1,5-NAPHTHYLENEDIAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H10N2
Molecular Weight	158.1998
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=CC=CC2=C(N)C=CC=C12

InChI

InChIKey=KQSABULTKYLFEV-UHFFFAOYSA-N

InChI=1S/C10H10N2/c11-9-5-1-3-7-8(9)4-2-6-10(7)12/h1-6H,11-12H2

HIDE SMILES / InChI

Molecular Formula	C10H10N2
Molecular Weight	158.1998
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25044901 | https://www.ncbi.nlm.nih.gov/pubmed/7049899 | http://onlinelibrary.wiley.com/doi/10.1002/3527600418.mb224362e3813/pdf

1,5-Naphthalenediamine is an organic amine which is used as an intermediate for the manufacture of 1,5-naphthalene diisocyanate and organic dyes. According to IARC monograph on the evaluation of the carcinogenic risk, there is a limited evidence for the carcinogenicity of 1,5-naphthalenediamine in experimental animals. 1,5-Naphthalenediamine is used for matrix-assisted laser desorption ionization-mass spectrometry of phospholipids.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Aryl hydrocarbon receptor 26 Target ID: CHEMBL5400 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9129166	Binding Agent 1064		4.0 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Comparison of biosensors based on entrapment of cholesterol oxidase and cholesterol esterase in electropolymerized films of polypyrrole and diaminonaphthalene derivatives for amperometric determination of cholesterol.	2003 Sep	12923606
Reductive electron injection into duplex DNA by aromatic amines.	2004 Dec 1	15563184
Synthesis and structure of the calixarene-like phosph(III)azane macrocycle [{P(mu-N(t)Bu)}2{1,5-(NH)2C10H6}]3.	2005 Aug 7	16027927
The formation of cucurbit[n]uril (n = 6, 7) complexes with amino compounds in aqueous formic acid studied by capillary electrophoresis.	2005 Jun	15880553
[Spectral analysis and photoluminescence properties of 1,5-naphthalene diamine derivative].	2006 Feb	16826895
Rapid sequencing and disulfide mapping of peptides containing disulfide bonds by using 1,5-diaminonaphthalene as a reductive matrix.	2006 Feb	16382486
Biological monitoring of exposure to 1,5-naphthalene diisocyanate and 4,4'-methylenediphenyl diisocyanate.	2006 Sep	16506043
New method for characterizing highly disulfide-bridged peptides in complex mixtures: application to toxin identification from crude venoms.	2007 Aug	17580849
A comparison of transcriptomic and metabonomic technologies for identifying biomarkers predictive of two-year rodent cancer bioassays.	2007 Mar	17114358
Application of genomic biomarkers to predict increased lung tumor incidence in 2-year rodent cancer bioassays.	2007 May	17311802
Rational selection of the optimum MALDI matrix for top-down proteomics by in-source decay.	2007 Nov 15	17939742
Screening of pi-basic naphthalene and anthracene amplifiers for pi-acidic synthetic pore sensors.	2008 Apr 2	18327940
Determination with matrix-assisted laser desorption/ionization tandem time-of-flight mass spectrometry of the extensive disulfide bonding in tarantula venom peptide Psalmopeotoxin I.	2009	19661560
Glycan tagging to produce bioactive ligands for a surface plasmon resonance study via immobilization on different surfaces.	2009 Apr	19267474
Use of short-term transcriptional profiles to assess the long-term cancer-related safety of environmental and industrial chemicals.	2009 Dec	19776212
5-Amino-1-naphthol: two-dimensional sheets built up from R(4)(4)(18) rings formed by O-H...N, N-H...O and pi-pi interactions.	2009 Nov	19893237
Phenazine-naphthalene-1,5-diamine-water (1/1/2).	2009 Nov 21	21578891
Mass spectrometric characterization and physiological actions of novel crustacean C-type allatostatins.	2009 Sep	19505516
Selective determination of dopamine with a cibacron blue/poly-1,5-diaminonaphthalene composite film.	2009 Sep 21	19720200
Selective reduction of C=C double bonds in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of microcystins.	2010	20065523
Preparation of poly(1,5 diamino naphthalene) nanobelts/nanodiscs through a "hard-soft combined templates" approach.	2010 Aug	21125886
Validation of a liquid chromatography-mass spectrometry method for determining the migration of primary aromatic amines from cooking utensils and its application to actual samples.	2010 Jan	19750402
In-source decay and fragmentation characteristics of peptides using 5-aminosalicylic acid as a matrix in matrix-assisted laser desorption/ionization mass spectrometry.	2010 Jun	20346696
Modulating the ground- and excited-state oxidation potentials of diaminonaphthalene by sequential N-methylation.	2010 Jun 7	20376874
MALDI-in source decay applied to mass spectrometry imaging: a new tool for protein identification.	2010 May 15	20397712
New advances in the understanding of the in-source decay fragmentation of peptides in MALDI-TOF-MS.	2010 Nov	20832332

Patents

Sample Use Guides

In Vivo Use Guide

In carcinogenicity and toxicology studies, 1,5-naphthalenediamine was administered to animals orally. Deaths occurred in the rats after doses of 200 mg/kg.

Route of Administration: Oral

In Vitro Use Guide

Displacement of [3H]TCDD from the rat hepatic cytosolic Ah receptor was determined using the hydroxylapatite method employing nine concentration of 1,5-Naphthalenediamine

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:40:02 GMT 2023` Edited by `admin` on `Fri Dec 15 16:40:02 GMT 2023`
Record UNII	13PD3J52LK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1,5-NAPHTHYLENEDIAMINE

Common Name

English

1,5-NAPHTHALENEDIAMINE [IARC]

Common Name

English

1,5-NAPHTHALENEDIAMINE [HSDB]

Common Name

English

NSC-401110

Code

English

1,5-DIAMINONAPHTHALENE

Systematic Name

English

1,5-NAPHTHALENEDIAMINE

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

218-817-8