One of the earliest syntheses of DMPEA (then referred to as "homoveratrylamine") was that of Pictet and Finkelstein, who made it in a multi-step sequence starting from vanillin.[1] A similar sequence was subsequently reported by Buck and Perkin,[2] as follows:
^Keller WJ; Ferguson GG (July 1977). "Effects of 3,4-dimethoxyphenethylamine derivatives on monoamine oxidase". Journal of Pharmaceutical Sciences. 66 (7): 1048–50. doi:10.1002/jps.2600660741. PMID 886445.
^Lundström J (December 1970). "Biosynthesis of mescaline and 3,4-dimethoxyphenethylamine in Trichocereus pachanoi Br&R". Acta Pharmaceutica Suecica. 7 (6): 651–66. PMID 5511715.
^Pummangura S; Nichols DE; McLaughlin JL (October 1977). "Cactus alkaloids XXXIII: beta-phenethylamines from the Guatemalan cactus Pilosocereus maxonii". Journal of Pharmaceutical Sciences. 66 (10): 1485–7. doi:10.1002/jps.2600661037. PMID 925910.
^Pardanani JH; McLaughlin JL; Kondrat RW; Cooks RG (1977). "Cactus alkaloids. XXXVI. Mescaline and related compounds from Trichocereus peruvianus". Lloydia. 40 (6): 585–90. PMID 600028.
External linksedit
DMPEA Entry in PiHKAL
DMPEA Entry in PiHKAL • info
December 20, 2023
dimethoxyphenethylamine, dmpea, chemical, compound, phenethylamine, class, analogue, major, human, neurotransmitter, dopamine, where, position, hydroxy, groups, have, been, replaced, with, methoxy, groups, also, closely, related, mescaline, which, trimethoxyph. 3 4 Dimethoxyphenethylamine DMPEA is a chemical compound of the phenethylamine class It is an analogue of the major human neurotransmitter dopamine where the 3 and 4 position hydroxy groups have been replaced with methoxy groups It is also closely related to mescaline which is 3 4 5 trimethoxyphenethylamine 3 4 Dimethoxyphenethylamine NamesPreferred IUPAC name 2 3 4 Dimethoxyphenyl ethan 1 amineIdentifiersCAS Number 120 20 7 Y3D model JSmol Interactive imageChEBI CHEBI 136995 YChEMBL ChEMBL26019 YChemSpider 8114 YECHA InfoCard 100 003 979PubChem CID 8421UNII IQF9T435OP YCompTox Dashboard EPA DTXSID8059506InChI InChI 1S C10H15NO2 c1 12 9 4 3 8 5 6 11 7 10 9 13 2 h3 4 7H 5 6 11H2 1 2H3 YKey ANOUKFYBOAKOIR UHFFFAOYSA N YInChI 1 C10H15NO2 c1 12 9 4 3 8 5 6 11 7 10 9 13 2 h3 4 7H 5 6 11H2 1 2H3Key ANOUKFYBOAKOIR UHFFFAOYABSMILES O c1ccc cc1OC CCN CPropertiesChemical formula C10H15NO2Molar mass 181 23 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Chemistry 1 1 Derivatives 2 Pharmacology 3 Occurrence 4 See also 5 References 6 External linksChemistry editOne of the earliest syntheses of DMPEA then referred to as homoveratrylamine was that of Pictet and Finkelstein who made it in a multi step sequence starting from vanillin 1 A similar sequence was subsequently reported by Buck and Perkin 2 as follows 3 4 Dimethoxybenzaldehyde veratraldehyde 3 4 Dimethoxycinnamic acid 3 4 Dimethoxyphenylpropionic acid 3 4 Dimethoxyphenylpropionamide 3 4 DimethoxyphenethylamineA much shorter synthesis is given by Shulgin and Shulgin 3 4 Derivatives edit A known use was in the synthesis of Bevantolol Pharmacology editDMPEA has some activity as a monoamine oxidase inhibitor 5 Occurrence editDMPEA occurs naturally along with mescaline in various species of cacti such as San Pedro and Peruvian Torch 6 7 8 See also edit3 Methoxytyramine MescalineReferences edit A Pictet and M Finkelstein 1909 Synthese des Laudanosins Ber 42 1979 1989 J S Buck and W H Perkin 1924 CCXVIII PS epiBerberine J Chem Soc Trans 125 1675 1686 A Shulgin and A Shulgin 1991 PiHKAL A Chemical Love Story pp 614 616 Transform Press Berkeley ISBN 0 9630096 0 5 Erowid Online Books PIHKAL 60 DMPEA Keller WJ Ferguson GG July 1977 Effects of 3 4 dimethoxyphenethylamine derivatives on monoamine oxidase Journal of Pharmaceutical Sciences 66 7 1048 50 doi 10 1002 jps 2600660741 PMID 886445 Lundstrom J December 1970 Biosynthesis of mescaline and 3 4 dimethoxyphenethylamine in Trichocereus pachanoi Br amp R Acta Pharmaceutica Suecica 7 6 651 66 PMID 5511715 Pummangura S Nichols DE McLaughlin JL October 1977 Cactus alkaloids XXXIII beta phenethylamines from the Guatemalan cactus Pilosocereus maxonii Journal of Pharmaceutical Sciences 66 10 1485 7 doi 10 1002 jps 2600661037 PMID 925910 Pardanani JH McLaughlin JL Kondrat RW Cooks RG 1977 Cactus alkaloids XXXVI Mescaline and related compounds from Trichocereus peruvianus Lloydia 40 6 585 90 PMID 600028 External links editDMPEA Entry in PiHKAL DMPEA Entry in PiHKAL info Retrieved from https en wikipedia org w index php title 3 4 Dimethoxyphenethylamine amp oldid 1017418437, wikipedia, wiki, book, books, library,
