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187305

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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3-Hydroxy-4-methoxyphenethylamine hydrochloride

Sigma-Aldrich

H3132

3-Hydroxy-4-methoxyphenethylamine hydrochloride

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)
The Pummerer cyclization route to the ibophyllidine alkaloids. Total synthesis of (?)-deethylibophyllidine.
Catena J, et al.
Tetrahedron Letters, 35(25), 4433-4436 (1994)
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
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
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)
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