocol and, instead of benzoic, cholic acid. It is formed in the liver of humans and some animals as a compound (conjugate) of cholic acid and glycine and therefore belongs to the so-called paired acids. In addition to glycine, cholic acid also conjugates with taurine, resulting in another paired acid - taurocholic.
In the intestine, it emulsifies fats by activating lipase and stimulating the absorption of free fatty acids. Up to 90-95% of glycocholic acid (in the form of cholic acid and other compounds) is absorbed in the intestines into the blood and returns to the liver through the portal vein, where cholic acid is transferred from the blood to the bile and again conjugated with glycine and taurine. During the day, the so-called enterohepatic circulation of bile acids occurs up to 10 times.
Taurocholic acid
Taurocholic acid is formed in the liver of humans and some animals as a compound (conjugate) of cholic acid and taurine and therefore belongs to the so-called paired acids. In addition to taurine, cholic acid also conjugates with glycine, resulting in another paired acid - glycocholic.
In the intestine, it emulsifies fats by activating lipase and stimulating the absorption of free fatty acids. Up to 90-95% of taurocholic acid (in the form of cholic acid and other compounds) is absorbed in the intestine into the blood and through the portal vein back to the liver, where cholic acid is transferred from the blood to the bile and again conjugated with taurine and glycine. During the day, the so-called enterohepatic circulation of bile acids occurs up to 10 times.
Bile salts dramatically reduce the surface tension at the fat/water interface, whereby they not only facilitate emulsification, but also stabilize the emulsion already formed. Bile acids activate the enzyme lipase, which catalyzes the hydrolysis of fats.
In the body, bile acids are in the form of amides at the carboxyl group and glycine residues are attached to them through a peptide bond.
10. Cholesterol is a representative of sterols, its conformational structure. Properties, role in the metabolism and structure of membranes, in the development of cardiovascular pathology.
Cholesterol is present in all animal lipids, blood, bile. A feature of its structure is the presence of a double bond in ring B between 5 and 6 carbon atoms. Its reduction leads to two stereoisomers - cholestanol and caprostan.
Cholesterol is a source of formation in the body of bile acids, corticosteroids, sex hormones, vitamin D 3, is a component of biological membranes
Approximately 20% of cholesterol enters the body with food. Most cholesterol is synthesized in the body from acetic acid.
Synthesis of cholesterol is carried out in the cells of almost all organs and tissues, however, cholesterol is formed in significant amounts in the liver (80%), the wall of the small intestine (10%) and skin (5%). Cholesterol is absent in plants, but there are other sterols - phytosterols
Violation of cholesterol metabolism leads to its deposition on the walls of blood vessels, as a result of which the elasticity of blood vessels decreases, atherosclerosis occurs, in addition, cholesterol can accumulate in the form of gallstones. However, there is not always a correlation between blood cholesterol levels and the severity of atherosclerosis.
An increase in the concentration of cholesterol in the blood is observed with diabetes mellitus, hypothyroidism, gout, obesity, with certain liver diseases, acute cerebrovascular accident
Reduced cholesterol is noted in a number of infectious diseases, intestinal diseases, hyperthyroidism
The ability of cholesterol to form esters with FFA is important:
 |
Cholesterol is insoluble in water, soluble in acetone, alcohol, ether, animal and vegetable fats. Cholesterol forms intensely colored products when interacting with strong acids. This property of cholesterol is used for its analytical determination.
*. Alkaloids, poisons and drugs. The structure and effect on the human body of nicotine, quinine, papaverine, morphine, atropine.
Alkaloids are nitrogen-containing substances of the main character, predominantly of plant origin.
Due to their high pharmacological activity, alkaloids are one of the most well-known group of natural compounds used in medicine since ancient times.
To date, more than 10,000 alkaloids of various structures are known.
One of the common features inherent in almost all alkaloids is the presence in their structure of a tertiary nitrogen atom, which determines the basic properties, which is reflected in their group name.
In plants, alkaloids are found in the form of salts with strong organic acids - citric, malic, succinic, oxalic, rarely acetic and propionic.
Salts of alkaloids, especially with mineral acids, are highly soluble in water, but insoluble in organic solvents.
Nicotine - 
a very toxic alkaloid, the content of which in tobacco leaves reaches 8%. Includes single bonded pyridine and pyrrolidine nuclei. Affects the autonomic nervous system, constricts blood vessels.
One of the products of nicotine oxidation under severe conditions is nicotinic acid, which is used for the synthesis of other drugs based on it.
à 
Quinine - 
the main alkaloid of cinchona bark with a strong bitter taste, which has antipyretic and analgesic properties, as well as a pronounced action against malarial plasmodia. This allowed for a long time to use quinine as the main treatment for malaria. Today, more effective synthetic drugs are used for this purpose, but for a number of reasons, quinine finds its use at the present time.
The composition of quinine includes 2 heterocyclic systems: quinoline and quinuclidine.
Papaverine - 
opium alkaloid, isoquinoline derivative, antispasmodic and hypotensive drug.
Morphine - 
the main alkaloid of opium, the content of which in opium is on average 10%, that is, significantly higher than all other alkaloids. Contained in poppy sleeping pills ( Papaver somniferum) and in other types of poppy. They contain only one stereoisomer - (−)-morphine. (+)-Morphine was synthesized and does not have the pharmacological properties of (−)-morphine.
The hydrochloride salt of morphine, morphine, is sometimes simplistically or erroneously referred to as morphine.
Atropine - 
anticholinergic (M - anticholinergic), plant alkaloid. Chemically, it is a racemic mixture of D- and L-tropic acid tropine esters. The L-stereoisomer of atropine is hyoscyamine. An alkaloid found in various plants of the nightshade family, such as belladonna ( Atropa belladonna) , henbane ( Hyoscyamus niger), different types of dope ( Datura stramonium), etc. The average lethal dose is 400 mg/kg.
*. Methylated xanthine derivatives - theobromine, theophylline, caffeine.
Xanthine - a purine base found in all tissues of the body. Colorless crystals, readily soluble in solutions of alkalis and acids, formamide, hot glycerin and poorly soluble in water, ethanol and ether.
Theobromine- a purine alkaloid, isomeric to theophylline. Colorless crystals of bitter taste, insoluble in water.
In medicine, theobromine is used to treat bronchopulmonary diseases. Also used is the double salt of T. with sodium salicylate, known as diuretin.
Experimental studies have shown that theobromine, which is so close in chemical composition to caffeine, has a similar effect with the latter, causing excitation of the heart muscle in therapeutic doses and increasing the amount of urine by irritating the renal epithelium.
To date, theobromine is used in toothpastes to provide enamel remineralization. On a molar level, the amount of theobromine (0.0011 mol/L) required to produce a cariostatic effect is 71 times less than the amount of fluoride (0.0789 mol/L) required in dentifrice to achieve a comparable effect. .
To obtain theobromine, either crushed cocoa seeds, freed from fat, or cocoa dust falling in chocolate factories are used. Cocoa mass is boiled with dilute sulfuric acid until most of the starch is converted into sugar, then lead carbon dioxide is added almost to complete neutralization, the precipitate is filtered and washed, having previously removed the sugar by fermentation; the filtrate is thickened, the settled brown mass is dissolved in hot nitric acid, the precipitate of lead is filtered off, and theobromine is precipitated from the nitric acid solution with ammonia.
Theophylline:
methylxanthine, a purine derivative, a heterocyclic alkaloid of plant origin, is found in camellia sinensis, from which tea is prepared, in Paraguayan holly (mate), in cocoa.
Caffeine:
purine alkaloid, colorless or white bitter crystals. It is a psychostimulant found in coffee, tea and many soft drinks.
Caffeine is found in plants such as coffee tree, tea, cocoa, mate, guarana, cola, and a few others. It is synthesized by plants to protect against insects that eat leaves, stems, and grains, and to encourage pollinators.
In animals and humans, it stimulates the central nervous system, increases cardiac activity, accelerates the pulse, causes constriction of blood vessels, and increases urination. This is due to the fact that caffeine blocks the enzyme phosphodiesterase, which destroys cAMP, which leads to its accumulation in cells. cAMP is a secondary mediator through which the effects of various physiologically active substances, primarily adrenaline, are carried out. Thus, the accumulation of cAMP leads to adrenaline-like effects.
In medicine, caffeine is used as part of a remedy for headaches, migraines, as a stimulant of respiration and cardiac activity in colds, to increase mental and physical performance, to eliminate drowsiness.
