1-Naphthaleneacetamide

For research use only. Not for therapeutic Use.

  • CAT Number: R068993
  • CAS Number: 86-86-2
  • Molecular Formula: C12H11NO
  • Molecular Weight: 185.226
  • Purity: ≥95%
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1-naphthaleneacetamide(CAS: 86-86-2) is a member of the class of naphthalenes that is naphthalene which is substituted by a 2-amino-2-oxoethyl group at position 1. It is a synthetic auxin that is widely used in agriculture to promote the growth of numerous fruits, for root cuttings and as a fruit thinning agent. It has a role as a synthetic auxin. It is a member of naphthalenes and a primary carboxamide.


Catalog Number R068993
CAS Number 86-86-2
Synonyms

NAD(TM), Rootene; 2-(1-Naphthyl)acetamide.

Molecular Formula C12H11NO
Purity ≥95%
Storage RT
IUPAC Name 2-naphthalen-1-ylacetamide
InChI InChI=1S/C12H11NO/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H2,13,14)
InChIKey XFNJVKMNNVCYEK-UHFFFAOYSA-N
SMILES C1=CC=C2C(=C1)C=CC=C2CC(=O)N
Reference

[1]. J Agric Food Chem. 1974 Jul-Aug;22(4):568-70. doi: 10.1021/jf60194a050.<br />
A fluorometric method for the determination of residues of 1-naphthaleneacetamide and 1-naphthaleneacetic acid on apples.<br />
Sigrist R, Temperli A, Hurter J.<br />
DOI: 10.1021/jf60194a050 PMID: 4840905 [Indexed for MEDLINE]<br />
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[2]. Anal Chim Acta. 2011 Aug 5;699(1):81-6. doi: 10.1016/j.aca.2011.05.012. Epub 2011 May 14.<br />
Quantitative analysis of multiple urinary biomarkers of carcinoid tumors through gold-nanoparticle-assisted laser desorption/ionization time-of-flight mass spectrometry.<br />
Kuo TR(1), Chen JS, Chiu YC, Tsai CY, Hu CC, Chen CC.<br />
Author information: (1)Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan.<br />
A simple technique for quantitative analysis of four urinary biomarkers, tryptophan (TRP), 5-hydroxytryptophan (5-HTP), 5-hydroxytryptamine (5-HT) and 5-hydroxyindole acetic acid (5-HIAA) of carcinoid tumors is developed using gold nanoparticles as the assisted matrix in surface-assisted laser desorption/ionization time-of-flight mass spectrometry (SALDI-TOF MS). The optimal SALDI conditions for the efficient ionization of those biomarkers are systematically explored by the adjustments of the concentrations of gold nanoparticles and internal standards. The mass spectra with strong signals and minimal background noise are obtained using 1-naphthaleneacetamide (NAD) as the internal standard. The calibration curves of the biomarker concentrations are determined using SALDI-TOF MS and the high linearity is obtained in all samples. For future clinical testing, multiplexed detection of those biomarkers in the urine samples of healthy males is performed. The successful quantitative detections of TRP, 5-HTP, 5-HT and 5-HIAA indicate that our technique provided great potentials to be developed a simple and rapid platform for the tumor biomarker detections.<br />
DOI: 10.1016/j.aca.2011.05.012 PMID: 21704761 [Indexed for MEDLINE]<br />
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[3]. J AOAC Int. 2008 Nov-Dec;91(6):1245-56.<br />
Determination of plant hormones in fertilizers by high-performance liquid chromatography with photodiode array detection: method development and single-laboratory validation.<br />
Gambino GL(1), Pagano P, Scordino M, Sabatino L, Scollo E, Traulo P, Gagliano G.<br />
Author information: (1)Ministero delle Politiche Agricole Alimentari e Forestali, Ispettorato Centrale per il Controllo della Qualit&agrave; dei Prodotti Agroalimentari, Laboratorio di Catania, Via Varese 45, 95123 Catania, Italy. [email protected]<br />
A simple and reliable high-performance liquid chromatographic method that uses photodiode array detection was developed for the simultaneous determination of 12 native and synthetic plant hormones, i.e., plant growth regulators (PGRs), in fertilizers, such as 1-naphthol, 2,4-dichlorophenoxyacetic acid, 4-(2,4-dichlorophenoxy)butyric acid, 4-chlorophenoxyacetic acid, indole-3-acetic acid, 4-(3-indolyl)butyric acid, dichlorprop, (4-chloro-2-methylphenoxy)acetic acid, alpha-naphthaleneacetic acid, 1-naphthaleneacetamide, beta-naphthoxyacetic acid, and thidiazuron. The method was experimentally validated for routine regulatory application, and the following analytical parameters were assessed for all PGRs studied: linearity; specificity; precision (relative standard deviation) and accuracy, both measured at 3 concentration levels (0.1, 0.05, and 0.01%, w/w); ruggedness; limit of detection; and limit of quantification. Results were satisfactory for all method validation parameters tested and for all PGRs studied, demonstrating the suitability of the method for the determination of PGRs in fertilizers. The uncertainty of measurement was also estimated at 3 concentration levels for all PGRs by using the approach of the International Organization for Standardization, described in its Guide to the Expression of Uncertainty in Measurement. The method was applied to 20 samples of liquid fertilizer with declared biostimulant properties.<br />
PMID: 19202783 [Indexed for MEDLINE]<br />
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[4]. J Neurosci. 2015 Apr 1;35(13):5409-21. doi: 10.1523/JNEUROSCI.4376-14.2015.<br />
GluA2 trafficking is involved in apoptosis of retinal ganglion cells induced by activation of EphB/EphrinB reverse signaling in a rat chronic ocular hypertension model.<br />
Dong LD(1), Gao F(2), Wang XH(1), Miao Y(1), Wang SY(1), Wu Y(1), Li F(1), Wu J(2), Cheng XL(3), Sun XH(2), Yang XL(1), Wang Z(4).<br />
Author information: (1)Institutes of Brain Science, Institute of Neurobiology, State Key Laboratory of Medical Neurobiology, Collaborative Innovation Center for Brain Science, Fudan University, Shanghai 200032, People&#39;s Republic of China, and. (2)Institutes of Brain Science, Eye &amp; ENT Hospital, State Key Laboratory of Medical Neurobiology, Shanghai Key Laboratory of Visual Impairment and Restoration, and Collaborative Innovation Center for Brain Science, Fudan University, Shanghai 200032, People&#39;s Republic of China, and. (3)First Affiliated Hospital of Yangtze University, Jingzhou 434000, People&#39;s Republic of China. (4)Institutes of Brain Science, Eye &amp; ENT Hospital, Institute of Neurobiology, State Key Laboratory of Medical Neurobiology, Shanghai Key Laboratory of Visual Impairment and Restoration, and Collaborative Innovation Center for Brain Science, Fudan University, Shanghai 200032, People&#39;s Republic of China, and [email protected].<br />
EphB1, expressed in M&uuml;ller cells, and ephrinB2, expressed in both M&uuml;ller cells and retinal ganglion cells (RGCs), constitute an EphB/ephrinB reverse signaling in RGCs. Whether and how this reverse signaling is involved in RGC apoptosis in a rat chronic ocular hypertension (COH) model was investigated. In the COH model, both EphB1 and ephrinB2 were significantly increased and the reverse signaling was activated, which was accompanied by increased protein levels of phosphorylated (p) src, GluA2, and p-GluA2. Intravitreal injection of EphB2-Fc, an activator of ephrinB2, induced an increase in TUNEL-positive signals in normal retinae. A coimmunoprecipitation assay demonstrated direct interactions among ephrinB2, p-src, and GluA2. Moreover, in COH rats the expression of GluA2 proteins on the surface of retinal cells was decreased. Such GluA2 endocytosis could be prevented by preoperational intravitreal injection of 4-amino-3-(4-chlorophenyl)-1-(t-butyl)-1H-pyrazolo [3,4-d] pyrimidine (PP2), an inhibitor of src family tyrosine kinases, and possibly involved the protein interacting with C kinase 1 and phosphorylation of GluA2. In normal rats, intravitreal injection of EphB2-Fc caused changes in these protein levels similar to those observed in COH rats, which all could be avoided by preinjection of PP2. Patch-clamp experiments further showed that the current-voltage relationship of AMPA receptor-mediated EPSCs of RGCs exhibited stronger inward rectification in EphB2-Fc-injected rats. Furthermore, preinjection of PP2 or N-[3-[[4-[(3-aminopropyl)amino]butyl]amino]propyl]-1-naphthaleneacetamide trihydrochloride) (Naspm), a Ca(2+)-permeable GluA2-lacking AMPA receptor inhibitor, remarkably inhibited RGC apoptosis in either EphB2-Fc-injected or COH rats. Together, elevated GluA2 trafficking induced by activated EphB2/ephrinB2 reverse signaling likely contributes to RGC apoptosis in COH rats.<br />
DOI: 10.1523/JNEUROSCI.4376-14.2015 PMCID: PMC6705403 PMID: 25834064 [Indexed for MEDLINE]

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