InChI=1S/C11H17NO/c1-9(12-2)8-10-6-4-5-7-11(10)13-3/h4-7,9,12H,8H2,1-3H3 |
OEHAYUOVELTAPG-UHFFFAOYSA-N |
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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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beta-adrenergic agonist
An agent that selectively binds to and activates beta-adrenergic receptors.
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beta-adrenergic agonist
An agent that selectively binds to and activates beta-adrenergic receptors.
bronchodilator agent
An agent that causes an increase in the expansion of a bronchus or bronchial tubes.
central nervous system stimulant
Any drug that enhances the activity of the central nervous system.
(via amphetamines )
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View more via ChEBI Ontology
1-(2-methoxyphenyl)-N-methylpropan-2-amine
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methoxyphenamine
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WHO MedNet
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méthoxyphénamine
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WHO MedNet
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methoxyphenaminum
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WHO MedNet
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metoxifenamina
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WHO MedNet
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2-Methoxymethamphetamine
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DrugCentral
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methoxiphenadrin
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DrugCentral
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methoxyphenamin
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DrugCentral
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OMMA
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ChEBI
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2803353
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Reaxys Registry Number
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Reaxys
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93-30-1
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CAS Registry Number
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DrugCentral
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Thevis M, Sigmund G, Koch A, Guddat S, Maurer HH, Schänzer W (2008) Doping control analysis of methoxyphenamine using liquid chromatography-tandem mass spectrometry. European journal of mass spectrometry (Chichester, England) 14, 145-152 [PubMed:18708694] [show Abstract] Methoxyphenamine (o-methoxy-N,alpha-dimethylphenethylamine, Orthoxine) used in earlier times as a bronchodilator is prohibited in sports according to the regulations of the World Anti-Doping Agency (WADA). The drug and several of its metabolites are commonly analysed in doping control screening assays using gas chromatography-mass spectrometry requiring extraction from urine specimens. A complementary method employing liquid chromatography-atmospheric pressure chemical ionisation-tandem mass spectrometry and direct injection of urine aliquots was developed, which provided a fast and sensitive alternative to confirm the presence of the prohibited compound and degradation products in sports drug testing samples. In particular, the chromatographic separation of the active drug from isomeric compounds such as the designer drug p-methoxymetamphetamine (PMMA) was of particular interest to unambiguously identify the applied substance and was accomplished using a C6-phenyl reverse-phase column with isocratic elution. The established procedure was validated for methoxyphenamine with regard to specificity, limit of detection (0.7 ng mL(-1)), intraday- and interday precision (2.5-5.8% and 10.8-16.2%, respectively) and its applicability was demonstrated with an authentic doping control sample which tested positive for the prohibited compound early in 2008. | Hsieh YC, Whang CW (2006) Analysis of ethambutol and methoxyphenamine by capillary electrophoresis with electrochemiluminescence detection. Journal of chromatography. A 1122, 279-282 [PubMed:16797572] [show Abstract] A capillary electrophoresis (CE) coupled with electrochemiluminescence (ECL) detection method for the analysis of ethambutol (EB) and methoxyphenamine (MP) has been investigated. Complete separation of EB and MP was achieved in 8 min using a background electrolyte of 20 mM sodium phosphate at pH 10.0 and a separation voltage of 9 kV. ECL detection was performed with an indium/tin oxide (ITO) working electrode biased at 1.4 V (versus a Pt wire reference) in a 200 mM sodium phosphate buffer (pH 8.0) containing 3.5 mM Ru(bpy)3(2+) (where bpy = 2,2'-bipyridyl). Linear correlation (r > or = 0.993) between ECL intensity and drug concentration was obtained in the range 2-50 ng/ml. The limits of detection (LODs) for EB and MP in water were 1.0 and 0.9 ng/ml, respectively. The relative standard deviation values on peak size (10 ng/ml level) and migration time for the two drugs were in the ranges 5-8 and 0.2-0.7% (n = 7), respectively. Applicability of the CE-ECL method to the analysis of human plasma spiked with EB and MP was examined. The LODs for EB and MP in plasma were 0.4 and 0.3 microg/ml, respectively. | Coutts RT, Bolaji OO, Su P, Baker GB (1994) Metabolism of methoxyphenamine in vitro by a CYP2D6 microsomal preparation. Drug metabolism and disposition: the biological fate of chemicals 22, 756-760 [PubMed:7835228] [show Abstract] Metabolism of methoxyphenamine (MP) was conducted in vitro using commercially available microsomes prepared from human AHH-1 TK+/-cells in which CYP2D6 had been expressed. This study has confirmed the involvement of CYP2D6 in the metabolism of MP to O-desmethylmethoxyphenamine (ODMP) and 5-hydroxymethoxyphenamine (5HMP), but not to N-desmethylmethoxyphenamine. It has also revealed that CYP2D6 catalyzes the formation of another, hitherto unknown, ring-hydroxylated metabolite of MP, isomeric with 5HMP. The analytical procedure used to identify and quantify MP metabolites involved an acetylation procedure that had distinct advantages. MP and its basic and amphoteric metabolites were all converted to neutral products that were efficiently extracted into organic solvent. The acetylated products also had good chromatographic properties and provided mass spectra that were readily interpretable. MP metabolism studies were also conducted with CYP2D6 microsomes in the presence of quinidine and quinine. The former was the more potent inhibitor of CYP2D6-catalyzed oxidations of MP. Its inclusion resulted in complete inhibition of metabolism of MP to ODMP, 5HMP, and its novel isomer. This study shows that the in vitro use of human cytochrome P450 isozyme preparations in drug metabolism studies can aid in the identification of possible in vivo metabolites of these drugs in humans and can provide information on putative drug-drug interactions. |
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