3,4-Dimethoxyphenethylamine Chemical Properties

Melting point:

12-15 °C

Boiling point:

188 °C15 mm Hg(lit.)

Density 

1.074 g/mL at 25 °C(lit.)

vapor pressure 

0.348-0.348Pa at 25℃

refractive index 

n20/D 1.546(lit.)

Flash point:

>230 °F

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

9.74±0.10(Predicted)

form 

Viscous Liquid

Specific Gravity

1.10

color 

Clear light yellow to orange or slightly brownish

PH

11.4 (100g/l, H2O, 20℃)

explosive limit

0.1-1.7%(V)

Water Solubility 

SOLUBLE

Sensitive 

Air Sensitive

InChIKey

ANOUKFYBOAKOIR-UHFFFAOYSA-N

LogP

0.77

CAS DataBase Reference

120-20-7(CAS DataBase Reference)

NIST Chemistry Reference

Benzeneethanamine, 3,4-dimethoxy-(120-20-7)

EPA Substance Registry System

Benzeneethanamine, 3,4-dimethoxy- (120-20-7)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-36-37/39

RIDADR 

UN 2735

WGK Germany 

3

RTECS 

SH2300000

F 

10

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29222900

Toxicity

mouse,LD50,intraperitoneal,181mg/kg (181mg/kg),Yakugaku Zasshi. Journal of Pharmacy. Vol. 97, Pg. 1117, 1977.

MSDS

• Language:English Provider:3,4-Dimethoxyphenethylamine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

3,4-Dimethoxyphenethylamine Usage And Synthesis

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

Occurrence

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

Uses

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

Uses

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.

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.]

3,4-Dimethoxyphenethylamine(120-20-7)Related Product Information

• 2,6-Dimethoxybenzaldehyde
• 1,1-Dimethoxyethane
• Diphenyldimethoxysilane
• Dimethyldimethoxysilane
• L-1-Phenylethylamine
• Ethylamine
• Dimethoxymethane
• (3,4-Dimethoxyphenyl)acetic acid
• 2-METHOXYETHYLAMINE
• Palmatine chloride
• D-TUBOCURARINE CHLORIDE
• 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride
• THEBAINE
• DL-6'-BROMOLAUDANOSIN
• Tetrahydropapaverine hydrochloride
• 3,4-Dibenzyloxyphenethylamine hydrochloride
• DL-LAUDANOSINE
• BRUCINE SULFATE