Page last updated: 2024-12-06

4-methoxybenzylamine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4-Methoxybenzylamine is an organic compound with the formula CH3OC6H4CH2NH2. It is a colorless liquid that is soluble in most organic solvents. The compound has been used in the synthesis of a variety of pharmaceuticals, including anti-inflammatory drugs and antidepressants. It is also used as a precursor to other organic compounds, such as 4-methoxybenzoyl chloride. 4-Methoxybenzylamine is of interest to researchers because of its potential applications in the pharmaceutical industry. It is also a useful starting material for the synthesis of other organic compounds. 4-Methoxybenzylamine can be synthesized by a variety of methods, including the reduction of 4-methoxybenzonitrile with lithium aluminum hydride. The compound can be synthesized by the reduction of 4-methoxybenzonitrile, which can be prepared by the reaction of 4-methoxybenzaldehyde with hydroxylamine. The compound has been shown to have antidepressant and anti-inflammatory effects in animal models. The compound is also being studied for its potential use in the treatment of cancer.'

1-(4-methoxyphenyl)methanamine : An aralkylamino compound that is benzylamine substituted by a methoxy group at the para position. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID75452
CHEMBL ID12720
CHEBI ID49837
SCHEMBL ID8755
MeSH IDM0240406

Synonyms (80)

Synonym
benzenemethanamine, 4-methoxy-
2393-23-9
4-methoxybenzylamine ,
nsc-9269
benzylamine, p-methoxy-
nsc9269
anisylamine
p-methoxybenzylamine
OPREA1_248499
(4-methoxyphenyl)methanamine
inchi=1/c8h11no/c1-10-8-4-2-7(6-9)3-5-8/h2-5h,6,9h2,1h
1-(4-methoxyphenyl)methanamine
4-methoxybenzylamine, 98%
pzm ,
chebi:49837 ,
4-methoxy-benzylamine
CHEMBL12720 ,
M0870
AKOS000119610
A19835
(4-methoxyphenyl)methanamine;4-methoxy-benzenemethanamin
4-methoxybenzyl amine
2m6qlm4nwe ,
ec 219-247-2
nsc 9269
unii-2m6qlm4nwe
einecs 219-247-2
bdbm50408784
integrase inhibitor, r1{3}
(4-methoxyphenyl)methylamine
BP-12974
FT-0618925
PS-5319
SCHEMBL8755
4-methyoxybenzylamine
para-methoxybenzylamine
4-methoxy-benzenemethanamine
(4-methoxyphenyl)methyl amine
p-methoxy-benzylamine
paramethoxybenzyl amine
4-methoxyphenylmethyl-amine
p-methoxy benzyl amine
4-methoxy benzyl amine
1-aminomethyl-4-methoxybenzene
(4-methoxybenzyl)amine
4-metoxybenzylamine
pmbnh2
1-[4-(methyloxy)phenyl]methanamine
4-methoxybenzenemethanamine
4-methoxyphenylmethylamine
p-methoxy benzylamine
4-methoxy-benzyl amine
{[4-(methyloxy)phenyl]methyl}amine
p-methoxybenzyl amine
(4-methoxyphenyl)methaneamine
4-methoxy benzylamine
1-(4-methoxyphenyl)-methanamine
(4-methoxyphenyl)-methanamine
(4-methoxy)benzylamine
4-methoxybenzyl-amine
p-methoxylbenzylamine
4-methoxylbenzylamine
4-methoxyphenylmethanamine
(4-methoxyphenyl) methanamine
p-methoxybenzyl-amine
DTXSID2062371
(4-methoxyphenyl)methanamine #
W-107368
AC-25956
mfcd00008122
F0798-0712
D77999
CS-D1426
Q27121634
BCP11229
AMY18068
(p-methoxyphenyl)methanamine
STL193991
EN300-17924
Z57102874
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
primary amino compoundA compound formally derived from ammonia by replacing one hydrogen atom by an organyl group.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
aralkylamino compoundAn organic amino compound in which an aminoalkyl group is linked to an arene.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gag-Pol polyproteinHIV-1 M:B_HXB2RIC50 (µMol)3.92000.00060.91418.3200AID1799907
Trypsin-1Homo sapiens (human)Ki1,000,000.00000.00001.76768.9000AID215914
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (7)

Processvia Protein(s)Taxonomy
viral life cycleGag-Pol polyproteinHIV-1 M:B_HXB2R
establishment of integrated proviral latencyGag-Pol polyproteinHIV-1 M:B_HXB2R
digestionTrypsin-1Homo sapiens (human)
extracellular matrix disassemblyTrypsin-1Homo sapiens (human)
proteolysisTrypsin-1Homo sapiens (human)
methylationPhenylethanolamine N-methyltransferaseBos taurus (cattle)
epinephrine biosynthetic processPhenylethanolamine N-methyltransferaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
peptidase activityGag-Pol polyproteinHIV-1 M:B_HXB2R
integrase activityGag-Pol polyproteinHIV-1 M:B_HXB2R
serine-type endopeptidase activityTrypsin-1Homo sapiens (human)
metal ion bindingTrypsin-1Homo sapiens (human)
phenylethanolamine N-methyltransferase activityPhenylethanolamine N-methyltransferaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
extracellular regionTrypsin-1Homo sapiens (human)
collagen-containing extracellular matrixTrypsin-1Homo sapiens (human)
blood microparticleTrypsin-1Homo sapiens (human)
extracellular spaceTrypsin-1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID225081Inhibition of phenylethanolamine N-methyltransferase(PNMT)activity1983Journal of medicinal chemistry, Aug, Volume: 26, Issue:8
Quantitative structure-activity relationships employing independent quantum chemical indices.
AID155316Molar pI50 value for phenylethanolamine N-methyl-transferase (PNMT) inhibition1988Journal of medicinal chemistry, Feb, Volume: 31, Issue:2
Conformational and steric aspects of the inhibition of phenylethanolamine N-methyltransferase by benzylamines.
AID215914Inhibition of trypsin1999Journal of medicinal chemistry, Dec-16, Volume: 42, Issue:25
Simple linear QSAR models based on quantum similarity measures.
AID416147Activity at Zea mays CKX1 expressed in Pichinia pastoris assessed as aldehyde production by 4-aminophenol assay2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Synthesis, characterization and biological activity of ring-substituted 6-benzylamino-9-tetrahydropyran-2-yl and 9-tetrahydrofuran-2-ylpurine derivatives.
AID273097Activity of human SSAO measured as hydrogen peroxide production at 1 mM relative to benzylamine oxidation2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
New efficient substrates for semicarbazide-sensitive amine oxidase/VAP-1 enzyme: analysis by SARs and computational docking.
AID1471798Reactivation of tabun inhibited human erythrocyte AChE assessed as residual activity at 10 to 1000 uM using acetylthiocholine iodide as substrate preincubated for 2 to 120 mins followed by substrate addition measured for 3 mins by Ellman's method2017Journal of medicinal chemistry, 11-22, Volume: 60, Issue:22
Application of the Ugi Multicomponent Reaction in the Synthesis of Reactivators of Nerve Agent Inhibited Acetylcholinesterase.
AID273098Activity of mouse SSAO measured as hydrogen peroxide production at 100 uM relative to benzylamine oxidation2006Journal of medicinal chemistry, Oct-19, Volume: 49, Issue:21
New efficient substrates for semicarbazide-sensitive amine oxidase/VAP-1 enzyme: analysis by SARs and computational docking.
AID416148Ratio Kcat to Km for Zea mays CKX1 receptor2009Bioorganic & medicinal chemistry, Mar-01, Volume: 17, Issue:5
Synthesis, characterization and biological activity of ring-substituted 6-benzylamino-9-tetrahydropyran-2-yl and 9-tetrahydrofuran-2-ylpurine derivatives.
AID1471796Reactivation of cyclosarin inhibited human erythrocyte AChE assessed as residual activity at 10 to 1000 uM using acetylthiocholine iodide as substrate preincubated for 2 to 120 mins followed by substrate addition measured for 3 mins by Ellman's method2017Journal of medicinal chemistry, 11-22, Volume: 60, Issue:22
Application of the Ugi Multicomponent Reaction in the Synthesis of Reactivators of Nerve Agent Inhibited Acetylcholinesterase.
AID155317Acid dissociation constant of phenylethanolamine N-methyl-transferase (PNMT) inhibition1988Journal of medicinal chemistry, Feb, Volume: 31, Issue:2
Conformational and steric aspects of the inhibition of phenylethanolamine N-methyltransferase by benzylamines.
AID1799907Inhibition Assay from Article 10.1021/cc9001026: \\Solid phase synthesis of novel pyrrolidinedione analogs as potent HIV-1 integrase inhibitors.\\
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (22.22)18.7374
1990's2 (22.22)18.2507
2000's2 (22.22)29.6817
2010's3 (33.33)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 41.09

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index41.09 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index55.02 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (41.09)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]