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Chemical Compound Review:

CHEMBL278663 1-(4-methoxyphenyl)propan-2- amine

Synonyms: SureCN264634, AG-G-40326, ANW-71105, HSDB 7594, NSC-32757, ...

Foster, B.C. et al., Smets, G. et al., Ask, A.L. et al., Lopatka, J.E. et al., Callaghan, P.D. et al., et al.

Kraemer, Wennig, Maurer,

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Disease relevance of A4070/0173407

5-Hydroxytryptophan (5-HTP) and p-methoxyamphetamine (p-MA) induce dose-dependent, lethal hyperthermia when applied intravenously to monoamine oxidase inhibitor (MAOI) pretreated rabbits [1].
Worldwide growth in p-methoxyamphetamine (PMA) usage amongst 'ecstasy' users indicates a proportionally greater incidence of acute toxicity compared to 3,4-methylenedioxymethamphetamine (MDMA) [2].

High impact information on A4070/0173407

In vivo analysis of serotonin clearance in rat hippocampus reveals that repeated administration of p-methoxyamphetamine (PMA), but not 3,4-methylenedioxymethamphetamine (MDMA), leads to long-lasting deficits in serotonin transporter function [3].
O-Demethylation of p-methoxyamphetamine (PMA) by CYP2D6 was characterized (Km = 59.2 +/- 22.4 microM, and Vmax = 29.3 +/- 16.6 nmol/mg/hr, N = 6 livers) [4].
The prevention by six reversible and selective monoamine oxidase-A (MAO-A) inhibitors (alpha-ethyl-tryptamine, harmaline, 4-methoxyamphetamine, amiflamine [FLA 336(+)], N-desmethylamiflamine [FLA 788(+)] and N,N-desmethylamiflamine [FLA 668(+)] of the phenelzine-induced irreversible MAO inhibition in the rat brain was examined [5].
p-Hydroxyamphetamine (PHA) and p-hydroxybenzoic acid (PHBA) have been isolated by gas-liquid chromatography (GC) as urinary metabolites of p-methoxyamphetamine (PMA) in dogs and rhesus monkeys [6].
2. The biotransformation of 4-methoxyamphetamine was inhibited by cobalt; the carbon source and other trace metals had no effect [7].

Chemical compound and disease context of A4070/0173407

In this article, we describe four cases of severe acute toxicity due to recreational use of amphetamines 3,4-methylene-dioxymethamphetamine, 3,4-methylenedioxyethylamphetamine, 3,4-methylenedioxyamphetamine, 4-methylthioamphetamine or p-methoxyamphetamine, with emphasis on the presenting symptoms and acute treatment in the emergency department [8].
The ability of various drugs to prevent the lethal effects of 4-methoxyamphetamine (PMA) and 3, 4-methylenedioxyamphetamine (MDA) were reduced by pretreatment with phentolamine and 6-hydroxydopamine suggesting that release of norepinephrine from peripheral adrenergic nerves contributed to their toxicity [9].

Associations of A4070/0173407 with other chemical compounds

The rate of biotransformation of 4-methoxyamphetamine and formation of 4-hydroxyamphetamine was greater in cultures incubated on 30 degrees angle brackets rather than flat [7].
5. O-Demethylation was the major metabolic route in the biotransformation of 4-methoxyamphetamine but occurred to a lesser extent with 3-methoxyamphetamine, and was only a trace pathway with 2-methoxyamphetamine [7].

Analytical, diagnostic and therapeutic context of A4070/0173407

The N-dehydroxybutyl metabolites of MB, MO-EA, HO-EA, and the bis-dealkyl metabolite PMA should be responsible for the positive immunoassay results [10].

References

Neuroleptic influence on hyperthermia induced by 5-hydroxytryptophan and p-methoxy-amphetamine in MAOI-pretreated rabbits. Fjalland, B. Psychopharmacology (Berl.) (1979) [Pubmed]
Repeated administration of the substituted amphetamine p-methoxyamphetamine produces reductions in cortical 5-HT transporter binding but not 5-HT content, unlike 3,4-methylenedioxyamethamphetamine. Callaghan, P.D., Farrand, K., Salem, A., Hughes, P., Daws, L.C., Irvine, R.J. Eur. J. Pharmacol. (2006) [Pubmed]
In vivo analysis of serotonin clearance in rat hippocampus reveals that repeated administration of p-methoxyamphetamine (PMA), but not 3,4-methylenedioxymethamphetamine (MDMA), leads to long-lasting deficits in serotonin transporter function. Callaghan, P.D., Owens, W.A., Javors, M.A., Sanchez, T.A., Jones, D.J., Irvine, R.J., Daws, L.C. J. Neurochem. (2007) [Pubmed]
Interactions of amphetamine analogs with human liver CYP2D6. Wu, D., Otton, S.V., Inaba, T., Kalow, W., Sellers, E.M. Biochem. Pharmacol. (1997) [Pubmed]
Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain. Ask, A.L., Fagervall, I., Ross, S.B. Naunyn Schmiedebergs Arch. Pharmacol. (1983) [Pubmed]
The metabolism of p-methoxyamphetamine in dog and monkey. O-demethylation as a major route. Hubbard, J.W., Midha, K.K., Cooper, J.K. Drug Metab. Dispos. (1977) [Pubmed]
Biotransformation of 2-, 3-, and 4-methoxy-amphetamines by Cunninghamella echinulata. Foster, B.C., Litster, D.L., Lodge, B.A. Xenobiotica (1991) [Pubmed]
Amphetamine toxicity in the emergency department. Smets, G., Bronselaer, K., De Munnynck, K., De Feyter, K., Van de Voorde, W., Sabbe, M. European journal of emergency medicine : official journal of the European Society for Emergency Medicine. (2005) [Pubmed]
The protective effects of methysergide, 6-hydroxydopamine and other agents on the toxicity of amphetamine, phentermine, MDA, PMA, and STP in mice. Lopatka, J.E., Brewerton, C.N., Brooks, D.S., Cook, D.A., Paton, D.M. Res. Commun. Chem. Pathol. Pharmacol. (1976) [Pubmed]
The antispasmodic drug mebeverine leads to positive amphetamine results by fluorescence polarization immunoassay (FPIA)--studies on the toxicological analysis of urine by FPIA and GC-MS. Kraemer, T., Wennig, R., Maurer, H.H. Journal of analytical toxicology. (2001) [Pubmed]

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