Morphine, N-oxide

Impurities in illicit morphine or heroin samples are important in establishing the manufacturing source of the drug. A16,17-Dehydroheroinium chloride (208) has been found(32l) in trace amounts in illicit heroin and may also be formed as a post-injection artefact during GC analysis of heroin samples. A synthesis from morphine-N-oxide by treatment with excess of hot acetyl chloride has been effected and 208 converted to 16-cyanoheroin (209) with aqueous KCN. 

Incubation of morphine and [14C-methyl]-5-adenosylmethionine with rabbit liver homogenates resulted in the detection of 2-methoxymorphine as a minor metabolite/446 Oxidation at C-2 may also have occurred in rat brain homogenates with the tentative identification of morphine-2,3-quinone as a minor morphine metabolite/447 Morphine-N-oxide (266) and its 3-glucuronide have been isolated 448 from guinea pig urine after morphine adminstration, and a- and /3-dihydromorphine (264 and 265) were also established as metabolites by gc/ms of extracts of the urine of several species. 

Fluoroacetylation Trifluoroacetic acid morphine-N-oxide, nor- morphine, pseudomorphine, 39 codeine morphine, codeine37... 

For investigations on morphine, its metabolites and conaeners (codeine, morphine-N-oxide,... 

Normorphine cannot be prepared like norcodeine, through the N-nitrosocompound, as nitrous acid oxidizes morphine to pseudomorphine [557]. Conversion of morphine-N-oxide to normorphine by dichromates is unsatisfactory owing to breakdown of the ring structure [556],... 

Interfering bromo-STP, codeine-N-oxide, ethylmorphine, 4-hydroxyamphetamine, morphine, morphine-N-oxide, normetanephrine, 2-phenethylamine, prolintane, STP... 

A patent has been published that covers the rearrangement of ethers of morphine and N-alkyl-normorphines to the corresponding derivatives of apomorphine and N-alkyl-norapomorphines by phosphoric acid at 125— 140 lO-Oxomorphine has been isolated as an oxidation production from solutions of morphine hydrochloride/ and morphine has been shown to be converted into morphine N-oxide and normorphine by guinea-pig liver microsomal preparations, which convert codeine, under similar conditions, into codeine AT-oxide, norcodeine, morphine, and normorphine/ ... 

Simultaneous acetylcodeine, amphetamine, benzphetamine, benzylmorphine, bromo-STP, buprenorphine, chlorphentermine, codeine, codeine-N-oxide, dextromoramide, dextropro-poxyphene, diamorphine, diethylpropion, dihydrocodeine, dihydromorphine, dimethylam-phetamine, dipipanone, ephedrine, epinephrine, ethoheptazine, ethylmorphine, etorphine, fencamfamin, fenfluramine, fentanyl, hydrocodone, 4-hydroxyamphetamine, levorphanol, mazindol, meperidine, mephentermine, mescaline, methadone, methamphetamine, meth-ylenediojQramphetamine, methylephedrine, monoacetylmorphine, morphine, morphine-3-glucuronide, morphine-N-oxide, naloxone, norcodeine, norlevorphanol, normetanephrine, normethadone, normorphine, norpethidine, norpseudoephedrine, noscapine, o codone, papaverine, pemoline, pentazocine, 2-phenethylamine, phenoperidine, phentermine, phenylephrine, phenylpropanolamine, pholcodeine, pipradol, piritramide, prolintane, pseudoephedrine, STP, thebacon, thebaine, trimethoxyamphetamine, tyramine... 

I Strong Analgesics A. Morphine-like compounds -The absolute configuration of morphine has been elucidated and is shov/n (1). The methoxymethyl ether of morphine proved less active than the parent while the essential inactivity of morphine N-oxide has been confirmed. ... 

Figure 6.28. N-oxides of Papaver alkaloids. Thebaine N-oxide, major isomer (1) minor isomer (2) codeine A -oxide. major isomer (3) minor isomer (4) morphine N-oxide, major isomer (5). 1 and 2 were isolated from P. bracteatum (thebaine-rich strain), 3, 4, and 5 were isolated from P. somniferum (Halle strain), courtesy of J. D. Phillipson and Pergamon Press, Ltd., copyright 1976.

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