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 biosynthesis of mescaline within the peyote cactus (Lophophora williamsii), but is also found in various other plant species.
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.
3-Methoxy-4,5-dihydroxyphenethylamine is the primary intermediate in the synthesis of the tetrahydroisoquinoline alkaloid lophophorine. 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.
Occurrence 3-Methoxy-4,5-dihydroxyphenethylamine has been found in the following plant species: Senegalia berlandieri, Echinopsis spachiana, Austrocylindropuntia cylindrica, Vachellia rigidula and Lophophora williamsii.Pubchem Taxonomy
See also Scaline
References
External links 3,4-DESMETHYL - Isomer Design