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Sigma-Aldrich

4-Methoxyphenethylamine

≥98%

Synonym(s):

2-(4-Methoxyphenyl)ethylamine, 4-Methoxyphenethylamine

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About This Item

Linear Formula:
CH3OC6H4CH2CH2NH2
CAS Number:
55-81-2
Molecular Weight:
151.21
Beilstein:
508967
EC Number:
200-245-5
MDL number:
MFCD00008192
UNSPSC Code:
12352100
PubChem Substance ID:
24851266
NACRES:
NA.22

Assay

≥98%

form

liquid

refractive index

n20/D 1.538 (lit.)

bp

138-140 °C/20 mmHg (lit.)
254-256 °C

density

1.031 g/mL at 20 °C (lit.)

SMILES string

COc1ccc(CCN)cc1

InChI

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

InChI key

LTPVSOCPYWDIFU-UHFFFAOYSA-N

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General description

4-Methoxyphenethylamine inhibits the monoamine oxidase-catalyzed deamination of both tyramine and tryptamine.

4-Methoxyphenethylamine is used as a precursor for the synthesis of other organic compounds by the alkylation reaction.

Application

4-Methoxyphenethylamine was used in the synthesis of :
  • pyrrolo[3,2-c]carbazole
  • poly(4-methoxyphenethylamine), required for the immobilization of nitrogenated bases and oligonucleotides
  • organopolyphosphazenes such as poly[bis(4-methoxy benzylamino)polyphosphazene] and poly[bis(4-methoxyphenethylamino)polyphosphazene]

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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Synthesis and characterization of novel polyorganophosphazenes substituted with 4-methoxybenzylamine and 4-methoxyphenethylamine for in vitro release of indomethacin and 5-fluorouracil.
Gudasi KB, et al.
Reactive functional Polymers, 66(10), 1149-1157 (2006)
Francielle B Silva et al.
International journal of molecular sciences, 9(7), 1173-1188 (2009-03-28)
This work describes the immobilization of purine and pyrimidine bases and immobilization/hybridization of synthetic oligonucleotides on graphite electrodes modified with poly(4-methoxyphenethylamine) produced in acid medium. The immobilization of adenine, guanine, cytosine and thymine on these modified electrodes was efficient, producing
The Pummerer cyclization route to the ibophyllidine alkaloids. Total synthesis of (?)-deethylibophyllidine.
Catena J, et al.
Tetrahedron Letters, 35(25), 4433-4436 (1994)
GC--MS analysis of N-(bromodimethoxybenzyl)-2-, 3-, and 4-methoxyphenethylamines: Inverse analogues of the psychoactive 25B-NBOMe drug
Almalki AJ, et al.
Forensic Chemistry, 21, 100277-100277 (2020)
W J Keller et al.
Journal of pharmaceutical sciences, 65(10), 1539-1540 (1976-10-01)
It has been established that the oxidative deamination of tyramine by monoamine xodase is inhibited by (+/-)-4-methoxy-beta-hydroxyphenethylamine and its N-methylated derivatives. This particular series of compounds does not inhibit the action of monoamine oxidase when tryptamine is used as the
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