1,10-Phenanthroline
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Basic information
- CAS
66-71-7- Standard SMILES
c1cnc2c(c1)ccc1cccnc12- InChIKey
DGEZNRSVGBDHLK-UHFFFAOYSA-N- Molecular formula
- C12H8N2
- Average molar mass
- 180.2 g/mol
- Monoisotopic mass
- 180.06874826
Overview
1,10-phenanthroline is a phenanthroline. It has a role as an EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor and an EC 2.7.1.1 (hexokinase) inhibitor.
Names & identifiers
- Preferred name
- 1,10-Phenanthroline
- IUPAC
- 1,10-phenanthroline
- English name
- o-Phenanthroline
- Molecular formula
- C12H8N2
- Molecular weight
- 180.21
Names & synonyms
1,10-phenanthroline66-71-7o-phenanthroline4,5-diazaphenanthreneorthophenanthroline1,10-o-phenanthrolinebeta-phenanthroline2-phenanthrolineDTXSID1025857O-PHEW4X6ZO7939NSC-4265
Show more names
1,10-Phen10-Phenanthroline1,10-Fenanthrolin1,10-Phenanthroline anhydrate4,5-Phenanthroline1,1-Phenanthroline
NSC-203545DTXCID405857CHEBI:44975(OP)2Cu(I)RefChem:410355200-629-2Phenanthrolinephen
Database identifiers
- CAS
66-71-7- PubChem CID
- 1318
- DTXSID
DTXSID1025857- ChEMBL
CHEMBL415879- ChEBI
CHEBI:44975- UNII
- W4X6ZO7939
- EC Number
- 200-629-2
- Nikkaji
- J4.844E
Properties
Computed structural propertiesFilling in
- XLogP
- 1.8
- Topological polar surface area
- 25.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 182
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
SpringerMaterials PropertiesAngular frequency
LogP1.93
Solubility>27 [ug/mL] (The mean of the results at pH 7.4)
Boiling Point> 300 °C
Melting Point117 °C
Vapor Pressure0.0000523 [mmHg]
Physical Description
Liquid
White solid; [Merck Index] Hygroscopic solid; [Sigma-Aldrich MSDS]
Ionization Efficiency
Positive
3.25
2.7
Agilent XCT
Electrospray ionization
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301: Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P273, P301+P316, P321, P330, P391, P405, and P501 (click each P-code to see the statement)
Danger
H301 (99.8%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P273, P301+P316, P321, P330, P391, P405, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Chemical: 1,10-Phenanthroline
1,10-Phenanthroline is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,10-Phenanthroline are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
1,10-Phenanthroline: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses kidney changes in intraperitoneal lethal-dose studies of mice (LD50 = 75 mg/kg); [RTECS] May cause irritation; Toxic by ingestion; [Sigma-Aldrich MSDS] See 2,2'-Bipyridine. See POLYCYCLIC AROMATIC HYDROCARBONS.
Hazard Classes and Categories
Acute Tox. 3 (99.8%)
Acute toxicity - category 3
Acute Tox. 3 *
Safety & protection
Protective Action Criteria (PAC)
0.25 [mg/m3]
2.7 [mg/m3]
16 [mg/m3]
Toxicology
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS.
Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.
Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other.
Agents that are capable of inserting themselves between the successive bases in DNA, thus kinking, uncoiling or otherwise deforming it and therefore preventing its proper functioning. They are used in the study of DNA.
Organic chemicals that form two or more coordination links with an iron ion. Once coordination has occurred, the complex formed is called a chelate. The iron-binding porphyrin group of hemoglobin is an example of a metal chelate found in biological systems.
Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES).
Uses & manufacturing
UsesUsed as an analytical reagent, metal chelator, and in organic synthesis; [Merck Index] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]
U.S. Production2023: <50,000 lb
Industry UsesDrier
General Manufacturing Information
Related reactions
1,045 records
Compound notes
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