Acridine orange (CHEM016069)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:13:14 UTC
Update Date2026-04-03 00:38:32 UTC
Accession NumberCHEM016069
Identification
Common NameAcridine orange
ClassSmall Molecule
DescriptionA member of the class of aminoacridines that is acridine carrying two dimethylamino substituents at positions 3 and 6. The hydrochloride salt is the fluorescent dye 'acridine orange', used for cell cycle determination.
Contaminant Sources
  • IARC Carcinogens Group 3
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,6-Bis(dimethylamino)acridineChEBI
3,6-Di(dimethylamino)acridineChEBI
Acridine orangeChEBI
Acridine orange baseChEBI
Brilliant acridine orange eChEBI
C.I. 46005bChEBI
C.I. solvent orange 15ChEBI
N,N,N',n'-tetramethyl-3,6-acridinediamineChEBI
Solvent orange 15ChEBI
Acridine diamine, tetramethylMeSH
Basic orange 3RnMeSH
C.I. basic orange 14MeSH
Orange base, acridineMeSH
Base, acridine orangeMeSH
N,N,N',n'-tetramethyl-3,6-acridinediamine hydrochlorideMeSH
Orange 3Rn, basicMeSH
Orange, acridineMeSH
Orange, rhodulineMeSH
Rhoduline orangeMeSH
Diamine, tetramethyl acridineMeSH
Tetramethyl acridine diamineMeSH
EuchrysineMeSH
Chemical FormulaC17H19N3
Average Molecular Mass265.360 g/mol
Monoisotopic Mass265.158 g/mol
CAS Registry Number494-38-2
IUPAC NameN3,N3,N6,N6-tetramethylacridine-3,6-diamine
Traditional Nameacridine orange
SMILESCN(C)C1=CC2=NC3=C(C=CC(=C3)N(C)C)C=C2C=C1
InChI IdentifierInChI=1S/C17H19N3/c1-19(2)14-7-5-12-9-13-6-8-15(20(3)4)11-17(13)18-16(12)10-14/h5-11H,1-4H3
InChI KeyDPKHZNPWBDQZCN-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentAcridines
Alternative Parents
Substituents
  • Acridine
  • Aminoquinoline
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP4.37ALOGPS
logP3.72ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)8.17ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area19.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity84.91 m³·mol⁻¹ChemAxon
Polarizability31.79 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ta-0490000000-b7a8d71677d5c76c63ceSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-2f0810585573991c88e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-ba30af201da1d7db1e96Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-0090000000-ca336db5bc3cc4d67ef1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-35fa5183816b1ea5153eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0090000000-aa454d77c0ee0149fcf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-0090000000-51ee3146d2ca9d3fe714Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0260299
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcridine_orange
Chemspider ID56136
ChEBI ID87346
PubChem Compound IDNot Available
Kegg Compound IDC19315
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24988915
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25025314
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25542136
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=26016416
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26034308
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=26163789