Acridine Orange Base
Basic information
- CAS
17251-70-6- Standard SMILES
CN(C)c1ccc2cc3ccc(N(C)C)cc3nc2c1- InChIKey
DPKHZNPWBDQZCN-UHFFFAOYSA-N- Molecular formula
- C17H19N3
- Average molar mass
- 265.35 g/mol
- Monoisotopic mass
- 265.15789761
Overview
Acridine orange free base is a 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. It has a role as a fluorochrome and a histological dye. It is an aromatic amine, a tertiary amino compound and a member of aminoacridines.
Names & identifiers
- Preferred name
- Acridine Orange Base
- IUPAC
- 3-N,3-N,6-N,6-N-tetramethylacridine-3,6-diamine
- English name
- AcridineOrangeForMicroscopicalStaining
- Molecular formula
- C17H20N3+
- Molecular weight
- 266.3608
Names & synonyms
Acridine orange494-38-2Acridine Orange Base3,6-Bis(dimethylamino)acridineWaxoline Orange AOranz akridinova3,6-Di(dimethylamino)acridineRhoduline OrangeC.I. No. 46005:1Oranz rozpoustedlova 15Basic Orange 14Acridine Orange NO
Show more names
AcridineOrangeForMicroscopicalStaining3,6-Acridinediamine, N,N,N,N-tetramethyl-, conjugate monoacid
Rhoduline Orange NOF30N4O6XVVDTXSID60197783NSC-194350Acridine Orange NAcridine Orange RAcridine Orange NSSumitomo Acridine Orange NO
Database identifiers
- CAS
17251-70-6、494-38-2- PubChem CID
- 62344
- DTXSID
DTXSID60197783- ChEMBL
CHEMBL81880- ChEBI
CHEBI:87346- UNII
- F30N4O6XVV
- EC Number
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 19.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 298
Experimental & physicochemical properties
Chemical Classes
Dyes -> Acridine Dyes
Dyes -> Acridine Dyes
Physical DescriptionSolid; [Sigma-Aldrich MSDS]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory Information
Chemical: 3,6-Acridinediamine, N,N,N',N'-tetramethyl-
Acridine orange: Does not have an individual approval but may be used under an appropriate group standard
Acridine orange base: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Has mutagenic potential that is enhanced by light; Acridine dyes are derived from 3,6-diaminoacridine, 9-(4'-aminophenyl)-3-aminoacridine, and 9-(4'-aminophenyl)-3,6-diaminoacridine. One of the oldest acridine dyes is chrysaniline. Acridine dyes have low light fastness. In the past they were used for printing on cotton. Currently, they are not commercially important. [Ullmann] See Acridine.
May cause irritation; Targets the blood; Mutagenic effects observed in laboratory experiments; [Sigma-Aldrich MSDS] See Acridine orange.
Safety & protection
Protective Action Criteria (PAC)
0.090 [mg/m3]
0.98 [mg/m3]
5.9 [mg/m3]
Toxicology
Carcinogen Classification
Acridine orange
Group 3: Not classifiable as to its carcinogenicity to humans
Volume 16: (1978) Some Aromatic Amines and Related Nitro Compounds – Hair Dyes, Colouring Agents and Miscellaneous Industrial Chemicals
1987
1987
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.
Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.
Uses & manufacturing
Uses
N,N,N',N'-Tetramethyl-3,6-acridinediamine, monohydrochloride. Cationic cytochemical stain specific for cell nuclei, especially DNA. It is used as a supravital stain and in fluorescence cytochemistry. It may cause mutations in microorganisms. [ChemIDplus]
A coloring agent; [IARC]
Related reactions
6 records
Compound notes
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