Compounds > 5-methyl-1,10-phenanthroline
Page last updated: 2024-12-06

5-methyl-1,10-phenanthroline

5-methyl-1,10-phenanthroline is a heterocyclic organic compound with the formula C13H10N2. It is a derivative of 1,10-phenanthroline, with a methyl group attached to the 5-position. It is a white solid that is soluble in organic solvents. 5-methyl-1,10-phenanthroline is used as a ligand in coordination chemistry. It forms complexes with transition metals, such as iron, copper, and zinc. These complexes have been studied for their potential applications in catalysis, sensing, and medicine. 5-methyl-1,10-phenanthroline has also been used as a reagent for the determination of metals in solution. '

Cross-References

ID SourceID
PubMed CID72791
CHEMBL ID98682
SCHEMBL ID371564
MeSH IDM0068328

Synonyms (30)

Synonym
5-methyl-[1,10]phenanthroline
CHEMBL98682 ,
nsc-4272
nsc4272
5-methylphenanthroline
3002-78-6
5-methyl-1,10-phenanthroline ,
1,10-phenanthroline, 5-methyl-
5-methyl-1,10-phenanthroline, >=99%
ujaqyozroifqho-uhfffaoysa-
inchi=1/c13h10n2/c1-9-8-10-4-2-6-14-12(10)13-11(9)5-3-7-15-13/h2-8h,1h3
iron(+2) cation; 5-methyl-1,10-phenanthroline; sulfate
M0300
einecs 221-099-9
nsc 4272
bdbm50401345
AKOS015899630
FT-0620583
DTXSID4062771
SCHEMBL371564
J-200078
AC-29167
mfcd00004982
AS-59411
CS-W004552
smssf-0625532
ams_cnc_id-110962535
2-bromo-5-(2,5-dimethyl)pyrrolidylpyridine
5-methyl-1,10-phenanthroline hydrate [for colorimetric determination of iron]
A846127
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
C-C chemokine receptor type 1Homo sapiens (human)IC50 (µMol)122.44650.00070.20022.5000AID716289
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
C-C chemokine receptor type 1Homo sapiens (human)EC50 (µMol)1.89761.50002.98566.3096AID716296
C-C chemokine receptor type 5Homo sapiens (human)EC50 (µMol)1,000.00000.00702.09365.0119AID716295
C-C chemokine receptor type 8Homo sapiens (human)EC50 (µMol)1.99760.48003.72297.9433AID716294
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (34)

Processvia Protein(s)Taxonomy
dendritic cell chemotaxisC-C chemokine receptor type 1Homo sapiens (human)
monocyte chemotaxisC-C chemokine receptor type 1Homo sapiens (human)
calcium ion transportC-C chemokine receptor type 1Homo sapiens (human)
intracellular calcium ion homeostasisC-C chemokine receptor type 1Homo sapiens (human)
exocytosisC-C chemokine receptor type 1Homo sapiens (human)
chemotaxisC-C chemokine receptor type 1Homo sapiens (human)
immune responseC-C chemokine receptor type 1Homo sapiens (human)
cell adhesionC-C chemokine receptor type 1Homo sapiens (human)
cell surface receptor signaling pathwayC-C chemokine receptor type 1Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerC-C chemokine receptor type 1Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationC-C chemokine receptor type 1Homo sapiens (human)
cell-cell signalingC-C chemokine receptor type 1Homo sapiens (human)
response to woundingC-C chemokine receptor type 1Homo sapiens (human)
negative regulation of gene expressionC-C chemokine receptor type 1Homo sapiens (human)
cytokine-mediated signaling pathwayC-C chemokine receptor type 1Homo sapiens (human)
positive regulation of cell migrationC-C chemokine receptor type 1Homo sapiens (human)
negative regulation of bone mineralizationC-C chemokine receptor type 1Homo sapiens (human)
positive regulation of osteoclast differentiationC-C chemokine receptor type 1Homo sapiens (human)
positive regulation of calcium ion transportC-C chemokine receptor type 1Homo sapiens (human)
chemokine-mediated signaling pathwayC-C chemokine receptor type 1Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeC-C chemokine receptor type 1Homo sapiens (human)
positive regulation of monocyte chemotaxisC-C chemokine receptor type 1Homo sapiens (human)
calcium-mediated signalingC-C chemokine receptor type 1Homo sapiens (human)
cell chemotaxisC-C chemokine receptor type 1Homo sapiens (human)
inflammatory responseC-C chemokine receptor type 1Homo sapiens (human)
MAPK cascadeC-C chemokine receptor type 5Homo sapiens (human)
dendritic cell chemotaxisC-C chemokine receptor type 5Homo sapiens (human)
calcium ion transportC-C chemokine receptor type 5Homo sapiens (human)
chemotaxisC-C chemokine receptor type 5Homo sapiens (human)
cellular defense responseC-C chemokine receptor type 5Homo sapiens (human)
cell surface receptor signaling pathwayC-C chemokine receptor type 5Homo sapiens (human)
G protein-coupled receptor signaling pathwayC-C chemokine receptor type 5Homo sapiens (human)
cell-cell signalingC-C chemokine receptor type 5Homo sapiens (human)
release of sequestered calcium ion into cytosol by sarcoplasmic reticulumC-C chemokine receptor type 5Homo sapiens (human)
calcium-mediated signalingC-C chemokine receptor type 5Homo sapiens (human)
signalingC-C chemokine receptor type 5Homo sapiens (human)
symbiont entry into host cellC-C chemokine receptor type 5Homo sapiens (human)
chemokine-mediated signaling pathwayC-C chemokine receptor type 5Homo sapiens (human)
response to cholesterolC-C chemokine receptor type 5Homo sapiens (human)
cellular response to lipopolysaccharideC-C chemokine receptor type 5Homo sapiens (human)
negative regulation of macrophage apoptotic processC-C chemokine receptor type 5Homo sapiens (human)
inflammatory responseC-C chemokine receptor type 5Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationC-C chemokine receptor type 5Homo sapiens (human)
immune responseC-C chemokine receptor type 5Homo sapiens (human)
cell chemotaxisC-C chemokine receptor type 5Homo sapiens (human)
chemotaxisC-C chemokine receptor type 8Homo sapiens (human)
cell adhesionC-C chemokine receptor type 8Homo sapiens (human)
G protein-coupled receptor signaling pathwayC-C chemokine receptor type 8Homo sapiens (human)
chemokine-mediated signaling pathwayC-C chemokine receptor type 8Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationC-C chemokine receptor type 8Homo sapiens (human)
immune responseC-C chemokine receptor type 8Homo sapiens (human)
cell chemotaxisC-C chemokine receptor type 8Homo sapiens (human)
calcium-mediated signalingC-C chemokine receptor type 8Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
phosphatidylinositol phospholipase C activityC-C chemokine receptor type 1Homo sapiens (human)
chemokine receptor activityC-C chemokine receptor type 1Homo sapiens (human)
protein bindingC-C chemokine receptor type 1Homo sapiens (human)
C-C chemokine receptor activityC-C chemokine receptor type 1Homo sapiens (human)
C-C chemokine bindingC-C chemokine receptor type 1Homo sapiens (human)
chemokine (C-C motif) ligand 7 bindingC-C chemokine receptor type 1Homo sapiens (human)
chemokine (C-C motif) ligand 5 bindingC-C chemokine receptor type 1Homo sapiens (human)
virus receptor activityC-C chemokine receptor type 5Homo sapiens (human)
actin bindingC-C chemokine receptor type 5Homo sapiens (human)
phosphatidylinositol phospholipase C activityC-C chemokine receptor type 5Homo sapiens (human)
chemokine receptor activityC-C chemokine receptor type 5Homo sapiens (human)
protein bindingC-C chemokine receptor type 5Homo sapiens (human)
coreceptor activityC-C chemokine receptor type 5Homo sapiens (human)
C-C chemokine receptor activityC-C chemokine receptor type 5Homo sapiens (human)
C-C chemokine bindingC-C chemokine receptor type 5Homo sapiens (human)
identical protein bindingC-C chemokine receptor type 5Homo sapiens (human)
chemokine (C-C motif) ligand 5 bindingC-C chemokine receptor type 5Homo sapiens (human)
chemokine receptor activityC-C chemokine receptor type 8Homo sapiens (human)
coreceptor activityC-C chemokine receptor type 8Homo sapiens (human)
C-C chemokine receptor activityC-C chemokine receptor type 8Homo sapiens (human)
C-C chemokine bindingC-C chemokine receptor type 8Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
plasma membraneC-C chemokine receptor type 1Homo sapiens (human)
external side of plasma membraneC-C chemokine receptor type 1Homo sapiens (human)
external side of plasma membraneC-C chemokine receptor type 1Homo sapiens (human)
cytoplasmC-C chemokine receptor type 1Homo sapiens (human)
cell surfaceC-C chemokine receptor type 5Homo sapiens (human)
endosomeC-C chemokine receptor type 5Homo sapiens (human)
plasma membraneC-C chemokine receptor type 5Homo sapiens (human)
external side of plasma membraneC-C chemokine receptor type 5Homo sapiens (human)
cell surfaceC-C chemokine receptor type 5Homo sapiens (human)
external side of plasma membraneC-C chemokine receptor type 5Homo sapiens (human)
cytoplasmC-C chemokine receptor type 5Homo sapiens (human)
plasma membraneC-C chemokine receptor type 8Homo sapiens (human)
external side of plasma membraneC-C chemokine receptor type 8Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (15)

Assay IDTitleYearJournalArticle
AID716300Ratio of ZnPhe EC50 to compound EC50 for human CCR1 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as IP3 turnover by liquid scintillation counting analysis2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716290Allosteric modulation at human CCR8 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as [3H]IP3 turnover by liquid scintillation counting analysis relative to basal level2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716288Displacement of [125I]-CCL3 from human CCR1 transfected in COS7 cells coexpressing chimeric Gqi4myr after 3 hrs relative to basal level2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716289Displacement of [125I]-CCL3 from human CCR1 transfected in COS7 cells coexpressing chimeric Gqi4myr after 3 hrs2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716294Allosteric modulation at human CCR8 transfected in COS7 cells assessed as [3H]IP3 turnover by liquid scintillation counting analysis2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716296Allosteric modulation at human CCR1 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as {3H]IP3 turnover by liquid scintillation counting analysis2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716293Binding affinity to Zn(II) after 2 hrs using FluoZin-3 by fuorescence assay2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716287Displacement of [125I]-CCL3 from human CCR5 transfected in COS7 cells coexpressing chimeric Gqi4myr after 3 hrs2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716297Allosteric modulation at human CCR1 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as [3H]IP3 turnover by liquid scintillation counting analysis relative to basal level2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID158223In vitro antimalarial activity against chloroquine-sensitive Plasmodium falciparum D10; Not determined2004Journal of medicinal chemistry, May-20, Volume: 47, Issue:11
In vitro antimalarial activity of a series of cationic 2,2'-bipyridyl- and 1,10-phenanthrolineplatinum(II) benzoylthiourea complexes.
AID158225In vitro antimalarial activity against chloroquine-sensitive Plasmodium falciparum K1; Not determined2004Journal of medicinal chemistry, May-20, Volume: 47, Issue:11
In vitro antimalarial activity of a series of cationic 2,2'-bipyridyl- and 1,10-phenanthrolineplatinum(II) benzoylthiourea complexes.
AID218537Inhibition of beta-hematin formation; Not active2004Journal of medicinal chemistry, May-20, Volume: 47, Issue:11
In vitro antimalarial activity of a series of cationic 2,2'-bipyridyl- and 1,10-phenanthrolineplatinum(II) benzoylthiourea complexes.
AID716295Allosteric modulation at human CCR5 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as [3H]IP3 turnover by liquid scintillation counting analysis2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID72977Ability to associate with ferriprotoporphyrin IX2004Journal of medicinal chemistry, May-20, Volume: 47, Issue:11
In vitro antimalarial activity of a series of cationic 2,2'-bipyridyl- and 1,10-phenanthrolineplatinum(II) benzoylthiourea complexes.
AID716291Ratio of ZnPhe EC50 to compound EC50 for human CCR8 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as IP3 turnover by liquid scintillation counting analysis2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (20.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)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: 20.64

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 Index20.64 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.80 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.64)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
1,10-phenanthroline
1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases		2.7730phenanthrolineEC 2.7.1.1 (hexokinase) inhibitor;
EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor
2,2'-dipyridyl
2,2'-Dipyridyl: A reagent used for the determination of iron.. 2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.		2.7430bipyridinechelator;
ferroptosis inhibitor
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		2.0210aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
cyclopentane
Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.		2.0810cycloalkane;
cyclopentanes;
volatile organic compound		non-polar solvent
4,4'-dimethyl-2,2'-bipyridine
4,4'-dimethyl-2,2'-bipyridine: structure in first source		2.4420
2,2'-dipyridylamine
dipyridin-2-ylamine: structure in first source		2.0610
5,5'-dimethyl-2,2'-bipyridyl
5,5'-dimethyl-2,2'-bipyridyl: structure in first source		2.0710bipyridines
platinum
Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.		2.0810elemental platinum;
nickel group element atom;
platinum group metal atom
neocuproine
neocuproine: Spectrophotometric determination of copper and ultramicro blood sugar determinations; structure; RN given refers to parent cpd. neocuproine : A member of the class of phenanthrolines that is 1,10-phenanthroline bearing two methyl substituents at positions 2 and 9.		2.0710phenanthrolineschelator;
copper chelator
1,7-phenanthroline
[no description available]		2.730phenanthroline
2,2',2''-terpyridine
2,2',2''-terpyridine: RN given refers to parent cpd. 2,2':6',2''-terpyridine : A tridentate heterocyclic ligand that binds metals at three meridional sites giving two adjacent 5-membered MN2C2 chelate rings.		2.0710terpyridineschelator
5-nitro-1,10-phenanthroline
5-nitro-1,10-phenanthroline: structure in first source		2.4420
bathophenanthroline
4,7-diphenyl-1,10-phenanthroline : A member of the class of phenanthrolines that is 1,10-phenanthroline bearing two phenyl substituents at positions 4 and 7.		2.0610benzenes;
phenanthrolines		chelator
3,4,7,8-tetramethyl-1,10-phenanthroline
[no description available]		2.7430
cobalt
Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.		1.9510cobalt group element atom;
metal allergen		micronutrient
emetine dihydrochloride
emetine dihydrochloride : The dihydrochloride salt of emetine.. emetine dihydrochloride hydrate : A hydrate that is the monohydrate of the dihydrochloride salt of emetine.		2.0210hydrochlorideanticoronaviral agent;
antimalarial;
antineoplastic agent;
antiprotozoal drug;
antiviral agent;
autophagy inhibitor;
emetic;
protein synthesis inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Benign Neoplasms
[description not available]		02.0610
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.0610
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