LYSERGIC ACID, 7-methyl-4,6,6a, 7,8,9-geksagidroindolo [4,3-f, g] quinoline-9-carboxylic to - that, C 16 H 16 O 2 N 2 :
Pier. weight 268,32; t ° pl 238 ° (with decomposition). Difficult a rastvorima in neutral organic solvents, it is easy — in pyridine. Is a part of alkaloids ergot (see) also it turns out from them at vigorous alkaline hydrolysis. During the splitting of L. to. 1-methyl-5-aminonaphthalene, quinoline, picric and propionic to - you are formed. Structure of L. to. it is confirmed with its synthesis [Vudvard (R. Century of Woodward), 1954].
L. to. it is physiologically poorly active. However a number of its derivatives possesses high fiziol, activity. The left-handed indole alkaloids which are contained in an ergot being derivative L. to., are physiologically active, and their dextroizomers — derivatives isolysergic to - you — do not show considerable activity.
In alkaloids of group of ergotamine, napr, in ergotamine, the ergozena, and groups of Ergotoxinum (in the ergokristena, the ergokriptena, the ergokornena) L. to. it is connected with amino acids. Ergotamine (see) and alkaloids of group of Ergotoxinum exert the stimulating impact on a myometrium and muscles of vessels, and also have alpha and adrenoceptor blocking properties.
Ergometrine (see) represents beta propanolamid L. to.; it stimulates muscles of a uterus, has weak vasoconstrictive effect, has no adrenoceptor blocking properties.
At partial recovery and accession of two hydrogen atoms to a kernel of L. to. their dihydrogenated derivatives are formed of alkaloids of an ergot — dihydroergotamine (see) and dihydroergotoxin (see). The dihydrogenated alkaloids have more expressed alpha and adrenoceptor blocking properties and exert the smaller stimulating impact on muscles of a uterus and vessels in comparison with initial alkaloids.
Diethyl amide L. to. (LSD) is one of the most active psychodisleptic substances (see). Already in small doses (1 mkg/kg) it causes in people temporary disturbance of century of N of with development of visual and auditory hallucinations, etc. Psychodisleptic properties are shown also by Etilamid and Morfolid L. to. In the USSR since 1967 the order of the Minister of Health of the USSR prohibited production, import and use on the person of diethyl amide L. to. and other its derivatives having psychodisleptic properties. Studying of such substances in an experiment on animals can be authorized only the special decision M3 of the USSR and Standing Committee on control of drugs. At a number of derivative L. to. antiserotoninovy properties are found. The most expressed antiserotoninovy activity among derivative L. to. possesses metisergid (1-methyl-butanolamid L. to.). It suppresses vasoconstrictive and pressor effects of serotonin and its influence on unstriated muscles of internals. Unlike diethyl amide L. to. influences c a little. N of page. Despite considerable similarity on chemical structure to alkaloids of an ergot, metisergid has weak influence and a myometrium and muscles of vessels. There are data on efficiency of a metisergid at migraine, a carcinoid syndrome, a dumping syndrome, allergic rhinitis and bronchial asthma.
V. V. Churyukanov.