Morphines apomorphines

The synthesis of three l,2,10,ll-tetrasubstituted./V-(n-propyl)noraporphines, using either the Bischler-Napieralski-Pschorr sequence or a Reissert alkylation-Pschorr cyclization, has been achieved.29 Patents have been taken out on the morphine-apomorphine rearrangement that is induced by phosphoric acid and which leads to N- alkylated norapomorphines.30 Other patents concern the vanadium-trichloride-induced cyclization of tetrahydrobenzylisoquinolines that are hydroxylated at C-7, to furnish a series of 1-hydroxylated aporphines such as thaliphorphine. 31,32... 

Chloromorphide was early recognized as an intermediate in the conversion of morphine to apomorphine [69, 72, 75], and both /3-chloromorphide and [xlvi] give yields of apomorphine comparable to those obtained from morphine under the same conditions [19, 74], The mechanism of the morphine -> apomorphine conversion is regarded by Small as being as follows [19] (see, however, Chap. XXII) ... 

On the basis of the above Small, Far is, and Mallonee [15] have advanced the following mechanism for the morphine -> apomorphine conversion. Three stages are envisaged ... 

On methylation apomorphine yields apo-i/i-coDEiNE (i/i-apocodeme, anocodeine, apomorphine methyl ether), CigHigOaN. C2H5. OH, crystallising in brilliant plates, m.p. 104-5-106-5°, or 122-5-124-5 dry), — 90° (EtOH), which is also produced when codeine or i/i-codeine is heated with oxalic acid or phosphoric acid. It stands in the same relation to codeine as apomorphine to morphine. 

For instance morphine (1) can be detected by the formation of various quinones via apomorphine as intermediate [4, 12, 13]. All morphines with an OH group in the 6-position and a double bond (codeine, ethylmorphine etc.) first undergo an acid-catalyzed rearrangement according to the following scheme [12] ... 

The Husemann and Erdmann identification reactions for morphine and codeine in the DAB 9 (German Pharmacopoeia) involve the formation of the red-colored ortho-quinone (8) via apomorphine (5) under the influence of nitric acid with the simultaneous nitration of the benzene ring [15]. 

Recently, it was found that single-housed mice that had been undergoing withdrawal for 48 hours (after removal of a subcutaneously implanted 75-mg morphine pellet) showed an elevation of attack and threat behavior that was doubled when these mice were challenged with amphetamine, cocaine, /-dopa, or apomorphine (figure 4) (Kantak and Miczek 1986 ... 

To identify the presence of undesirable specific organic compounds present as impurities in a number of pharmaceutical substances, namely morphine in apomorphine hydrochloride hydrazine in carbidopa 3-aminopropanol in dexampanthenol etc.,... 

Procedure Prepare the chromatogrphic tank by lining the walls with sheets of filter paper pour the mobile-phase into the tank, saturating the filter paper in the process, to a depth of 5 to 10 mm, close the tank and allow it to stand at 20° to 25 °C for 1 hour for equilibration of the mobile-phase in the chromatank. Apply separately to the TLC plate 5 (il of each of two solutions (1) and (2) of apomorphine hydrochloride and (3) of morphine in the form of circular spots about 2 to 6 mm in diameter, and 15 to 20 mm from one end of the plate and not nearer than 10 mm to the sides the two spots must be at least 10 mm apart. Mark the sides of the plate 15 cm from the line of application. Allow the solvent to evaporate and place in the chromatank,... 

Apomorphine hydrochloride (44 Apokyn ) Morphine (43) Alkaloid Semi-synthetic NP Plant Parkinson s disease Potent dopamine receptor agonist 403 16... 

Apomorphine hydrochloride (44 Apokyn Bertek, 2004), is a semisynthetic derivative of opium alkaloid morphine (43) isolated from poppy (Papaver somniferum), and it has long been known for its erectile activity at the effective dose of 2-6 mg physicians discovered the effect over 100 years ago, but found the drug, at a much higher dose (ca. 200 mg), to be more suitable for poison victims as an emetic because it also causes serious nausea and vomiting. Apomorphine exerts its erectile effect at the central nervous system the drug has been found to be a non-selective dopamine agonist which activates both Di-like and D2-like... 

Morphine (13) Apomorphine (36) Benzyltetrahydro-isoquinoline alkaloid Parkinson s disease... 

The most known narcotics are the opium alkaloids such as morphine, codeine, thebaine, papaverine, noscapine and their derivatives and modified compounds such as nalmorphine, apomorphine, apomopholcodine, dihydrocodeine, hydro-morphone and heroine, also known as diamorphine. Synthetic narcotics share the structural skeleton of morphine and include dextromethorphan, pentazocine, phenazocine meperidine (pethidine), phentanyl, anfentaitil, remifentalin, methadone, dextropropoxyphene, levoproxyphene, dipipanone, dextromoramide, meptazinol and tramadol. Thebaine derivatives are also modified narcotics and include oxycodone, oxymorphone, etorphine, buprenorphine, nalbuphine, naloxone or naltrexone. Narcotics can be semi-synthesized or totally synthesized from the morphine and thebaine model. The compounds serve various purposes in clinical practise. 

Apomorphine, a derivative of morphine, acts directly on the CTZ. It also is more effective if water is first administered before oral or subcutaneous dosing. Excessive dosage may cause respiratory depression and circulatory collapse. Opioid antagonists such as naloxone usually reverse the depressant actions of apomorphine. Because of the possibility of respiratory depression, apomorphine is infrequently used as an emetic. 

B. Two medicines, ipecac and apomorphine, induce vomiting. Metoclopramide is a prokinetic with antiemetic properties and therefore would have the opposite of the desired effect. Morphine is an opioid with analgesic and sedating properties. Promethazine and ondansetron are also antiemetics, not emetics. 

Spinal KAtp channels were shown to be involved in the antinociception produced by intrathecally (i.t.) administered morphine, norepinephrine, apomorphine and carbachol as deduced from the dose-dependent inhibition by i.t. glibenclamide. 

Well over a hundred years ago it was discovered that morphine, when treated with a strong acid, gave rise to the compound apomor-phine, an aporphine. It is now known that the lower of the two aromatic rings of apomorphine is the result of the rearomatization of the benzyl group, which was compromised by the ortho-4a attack men-... 

Apomorphine hydrochloride (Figure 44.2), an alkaloid obtained in the laboratory by rearrangements within the morphine molecule, is a grayish-white, glistening, light-sensitive, and air-sensitive crystalline powder, soluble in both water and alcohol in the proportions of about 1 50 it is available in small amounts in bulk and more easily as 5 mg (1/12 grain) tablets. 

Morphine, C17H19N03, 2 1/2 to 2% — The principal alkaloid, occurring in the drug in the form of the tribasic meconate. Its properties are anodyne, hypnotic, and narcotic. From it, by a process of dehydration by heat and hydrochloric acid, is prepared the artificial alkaloid apomorphine, a powerful emetic and expectorant. 

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