4-Amino-1,8-naphthalimide
Basic information
- CAS
1742-95-6- Standard SMILES
Nc1ccc2c3c(cccc13)C(=O)NC2=O- InChIKey
SSMIFVHARFVINF-UHFFFAOYSA-N- Molecular formula
- C12H8N2O2
- Average molar mass
- 212.2 g/mol
- Monoisotopic mass
- 212.0585775
Overview
4-amino-1,8-naphthalimide is a dicarboximide and a benzoisoquinoline.
Names & identifiers
- Preferred name
- 4-Amino-1,8-naphthalimide
- IUPAC
- 6-aminobenzo[de]isoquinoline-1,3-dione
- English name
- 4-AMINO-1,8-NAPHTHALIMIDE
- Molecular formula
- C12H8N2O2
- Molecular weight
- 212.2
Names & synonyms
4-Amino-1,8-naphthalimide1742-95-64-Aminonaphthalimide6-AMINO-BENZO[DE]ISOQUINOLINE-1,3-DIONE6-aminobenzo[de]isoquinoline-1,3-dione4-Aminonaphthalene-1,8-dicarboximideDFP 14-amino1,8-naphthalimide6-Amino-1H-benz(de)isoquinoline-1,3(2H)-dioneS529AR2S8BDTXSID6061941CHEBI:40071
Show more names
dfp14-ANITIMTEC-BB SBB0034254-amino-naphthalimid4-Amino-1,8-naphthalimide,98%4-AMINO-1,8-NAPHTHALIMIDE 98%
D-1226-AMINO-BENZO(DE)ISOQUINOLINE-1,3-DIONE6-aminobenzo(de)isoquinoline-1,3-dioneRefChem:517404DTXCID3035559217-110-16-Amino-1H-benzo[de]isoquinoline-1,3(2H)-dione1H-Benz[de]isoquinoline-1,3(2H)-dione, 6-amino-
Database identifiers
- CAS
1742-95-6- PubChem CID
- 1720
- DTXSID
DTXSID6061941- ChEMBL
CHEMBL338790- ChEBI
CHEBI:40071- UNII
- S529AR2S8B
- EC Number
- 217-110-1
- Nikkaji
- J203.150G
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 72.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 342
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 360 °C · 360 °C
- Boiling point
- 352.04 °C · 352.04°C (rough estimate)
- Density
- 1.105 g/mL · 1.105 g/mL at 25 °C(lit.)
- vapor pressure
- 0 Pa · 0Pa at 25℃
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in DMSO
- form
- Orange solid.
- pka
- 9.53 · 9.53±0.20(Predicted)
- color
- Yellow to brown
- Water Solubility
- 354 mg/L · 354mg/L at 25℃
- Cosmetics Ingredients Functions
- HAIR DYEING
- InChI
- 1S/C12H8N2O2/c13-9-5-4-8-10-6(9)2-1-3-7(10)11(15)14-12(8)16/h1-5H,13H2,(H,14,15,16)
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 (47%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 83 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
REACH registered substance: 4-aminonaphthalene-1,8-dicarboximide (EC: 217-110-1)
1H-Benzdeisoquinoline-1,3(2H)-dione, 6-amino-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesSkin Irrit. 2 (47%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- DE4081000
- hs_code
- 29251995
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-37/39
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationChemicals and drugs that inhibit the action of POLY(ADP-RIBOSE)POLYMERASES.
Uses & manufacturing
General Manufacturing Information1H-Benz[de]isoquinoline-1,3(2H)-dione, 6-amino-: ACTIVE
Applications
DescriptionThe poly(ADP-ribose) polymerases (PARPs) form a family of enzymes with roles in DNA repair and apoptosis, particularly in response to reactive oxygen and nitrogen species. 4-amino-1,8-Naphthalimide (4-ANI) is an inhibitor of PARP (IC50 = 180 nM). It blocks radiation-induced PARP in cancer cells, potentiating the cytotoxicity of γ-radiation, although it is not cytotoxic in the absence of radiation. 4-ANI is used to study the role of PARP activity in various cell systems.
UsesThe poly(ADP-ribose) polymerases (PARPs) form a family of enzymes with roles in DNA repair and apoptosis, particularly in response to reactive oxygen and nitrogen species. 4-amino-1,8-Naphthalimide (4-ANI) is an inhibitor of PARP (IC50 = 180 nM). It blocks radiation-induced PARP in cancer cells, potentiating the cytotoxicity of γ-radiation, although it is not cytotoxic in the absence of radiation. 4-ANI is used to study the role of PARP activity in various cell systems.
Upstream & downstream products
Upstream raw materials
Suppliers
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Related reactions
3 records
Compound notes
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