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270229

Sigma-Aldrich

3-Methoxyphenethylamine

97%

Synonym(s):

2-(3-Methoxyphenyl)ethylamine

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About This Item

Linear Formula:
CH3OC6H4CH2CH2NH2
CAS Number:
2039-67-0
Molecular Weight:
151.21
Beilstein:
775202
EC Number:
218-017-9
MDL number:
MFCD00008187
UNSPSC Code:
12352100
PubChem Substance ID:
24856363
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.538 (lit.)

bp

118-119 °C/6 mmHg (lit.)

density

1.038 g/mL at 25 °C (lit.)

SMILES string

COc1cccc(CCN)c1

InChI

1S/C9H13NO/c1-11-9-4-2-3-8(7-9)5-6-10/h2-4,7H,5-6,10H2,1H3

InChI key

WJBMRZAHTUFBGE-UHFFFAOYSA-N

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General description

The spectral binding affinity for 3-methoxyphenethylamine was studied to examine the determinants of P450 2D6 catalysis.

Application

3-Methoxyphenethylamine was used in the perfluorooctanesulfonic acid catalyzed Pictet-Spengler reaction. It was also used in the synthesis of 1,3-oxazepines via palladium-catalyzed intramolecular coupling.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tetrahedron, 62, 9002-9002 (2006)
Tetrahedron Letters, 48, 835-835 (2007)
G P Miller et al.
Biochemistry, 40(47), 14215-14223 (2001-11-21)
Cytochrome P450 (P450) 2D6 oxidizes a wide variety of drugs typically at a distance of 5-7 A from a basic nitrogen on the substrate. To investigate the determinants of P450 2D6 catalysis, we analyzed the binding and oxidation of phenethylamine
P T Wong et al.
Neuroreport, 5(1), 53-56 (1993-10-25)
The effects of death and various treatments that affect the status of nigrostriatal neurones on striatal release of dopamine (DA) and 5-hydroxytryptamine (5-HT) and their metabolites 3,4-dihydroxyphenylacetic acid (DOPAC), 3-methoxy-4-hydroxyphenylethylamine (3-MT), homovanillic acid (HVA) and 5-hydroxyindoleacetic acid (5-HIAA) were studied
Anita H Lewin et al.
Bioorganic & medicinal chemistry, 16(15), 7415-7423 (2008-07-08)
A cell line in which RD-HGA16 cells were stably transfected with the hTAAR 1 receptor was created and utilized to carry out a systematic evaluation of a series of beta-phenethylamines. Fair agreement was observed with data obtained for aryl and

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