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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H13NO4
Molecular Weight 211.2145
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3-O-METHYLDOPA

SMILES

COC1=CC(C[C@H](N)C(O)=O)=CC=C1O

InChI

InChIKey=PFDUUKDQEHURQC-ZETCQYMHSA-N
InChI=1S/C10H13NO4/c1-15-9-5-6(2-3-8(9)12)4-7(11)10(13)14/h2-3,5,7,12H,4,11H2,1H3,(H,13,14)/t7-/m0/s1

HIDE SMILES / InChI

Molecular Formula C10H13NO4
Molecular Weight 211.2145
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

3-O-methyldopa (3-OMD) is a metabolite of L-3,4-dihydroxyphenylalanine (L-DOPA), a drug used for the treatment of Parkinson's disease patients. 3-OMD is formed by catechol-O-methyltransferase. 3-OMD may be responsible for the side effects of L-DOPA.

CNS Activity

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
PubMed

PubMed

TitleDatePubMed
Metabolic fate of l-[14C] DOPA in cerebrospinal fluid and blood plasma of humans.
1967 Feb
3-O-methyldopa, a new precursor of dopamine.
1971 Apr 23
Demethylation of 3-O-methyldopa.
1971 Oct
Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology.
1992 Dec
Aromatic L-amino acid decarboxylase deficiency: clinical features, diagnosis, and treatment of a new inborn error of neurotransmitter amine synthesis.
1992 Oct
Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis.
2006 Jan
The role of 3-O-methyldopa in the side effects of L-dopa.
2008 Mar

Sample Use Guides

In Vivo Use Guide
mice: 200 or 400 mg/kg (ip) rats: 3, 10 or 30 mg/kg (ip) rats: 1 uM (icv)
Route of Administration: intracerebroventricular, intraperitoneal
In Vitro Use Guide
The number of tyrosine hydroxylase-positive dopaminergic neurons was not affected by L-DOPA treatment in mesencephalic neurons alone. However, the increase in viability of dopaminergic neurons in the presence of astrocytes was further enhanced after methyl-L-DOPA treatment (25 µM) in mixed cultured mesencephalic neurons and striatal astrocytes. The neuroprotective effect of 25 µM L-DOPA was almost completely inhibited by simultaneous treatment with 3-O-methyl-DOPA (10 or 100 µM).
Substance Class Chemical
Created
by admin
on Tue Oct 22 15:40:36 UTC 2019
Edited
by admin
on Tue Oct 22 15:40:36 UTC 2019
Record UNII
V3O7J20DWN
Record Status Validated (UNII)
Record Version
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Name Type Language
3-O-METHYLDOPA
MI  
Common Name English
L-3-MTO
Common Name English
OM-DOPA
Common Name English
3-O-METHYLDOPA [MI]
Common Name English
OMD
Common Name English
(-)-3-O-METHYLDOPA
Common Name English
L-3-METHOXY-4-HYDROXYPHENYLALANINE
Common Name English
3-(4-HYDROXY-3-METHOXYPHENYL)-L-ALANINE
Systematic Name English
3-METHOXY-L-TYROSINE
Systematic Name English
Code System Code Type Description
PUBCHEM
9307
Created by admin on Tue Oct 22 15:40:36 UTC 2019 , Edited by admin on Tue Oct 22 15:40:36 UTC 2019
PRIMARY
WIKIPEDIA
3-O-Methyldopa
Created by admin on Tue Oct 22 15:40:36 UTC 2019 , Edited by admin on Tue Oct 22 15:40:36 UTC 2019
PRIMARY
CAS
300-48-1
Created by admin on Tue Oct 22 15:40:36 UTC 2019 , Edited by admin on Tue Oct 22 15:40:36 UTC 2019
PRIMARY
MESH
C008404
Created by admin on Tue Oct 22 15:40:36 UTC 2019 , Edited by admin on Tue Oct 22 15:40:36 UTC 2019
PRIMARY
MERCK INDEX
M7398
Created by admin on Tue Oct 22 15:40:36 UTC 2019 , Edited by admin on Tue Oct 22 15:40:36 UTC 2019
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
RACEMATE -> ENANTIOMER
Related Record Type Details
PARENT -> METABOLITE
When decarboxylation of levodopa is prevented by carbidopa, COMT becomes the major metabolizing enzyme for levodopa, catalyzing its metabolism to 3-methoxy-4-hydroxy-L-phenylalanine (3-OMD).