22331-70-0

Basic information

• Product Name: p-methoxy-N,alpha-dimethylphenethylamine
• Synonyms: p-methoxy-N,alpha-dimethylphenethylamine;1-(4-METHOXYPHENYL)-N-METHYLPROPAN-2-AMINE;4-Methoxy-N,α-dimethylbenzeneethanamine;N,1-Dimethyl-2-(4-methoxyphenyl)ethanamine;N,α-Dimethyl-4-methoxybenzeneethanamine;N-Methyl-1-(4-methoxyphenyl)-2-propanamine;N-Methyl-2-(4-methoxyphenyl)-1-methylethylamine;N-Methyl-3-(4-methoxyphenyl)propane-2-amine
• CAS NO: 22331-70-0
• Molecular Formula: C₁₁H₁₇NO
• Molecular Weight: 179.25878
• EINECS: 244-917-6
• Mol File: 22331-70-0.mol

Chemical Properties

• Melting Point: 175-176 °C
• Boiling Point: 262.9°Cat760mmHg
• Flash Point: 106.6°C
• Appearance: /
• Density: 0.951g/cm³
• PKA: 10.53±0.10(Predicted)
• CAS DataBase Reference: p-methoxy-N,alpha-dimethylphenethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: p-methoxy-N,alpha-dimethylphenethylamine(22331-70-0)
• EPA Substance Registry System: p-methoxy-N,alpha-dimethylphenethylamine(22331-70-0)

Safety Data

• Hazardous Substances Data: 22331-70-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
p-methoxy-N,alpha-dimethylphenethylamine is used as a research chemical for studying the effects of psychoactive substances on the central nervous system. Its structural similarity to MDMA allows scientists to investigate the mechanisms of action and potential therapeutic applications of entactogens.
Used in Forensic Toxicology:
As an illegal psychedelic drug, p-methoxy-N,alpha-dimethylphenethylamine is used in forensic toxicology to identify and analyze its presence in biological samples. This helps in understanding the extent of its abuse and the associated risks of intoxication and fatalities.

Upstream product

• 50-00-0 formaldehyd 
• 64-13-1 2-amino-1-(4-methyoxyphenyl)propane 
• 122-84-9 4-methoxybenzyl methyl ketone 
• 74-89-5 methylamine 
• 74-88-4 methyl iodide 
• 126002-14-0 N-[2-(4-methoxyphenyl)-1-methyl-ethyl]formamide 
• 593-51-1 methylamine hydrochloride 
• 2749-94-2 1-methoxy-4-(prop-1-yn-1-yl)benzene 
• 2746-25-0 p-Methoxybenzyl bromide 
• 104-01-8 4-Methoxyphenylacetic acid 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 

Downstream Products

• 78469-72-4 Formyl(N,α-dimethyl-p-methoxy)phenylethylamin 
• 78469-71-3 Formyl(N-methoxymethyl-α-methyl-p-methoxy)phenylethylamin 
• 147282-88-0 N-<1-(4-Methoxyphenyl)prop-2-yl>-N-methylcarbamidsaeureethylester 
• 69792-61-6 N,N-dimethyl-1-(4-hydroxyphenyl)-2-propylamine 
• 1268369-38-5 C₁₃H₁₆F₃NO₂ 

Relevant articles and documents

Ind2TiMe2-catalyzed addition of methyl- and ethylamine to alkynes

We describe a very simple hydrogenation-like experimental protocol for the addition of gaseous methyl- and ethylamine to alkynes in the presence of Ind2TiMe2 as the catalyst. For efficient hydroamination reactions it is sufficient to stir a mixture of the alkyne and the catalyst in toluene at temperatures between 80°C (terminal alkynes) and 105°C (internal alkynes) under a constant pressure of 1 atm of the corresponding amine. After subsequent reduction of the initially formed imines, methyl- and ethylamine derivatives are the final products of the described one-pot reaction sequences. In the case of 2-alkyl-1-phenylalkynes as starting materials, biologically interesting 2-phenylethylamine derivatives possessing a small methyl or ethyl substituent at the N atom are easily accessible by the new reaction protocol. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Synthesis and structure-activity relationships of trisubstituted phenyl urea derivatives as neuropeptide Y5 receptor antagonists

1-((1R,2R)-2-Hydroxy-1-methyl-2-phenylethyl)-1-methyl-3-(4-phenoxyphenyl)urea (1) was identified as a hit from the screening of the neuropeptide Y5 (NPY5) receptor. This lead was optimized for in vitro potency by changing the stereochemistry, the phenylethyl segment, the urea portion, and the 4-phenoxyphenyl group on the molecule. Over 40 analogues of 1 were prepared to study the structure-activity relationship for this series. The most potent compounds in this class have IC50S less than 0.1 nM at the NPY5 receptor (e.g., 40f, 44a, and 47). To determine the functional activity for this series of compounds, selected analogues were tested in a cellular assay measuring forskolin-induced cyclic AMP accumulation in 293 cells transfected with the human NPY5 receptor. All urea analogues tested in the functional assay acted as antagonists (e.g., 1, 32, 40a, and 44e).

POTENTIAL ANTIDEPRESSANTS: 1-(4-(AMINOALKOXY)PHENYL)-2-PROPYLAMINES

1-(4-Hydroxyphenyl)-2-propylamine (X) and its N-monomethyl (XI) and N,N-dimethyl (XII) derivatives were O-alkylated with six tert.aminoalkyl chlorides to aminoalkyl ethers Ia-VIc.In cases of X and XI the reactions were complicated by O,N-dialkylation leading to isolation of triamino ethers XVI and XVII. 1-(4-Hydroxyphenyl)propan-2-one was alkylated with 2-dimethylaminoethyl chloride and the ether XIII was obtained.An attempt to transform 4-(2-dimethylaminoethoxy)benzaldehyde to the 1-aryl-2-nitropropene XIV by heating with nitroethane in acetic acid in the presence of ammonium acetate resulted in the formation of 4-(2-dimethylaminoethoxy)benzonitrile (XV).In the form of salts the amino ethers prepared were tested for antidepressant activity but proved little active or inactive.

ASYMMETRIC SYNTHESIS IX: PREPARATION OF CHIRAL α-SUBSTITUTED PHENETHYLAMINES

(S)-N-methyl-α-methyl-phenethylamines 5a-d were obtained in 56-62 percent e.e. from chiral synthon (-)-N-cyanomethyl-4-phenyl-1,3-oxazolidine-1.