3,4-Dimethoxyphenethylamine

Description

3,4-Dimethoxyphenylethylamine, also known as 3,4-DMPEA or DMPEA is an endogenous metabolite found in urine that belongs to both the phenethylamine and catecholamine families. DMPEA is an analogue of dopamine (3,4-dihydroxyphenethylamine), with a substitution of the hydroxy groups with methoxy groups. It is also structurally similar to mescaline (3,4,5-trimethoxyphenylethylamine) and occurs naturally alongside it in various species of cacti such as the San Pedro and Peruvian Torch. DMPEA received wide attention after it was proposed as a biomarker in schizophrenic patients urine, however later studies revealed that DMPEA is also excreted by non-schizophrenics. DMPEA has little known bioactivity, but it has some action as a monoamine oxidase inhibitor. It has also been shown to have neurotoxic effects, especially in the nigrostriatal system and among dopaminergic neurons. DMPEA appears to be an inhibitor of mitochondrial complex I.

Chemical properties

3,4-Dimethoxyphenethylamine is clear yellowish oil

Occurence

3,4-Dimethoxyphenethylamine occurs naturally along with mescaline in various species of cacti such as San Pedro and Peruvian Torch.

Occurrence

3,4-Dimethoxyphenethylamine is a natural product found in Pilosocereus leucocephalus, Vachellia rigidula, and Ototropis elegans with data available.

The Uses of 3,4-Dimethoxyphenethylamine

3,4-Dimethoxyphenethylamine is a methylated metabolite of Dopamine (D533780); a potent inhibitor of brain mitochondrial respiration used in Parkinson’s disease studies.

The Uses of 3,4-Dimethoxyphenethylamine

Precursor for the synthesis of isoquinolines.

Definition

ChEBI: An aromatic ether that is the derivative of 2-phenylethylamine with methoxy substituents at the 3- and 4-positions. It is an alkaloid isolated from the Cactaceae family.

Pharmacology

3,4-Dimethoxyphenethylamine has some activity as a monoamine oxidase inhibitor.

Production technology

One kind 3, 4-dimethoxy-phenylethylamine production technology, it is characterized in that with 3, 4-dihydroxyl Benzyl Chloride and methyl-sulfate are raw material, under sodium hydroxide exists, there is etherification reaction generate 3, 4-dimethoxy Benzyl Chloride, 3, 4-dimethoxy Benzyl Chloride generates 3 with prussiate generation cyanogenation again, 4-dimethoxy cyanobenzene, crystallisation by cooling obtains 3 in acetone, 4-dimethoxy cyanobenzene crystal, in a solvent 3, 4-dimethoxy cyanobenzene catalytic ammoniation hydrogenation generates 3, 4-dimethoxy-phenylethylamine, product after ammonification hydrogenation obtains product 3 through underpressure distillation, 4-dimethoxy-phenylethylamine.

Flammability and Explosibility

Not classified

Safety Profile

Poison by intravenous and intraperitoneal routes. When heated to decomposition it emits toxic fumes of NOx.

Purification Methods

Purify the amine by fractionation through an efficient column in an inert atmosphere as it is a relatively strong base. [Horner & Sturm Justus Liebigs Ann Chem 608 12819 1957, Jung et al. J Am Chem Soc 75 4664 1953.] The hydrochloride has m 152o, 154o, 156o (from EtOH, Me2CO or EtOH/Et2O), the picrate has m 165-167o(dec), and the 4-nitrobenzoyl derivative has m 147o [Buck J Am Chem Soc 55 2593 1933]. [Beilstein 13 H 800, 13 IV 2604.]