ChemFOnt: Showing chemical card for 4-Methoxytyramine (CFc000007717)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:10 UTC

Chemfont ID

CFc000007717

Molecule Identification

Common Name

4-Methoxytyramine

Definition

4-Methoxytyramine is a catecholamine derivative. Catecholamines are important components of the central nervous system. A number of diseases are characterized by abnormal levels of catecholamines. For example, patients with Parkinson's disease have lower levels of dopamine than normal. L-3,4-Dihydroxyphennylalanune (L-Dopa), a catechol a-amino acid, is widely used in the treatment of Parkinson's disease. When L-Dopa is given orally to patients, the most prominent metabolite is 3-methoxy-4-hydroxyphenylalanine. However, a part of L-Dopa is methylated to 3-hydroxy-4-methylphenylalanine and to 3-hydroxy-4-methoxyphenethylamine. It has been reported that 4-O-methylation of catecholamines is implicated in some neuropsychiatric disorders and thus 3-hydroxy-4-methoxyphenethylamine appears to be the endogenous "toxin" in Parkinson's disease. Consequently, the determination of plasma levels of 3-hydroxy-4-methoxyphenethylamine is important following oral L-Dopa therapy (PMID: 6518609 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Hydroxy-4-methoxyphenethylamine	MeSH
3-Hydroxy-4-methoxyphenethylamine hydrochloride	MeSH
3-Hydroxy-4-methoxy-benzeneethanamine	HMDB
4-(2-Aminoethyl)guaiacol hydrochloride	HMDB
4-Methoxy-3-hydroxyphenethylamine hydrochloride	HMDB
4-O-Methyldopamine	HMDB
5-(2-Aminoethyl)-2-methoxyphenol	HMDB
5-Hydroxy-4-methoxy-benzeneethanamine	HMDB
Lopac-H-3132	HMDB

Chemical Formula

C₉H₁₃NO₂

Average Molecular Weight

167.205

Monoisotopic Molecular Weight

167.094628665

IUPAC Name

5-(2-aminoethyl)-2-methoxyphenol

Traditional Name

5-(2-aminoethyl)-2-methoxyphenol

CAS Registry Number

3213-30-7

SMILES

COC1=C(O)C=C(CCN)C=C1

InChI Identifier

InChI=1S/C9H13NO2/c1-12-9-3-2-7(4-5-10)6-8(9)11/h2-3,6,11H,4-5,10H2,1H3

InChI Key

WJXQFVMTIGJBFX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenethylamine
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
2-arylethylamine
Aralkylamine
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Ether
Hydrocarbon derivative
Primary amine
Amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 6518609)

Source

Endogenous

Endogenous (HMDB: HMDB0012162)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.68 g/L	ALOGPS
logP	-0.06	ALOGPS
logP	0.45	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	10.24	ChemAxon
pKa (Strongest Basic)	9.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	55.48 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.73 m³·mol⁻¹	ChemAxon
Polarizability	18.18 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon