ContaminantDB: Acridine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:59:16 UTC

Update Date

2026-03-31 17:55:07 UTC

Accession Number

CHEM000562

Identification

Common Name

Acridine

Class

Small Molecule

Description

Acridine is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. (4)

Contaminant Sources

STOFF IDENT Compounds
Suspected Compounds
T3DB toxins

Contaminant Type

Aromatic Hydrocarbon
Food Toxin
Natural Compound
Organic Compound
Pollutant
Polycyclic Aromatic Hydrocarbon

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
10-Azaanthracene	ChEBI
2,3,5,6-Dibenzopyridine	ChEBI
2,3-Benzoquinoline	ChEBI
9-Azaanthracene	ChEBI
Acrydine	ChEBI
Akridin	ChEBI
Benzo[b]quinoline	ChEBI
Dibenzo[b,e]pyridine	ChEBI

Chemical Formula

C₁₃H₉N

Average Molecular Mass

179.217 g/mol

Monoisotopic Mass

179.073 g/mol

CAS Registry Number

260-94-6

IUPAC Name

acridine

Traditional Name

acridine

SMILES

C1=CC2=CC3=CC=CC=C3N=C2C=C1

InChI Identifier

InChI=1S/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H

InChI Key

DZBUGLKDJFMEHC-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridines

Alternative Parents

Substituents

Acridine
Benzenoid
Pyridine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acridines (CHEBI:36420 )
polycyclic heteroarene (CHEBI:36420 )
mancude organic heterotricyclic parent (CHEBI:36420 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

genotoxin

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colorless solid.

Experimental Properties

Property	Value
Melting Point	108°C
Boiling Point	Not Available
Solubility	0.0384 mg/mL at 25°C [BANWART,WL et al. (1982)]

Predicted Properties

Property	Value	Source
Water Solubility	0.039 g/L	ALOGPS
logP	3.51	ALOGPS
logP	3.51	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	6.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.89 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	56.06 m³·mol⁻¹	ChemAxon
Polarizability	20.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0900000000-60709f13538ebb5bf03c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0fb9-0900000000-e0c1bf58e0cb2bf829ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-003r-0900000000-eae554919803e4683fdb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0900000000-9e670fdb36b28daad5dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-8173a227a1d988a8e1a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-422dd5d409aa20c1ff0e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-0900000000-a5b0ca159a9258ef014d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-05d700c59ef99ce33b11	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-2356d93638ed7ee93521	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000000-11523a8602aa0962e990	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-594469afea8b2ce91c8c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-594469afea8b2ce91c8c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-72311cdd3bfe34545a89	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-9417270887d6a1e93e91	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-9417270887d6a1e93e91	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000000-063b6148248bc2509b93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8c0deb449c1b4d81b5d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-8c0deb449c1b4d81b5d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-8c0deb449c1b4d81b5d9	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-3900000000-cea0879ccb7e90ce2a83	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (4) ; inhalation (4)

Mechanism of Toxicity

The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (4, 5, 2, 3)

Metabolism

PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (4)

Toxicity Values

LD50: 400 mg/kg (Subcutaneous, Mouse) (6) LD50: 500 mg/kg (Oral, Mouse) (6) LD50: 100 mg/kg (Intravenous, Rabbit) (6)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC. IARC has evaluated related PAHs (7).

Uses/Sources

PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (4)

Minimum Risk Level

Not Available

Health Effects

PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (4)

Symptoms

Acute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (1)

Treatment

There is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (4)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0247968

FooDB ID