3-O-METHYLDOPA

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6029941 | https://www.ncbi.nlm.nih.gov/pubmed/17713853 | https://www.ncbi.nlm.nih.gov/pubmed/22863920

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17713853/	Activator 1430
neuron death 3 Target ID: GO:0070997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27456338	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Aromatic L-amino-acid decarboxylase (AADC) deficiency 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27216367	Diagnostic		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Metabolic fate of l-[14C] DOPA in cerebrospinal fluid and blood plasma of humans.	1967 Feb	6029941
3-O-methyldopa, a new precursor of dopamine.	1971 Apr 23	4927759
Demethylation of 3-O-methyldopa.	1971 Oct	5158231
Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology.	1992 Dec	1281049
Aromatic L-amino acid decarboxylase deficiency: clinical features, diagnosis, and treatment of a new inborn error of neurotransmitter amine synthesis.	1992 Oct	1357595
Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis.	2006 Jan	16288991
The role of 3-O-methyldopa in the side effects of L-dopa.	2008 Mar	17713853

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: Other

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).

Name

Type

Language

3-O-METHYLDOPA

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

CHEBI

82913