JNJ 1661010 Chemical Properties

Density 

1.340±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO: ≥28mg/mL

form 

solid

pka

13.94±0.70(Predicted)

color 

Off-white

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.

Safety Information

WGK Germany 

1

JNJ 1661010 Usage And Synthesis

Solubility

JNJ 1661010 is soluble to 100 mM in DMSO and to 10 mM in ethanol.

Description

JNJ-1661010 (681136-29-8) is a potent and selective FAAH inhibitor. Initially forms a covalent adduct with FAAH but is slowly released, IC50 = 12 nM. 100-fold selectivity for FAAH-1 over FAAH-2. Cell permeable and active in vivo. JNJ-1661010 displays analgesic activity in various animal models.

Uses

JNJ-1661010, is used to examine the contribution of endocannabinoid signaling in experimental fibrosis. In biological studies, this compound had shown to elevate the levels of arachidonoyl ethanolamide (AEA) in rat brains.

Definition

ChEBI: JNJ-1661010 is a N-arylpiperazine.

Biological Activity

Selective, reversible inhibitor of fatty acid amide hydrolase (FAAH) (IC 50 = 12nM). Brain penetrant and active in vivo .

Synthesis

GENERAL STEPS: A solution of 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (1.00 g, 4.06 mmol) and triethylamine (0.565 mL, 4.06 mmol) in tetrahydrofuran (20 mL) was added to a 25 mL round bottom flask. The reaction mixture was cooled to 0°C in an ice bath, followed by slow dropwise addition of phenyl isocyanate (0.529 mL, 4.87 mmol). After the dropwise addition was completed, the ice bath was removed and the reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, diisopropyl ether (40 mL) was added to the mixture to precipitate the product. The solid was collected by filtration and recrystallized with a mixed solvent of hexane and ethyl acetate (1:1, v/v) to afford N-phenyl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide 1.19 g in 80.4% yield as a white solid. The structure of the product was confirmed by 1H-NMR (CDCl3): δ 3.70 (8H, s), 6.43 (1H, s), 7.06-7.11 (1H, m), 7.29-7.46 (7H, m), 8.17-8.21 (2H, m).

storage

Store at +4°C

References

[1] MARK J KARBARZ. Biochemical and biological properties of 4-(3-phenyl-[1,2,4] thiadiazol-5-yl)-piperazine-1-carboxylic acid phenylamide, a mechanism-based inhibitor of fatty acid amide hydrolase.[J]. Anesthesia and analgesia, 2009, 108 1: 316-329. DOI:10.1213/ane.0b013e31818c7cbd

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