ИЗОТОНИТАЗЕН Маргилан
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Маргила́н (узб. Marg‘ilon/Марғилон) — город в Ферганской области Узбекистана. В основе названия таджикское «Марғ» — «луг, лужайка, поляна» «зеленая трава», «зеленая низменность») и древнеиранского суффикса «Лон» («местность»). При слиянии этих 2-х слов получается «Маргилон» — «зеленая местность». Маргилан является одним из древних городов Ферганской долины.
Etonitazene is an analgesic drug, first reported in , \\\\\\\\\[1\\\\\\\\\] that has been shown to have approximately one thousand to one thousand five hundred times the potency of morphine in animal models, but only sixty times the potency in humans. Because it is characterized by a strong dependency potential and a tendency to produce profound respiratory depression , it is not used in humans. It is, however, useful in animal models for addiction studies, particularly those requiring the animals to drink or ingest the agent, because it is not as bitter as opiate salts like morphine sulfate. Illicit production and sale of etonitazene has been limited. Identified on the Moscow illegal drug market in , it was primarily smoked in laced cigarettes. The drug resulted in an unconfirmed number of deaths due to its uncertain potency. If a carboxide moiety is placed onto the carbon between the benzimidazole and the p -ethoxybenzyl, compounds up to four times more potent were discovered. A publication \\\\\\\\\[9\\\\\\\\\] has shown the possibility the previously assumed binding position of the benzimidazole class acting as a semi-rigid fentanyl analogue may be incorrect. Based on a large scale analysis of known opioid receptor ligands a template was created through manual overlaying and alignment which has identified several mu-specific areas within the receptor. In this analysis it is noted etonitazene now more closely matches another separate mu-specific region sharing very only a small area in common with the fentanyl class. Of these analogues, only etonitazene and clonitazene are explicitly listed under UN conventions and so are controlled throughout the world. Etonitazene has proved very important in mapping out the opiate receptor; some experimental compounds in which phenolic groupings have been replaced with nitro groupings have proved more active than the parent compound. Etonitazene and its related opioid agonist benzimidazoles were discovered in the late s, \\\\\\\\\[10\\\\\\\\\] \\\\\\\\\[11\\\\\\\\\] \\\\\\\\\[12\\\\\\\\\] \\\\\\\\\[13\\\\\\\\\] \\\\\\\\\[14\\\\\\\\\] \\\\\\\\\[15\\\\\\\\\] by a team of Swiss researchers working at the pharmaceutical firm CIBA now Novartis. This finding encouraged the group to begin a comprehensive systematic study of 2-benzylbenzimidazoles and to establish the structure-activity relationship of this new family of analgesics. Two general synthetic methods were developed for the preparation of these compounds. The first method involved the condensation of o-phenylenediamine with phenylacetonitrile to form a 2-benzylbenzimidazole. The benzimidazole is then alkylated with the desired 1-chlorodialkylaminoethane, forming the final product. This particular procedure was most useful for the preparation of benzimidazoles that lacked substituents on the benzene rings. A diagram of this method is displayed below. The 2-nitro substituent o n the 2,4-dinitroaniline compound is then selectively reduced to the corresponding primary amine by utilizing ammonium sulfide as the reducing agent. The ammonium sulfide can be formed in situ by the addition of concentrated aqueous ammonium hydroxide followed by saturation of the solution with hydrogen sulfide gas. The imino ether, 2- 4-Ethoxyphenyl -acetimidic acid ethyl ester hydrochloride, is prepared by dissolving the 4-substituted benzyl cyanide in a mixture of anhydrous ethanol and chloroform and then saturating this solution with dry hydrogen chloride gas. This procedure is particularly useful in the preparation of the 4-, 5-, 6-, and 7-nitrobenzimidazoles. Varying the choice of the substituted phenylacetic acid imino ether affords compounds with a diversity of substituents on the benzene ring at the 2- position. A diagram of this particular synthesis as it applies to the preparation of etonitazene is shown below. A particularly novel, high-yielding synthesis of etonitazene was developed by FI Carroll and MC Coleman in the mids \\\\\\\\\[17\\\\\\\\\] The authors were tasked with the preparation of large quantities of etonitazene, but found the conventional synthesis to be inadequate. The problem with the conventional synthesis was the lability of the imino ether reactant, 2- 4-Ethoxyphenyl -acetimidic acid ethyl ester prepared by reacting 4-ethoxyphenylacetonitrile with ethanolic HCl. The imino ether necessitated the use of anhydrous reaction conditions and was inconvenient to prepare in large quantities. This led the authors to experiment with the use of a coupling reagent, EEDQ N-Ethoxycarbonylethoxy-1,2-dihydroquinoline , in order to promote the condensation of 2- 2-diethylaminoethylamino nitroaniline with 4-ethoxyphenylacetic acid. In addition to the impressive improvement in yield over the conventional procedure, the work up procedure was greatly simplified since quinoline , carbon dioxide , and ethanol were the only by-products formed. A diagram of this procedure is shown below. A publication \\\\\\\\\[18\\\\\\\\\] \\\\\\\\\[J. The three component synthesis of the direct etonitazene precursor, 2- 4-Ethoxybenzyl nitro-1H-benzoimidazole, consists of a 2-Bromo- or 2-Iodonitro-phenylamine 1. The 2-Halonitro-phenylamine requires a bromo or iodo group for optimal activity. In addition to these three components, the reaction was optimized in the presence of 0. The secondary amine nitrogen of 2- 4-Ethoxybenzyl nitro-1H-benzoimidazole was then alkylated with 2-Chloroethyl diethylamine to form etonitazene. From Wikipedia, the free encyclopedia. Etonitazene Clinical data ATC code none. IUPAC name. Interactive image. Deseret News. Salt Lake City. Archived from the original on March 7, Social Services LLC. Archived from the original on 23 March European Journal of Pharmacology. ACS Omega. Helvetica Chimica Acta in German. Synthesis of phenyl-\\\\\\\\\[1-aminoalkyl-benzimidazolyl- 2 \\\\\\\\\]-acetic acid esters and amides\\\\\\\\\]. Synthesis of new 2-amino-benzimidazole\\\\\\\\\]. Synthese von 1-Aminoalkylbenzyl-benzimidazolen' \\\\\\\\\[Benzimidazole derivatives and related heterocycles II. Synthesis of 1-aminoalkylbenzyl-benzimidazoles\\\\\\\\\]. An improved synthesis'. Journal of Medicinal Chemistry. The Journal of Organic Chemistry. Opioid receptor modulators. Namespaces Article Talk. Views Read Edit View history. Help Learn to edit Community portal Recent changes Upload file. Download as PDF Printable version. Wikimedia Commons.
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Etonitazene is an analgesic drug, first reported in , that has been shown to have approximately one thousand to one thousand five hundred times the potency of morphine in animal models, but only sixty times the potency in humans. One of several benzimidazole opioids, etonitazene is structurally related to clonitazene, in which the p-ethoxybenzyl group is replaced by a p-chlorobenzyl group; however, clonitazene itself is only three times as potent as morphine.
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