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Chemical Compound Review:

CTK8H0512 N-(1-phenylpropan-2- yl)hydroxylamine

Synonyms: AC1L23GP, 63-90-1, 4490-17-9, N-Hydroxyamphetamine, 4490-17-9 (hydrochloride), ...

Gal, J. et al., Paulsen-Sörman, U. et al., Kawalek, J.C. et al., Mahy, J.P. et al., Peyronneau, M.A. et al., et al.

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High impact information on N-Hydroxyamphetamine

Various N-alkylhydroxylamines such as N-hydroxyamphetamine react with prostaglandin synthase (PGHS) from sheep seminal vesicles, with the formation of new complexes characterized by a Soret peak around 421 nm [1].
A P450 Fe(II)-(RNO) complex was obtained upon oxidation of N-hydroxyamphetamine, catalyzed by P450-NF25-containing yeast microsomes [2].
The reconstituted liver microsomal hydroxylation system was used to study the formation of a metabolite-cytochrome P-450 complex absorbing maximally at 455 nm, with benzphetamine and N-hydroxyamphetamine as substrates [3].
In microsomes obtained from phenobarbital-treated rats, pronounced differences in the kinetics of complex formation were observed between the enantiomeric C-nitroso compounds, but not between the isomers of N-hydroxyamphetamine [4].
The role of N-hydroxyamphetamine in the metabolic deamination of amphetamine [5].

Associations of N-Hydroxyamphetamine with other chemical compounds

The stereoselective formation of the major metabolites N-hydroxyamphetamine and 1-phenyl-2-propanol in incubations of amphetamine with 9,000 X g supernatant fractions of rabbit liver has been studied using deuterium labelling in conjunction with selected-ion-monitoring gas chromatography/mass spectrometry [6].

References

Formation of prostaglandin synthase-iron-nitrosoalkane inhibitory complexes upon in situ oxidation of N-substituted hydroxylamines. Mahy, J.P., Mansuy, D. Biochemistry (1991) [Pubmed]
Optimization of yeast-expressed human liver cytochrome P450 3A4 catalytic activities by coexpressing NADPH-cytochrome P450 reductase and cytochrome b5. Peyronneau, M.A., Renaud, J.P., Truan, G., Urban, P., Pompon, D., Mansuy, D. Eur. J. Biochem. (1992) [Pubmed]
Reconstituted liver microsomal enzyme system that hydroxylates drugs, other foreign compounds, and endogenous substrates. IX. The formation of a 455-nm metabolite-cytochrome P-450 complex. Kawalek, J.C., Levin, W., Ryan, D., Lu, A.Y. Drug Metab. Dispos. (1976) [Pubmed]
Cytochrome P-455 nm complex formation in the metabolism of phenylalkylamines. IX. A comparative study with enantiomeric 2-nitroso-1-phenylpropane in microsomes and a reconstituted cytochrome P-450 system from rat liver. Paulsen-Sörman, U., Jönsson, K.H., Lindeke, B. Chem. Biol. Interact. (1988) [Pubmed]
The role of N-hydroxyamphetamine in the metabolic deamination of amphetamine. Wright, J., Cho, A.K., Gal, J. Life Sci. (1977) [Pubmed]
In vitro metabolism of amphetamine: an apparent enantiomeric interaction. Gal, J., Wright, J., Cho, A.K. Res. Commun. Chem. Pathol. Pharmacol. (1976) [Pubmed]

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