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.

Quick Facts Names, Identifiers ...

3,4-Dimethoxyphenethylamine

Names
Preferred IUPAC name 2-(3,4-Dimethoxyphenyl)ethan-1-amine
Identifiers
CAS Number	120-20-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:136995 Y
ChEMBL	ChEMBL26019 Y
ChemSpider	8114 Y
ECHA InfoCard	100.003.979
PubChem CID	8421
UNII	IQF9T435OP Y
CompTox Dashboard (EPA)	DTXSID8059506
InChI 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
SMILES O(c1ccc(cc1OC)CCN)C
Properties
Chemical formula	C10H15NO2
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). Y verify (what is YN ?) Infobox references

Close

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]

DMPEA has some activity as a monoamine oxidase inhibitor.^[5]

DMPEA occurs naturally along with mescaline in various species of cacti such as San Pedro and Peruvian Torch.^[6][7][8]

• 3-Methoxytyramine
• Mescaline