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Chemical Compound Review:

SureCN274906 4-(2-methylaminoethyl)phenol

Synonyms: AG-F-29859, CHEBI:17458, HMDB03633, ANW-58674, NSC-113958, ...

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Disease relevance of WIN 5582

Evidence that N-methyltyramine does not cause Phalaris aquatica-related sudden death in ruminants [1].

High impact information on WIN 5582

Analysis and prediction of absorption profile including hepatic first-pass metabolism of N-methyltyramine, a potent stimulant of gastrin release present in beer, after oral ingestion in rats by gastrointestinal-transit-absorption model [2].
Traces of 3,4-dimethoxyphenethylamine (TLC and mass spectrometry), tyramine (TLC), and N-methyltyramine (TLC) were identified [3].
Thus, the decomposition of the specific MAO-A-substrates noradrenaline and adrenaline as well as of N-methyltyramine itself is inhibited [4].
Nitrosation of N-methyltyramine and N-methyl-3-aminomethylindole, two barley malt alkaloids [5].

Biological context of WIN 5582

The nitrosation products of N-methyltyramine were p-hydroxy-m-nitro-N-nitroso-N-methyl-2-phenylethylamine and p-hydroxy-N-nitroso-N-methyl-2-phenylethylamine [5].

Gene context of WIN 5582

Given orally, both substances influence the monoamine oxidase type A (MAO-A): N-methyltyramine acts as a competitive substrate, and 2-Me THBC is one of the most effective MAO-A-inhibitors [4].

Analytical, diagnostic and therapeutic context of WIN 5582

The dose of NMT giving maximal gastrin-releasing activity was 25 microg/kg, and the 50% effective dose was approximately 10 microg/kg on oral administration to rats [6].

References

Evidence that N-methyltyramine does not cause Phalaris aquatica-related sudden death in ruminants. Bourke, C., Colegate, S., Culvenor, R. Aust. Vet. J. (2006) [Pubmed]
Analysis and prediction of absorption profile including hepatic first-pass metabolism of N-methyltyramine, a potent stimulant of gastrin release present in beer, after oral ingestion in rats by gastrointestinal-transit-absorption model. Kimura, T., Iwasaki, N., Yokoe, J.I., Haruta, S., Yokoo, Y., Ogawara, K.I., Higaki, K. Drug Metab. Dispos. (2000) [Pubmed]
Cactus alkaloids XXXIII: beta-phenethylamines from the Guatemalan cactus Pilosocereus maxonii. Pummangura, S., Nichols, D.E., McLaughlin, J.L. Journal of pharmaceutical sciences. (1977) [Pubmed]
Toxicity of Palicourea marcgravii: combined effects of fluoroacetate, N-methyltyramine and 2-methyltetrahydro-beta-carboline. Kemmerling, W. Z. Naturforsch., C, J. Biosci. (1996) [Pubmed]
Nitrosation of N-methyltyramine and N-methyl-3-aminomethylindole, two barley malt alkaloids. Mangino, M.M., Libbey, L.M., Scanlan, R.A. IARC Sci. Publ. (1982) [Pubmed]
Isolation from beer and structural determination of a potent stimulant of gastrin release. Yokoo, Y., Kohda, H., Kusumoto, A., Naoki, H., Matsumoto, N., Amachi, T., Suwa, Y., Fukazawa, H., Ishida, H., Tsuji, K., Nukaya, H. Alcohol Alcohol. (1999) [Pubmed]

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