6-Chloro-2-methoxy-9-acridinamine
Basic information
- CAS
3548-09-2- Standard SMILES
COc1ccc2nc3cc(Cl)ccc3c(N)c2c1- InChIKey
IHHSSHCBRVYGJX-UHFFFAOYSA-N- Molecular formula
- C14H11ClN2O
- Average molar mass
- 258.7 g/mol
- Monoisotopic mass
- 258.0559907
Names & identifiers
- Preferred name
- 6-Chloro-2-methoxy-9-acridinamine
- IUPAC
- 6-chloro-2-methoxyacridin-9-amine
- English name
- 9-Amino-6-chloro-2-methoxyacridine
- Molecular formula
- C14H11ClN2O
- Molecular weight
- 258.7
Names & synonyms
9-Amino-6-chloro-2-methoxyacridine3548-09-26-Chloro-2-methoxy-9-acridinamine2-methoxy-6-chloro-9-aminoacridine9-amino-2-methoxy-6-chloroacridine9-amino-3-chloro-7-methoxyacridine9-Acridinamine, 6-chloro-2-methoxy-ACRIDINE, 9-AMINO-3-CHLORO-7-METHOXY-Acridine, 9-amino-6-chloro-2-methoxy-DTXSID90188987NSC-15300R9EB8YPL49
Show more names
6-chloro-2-methoxy-9-acridinamin3-Chloro-7-methoxy-9-aminoacridine2-Methoxy-6-chloroacridine-9-amine5-amino-2-chloro-7-methoxyacridine
G-185RefChem:549166DTXCID50111478636-858-36-chloro-2-methoxyacridin-9-amineACMANSC 15300G 185
Database identifiers
- CAS
3548-09-2- PubChem CID
- 19080
- DTXSID
DTXSID90188987- ChEMBL
CHEMBL76954- UNII
- R9EB8YPL49
- EC Number
- 636-858-3
- Nikkaji
- J55.087F
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 48.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 302
Physicochemical properties
- Melting point
- 250 °C · >250°C
- Boiling point
- 475.1 · 475.1±35.0 °C(Predicted)
- Density
- 1.367 · 1.367±0.06 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- Solubility Insoluble in water; soluble in N, N-dimethylformamide, dimethyl sulfoxide
- form
- Solid
- pka
- 8.6 · 8.6(at 25℃)
- color
- Yellow
- PH Range
- Weak blue B uorescence (7.5) to strong blue B uorescence (9.8)
- Appearance
- Solid Powder
- λmax
- 412 nm · 412nm
- Biological Applications
- Antimalarial; bactericidal; detection of cancer cells,nucleic acids; treating malformed proteins causing neurodegenerative disease
- Major Application
- Sensors, detection method for DNA amplification, inhibition of neurode-generative diseases, RNA hydrolysis, fluorescent probes, primers for nucleic acid sequencing, synthesis of nucleic acids, antimalerial agent
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- 3
- rtecs
- AR7330000
- risk_code
- 36/37/38-40
- Signal word
- Warning
- Symbol(GHS)
- GHS08,GHS07
- hazard_code
- Xn
- safety_code
- 22-26-36
- Hazard statements
- H315-H319-H335-H351
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P-P201-P202-P281-P308+P313-P405-P501
Chemistry & industry
Pharmacology
Metabolism/Metabolites9-Amino-6-chloro-2-methoxyacridine is a known human metabolite of qun.
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.
Agents that are capable of inserting themselves between the successive bases in DNA, thus kinking, uncoiling or otherwise deforming it and therefore preventing its proper functioning. They are used in the study of DNA.
Applications
Description9-Amino-6-chloro-2-methoxyacridine (ACMA) is a cell-permeable fluorescent probe for labeling DNA with selectivity for poly(dA-dT) sequences. ACMA fluorescence is quenched when a pH gradient is established, a property that has been utilized in animal- and plant-based studies. It also inhibits acetylcholinesterase with a Ki value of 49 nM.
Uses9-Amino-6-chloro-2-methoxyacridine is a nucleic acid stain.
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