Page last updated: 2024-12-06

4-fluorobenzylamine

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

4-Fluorobenzylamine is a versatile synthetic building block used in the synthesis of various pharmaceuticals and other organic molecules. Its synthesis is typically achieved through the reduction of 4-fluorobenzonitrile, which is readily available. 4-Fluorobenzylamine has been studied for its potential pharmacological applications, particularly as a precursor to serotonin reuptake inhibitors and other neuroactive compounds. Its unique structure, with a fluorine atom adjacent to the benzyl amine group, imparts specific properties that make it attractive for medicinal chemistry. 4-Fluorobenzylamine's importance lies in its role as a key intermediate in the development of new drugs, particularly in areas like neurology and psychiatry.'

Cross-References

ID SourceID
PubMed CID67326
CHEMBL ID12392
SCHEMBL ID21063
SCHEMBL ID2532551
MeSH IDM0295824

Synonyms (64)

Synonym
p-fluorobenzylamine
4-fluorobenzylamine ,
benzenemethanamine, 4-fluoro-
140-75-0
benzylamine, p-fluoro-
nsc-158269
nsc158269
1TNH
4-fluorobenzylamine, 97%
bdbm50113835
integrase inhibitor, r1{2}
CHEMBL12392 ,
4-fluoro-benzylamine
(4-fluorophenyl)methanamine
1-(4-fluorophenyl)methanamine
STK862565
F0252
AKOS000120302
A22214
4-fluorophenyl)methanamine;4-fluoro-benzenemethanamin;benzylamine, p-fluoro-
p-fluorobenzyl amine
4-(18f)-fluorobenzylamine
p-(18f)-fluorobenzylamine
einecs 205-430-4
nsc 158269
FT-0618437
AM20020467
c7h8fn
SCHEMBL21063
DTXSID7059698
4-fluoro benzylamine
4-fluorobenzenemethanamine
(4-fluorobenzyl)amine
[(4-fluorophenyl)methyl]amine
4-flourobenzylamine
(4-fluorophenyl)-methanamine
p-fluoro-benzylamine
4-fluoro benzyl amine
4-fluorobenzyl-amine
4-fluoro-benzyl amine
(4-fluorophenyl)methan amine
para fluorobenzylamine
4-fluoro-benzene methanamine
para-fluoro-benzylamine
para-fluorobenzylamine
(4-fluorobenzyl) amine
4-flourobenzyl amine
p-fluoro benzylamine
4-fluorobenzyl amine
(4-fluoro-benzyl)-amine
4-fluorbenzylamine
SCHEMBL2532551
Q-200471
(4-fluorophenyl)methanamine #
PS-9203
mfcd00008120
F2190-0390
AC-9771
D90651
EN300-16220
4-fluorobenzyl--d4-amine
PD041675
CS-W019800
Z54748266
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (13)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TRYPSINBos taurus (cattle)Ki430.0000100.000011,466.000032,500.0000AID977610
Chain A, TRYPSINBos taurus (cattle)Ki430.0000100.000011,466.000032,500.0000AID977610
Chain A, TRYPSINBos taurus (cattle)Ki430.0000100.000011,466.000032,500.0000AID977610
Chain A, TRYPSINBos taurus (cattle)Ki430.0000100.000011,466.000032,500.0000AID977610
Chain A, TRYPSINBos taurus (cattle)Ki430.0000100.000011,466.000032,500.0000AID977610
Chain A, TRYPSINBos taurus (cattle)Ki430.0000100.000011,466.000032,500.0000AID977610
Cationic trypsinBos taurus (cattle)Ki0.43000.00001.07539.0000AID214878
Gag-Pol polyproteinHIV-1 M:B_HXB2RIC50 (µMol)4.05000.00060.91418.3200AID1799907
Lysyl oxidase homolog 2Homo sapiens (human)IC50 (µMol)26.00000.06600.56494.2600AID1430567
[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 (40)

Processvia Protein(s)Taxonomy
proteolysisCationic trypsinBos taurus (cattle)
digestionCationic trypsinBos taurus (cattle)
viral life cycleGag-Pol polyproteinHIV-1 M:B_HXB2R
establishment of integrated proviral latencyGag-Pol polyproteinHIV-1 M:B_HXB2R
methylationPhenylethanolamine N-methyltransferaseBos taurus (cattle)
epinephrine biosynthetic processPhenylethanolamine N-methyltransferaseBos taurus (cattle)
inflammatory responseMembrane primary amine oxidaseHomo sapiens (human)
cell adhesionMembrane primary amine oxidaseHomo sapiens (human)
amine metabolic processMembrane primary amine oxidaseHomo sapiens (human)
response to antibioticMembrane primary amine oxidaseHomo sapiens (human)
negative regulation of primary amine oxidase activityMembrane primary amine oxidaseHomo sapiens (human)
regulation of autophagyHistone acetyltransferase KAT8Homo sapiens (human)
negative regulation of epithelial to mesenchymal transitionHistone acetyltransferase KAT8Homo sapiens (human)
neurogenesisHistone acetyltransferase KAT8Homo sapiens (human)
myeloid cell differentiationHistone acetyltransferase KAT8Homo sapiens (human)
negative regulation of type I interferon productionHistone acetyltransferase KAT8Homo sapiens (human)
post-embryonic hemopoiesisHistone acetyltransferase KAT8Homo sapiens (human)
transcription initiation-coupled chromatin remodelingHistone acetyltransferase KAT8Homo sapiens (human)
negative regulation of DNA-templated transcriptionHistone acetyltransferase KAT8Homo sapiens (human)
positive regulation of DNA-templated transcriptionHistone acetyltransferase KAT8Homo sapiens (human)
oogenesisHistone acetyltransferase KAT8Homo sapiens (human)
regulation of mRNA processingHistone acetyltransferase KAT8Homo sapiens (human)
positive regulation of transcription initiation by RNA polymerase IIHistone acetyltransferase KAT8Homo sapiens (human)
positive regulation of skeletal muscle satellite cell differentiationHistone acetyltransferase KAT8Homo sapiens (human)
regulation of mitochondrial transcriptionHistone acetyltransferase KAT8Homo sapiens (human)
regulation of transcription by RNA polymerase IIHistone acetyltransferase KAT8Homo sapiens (human)
negative regulation of transcription by RNA polymerase IILysyl oxidase homolog 2Homo sapiens (human)
response to hypoxiaLysyl oxidase homolog 2Homo sapiens (human)
epithelial to mesenchymal transitionLysyl oxidase homolog 2Homo sapiens (human)
endothelial cell proliferationLysyl oxidase homolog 2Homo sapiens (human)
sprouting angiogenesisLysyl oxidase homolog 2Homo sapiens (human)
positive regulation of epithelial to mesenchymal transitionLysyl oxidase homolog 2Homo sapiens (human)
peptidyl-lysine oxidationLysyl oxidase homolog 2Homo sapiens (human)
collagen fibril organizationLysyl oxidase homolog 2Homo sapiens (human)
positive regulation of chondrocyte differentiationLysyl oxidase homolog 2Homo sapiens (human)
protein modification processLysyl oxidase homolog 2Homo sapiens (human)
endothelial cell migrationLysyl oxidase homolog 2Homo sapiens (human)
negative regulation of DNA-templated transcriptionLysyl oxidase homolog 2Homo sapiens (human)
response to copper ionLysyl oxidase homolog 2Homo sapiens (human)
heterochromatin organizationLysyl oxidase homolog 2Homo sapiens (human)
negative regulation of stem cell population maintenanceLysyl oxidase homolog 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (28)

Processvia Protein(s)Taxonomy
endopeptidase activityCationic trypsinBos taurus (cattle)
serine-type endopeptidase activityCationic trypsinBos taurus (cattle)
protein bindingCationic trypsinBos taurus (cattle)
metal ion bindingCationic trypsinBos taurus (cattle)
serpin family protein bindingCationic trypsinBos taurus (cattle)
peptidase activityGag-Pol polyproteinHIV-1 M:B_HXB2R
integrase activityGag-Pol polyproteinHIV-1 M:B_HXB2R
phenylethanolamine N-methyltransferase activityPhenylethanolamine N-methyltransferaseBos taurus (cattle)
copper ion bindingMembrane primary amine oxidaseHomo sapiens (human)
calcium ion bindingMembrane primary amine oxidaseHomo sapiens (human)
protein bindingMembrane primary amine oxidaseHomo sapiens (human)
primary amine oxidase activityMembrane primary amine oxidaseHomo sapiens (human)
identical protein bindingMembrane primary amine oxidaseHomo sapiens (human)
protein heterodimerization activityMembrane primary amine oxidaseHomo sapiens (human)
quinone bindingMembrane primary amine oxidaseHomo sapiens (human)
aliphatic amine oxidase activityMembrane primary amine oxidaseHomo sapiens (human)
histone H4K5 acetyltransferase activityHistone acetyltransferase KAT8Homo sapiens (human)
histone H4K8 acetyltransferase activityHistone acetyltransferase KAT8Homo sapiens (human)
histone H4K16 acetyltransferase activityHistone acetyltransferase KAT8Homo sapiens (human)
transcription coactivator activityHistone acetyltransferase KAT8Homo sapiens (human)
protein bindingHistone acetyltransferase KAT8Homo sapiens (human)
histone H4 acetyltransferase activityHistone acetyltransferase KAT8Homo sapiens (human)
enzyme bindingHistone acetyltransferase KAT8Homo sapiens (human)
histone H4K5 acetyltransferase activityHistone acetyltransferase KAT8Homo sapiens (human)
histone H4K8 acetyltransferase activityHistone acetyltransferase KAT8Homo sapiens (human)
metal ion bindingHistone acetyltransferase KAT8Homo sapiens (human)
histone H4K16 acetyltransferase activityHistone acetyltransferase KAT8Homo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingHistone acetyltransferase KAT8Homo sapiens (human)
peptide-lysine-N-acetyltransferase activityHistone acetyltransferase KAT8Homo sapiens (human)
protein propionyltransferase activityHistone acetyltransferase KAT8Homo sapiens (human)
transcription coregulator activityHistone acetyltransferase KAT8Homo sapiens (human)
chromatin bindingHistone acetyltransferase KAT8Homo sapiens (human)
protein-lysine 6-oxidase activityLysyl oxidase homolog 2Homo sapiens (human)
copper ion bindingLysyl oxidase homolog 2Homo sapiens (human)
calcium ion bindingLysyl oxidase homolog 2Homo sapiens (human)
protein bindingLysyl oxidase homolog 2Homo sapiens (human)
oligosaccharide bindingLysyl oxidase homolog 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (24)

Processvia Protein(s)Taxonomy
serine protease inhibitor complexCationic trypsinBos taurus (cattle)
cytoplasmMembrane primary amine oxidaseHomo sapiens (human)
plasma membraneMembrane primary amine oxidaseHomo sapiens (human)
microvillusMembrane primary amine oxidaseHomo sapiens (human)
cell surfaceMembrane primary amine oxidaseHomo sapiens (human)
membraneMembrane primary amine oxidaseHomo sapiens (human)
early endosomeMembrane primary amine oxidaseHomo sapiens (human)
endoplasmic reticulumMembrane primary amine oxidaseHomo sapiens (human)
Golgi apparatusMembrane primary amine oxidaseHomo sapiens (human)
early endosomeMembrane primary amine oxidaseHomo sapiens (human)
plasma membraneMembrane primary amine oxidaseHomo sapiens (human)
endoplasmic reticulumMembrane primary amine oxidaseHomo sapiens (human)
Golgi apparatusMembrane primary amine oxidaseHomo sapiens (human)
nucleusHistone acetyltransferase KAT8Homo sapiens (human)
chromosomeHistone acetyltransferase KAT8Homo sapiens (human)
kinetochoreHistone acetyltransferase KAT8Homo sapiens (human)
nucleusHistone acetyltransferase KAT8Homo sapiens (human)
nucleoplasmHistone acetyltransferase KAT8Homo sapiens (human)
mitochondrionHistone acetyltransferase KAT8Homo sapiens (human)
nuclear matrixHistone acetyltransferase KAT8Homo sapiens (human)
NSL complexHistone acetyltransferase KAT8Homo sapiens (human)
MSL complexHistone acetyltransferase KAT8Homo sapiens (human)
histone acetyltransferase complexHistone acetyltransferase KAT8Homo sapiens (human)
MLL1 complexHistone acetyltransferase KAT8Homo sapiens (human)
chromatinHistone acetyltransferase KAT8Homo sapiens (human)
NuA4 histone acetyltransferase complexHistone acetyltransferase KAT8Homo sapiens (human)
collagen-containing extracellular matrixLysyl oxidase homolog 2Homo sapiens (human)
basement membraneLysyl oxidase homolog 2Homo sapiens (human)
extracellular spaceLysyl oxidase homolog 2Homo sapiens (human)
nucleusLysyl oxidase homolog 2Homo sapiens (human)
nucleoplasmLysyl oxidase homolog 2Homo sapiens (human)
endoplasmic reticulumLysyl oxidase homolog 2Homo sapiens (human)
membraneLysyl oxidase homolog 2Homo sapiens (human)
collagen-containing extracellular matrixLysyl oxidase homolog 2Homo sapiens (human)
chromatinLysyl oxidase homolog 2Homo sapiens (human)
collagen-containing extracellular matrixLysyl oxidase homolog 2Homo sapiens (human)
extracellular spaceLysyl oxidase homolog 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID273099Binding affinity to human SSAO2006Journal 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.
AID1430567Inhibition of full length recombinant human LOXL2 expressed in CHO cells assessed as reduction in H2O2 production using DAP as substrate preincubated for 2 hrs followed by substrate addition measured every 2 minutes for 50 minutes by Amplex red dye based 2017ACS medicinal chemistry letters, Apr-13, Volume: 8, Issue:4
Small Molecule Lysyl Oxidase-like 2 (LOXL2) Inhibitors: The Identification of an Inhibitor Selective for LOXL2 over LOX.
AID214878Binding affinity against bovine trypsin2002Journal of medicinal chemistry, Jun-06, Volume: 45, Issue:12
Simple, intuitive calculations of free energy of binding for protein-ligand complexes. 1. Models without explicit constrained water.
AID215916Binding affinity against trypsin2002Journal of medicinal chemistry, Jun-20, Volume: 45, Issue:13
SMall Molecule Growth 2001 (SMoG2001): an improved knowledge-based scoring function for protein-ligand interactions.
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.
AID1244806Antibacterial activity against Staphylococcus aureus ATCC 6538 after 18 hrs by serial microdilution method2015Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18
The effect of complexation of 3-formylrifamycin SV macrocyclic ether derivatives with metal cations and small nitrogen-containing organic molecules on antibacterial activity against S. aureus and S. epidermidis.
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.
AID1244813Antibacterial activity against Staphylococcus aureus ATCC 4163 after 18 hrs by serial microdilution method2015Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18
The effect of complexation of 3-formylrifamycin SV macrocyclic ether derivatives with metal cations and small nitrogen-containing organic molecules on antibacterial activity against S. aureus and S. epidermidis.
AID1244820Antibacterial activity against Staphylococcus aureus ATCC 25923 after 18 hrs by serial microdilution method2015Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18
The effect of complexation of 3-formylrifamycin SV macrocyclic ether derivatives with metal cations and small nitrogen-containing organic molecules on antibacterial activity against S. aureus and S. epidermidis.
AID1244827Antibacterial activity against Staphylococcus epidermidis ATCC 12228 after 18 hrs by serial microdilution method2015Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18
The effect of complexation of 3-formylrifamycin SV macrocyclic ether derivatives with metal cations and small nitrogen-containing organic molecules on antibacterial activity against S. aureus and S. epidermidis.
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.
AID1507709Inhibition of N-terminal His6-tagged KAT8 catalytic domain (125 to 458 residues) (unknown origin) expressed in Escherichia coli BL21(DE3) using SGRGKGGKGLGKGGAKRHRK-NH2 as substrate after 5 mins in presence of Ac-CoA by fluorescence assay2017European journal of medicinal chemistry, Aug-18, Volume: 136The relevance of K
AID273100Binding affinity to mouse SSAO2006Journal 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.
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.
AID1244834Antibacterial activity against Staphylococcus epidermidis ATCC 49134 after 18 hrs by serial microdilution method2015Bioorganic & medicinal chemistry letters, Sep-15, Volume: 25, Issue:18
The effect of complexation of 3-formylrifamycin SV macrocyclic ether derivatives with metal cations and small nitrogen-containing organic molecules on antibacterial activity against S. aureus and S. epidermidis.
AID225081Inhibition of phenylethanolamine N-methyltransferase(PNMT)activity1983Journal of medicinal chemistry, Aug, Volume: 26, Issue:8
Quantitative structure-activity relationships employing independent quantum chemical indices.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB1994Nature structural biology, Oct, Volume: 1, Issue:10
Prediction of new serine proteinase inhibitors.
AID1811Experimentally measured binding affinity data derived from PDB1994Nature structural biology, Oct, Volume: 1, Issue:10
Prediction of new serine proteinase inhibitors.
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 (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (15.38)18.7374
1990's2 (15.38)18.2507
2000's3 (23.08)29.6817
2010's5 (38.46)24.3611
2020's1 (7.69)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.12

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index34.12 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index39.48 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.12)

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%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]