874902-19-9

Basic information

• Product Name: 5-[[(1,1'-BIPHENYL)-4-YL]METHYL]-N,N-DIMETHYL-1H-TETRAZOLE-1-CARBOXAMIDE
• Synonyms: LY 2183240;5-[[(1,1'-BIPHENYL)-4-YL]METHYL]-N,N-DIMETHYL-1H-TETRAZOLE-1-CARBOXAMIDE;5-(biphenyl-4-ylMethyl)-N,N-diMethyl-1H-tetrazole-1-carboxaMide;LY-2183240 MN-25;1H-Tetrazole-1-carboxamide, 5-([1,1′-biphenyl]-4-ylmethyl)-N,N-dimethyl-;5-Biphenyl-4-ylmethyl-tetrazole-1-carboxylic acid dimethylamide;N,N-dimethyl-5-[(4-phenylphenyl)methyl]tetrazole-1-carboxamide;LY2183240/LY-2183240
• CAS NO: 874902-19-9
• Molecular Formula: C17H17N5O
• Molecular Weight: 307.34978
• Mol File: 874902-19-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 87-88℃
• Boiling Point: 506.103 °C at 760 mmHg
• Flash Point: 259.882 °C
• Appearance: /
• Density: 1.21
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.64
• Storage Temp.: Store at +4°C
• Solubility: Soluble in DMSO (greater than 25 mg/ml) or in Ethanol (up to 15 mg/ml).
• PKA: 0.01±0.10(Predicted)
• Stability: Stable for 1 year as supplied. Solutions in DMSO of ethanol may be stored at -20°C for up to 1 month
• CAS DataBase Reference: 5-[[(1,1'-BIPHENYL)-4-YL]METHYL]-N,N-DIMETHYL-1H-TETRAZOLE-1-CARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[[(1,1'-BIPHENYL)-4-YL]METHYL]-N,N-DIMETHYL-1H-TETRAZOLE-1-CARBOXAMIDE(874902-19-9)
• EPA Substance Registry System: 5-[[(1,1'-BIPHENYL)-4-YL]METHYL]-N,N-DIMETHYL-1H-TETRAZOLE-1-CARBOXAMIDE(874902-19-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 874902-19-9(Hazardous Substances Data)

Usage

Description

LY-2183240 (874902-19-9) is highly potent inhibitor of cellular anandamide uptake (IC50 = 0.27nM1, 15nM2). LY-2183240 has also been found2-4 to be an inhibitor of fatty acid amide hydrolase (FAAH) – IC50 = 14nM4, diacylglycerol lipase (DAGL) and monoacylglycerol lipase (MAGL) – IC50 = 5.3 nM3.

Uses

LY2183240 is a potent inhibitor of FAAH activity, and the uptake and enzymatic hydrolysis of anandamide. Synthetic Cannabinoids

Biological Activity

Novel and highly potent blocker of anandamide uptake (IC 50 = 270 pM). Inhibits fatty acid amide hydrolase (FAAH) activity (IC 50 = 12.4 nM). Following i.p. administration in rats, increases brain anandamide concentration and exerts antinociceptive effects in formalin model of pain.

References

1) Moore et al., (2005), Identification of a high-affinity binding site involved in the transport of endocannabinoids; Proc. Natl. Acad. Sci. USA, 102 17852 2) Ortar et al. (2008), Carbamoyl tetrazoles as inhibitors of endocannabinoid inactivation: A critical revision; Eur. .J. Med. Chem., 43 62 3) Alexander and Cravatt (2006), The putative endocannabinoid transport blocker LY2183240 is a potent inhibitor of FAAH and several other brain serine hydrolases; J. Am. Chem. Soc., 128 9699 4) Dickason-Chesterfield et al. (2006), Pharmacological Characterization of Endocannabinoid Transport and Fatty Acid Amide Hydrolase Inhibitors; Cell. Mol. Neurobiol., 26 405

InChI:InChI=1/C17H17N5O/c1-21(2)17(23)22-16(18-19-20-22)12-13-8-10-15(11-9-13)14-6-4-3-5-7-14/h3-11H,12H2,1-2H3

Upstream product

• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 31603-77-7 4-biphenylacetonitrile 

Relevant articles and documents

The putative endocannabinoid transport blocker LY2183240 is a potent inhibitor of FAAH and several other brain serine hydrolases

How lipid transmitters move within and between cells to communicate signals remains an important and largely unanswered question. Integral membrane transporters, soluble lipid-binding proteins, and metabolic enzymes have all been proposed to collaborative

INHIBITORS OF FATTY ACID AMIDE HYDROLASE AND MONOACYLGLYCEROL LIPASE FOR MODULATION OF CANNABINOID RECEPTORS

Disclosed are compounds and compositions that inhibit the action of fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MGL), methods of inhibiting FAAH and MGL, methods of modulating cannabinoid receptors, and methods of treating various disorders related to modulation of cannabinoid receptors.