3-Methoxy-4,5-dihydroxyphenethylamine
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| IUPAC name
5-(2-aminoethyl)-3-methoxybenzene-1,2-diol
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3D model (JSmol)
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PubChem CID
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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).
Infobox references
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3-Methoxy-4,5-dihydroxyphenethylamine (3-MeO-4,5-diOH-PEA) 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]
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]
Occurence
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]
References
- ^ a b Kirschner, Gwendolyn K. (2023). "Breaking bad buttons: mescaline biosynthesis in peyote". The Plant Journal. 116 (3): 633–634. doi:10.1111/tpj.16503. ISSN 0960-7412. PMID 37861456.
- ^ a b Li, Ginny; Facchini, Peter J. (2024-12-01). "New frontiers in the biosynthesis of psychoactive specialized metabolites". Current Opinion in Plant Biology. 82 102626. doi:10.1016/j.pbi.2024.102626. ISSN 1369-5266. PMID 39288539.
- ^ a b Lembong, Elazmanawati; Nurmilah, Siti; Utama, Gemilang Lara (2025-10-01). "Metabolomic fingerprinting of Indonesian beetroot across Java agroecological zones: A tool for geographical authentication and quality assessment". Food Chemistry: X. 31: 102990. doi:10.1016/j.fochx.2025.102990. ISSN 2590-1575. PMC 12640041.
{{cite journal}}: CS1 maint: article number as page number (link) - ^ a b Watkins, Jacinta L.; Li, Qiushi; Yeaman, Sam; Facchini, Peter J. (2023). "Elucidation of the mescaline biosynthetic pathway in peyote (Lophophora williamsii)". The Plant Journal. 116 (3): 635–649. doi:10.1111/tpj.16447. ISSN 1365-313X.
- ^ Clement, Beverly A.; Goff, Christina M.; Forbes, T. David A. (1997-09-01). "Toxic amines and alkaloids from Acacia berlandieri". Phytochemistry. 46 (2): 249–254. doi:10.1016/S0031-9422(97)00240-9. ISSN 0031-9422.
- ^ Turner, William; Heyman, Jack (1960-12-01). "Notes: The Presence of Mescaline in Opuntia cylindrica". The Journal of Organic Chemistry. 25 (12): 2250–2251. doi:10.1021/jo01082a623. ISSN 0022-3263.
- ^ Clement, Beverly A; Goff, Christina M; Forbes, T. David A (1998-11-05). "Toxic amines and alkaloids from acacia rigidula". Phytochemistry. 49 (5): 1377–1380. doi:10.1016/S0031-9422(97)01022-4. ISSN 0031-9422.
- ^ Pummangura, S.; McLaughlin, J. L.; Schifferdecker, R. C. (March 1, 1982). "Cactus Alkaloids. LI. Lack of Mescaline Translocation in Grafted Trichocereus". Journal of Natural Products. 45 (2): 224–225. doi:10.1021/np50020a022. Retrieved 2026-03-01.
- ^ Pubchem Taxonomy