Naptalam | CAS# 132-66-1

MedKoo Cat#: 571590 | Name: Naptalam

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Naptalam is an herbicide.

Chemical Structure

Naptalam

CAS#132-66-1

Theoretical Analysis

MedKoo Cat#: 571590

Name: Naptalam

CAS#: 132-66-1

Chemical Formula: C18H13NO3

Exact Mass: 291.0895

Molecular Weight: 291.31

Elemental Analysis: C, 74.22; H, 4.50; N, 4.81; O, 16.48

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100mg	USD 230.00

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Related CAS #

No Data

Synonym

NSC 204421; NSC204421; NSC-204421

IUPAC/Chemical Name

Benzoic acid, 2-((1-naphthalenylamino)carbonyl)- (9CI)

InChi Key

JXTHEWSKYLZVJC-UHFFFAOYSA-N

InChi Code

InChI=1S/C18H13NO3/c20-17(14-9-3-4-10-15(14)18(21)22)19-16-11-5-7-12-6-1-2-8-13(12)16/h1-11H,(H,19,20)(H,21,22)

SMILES Code

O=C(O)C1=CC=CC=C1C(NC2=C3C=CC=CC3=CC=C2)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

N-1-Naphthylphthalamic acid is a polar auxin transport inhibitor.

In vitro activity:

Here this study presents cryo-electron microscopy structures of PIN3 from Arabidopsis thaliana in the apo state and in complex with its substrate indole-3-acetic acid and the inhibitor N-1-naphthylphthalamic acid (NPA). The structural and functional analyses, along with computational studies, reveal the structural basis for the recognition of indole-3-acetic acid and NPA and elucidate the molecular mechanism of NPA inhibition on PIN-mediated auxin transport. Reference: Nature. 2022 Sep;609(7927):616-621. https://pubmed.ncbi.nlm.nih.gov/35917926/

In vivo activity:

This study tested the hypothesis that the NPA-binding protein (NBP) is associated with the actin cytoskeleton in vitro and that an intact actin cytoskeleton is required for polar auxin transport in vivo. Phalloidin increased both filamentous actin (F-actin) and NPA-binding activity, while cytochalasin D and Tris decreased both F-actin and NPA-binding activity in cytoskeletal pellets. The microtubule stabilizing drug taxol increased pelletable tubulin, but did not alter either the amount of pelletable actin or NPA-binding activity. Treatment of etiolated zucchini hypocotyls with cytochalasin D decreased the amount of auxin transport and its regulation by NPA. Reference: Plant J. 1998 Feb;13(3):291-301. https://pubmed.ncbi.nlm.nih.gov/11536873/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	85.82
	DMF:PBS (pH 7.2) (1:3)	0.3	0.86
	DMSO	24.2	82.95

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 291.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Su N, Zhu A, Tao X, Ding ZJ, Chang S, Ye F, Zhang Y, Zhao C, Chen Q, Wang J, Zhou CY, Guo Y, Jiao S, Zhang S, Wen H, Ma L, Ye S, Zheng SJ, Yang F, Wu S, Guo J. Structures and mechanisms of the Arabidopsis auxin transporter PIN3. Nature. 2022 Sep;609(7927):616-621. doi: 10.1038/s41586-022-05142-w. Epub 2022 Aug 2. Erratum in: Nature. 2022 Oct;610(7930):E2. PMID: 35917926. 2. Marasek-Ciolakowska A, Dziurka M, Kowalska U, Góraj-Koniarska J, Saniewski M, Ueda J, Miyamoto K. Mode of Action of 1-Naphthylphthalamic Acid in Conspicuous Local Stem Swelling of Succulent Plant, Bryophyllum calycinum: Relevance to the Aspects of Its Histological Observation and Comprehensive Analyses of Plant Hormones. Int J Mol Sci. 2021 Mar 18;22(6):3118. doi: 10.3390/ijms22063118. PMID: 33803750; PMCID: PMC8003132. 3. Butler JH, Hu S, Brady SR, Dixon MW, Muday GK. In vitro and in vivo evidence for actin association of the naphthylphthalamic acid-binding protein from zucchini hypocotyls. Plant J. 1998 Feb;13(3):291-301. doi: 10.1046/j.1365-313x.1998.00017.x. PMID: 11536873.

In vitro protocol:

In vivo protocol:

1. Butler JH, Hu S, Brady SR, Dixon MW, Muday GK. In vitro and in vivo evidence for actin association of the naphthylphthalamic acid-binding protein from zucchini hypocotyls. Plant J. 1998 Feb;13(3):291-301. doi: 10.1046/j.1365-313x.1998.00017.x. PMID: 11536873.

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