3,4-Dimethoxyphenethylamine
Names
Preferred IUPAC name
2-(3,4-Dimethoxyphenyl)ethan-1-amine
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.003.979
UNII
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
Y Key: ANOUKFYBOAKOIR-UHFFFAOYSA-N
Y InChI=1/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3
Key: ANOUKFYBOAKOIR-UHFFFAOYAB
Properties
C10 H15 NO2
Molar mass
181.23 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
3,4-Di methoxy phenethylamine (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.
Chemistry
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:
3,4-Dimethoxybenzaldehyde (veratraldehyde) → 3,4-Dimethoxycinnamic acid → 3,4-Dimethoxyphenylpropionic acid → 3,4-Dimethoxyphenylpropionamide → 3,4-Dimethoxyphenethylamine
A much shorter synthesis is given by Shulgin and Shulgin:[ 3] [ 4]
Derivatives
A known use was in the synthesis of Bevantolol .
Pharmacology
DMPEA has some activity as a monoamine oxidase inhibitor .[ 5]
Occurrence
DMPEA occurs naturally along with mescaline in various species of cacti such as San Pedro and Peruvian Torch .[ 6] [ 7] [ 8]
See also
References
^ A. Pictet and M. Finkelstein (1909). "Synthese des Laudanosins." Ber. 42 1979-1989.
^ J. S. Buck and W. H. Perkin (1924). "CCXVIII. Ψ-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 .
^ 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 links