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MedKoo Cat#: 596523 | Name: Diphenamid

Description:

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

Diphenamid is a chemical compound from the group of acetamides and a herbicide. The effect is based on inhibition of acetyl-CoA carboxylase. Do not confuse with anti-inflammatory agent difenpiramide.

Chemical Structure

Diphenamid
Diphenamid
CAS#957-51-7

Theoretical Analysis

MedKoo Cat#: 596523

Name: Diphenamid

CAS#: 957-51-7

Chemical Formula: C16H17NO

Exact Mass: 239.1310

Molecular Weight: 239.32

Elemental Analysis: C, 80.30; H, 7.16; N, 5.85; O, 6.69

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Synonym
Diphenamid; Fenam; Caswell No. 395; Enide 50; Enide 50W; Rideon; Trefmid; U 4513;
IUPAC/Chemical Name
N,N-dimethyl-2,2-diphenylacetamide
InChi Key
QAHFOPIILNICLA-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H17NO/c1-17(2)16(18)15(13-9-5-3-6-10-13)14-11-7-4-8-12-14/h3-12,15H,1-2H3
SMILES Code
O=C(N(C)C)C(C1=CC=CC=C1)C2=CC=CC=C2
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:
Diphenamid is an inhibitor of acetyl-CoA carboxylase.
In vitro activity:
TBD
In vivo activity:
The insect repellent DEET and the structurally related herbicide diphenamid both cause ataxia associated with a spongiform myelinopathy largely confined to the rat cerebellar roof nuclei. This local myelinopathy was accompanied by the formation of neuronal cytoplasmic clefts and was produced by a single dose of 1 to 3 g/kg N,N-diethyl-m-toluamide (DEET). These dose levels also produced a severe and often fatal prostration and clear electrophysiological signs of prolonged suppressed seizure activity. Diphenamid produced an identical myelinopathy after doses of 0.8 to 1.5 g/kg but without the severe prostration, suppressed seizures, or neuronal clefts. Reference: Fundam Appl Toxicol. 1992 Jan;18(1):79-88. https://pubmed.ncbi.nlm.nih.gov/1601213/

Preparing Stock Solutions

The following data is based on the product molecular weight 239.32 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.

Recalculate based on batch purity %
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. Verschoyle RD, Brown AW, Nolan C, Ray DE, Lister T. A comparison of the acute toxicity, neuropathology, and electrophysiology of N,N-diethyl-m-toluamide and N,N-dimethyl-2,2-diphenylacetamide in rats. Fundam Appl Toxicol. 1992 Jan;18(1):79-88. doi: 10.1016/0272-0590(92)90198-q. PMID: 1601213.
In vitro protocol:
TBD
In vivo protocol:
1. Verschoyle RD, Brown AW, Nolan C, Ray DE, Lister T. A comparison of the acute toxicity, neuropathology, and electrophysiology of N,N-diethyl-m-toluamide and N,N-dimethyl-2,2-diphenylacetamide in rats. Fundam Appl Toxicol. 1992 Jan;18(1):79-88. doi: 10.1016/0272-0590(92)90198-q. PMID: 1601213.
1: Guo W, Bian Z, Zhang D, Tang G, Liu W, Wang J, Li Z, Yang F. Simultaneous determination of herbicide residues in tobacco using ultraperformance convergence chromatography coupled with solid-phase extraction. J Sep Sci. 2015 Mar;38(5):858-63. doi: 10.1002/jssc.201401063. Epub 2015 Feb 4. PubMed PMID: 25546570. 2: Yang X, Guschina IA, Hurst S, Wood S, Langford M, Hawkes T, Harwood JL. The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber. Pest Manag Sci. 2010 Jul;66(7):794-800. doi: 10.1002/ps.1944. PubMed PMID: 20533380. 3: Liang HC, Li XZ, Yang YH, Sze KH. Comparison of the degradations of diphenamid by homogeneous photolysis and heterogeneous photocatalysis in aqueous solution. Chemosphere. 2010 Jun;80(4):366-74. doi: 10.1016/j.chemosphere.2010.04.054. Epub 2010 May 21. PubMed PMID: 20494398. 4: Mayer-Helm B, Hofbauer L, Müller J. Method development for the determination of selected pesticides on tobacco by high-performance liquid chromatography-electrospray ionisation-tandem mass spectrometry. Talanta. 2008 Feb 15;74(5):1184-90. doi: 10.1016/j.talanta.2007.08.033. Epub 2007 Sep 2. PubMed PMID: 18371768. 5: Czescik A, Malo DL, Duart MJ, Zamora LL, Fos GM, Calatayud JM. Photo-induced chemiluminescence-based determination of diphenamid by using a multicommuted flow system. Talanta. 2007 Oct 15;73(4):718-25. doi: 10.1016/j.talanta.2007.04.044. Epub 2007 May 10. PubMed PMID: 19073093. 6: Liu H, Dang Y, Zhang S, Liu H, Qu L, Liao X, Zhao Y, Wu Y. Determination of diphenamide, napropamide and metolachlor in tobacco by gel permeation chromatographic clean-up and high performance liquid chromatography. Ann Chim. 2005 May;95(5):369-74. PubMed PMID: 16477944. 7: Aharonson N, Katan J. Delayed and enhanced biodegradation of soil-applied diphenamid, carbendazim, and aldicarb. Arch Insect Biochem Physiol. 1993;22(3-4):451-66. PubMed PMID: 8467100. 8: Verschoyle RD, Brown AW, Nolan C, Ray DE, Lister T. A comparison of the acute toxicity, neuropathology, and electrophysiology of N,N-diethyl-m-toluamide and N,N-dimethyl-2,2-diphenylacetamide in rats. Fundam Appl Toxicol. 1992 Jan;18(1):79-88. PubMed PMID: 1601213. 9: Sato F, Takeda S, Yamada Y. A comparison of effects of several herbicides on photoautotrophic, photomixotrophic and heterotrophic cultured tobacco cells and seedlings. Plant Cell Rep. 1987 Dec;6(6):401-4. doi: 10.1007/BF00272768. PubMed PMID: 24248918. 10: Medved' IL. [Data on establishing the maximum permissible concentration of difenamid in the air of a work area]. Gig Sanit. 1983 May;(5):77-8. Russian. PubMed PMID: 6873680. 11: Novakova S, Strateva A. [Toxicologic characteristics of several pesticides and standards for them in water]. Probl Khig. 1983;8:116-20. Russian. PubMed PMID: 6672816. 12: Horowitz M. Herbicidal treatments for control of Papaver somniferum L. Bull Narc. 1980;32(1):33-43. PubMed PMID: 6905769. 13: Horowitz M. Herbicidal treatments for control of Cannabis sativa L. Bull Narc. 1977 Jan-Mar;29(1):75-84. PubMed PMID: 585583. 14: Payne WR Jr, Pope JD Jr, Benner JE. An integrated method for trifluralin, diphenamid, and paraquat in soil and runoff from agricultural land. J Agric Food Chem. 1974 Jan-Feb;22(1):79-82. PubMed PMID: 4811639. 15: Pinthus MJ, Eshel Y, Shchori Y. Field and vegetable crop mutants with increased resistance to herbicides. Science. 1972 Aug 25;177(4050):715-6. PubMed PMID: 17829159. 16: Schultz DP, Tweedy BG. The effect of light and humidity on absorption and degradation of diphenamid in tomatoes. J Agric Food Chem. 1972 Jan-Feb;20(1):10-3. PubMed PMID: 5059929. 17: Rosen JD. The photolysis of diphenamid. Bull Environ Contam Toxicol. 1967 Nov;2(6):349-54. doi: 10.1007/BF01684410. PubMed PMID: 24189959. 18: Heidelberger C, Iype PT. Diphenamid metabolism in plants. Science. 1967 Jan 13;155(3759):210-7. PubMed PMID: 17738227. 19: McMahon RE, Sullivan HR. The metabolism of the herbicide diphenamid in rats. Biochem Pharmacol. 1965 Jul;14(7):1085-92. PubMed PMID: 5854738.