Hyoscyamine (chemical) - C 17 H 13 NO 3 ( fr. and eng. Hyoscyamine , him. Hyoscyamin ) is an alkaloid isomeric with atropine , M-holinoblokator , found in the seeds and juice of henbane ( Hyoscyamus niger ) and other species of the genus Hyoscyamus , in seeds of belladonna ( Atropa belladonna ) and datura ( Datura stramonium ), in leaves and stem of the io-io-iradia iradia iladia iradia , and datura ( Datura stramonium ), in the leaves and stem of the Dubo-i'oia-iradia iradia , and Datura in the rhizome of Scopolia japonica and Scopolia carniolica . Its content in seeds reaches 0.5%.
| Hyoscyamine | |
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| Chemical compound | |
| IUPAC | (8-methyl-8-azabicyclo [3.2.1] oct-3-yl) 3-hydroxy-2-phenyl-propanoate |
| Gross formula | C 17 H 23 NO 3 |
| Molar mass | 289.375 g / mol |
| CAS | |
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| ATH | |
| Pharmacokinetics | |
| Bioavailable | 50% protein |
| Metabolism | Liver |
| The period is half out. | 3-5 h |
| Excretion | Urine |
| Mode of administration | |
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To obtain hyoscyamine, henbane seeds are extracted with boiling 90% alcohol , acidified with tartaric acid , the alcohol is distilled from the extract; the top, green, oily layer of the remaining liquid is shaken with dilute sulfuric acid , the acidic extract is almost neutralized by potash , filtered and evaporated to a syrupy density. Upon the addition of alcohol, a potassium sulphate is precipitated, which is separated, and the residue, after distillation of the alcohol, is extracted with chloroform in the presence of potash. Hyoscyamine is again extracted from chloroform with sulfuric acid, the sulphate of salt is purified with animal charcoal, decomposed with chalk, and hyoscyamine is finally extracted with chloroform (Duquenel). Pure hyoscyamine crystallizes in shiny needles (from diluted alcohol) or prisms (from chloroform), melts at 108.5 °, the alcohol solution rotates it to the left - [α] D = 21 °. Like atropine , hyoscyamine acts in an expanding manner on the pupil of the eye. With prolonged heating above the melting point (Schmidt) or under the action of caustic alkalis on its alcohol solution (Wil and Bredig), hyoscyamine goes to atropine , which, according to Ladenburg, stands in the same relation to hyoscyamine as grape acid to tartaric . With the energetic action of acids, or caustic alkalis, hyoscyamine gives the same products as atropine (Ladenburg).
Pharmacological properties
In medicine, pure, crystalline and amorphous is used, which is a brown residue, after the isolation of crystalline hyoscyamine. Its physiological effect on the eyes and heart is very similar to the effect of atropine , it affects the nervous system depressingly, why it is often used in various preparations, as a soothing pain and in psychiatry. Pure crystalline hyoscyamine is taken orally in very small doses, from 0.001 to 0.003 g; outside in eye drops, etc. The most recommended is hyoscyamine sulfate (Hyosciaminum sulfuricum purum). In the Russian pharmaceutical industry, hyoscyamine and its salts did not belong to official preparations, but were part of many drugs required for pharmacies: extractum Hyosciami (henbane leaf extract), the very seeds and leaves are henbane; oleum Hyosciami (bleached oil), ointment and patch with henbane extract (unguentum et emplastrum Hyosciami).
Hyoscyamine, like other atropine alkaloids, is a non-selective blocker of m-cholinergic receptors. Reduces the secretion of gastric glands, salivary glands, glands of the mucous membrane of the pharynx, trachea, bronchi, sweat glands. Reduces the tone and motility of the smooth muscles of the gastrointestinal tract, lowers the tone of the bronchi, biliary tract, urinary tract. Increases the frequency of contractions of the heart and cardiac output. Causes dilated pupils, increased intraocular pressure, accommodation paralysis.
Indications: urinary tract spasm, cystitis , renal colic, irritable bowel syndrome , spastic colitis, mucosal colitis, acute enterocolitis, biliary colic; gastric ulcer and duodenal ulcer, pylorospasm, cholelithiasis, cholecystitis, acute pancreatitis, hypersalivation; bronchial asthma, for the prevention of broncho-and laryngism; atrioventricular block; poisoning with m-cholinomimetics ( mushroom ), acetylcholinesterase inhibitors.
Contraindications: glaucoma , obstructive conditions of the gastrointestinal tract and urinary tract, intestinal atony, acute ulcerative colitis , toxic megacolon in ulcerative colitis, arterial hypotension, acute bleeding, myasthenia gravis , hypersensitivity to hyoscyamine, tachyarrhythmia.
It is used with caution in patients with polyneuropathy, hyperthyroidism, coronary artery disease, arrhythmias, tachycardia, arterial hypertension, chronic heart failure, kidney disease, as well as diaphragmatic hernia in combination with reflux esophagitis.
Symptoms of poisoning: palpitations , dry mouth, vomiting , hyperthermia, blurred vision, pain in the eyes, dilated pupils and their weak reaction to light, photophobia, euphoria , confusion and hallucinations (up to the development of the delirious state). Tachyarrhythmias, coma and death can occur.
Sources
- Hyoscyamine in Vidal database
- Hyoscyamine // Encyclopedic Dictionary of Brockhaus and Efron : in 86 tons (82 tons and 4 add.). - SPb. , 1890-1907.