Ethyl morphine

PYRROLEANDPYRROLEDERIVATIVES] (Vol20) (+)-N-(2-Hydroxy-3-[ql(4-hydroxyphenoxy)propylamino)ethyl morphine-4-caiboxamide... 

Molecular modifications of the morphine skeleton have produced numerous derivatives with antitussive properties, some of which have become commercially significant. Ethyknorphine [76-58-4] (29), a simple homologue of codeine, is prepared by ethylating morphine. It is pharmacologically similar to codeine but is seldom used clinically. Pholcodine [509-67-1] (30), the morpholinoethyl derivative of morphine, is used as an antitussive in a number of European countries. It is about one and a half times as potent as codeine, has Htde or no analgesic activity, and produces minimal physical dependence. The compound is prepared by the amino alkylation of morphine (48). 

Years later, in 1898, Heinrich Dreser, a chemist working for Bayer Laboratories, conducted a series of clinical tests with the previously discovered tetra-ethyl morphine (now renamed... 

Ethyl morphine N-demethylation nmol HCHO 100g 1 body weight 10 min-1... 

Other opioids such as buprenorphine, norbuprenorphine, dihydrocodeine, ethyl-morphine, fentanyl, methadone, methadone primary metabolite, and pentazocine have been identified in hair of drug users. Data from the literature are summarized below ... 

An aliquot of this together with homatropine HBr (II) and ethyl morphine (III) (as internal standards) in chloroform was analyzed by GLC. 

Derivation Action of hydrochloric acid on ethyl-morphine, which is made by action of ethyl iodide on morphine in alkaline solution. 

Morphlne-3 ethyl ether (ethyl, morphine codethylin) 93 HaO prisms 364, 367-9, 371, 378, 385-6, 389... 

The reaction between silver oxide and the quaternary salts of morphine and codeine was first investigated, inconclusively, by How [2]. Grimaux, by heating codeine [i] methiodide with silver oxide or potassium hydroxide, obtained a-codeimethine [n] dionin methine likewise could be prepared from dionin (ethyl morphine) methiodide [3-4]. The reaction presumably proceeds by elimination of water from the methohydroxide, and Hesse found that evaporation of codeine methohydroxide solutions over concentrated sulphuric acid affords a-codeimethine [5]. 

Children are generally more sensitive than adults (codeine should not be given to children less than Vi year old). The main risk of poisoning is the CNS-effect and respiratory depression, which can come late (especially for ethyl-morphine). An effective antidote is Naloxone (Narcan) ... 

ETHYL MORPHINE This semisynthetic derivate has an ethyl group instead of the methyl in codeine and is used on a large scale in cough syrups. 

Ucations, a, p, y, of aoetyl-morpliin, CitH,b(C,H30)N 03, are formed. Similarly substituted butjrryl-, benzoyl-, succinyl-, camphoryl-, methyl-, and ethyl-morphin are also known. 

C-3 phenolic hydroxyl C-6 allylic alcohol and C = C between C-7 and C-8 as depicted in the following stmcture(s). It is, however, pertinent to mention here that several synthesized structural analogues even before 1930 are still constituted as vital and potential drugs in the therapeutic armamentarium, for instance codeine ethyl morphine (Dionin ) diacetyl morphine (heroin) hydromorphone... 

The control of pharmaceutics is the field where analytical isotachophorcsis has already proved to be advantageous, particularly due to its rapid and simplicity. Inorganic and organic components may be determined in one analysis only. This is illustrated by the analysis of a pharmaceutical preparation in which the sodium, calcium and ethyl morphine content must be controlled (Fig. 30) and by the analysis of an infusion solution in which the sodiiun, calcium and procaine contents are controlled (Fig. 31). 

Liver and lung NADPH-cytochrome P-450 reductases (EC 1.6.2.4) of well bled male Akkaraman sheep appear to have a similar kinetic and spectral properties (Isgan and Arin 1988). Both reductases supported aniline 4-hydroxylation and ethyl-morphine N-demethylation reactions to the same extent in the constituted systems. However, sheep lung reductase appeared only 36.5 and 14.8 % as effective in catalysing benzo[a]pyrene reaction as an equivalent amount of reductase from fiver in the presence of fiver cytochrome P-450 and 3MC-treated rat fiver cytochrome P-448, respectively. 

In adult rats, the magnitude of the sex difference in microsomal drug metabolism is dependent upon the drug substrate examined. Microsomes from male rats are 3 to 4 times as active as those from females in the metabolism of ethyl-morphine, hexobarbital, and aminopyrine, but only about twice as active in the metabolism of cocaine or p-nitroanisole. There is no appreciable sex difference in the metabolism of zoxazolamine or aniline by rat-liver microsomes nor in the duration of zoxazolamine paralysis in vivo. Similarly, there is very little sex difference in the cytochrome P-4S0 content or in NADPH cytochrome c reductase activity. 

Like codeine and unlike morphine and diamorphine, ethylmorphine is extracted from alkaline solution by chloroform and assay of its salts and preparations is effected by normal alkaloidal extraction technique. Ethyl-morphine hydrochloride, Ci9H2303N,HCl,2H20, Mol. Wt. 385-9. 1 ml... 

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