Acridine Orange base - ≥75% , CAS No.494-38-2

CAS: 494-38-2 Cat. No.: A121748 Molecular Weight: 265.35

GRADE & PURITY ≥75%

Synonyms

F30N4O6XVV | Oranz akridinova | 2,8-Bisdimethylaminoacridine | C.I. Solvent Orange 15 | C.I. 46005B | N,N,N(sup 1),N(sup 1)-Tetramethylacridinediamine | [6-(dimethylamino)acridin-3-yl]-dimethyl-amine | F19170 | NSC 194350 | 4-22-00-05490 (Beilstein Handbo

Storage

Room temperature

Shipped In

Normal

Overview

When bound to DNA, it emits green fluorescence (Em=525 nm) and when bound to RNA, it emits red fluorescence (Em=~650 nm).
A fluorescent nucleic acid binding dye which interacts with both DNA and RNA.

Specifications

Synonyms

F30N4O6XVV | Oranz akridinova | 2, 8-Bisdimethylaminoacridine | C.I. Solvent Orange 15 | C.I. 46005B | N, N, N(sup 1), N(sup 1)-Tetramethylacridinediamine | [6-(dimethylamino)acridin-3-yl]-dimethyl-amine | F19170 | NSC 194350 | 4-22-00-05490 (Beilstein Handbo

Specifications & Purity

≥75%

Storage

Room temperature

Shipped In

Normal

Purity

≥75%

Names and Identifiers

• Pubchem Sid: 488183564
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488183564
• Canonical Smiles: CN(C)C1=CC2=C(C=C1)C=C3C=CC(=CC3=N2)N(C)C
• IUPAC Name: 3-N,3-N,6-N,6-N-tetramethylacridine-3,6-diamine
• InChIKey: DPKHZNPWBDQZCN-UHFFFAOYSA-N
• INCHI: 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
• Isomeric SMILES: CN(C)C1=CC2=C(C=C1)C=C3C=CC(=CC3=N2)N(C)C
• WGK Germany: 3
• RTECS: AR7600000
• Molecular Weight: 265.35
• Reaxy-Rn: 20916
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=20916&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Quinolines and derivatives
      • Subclass Benzoquinolines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Quinolines and derivatives
• Subclass: Benzoquinolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Acridines
• Alternative Parents: Aminoquinolines and derivatives Dialkylarylamines Pyridines and derivatives Benzenoids Heteroaromatic compounds Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• 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
• Description: This compound 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.
• External Descriptors: aminoacridines - tertiary amino compound - aromatic amine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

APP Tclin Amyloid-beta A4 protein (1 Activities)

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APP Tclin Amyloid-beta A4 protein (8510 Activities)

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TERT Tchem Telomerase reverse transcriptase (2428 Activities)

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A498 (42825 Activities)

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ACHN (49357 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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KM12 (47707 Activities)

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M14 (47487 Activities)

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MCF7 (126967 Activities)

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MOLT-4 (49676 Activities)

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OVCAR-3 (48710 Activities)

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OVCAR-4 (44535 Activities)

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OVCAR-5 (45555 Activities)

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OVCAR-8 (47708 Activities)

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PC-3 (62116 Activities)

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RPMI-8226 (44974 Activities)

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RXF 393 (41971 Activities)

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SF-295 (48000 Activities)

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SK-MEL-2 (46422 Activities)

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SK-MEL-28 (48833 Activities)

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SK-MEL-5 (47095 Activities)

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SK-OV-3 (52876 Activities)

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SN12C (47755 Activities)

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SNB-19 (46794 Activities)

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TK-10 (45540 Activities)

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U-251 (51189 Activities)

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UACC-257 (46019 Activities)

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UACC-62 (47335 Activities)

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UO-31 (46270 Activities)

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786-0 (47912 Activities)

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A549 (127892 Activities)

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NCI/ADR-RES (33767 Activities)

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T47D (39041 Activities)

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EKVX (44102 Activities)

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NCI-H322M (45589 Activities)

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HCC 2998 (41480 Activities)

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HCT-116 (91556 Activities)

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HOP-92 (41141 Activities)

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Hs-578T (29457 Activities)

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NCI-H460 (60772 Activities)

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SF-268 (49410 Activities)

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IGROV-1 (47897 Activities)

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LOX IMVI (44321 Activities)

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HOP-62 (47048 Activities)

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MDA-MB-435 (38290 Activities)

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Associated Targets(non-human)

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

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Pasteurella multocida (1166 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Rattus norvegicus (775804 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Melt Point(°C): 165°C(dec.)(lit.)
• Molecular Weight: 265.350 g/mol
• XLogP3: 3.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 265.158 Da
• Monoisotopic Mass: 265.158 Da
• Topological Polar Surface Area: 19.400 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 298.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Juan Wu, Xi Wang, Binglong Zhu, Qinting He, Yaheng Zhang, Wei Jiang.  (2022)  Synthesis and characterization of magnetic polymeric nanocomposites for pH-sensitive controlled release of methotrexate.  JOURNAL OF BIOMATERIALS SCIENCE-POLYMER EDITION,      [PMID:35727073] [10.1080/09205063.2022.2093053]

2. Ying Gong, Jiping Chen, Rongping Pu.  (2019)  The enhanced removal and phytodegradation of sodium dodecyl sulfate (SDS) in wastewater using controllable water hyacinth.  INTERNATIONAL JOURNAL OF PHYTOREMEDIATION,      [PMID:31044608] [10.1080/15226514.2019.1606779]

3. Dong Zhou.  (2018)  Ecotoxicity of bisphenol S to Caenorhabditis elegans by prolonged exposure in comparison with bisphenol A.  ENVIRONMENTAL TOXICOLOGY AND CHEMISTRY,  37  (10): (2560-2565).  [PMID:29923629] [10.1002/etc.4214]

4. Juan Wu, Wei Jiang, Yewen Shen, Wei Jiang, Renbing Tian.  (2016)  Synthesis and characterization of mesoporous magnetic nanocomposites wrapped with chitosan gatekeepers for pH-sensitive controlled release of doxorubicin.  Materials Science & Engineering C-Materials for Biological Applications,      [PMID:27770872] [10.1016/j.msec.2016.08.054]

5. Ruijing Li, Weili Yang, Xingxue Yan, Xinkui Zhou, Xiaorui Song, Cuihua Liu, Yaodong Zhang, Jitong Li.  (2024)  Folic acid mitigates the developmental and neurotoxic effects of bisphenol A in zebrafish by inhibiting the oxidative stress/JNK signaling pathway.  ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY,      [PMID:39566264] [10.1016/j.ecoenv.2024.117363]

6. Yue Tao, Xiaodong Yi, Yanyan Gu, Rongyi Yang, Zixu Li, Xiangyong Guo, Donglin Zhao, Ying Zhang.  (2024)  Neurotoxicity of dibutyl phthalate in zebrafish larvae: Decreased energy acquisition by neurons.  FOOD AND CHEMICAL TOXICOLOGY,      [PMID:38621509] [10.1016/j.fct.2024.114666]

7. Yiyun Liu, Qi-Ping Tang, Si-Jia Zuo, Yuan Ding, Feng-Yi Guo, Bao-Fu Zhang, Qin-Hong Zhou, Dongmei Xie, De-Sheng Pei.  (2025)  Synergistic neurotoxicity of polystyrene nanoparticles and MEHP in zebrafish (Danio rerio).  ENVIRONMENTAL POLLUTION,      [PMID:40609886] [10.1016/j.envpol.2025.126765]

8. Wang Xi, Wu Juan, Sun Haibin, Lu Bingyan, Huang Jingjing, Liu Qiaoling, Li Tingting.  (2025)  Fabrication of Ag-armed iron oxide magnetic Janus nanoparticles for enhanced elimination of robust biofilm under magnetic field.  JOURNAL OF MATERIALS SCIENCE,      [PMID:] [10.1007/s10853-025-10983-7]

9. Ruijing Li, Weili Yang, Lijuan Zheng, Xingxue Yan, Cuihua Liu, Yaodong Zhang, Jitong Li.  (2025)  Gastrodin alleviates alcohol-induced developmental and neurotoxic effects in zebrafish larvae by suppressing ferroptosis via regulating the Nrf2/GPX4 signaling pathway.  TOXICOLOGY AND APPLIED PHARMACOLOGY,      [PMID:41371372] [10.1016/j.taap.2025.117684]