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
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
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 Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2095205 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14459693 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Fine structural specificity differences of trimethoprim allergenic determinants. | 1996 Oct |
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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 |
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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 |
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2-(4-Chloro-phen-yl)-5-(3,4-dimethoxy-pheneth-yl)-6,7-dihydro-pyrazolo[1,5-a]pyrazin-4(5H)-one. | 2009 Jun 6 |
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Structure-activity relationships of anthraquinone derivatives derived from bromaminic acid as inhibitors of ectonucleoside triphosphate diphosphohydrolases (E-NTPDases). | 2009 Mar |
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An overview of Indian research in schizophrenia. | 2010 Jan |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27614
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14459693
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.
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PiHKAL
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3,4-DIMETHOXYPHENETHYLAMINE
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204-376-9
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)