N-Hydroxyamphetamine

Autoxidation of N-hydroxyamphetamine gives the nitroso-derivative which isomerizes to the corresponding oxime. A variety of AT-oxygenated products which might arise by oxidation, in vitro or in vivo, of 3,4-dimethoxyamphetamine and its V-alkyl derivatives have been prepared. A similar study has been carried out on the metabolic oxidation products of norephedrine. ... 

Lindeke, B., E. Anderson, G. Lundkvist, H. Jonsson, and S.O. Eriksson (1975). Autoxidation of N-hydroxyamphetamine and N-hydroxyphen-termine The formation of 2-nitroso-l-phenyl-propanes and l-phenyl-2-propanone oxime. Acta Pharm. Suec. 12, 183-198. 

N-hydroxyamphetamine [5]. (Note added in proof Since this paper... 

Beckett AH and Al-Sarraj S, The identification, properties and analysis of N-hydroxyamphetamine, a metabolite of amphetamine,... 

Hydroquinone (C6H6O2) p-Hydroxy-y-aminobutyric acid (C4H9NO3) N-hydroxyamphetamine (C9H13NO) 4-Hydroxyamphetamine (Paredrine) (C9H13NO)... 

Why more appealing For one thing, oxidative changes are much more common in the body than reductive changes. For another, the conversion of amphetamine to N-hydroxyamphetamine is an intermediate in the conversion of amphetamine to phenylacetone, a known metabolic process in several animal species. And that intermediate, N-hydroxyamphetamine, is a material that gives the famous cytochrome P-450 complex that has fascinated biochemists studying the so-called NADPH-dependent metabolism. 

N-hydroxyamphetamine, is a material that gives the famous cytochrome P-450 complex that has fascinated biochemists studying the so-called NADPH-dependent metabolism. 

EXTENSIONS AND COMMENT ARY Here is another example of the presentation of a compound for which there has not yet been an effective level determined. Why For a very good reason. This is an example of a whole class of compounds that I have called the pseudos, or the -compounds. Pseudo- as a prefix in the literary world generally stands for false. A pseudopod is a thing that looks like a foot, but isn t one. A pseudonym is a fictitious name. But in chemistry, it has quite a different meaning. If something has a common name, and there is a second form (or isomer, or shape, or orientation) that is possible and it doesn t have a common name, it can be given the name of the first form with a pseudo- attached. Ephedrine is the erythro-isomer of N-methyl-13-hydroxyamphetamine. There is a second stereoisomer, the threo- isomer, but it has no trivial name. So it is called pseudoephedrine, or the Sudafed of sinus decongestant fame. 

The main metabolic reaction is the deamination of amphetamine with the formation of phenylacetone, which is subsequently oxidized to benzoic acid, then conjugated with glycine to form hippuric acid. Side reactions include aromatic hydroxylation to form 4-hydroxyamphetamine (an active metabolite), the stereoselective [i-hydroxy-lation for the isomer (+) of amphetamine leading to the formation of norephedrine (phenylpropanolamine) and finally the N-oxidation leading to the formation of a hydroxylamine derivative. The products of the hydroxyl and aromatic N-oxides can be conjugated with sulfate or glucuronic acid [18]. 

The N-hydroxylation reaction is not restricted to o-substi-tuted primary amines such as phentermine. Amphetamine has been observed to undergo some N-hydroxylation in vitro to (V-hydroxyamphetamine.- - /V-Hydroxyamphetamine is, however, susceptible to further conversion to the imine or oxidation to the oxime intermediate. Note that the oxime intermediate arising from this N-oxidation pathway can undergo hydrolytic cleavage to yield phenylacetone. the same product obtained by the a-carbon hydroxylation (carbi-... 

Aral, Y. Kim, S.Y. Kinemuchi, H. Tadano, T. Satoh, S. and Satoh, N. Inhibition of brain type A monoamine oxidase and 5-hydroxytryptamine uptake by two amphetamine metabolites, p-hydroxyamphetamine and p-hydroxynorephedrine. JNeurochem 55 403-408, 1990. 

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

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... 

---