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Details

Stereochemistry ACHIRAL
Molecular Formula C10H15NO2
Molecular Weight 181.2316
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DMPEA

SMILES

COC1=C(OC)C=C(CCN)C=C1

InChI

InChIKey=ANOUKFYBOAKOIR-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C10H15NO2
Molecular Weight 181.2316
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Homoveratrylamine (3,4-dimethoxyphenethylamine, DMPEA) is an analog of the major neurotransmitter dopamine where 3- and 4- position hydroxyl groups are replaced with methoxy groups. DMPEA is a metabolite of dopamine and is reported to be produced at elevated levels in patients with schizophrenia and Parkinson's disease. DMPEA inhibited monoamine oxidase and demonstrated no peripheral and central antidopaminergic activity in vivo.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
In vivo experiments with DMPEA were performed on mice. Compound was administered intraperitoneally at doses 25-200 mg/kg.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Brain mitochondria, containing monoamine oxidase, were prepared from Wistar female rats. Monoamine oxidase activity was determined in the presence and absence of the DMPEA by manometric technique. The main compartment of Warburg flasks contained 0.8 ml of a 0.1 M buffered solution of the homoveratrylamine, 1 ml of mitochondrial suspension (representing 500 mg wet weight of original brain tissue), and sufficient 0.01 M phosphate buffer (pH 7.4) to make a total volume of 2.7 ml. All aliquots for a given run were taken from the same mitochondrial preparation. The side arm of each flask contained 0.3 ml of 0.1 M tyramine or tryptamine hydrochloride. After the flasks were allowed to equilibrate for 15 min at 37°, the manometer valves were closed and the side arm contents of each were tipped in. Manometers were set at 150 mm, and readings were taken at 15-min intervals for 90 min. Values for the 90-min reaction period were obtained for each flask and were multiplied by the respective flask constants after adjusting for changes in the thermobarometer. The total microliters of oxygen uptake for each flask was thus obtained.
Substance Class Chemical
Record UNII
IQF9T435OP
Record Status Validated (UNII)
Record Version