3-Methoxy-4,5-dihydroxyphenethylamine
Chemical compound
From Wikipedia, the free encyclopedia
3-Methoxy-4,5-dihydroxyphenethylamine (3-MeO-4,5-diOH-PEA), also known as 4-O-,5-O-didesmethylmescaline, is a phenylethylamine alkaloid and an important intermediate metabolite in the final biosynthesis of mescaline in the peyote cactus (Lophophora williamsii),[1] as well as in other cacti such as Echinopsis pachanoi, Echinopsis lageniformis, and Echinopsis peruvianus.[2] It was found in Beta vulgaris as a metabolite.[3]
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| Names | |
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| IUPAC name
5-(2-aminoethyl)-3-methoxybenzene-1,2-diol | |
| Other names
4-O-,5-O-Didesmethylmescaline; 3,4-Dihydroxy-5-methoxyphenethylamine; 3,4-DESMETHYL | |
| Identifiers | |
3D model (JSmol) |
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| Properties | |
| C9H13NO3 | |
| Molar mass | 183.207 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis
Mescaline biosynthesis in Lophophora williamsii begins with the conversion of L-tyrosine to L-DOPA by LwCYP76AD94, which is decarboxylated to dopamine (LwTYDC), which is then 3-O-methylated to 3-methoxytyramine by one of two O-methyltransferases (LwOMT2 or LwOMT6), 5-hydroxylated by cytochrome CYP76AD131 to 3-methoxy-4,5-dihydroxyphenylethylamine, then methylated by LwOMT2 at position 5 to form 3,5-dimethoxy-4-hydroxyphenylethylamine and finally by LwOMT10 at position 4 to form mescaline.[2][1][4]
3-Methoxy-4,5-dihydroxyphenethylamine is the primary intermediate in the synthesis of Lophophora williamsii tetrahydroisoquinoline alkaloids. This process likely involves the enzyme LwOMT10, which catalyzes methylation at position 4 or 5 to yield 3,4-dimethoxy-5-hydroxyphenethylamine. The latter is subsequently N-methylated by LwNMT to form N-methyl-3,4-dimethoxy-5-hydroxyphenethylamine, which is eventually converted into lophophorine.[4]
Occurrence
3-Methoxy-4,5-dihydroxyphenethylamine has been found in Senegalia berlandieri, Echinopsis spachiana, Austrocylindropuntia cylindrica,Beta vulgaris, and Vachellia rigidula and was identified as an important intermediate metabolite in Lophophora williamsii.[5][6][7][8][9][3]