Structure via PubChem · Public domain (PubChem)
homoveratrylamine
Sign in to saveAlso known as beta-(3,4-Dimethyoxyphenyl)ethylamine, O,O-Dimethyldopamine, Dopamine dimethyl ether, Dimethylmescaline, Dimethoxyphenylethylamine, Dimethoxydopamine, DMPEA
3,4-Dimethoxyphenethylamine (DMPEA or 3,4-DMPEA), also known as homoveratrylamine, 3-desmethoxymescaline, or '''O,O-dimethyldopamine''', is a chemical compound of the phenethylamine family. 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 (3,4,5-trimethoxyphenethylamine; 3,4,5-TMPEA) and to 3,4-dimethoxyamphetamine (3,4-DMA).
Chemical data
- Formula
- C10H15NO2
- Molecular weight
- 181.23 g/mol
- IUPAC name
- 2-(3,4-dimethoxyphenyl)ethanamine
- SMILES
- COC1=C(C=C(C=C1)CCN)OC
- InChIKey
- ANOUKFYBOAKOIR-UHFFFAOYSA-N
- XLogP
- 0.8
- Polar surface area
- 44.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
28 papers- Self-assembly of 3,5-bis(ethoxycarbonyl)pyrazolate anions and ammonium cations of beta-phenylethylamine or homoveratrylamine into hetero-double-stranded helical structures.Organic & biomolecular chemistry · 2009
- A computational model for selectivity evaluation of 2-(3,4-dimethoxyphenyl)ethylamine (homoveratrylamine) imprinted polymers towards biogenic compounds.Analytica chimica acta · 2011
- Effects of homoveratrylamine on the operant behavior of rats. Potentiation by phenelzine.Acta physiologica latino americana · 1969
- Effects of homoveratrylamine (3,4-dimethoxyphenylethylamine) on the histamine responses and on the histaminolytic power of hog kidney diamine oxidase (DAO).Psychopharmacologia · 1967
- Total synthesis of lamellarin G trimethyl ether through enaminone cyclocondensation.Organic & biomolecular chemistry · 2023
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 181.11
Show 5 more facts
- melting point
- 11
- found in taxon
- Vachellia rigidula
- chemical formula
- C₁₀H₁₅NO₂
- canonical SMILES
- COC1=C(C=C(C=C1)CCN)OC
- Commons category
- 3,4-Dimethoxyphenethylamine
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
12 sectionsContents
- Use and effects
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Synthesis
- Derivatives
- Natural occurrence
- See also
- References
- External links
3,4-Dimethoxyphenethylamine (DMPEA or 3,4-DMPEA), also known as homoveratrylamine, 3-desmethoxymescaline, or '''O,O-dimethyldopamine', is a chemical compound of the phenethylamine family. 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 (3,4,5-trimethoxyphenethylamine; 3,4,5-TMPEA) and to 3,4-dimethoxyamphetamine (3,4-DMA).
==Use and effects== According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, DMPEA is inactive in humans at doses of up to 1,000mg orally and at a dose of 10mg intravenously.
Excerpted from Wikipedia’s “homoveratrylamine” article, available under the CC BY-SA 4.0 licence.