Common Name |
Homoveratric acid
Description |
Homoveratric acid is the main metabolite of 3,4-dimethoxyphenylethylamine (DMPEA) in urine. It has been suggested that DMPEA and other amines are in higher concentrations in drug-free schizophrenics than in normal subjects. DMPEA is a the di-methylated metabolite of L-DOPA, the major treatment for Parkinsons disease (PD). (PMID 7059639 , 14311254 , 588645 , 10834300 ).
Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms |
Value |
Source |
(3,4-Dimethoxyphenyl)acetateHMDB
(3,4-Dimethoxyphenyl)acetic acidHMDB
3,4-DimethoxybenzeneacetateHMDB
3,4-Dimethoxybenzeneacetic acidHMDB
3,4-DimethoxyphenylacetateHMDB
3,4-Dimethoxyphenylacetic acidHMDB
HomoveratrateHMDB
Chemical Formlia |
C10H12O4
Average Molecliar Weight |
196.1999
Monoisotopic Molecliar Weight |
196.073558872
IUPAC Name |
2-(3,4-dimethoxyphenyl)acetic acid
Traditional Name |
3,4-dimethoxyphenylacetic acid
CAS Registry Number |
93-40-3
SMILES |
COC1=CC=C(CC(O)=O)C=C1OC
InChI Identifier |
InChI=1S/C10H12O4/c1-13-8-4-3-7(6-10(11)12)5-9(8)14-2/h3-5H,6H2,1-2H3,(H,11,12)
InChI Key |
WUAXWQRULBZETB-UHFFFAOYSA-N
Chemical Taxonomy |
Description |
This compound belongs to the class of chemical entities known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
Kingdom |
Chemical entities
Super Class |
Organic compounds
Class |
Benzenoids
Sub Class |
Benzene and substituted derivatives
Direct Parent |
Dimethoxybenzenes
Alternative Parents |
Phenoxy compounds
Anisoles
Alkyl aryl ethers
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
Substituents |
O-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Phenol ether
Alkyl aryl ether
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound
Molecliar Framework |
Aromatic homomonocyclic compounds
External Descriptors |
monocarboxylic acid (CHEBI:86655 )
Ontology |
Status |
Detected and Quantified
Origin |
Endogenous
Biofunction |
Not Available
Application |
Not Available
Cellliar locations |
Cytoplasm
Physical Properties |
State |
Solid
Experimental Properties |
Property |
Value |
Reference |
Melting Point96 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties |
Property |
Value |
Source |
Water Solubility1.21 mg/mLALOGPS
logP1.58ALOGPS
logP1.3ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.86ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.29 m3·mol-1ChemAxon
Polarizability19.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
Spectra |
Spectra |
Spectrum Type |
Description |
Splash Key |
|
LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0900000000-2a12c40170fec46f4a14View in MoNA
LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Negative (Annotated)splash10-00di-0900000000-5debb25eef3cd12b8c67View in MoNA
LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Negative (Annotated)splash10-00dl-9800000000-dcdcc653f9617b708e09View in MoNA
LC-MS/MS |
LC-MS/MS Spectrum – EI-B (HITACHI M-52) , Positivesplash10-0006-1900000000-b8fad1a07cec70a67baaView in MoNA
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
1D NMR |
1H NMR SpectrumNot Available
2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
Biological Properties |
Cellliar Locations |
Cytoplasm
Biofluid Locations |
Blood
Urine
Tissue Location |
Not Available
Pathways |
Not Available
Normal Concentrations |
Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified0.687 +/- 0.175 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified0.5 +/- 0.155 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified0.691 +/- 0.164 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified0.908 +/- 0.314 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified0.645 +/- 0.129 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified0.904 +/- 0.193 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified0.594 +/- 0.174 uMAdlit (>18 years old)Male
Normal
19812218
details
BloodDetected and Quantified2.613 +/- 2.137 uMAdlit (>18 years old)Male
Normal
19812218
details
UrineDetected and Quantified0.072 +/- 0.01 umol/mmol creatinineAdlit (>18 years old)Male
Normal
19812218
details
|
Abnormal Concentrations |
|
Not Available
Associated Disorders and Diseases |
Disease References |
None
Associated OMIM IDs |
None
External Links |
DrugBank ID |
Not Available
DrugBank Metabolite ID |
Not Available
Phenol Explorer Compound ID |
575
Phenol Explorer Metabolite ID |
Not Available
FoodDB ID |
FDB000317
KNApSAcK ID |
Not Available
Chemspider ID |
6872
KEGG Compound ID |
Not Available
BioCyc ID |
Not Available
BiGG ID |
Not Available
Wikipedia Link |
Not Available
NuGOwiki Link |
HMDB00434
Metagene Link |
HMDB00434
METLIN ID |
5423
PubChem Compound |
7139
PDB ID |
Not Available
ChEBI ID |
Not Available
Product: UNC3866
References |
Synthesis Reference |
Aboulezz, A. F.; Quelet, R. Derivatives of veratrole. Synthesis of homoveratric acid and some substituted diphenylmethane and fluorenone derivatives. Journal of Chemistry of the United Arab Republic (1962), 5(2), 137-46. |
Material Safety Data Sheet (MSDS) |
Not Available |
General References |
- Hempel K, Ullrich H, Philippu G: Quantitative investigation on the urinary excretion and metabolism of 3,4-dimethoxyphenylethylamine in schizophrenics and normal individuals. Biol Psychiatry. 1982 Jan;17(1):49-59. [PubMed:7059639 ]
- PROENCA J, WENNER J: [ON THE EFFECT OF NIKETHAMIDE AND HOMOVERATRIC ACID DIMETHYLAMIDE ON RESPIRATION IN INFANTS]. Monatsschr Kinderheilkd. 1965 Apr;113:341-3. [PubMed:14311254 ]
- Friedhoff AJ, Park S, Schweitzer JW, Burdock EI, Armour M: Excretion of 3,4-dimethoxyphenethylamine (DMPEA) by acute schizophrenics and controls. Biol Psychiatry. 1977 Oct;12(5):643-54. [PubMed:588645 ]
- Charlton CG, Crowell B Jr: Effects of dopamine metabolites on locomotor activities and on the binding of dopamine: relevance to the side effects of L-dopa. Life Sci. 2000 Apr 21;66(22):2159-71. [PubMed:10834300 ]
|
PMID: 19479584