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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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Fine structural specificity differences of trimethoprim allergenic determinants.
1996 Oct
Inhibition of brain mitochondrial respiration by dopamine and its metabolites: implications for Parkinson's disease and catecholamine-associated diseases.
2004 Nov
[Syntheses and ring-closures of difunctional tetrahydroisoquinolines].
2006
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
The structure of ammonium pyrazolates in the solid state.
2006 Dec
4-[2-(3,4-Dimethoxy-phenethyl-amino)prop-oxy]-2-methoxy-benzamide.
2008 May 24
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
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:31:03 UTC 2023
Edited
by admin
on Fri Dec 15 15:31:03 UTC 2023
Record UNII
IQF9T435OP
Record Status Validated (UNII)
Record Version
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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 UTC 2023 , Edited by admin on Fri Dec 15 15:31:03 UTC 2023
Code System Code Type Description
WIKIPEDIA
3,4-DIMETHOXYPHENETHYLAMINE
Created by admin on Fri Dec 15 15:31:03 UTC 2023 , Edited by admin on Fri Dec 15 15:31:03 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-376-9
Created by admin on Fri Dec 15 15:31:03 UTC 2023 , Edited by admin on Fri Dec 15 15:31:03 UTC 2023
PRIMARY
NSC
16948
Created by admin on Fri Dec 15 15:31:03 UTC 2023 , Edited by admin on Fri Dec 15 15:31:03 UTC 2023
PRIMARY
NSC
6328
Created by admin on Fri Dec 15 15:31:03 UTC 2023 , Edited by admin on Fri Dec 15 15:31:03 UTC 2023
PRIMARY
CAS
120-20-7
Created by admin on Fri Dec 15 15:31:03 UTC 2023 , Edited by admin on Fri Dec 15 15:31:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID8059506
Created by admin on Fri Dec 15 15:31:03 UTC 2023 , Edited by admin on Fri Dec 15 15:31:03 UTC 2023
PRIMARY
CHEBI
136995
Created by admin on Fri Dec 15 15:31:03 UTC 2023 , Edited by admin on Fri Dec 15 15:31:03 UTC 2023
PRIMARY
FDA UNII
IQF9T435OP
Created by admin on Fri Dec 15 15:31:03 UTC 2023 , Edited by admin on Fri Dec 15 15:31:03 UTC 2023
PRIMARY
PUBCHEM
8421
Created by admin on Fri Dec 15 15:31:03 UTC 2023 , Edited by admin on Fri Dec 15 15:31:03 UTC 2023
PRIMARY
RS_ITEM_NUM
1225237
Created by admin on Fri Dec 15 15:31:03 UTC 2023 , Edited by admin on Fri Dec 15 15:31:03 UTC 2023
PRIMARY
NSC
26152
Created by admin on Fri Dec 15 15:31:03 UTC 2023 , Edited by admin on Fri Dec 15 15:31:03 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY