Acridine Orange Base

HCID 62344CAS 17251-70-6

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Basic information

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: 610-452-6
Nikkaji: J1.559H

Properties

Computed structural properties

XLogP: 3.4
Topological polar surface area: 19.4 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 20
Formal charge: 0
Complexity: 298

Experimental & physicochemical properties

Chemical Classes · 2 items

Dyes -> Acridine Dyes

Physical DescriptionSolid; [Sigma-Aldrich MSDS]

Safety & regulation

Hazard information

Regulatory Information · 3 items

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 · 2 items

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) · 3 items

0.090 [mg/m3]

0.98 [mg/m3]

5.9 [mg/m3]

Toxicology

Carcinogen Classification · 5 items

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

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

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 · 2 items

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]