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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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
3,4-dimethoxyphenethylamine (DMPEA) and schizophrenia.
1979 Feb
Fine structural specificity differences of trimethoprim allergenic determinants.
1996 Oct
Contribution of aldehyde oxidizing enzymes on the metabolism of 3,4-dimethoxy-2-phenylethylamine to 3,4-dimethoxyphenylacetic acid by guinea pig liver slices.
2006
Evaluation of dimethoxydop-NU as a novel anti-tumor agent.
2007 Dec
Self-assembly of 3,5-bis(ethoxycarbonyl)pyrazolate anions and ammonium cations of beta-phenylethylamine or homoveratrylamine into hetero-double-stranded helical structures.
2009 Aug 21
Enhancement of 5-aminopenta-2,4-dienals electrophilicity via activation by O,N-bistrifluoroacetylation. application to an N-acyl Pictet-Spengler reaction.
2009 Dec 18
Structure-activity relationships of anthraquinone derivatives derived from bromaminic acid as inhibitors of ectonucleoside triphosphate diphosphohydrolases (E-NTPDases).
2009 Mar
An overview of Indian research in schizophrenia.
2010 Jan
(E)-N-(3,4-Dimethoxy-pheneth-yl)-3-methoxy-but-2-enamide.
2010 Jan 23
Selective electrochemical discrimination between dopamine and phenethylamine-derived psychotropic drugs using electrodes modified with an acyclic receptor containing two terminal 3-alkoxy-5-nitroindazole rings.
2010 Jun
Patents

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
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.
Name Type Language
DMPEA
Common Name English
3,4-DIMETHOXYPHENETHYLAMINE
Systematic Name English
3,4-DI-O-METHYLDOPAMINE
Systematic Name English
DOPAMINE DIMETHYL ETHER
Systematic Name English
NSC-26152
Code English
O,O-DIMETHYLDOPAMINE
Common Name English
DOPAMINE HYDROCHLORIDE IMPURITY C [EP IMPURITY]
Common Name English
3,4-DIMETHOXY-.BETA.-PHENYLETHYLAMINE
Systematic Name English
3,4-DIMETHOXYPHENYLETHYLAMINE
Systematic Name English
HOMOVERATRYLAMINE
Common Name English
BENZENEETHANAMINE, 3,4-DIMETHOXY-
Systematic Name English
NSC-16948
Code English
2-(3,4-DIMETHOXYPHENYL)ETHYLAMINE
Systematic Name English
NSC-6328
Code English
3,4-DIMETHOXYBENZENEETHANAMINE
Systematic Name English
DOPAMINE IMPURITY C
Common Name English
Classification Tree Code System Code
WIKIPEDIA PiHKAL
Created by admin on Fri Dec 15 15:31:03 GMT 2023 , Edited by admin on Fri Dec 15 15:31:03 GMT 2023
Code System Code Type Description
WIKIPEDIA
3,4-DIMETHOXYPHENETHYLAMINE
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ECHA (EC/EINECS)
204-376-9
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NSC
16948
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NSC
6328
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CAS
120-20-7
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EPA CompTox
DTXSID8059506
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CHEBI
136995
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FDA UNII
IQF9T435OP
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PUBCHEM
8421
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RS_ITEM_NUM
1225237
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NSC
26152
Created by admin on Fri Dec 15 15:31:03 GMT 2023 , Edited by admin on Fri Dec 15 15:31:03 GMT 2023
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