N piperidin 1 yl 5 4 iodophenyl 1 2 4 dichlorophenyl 4 methyl 1h pyrazole 3 carboxamide am251

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N-(Piperidin-1-yl) -5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (AM251) is a synthetic organic compound. It functions as an antagonist for the cannabinoid receptor type 1 (CB1).

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AM251 (139 citations)

6 protocols using n piperidin 1 yl 5 4 iodophenyl 1 2 4 dichlorophenyl 4 methyl 1h pyrazole 3 carboxamide am251

Pharmacological Modulation of Synaptic Signaling

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Unless specified otherwise, all drugs were prepared as concentrated stock solutions and stored at −20 or −80°C before use. Picrotoxin, guanosine 5′-[β-thio] diphosphate trilithium salt (GDP-βS), guanosine 5’-[γ-thio]triphosphate tetralithium salt (GTP-γS), and 6-Cyano-7- nitroquinoxaline-2,3-dione disodium salt hydrate (CNQX) were purchased from Sigma-Aldrich. JZL184 was synthesized at Scripps Research Institute (Long et al., 2009 (link)). N-(Piperidin-1-yl) -5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (AM251), 7-(hydroxyimino)cyclopropa[b]chromen-1a-carboxylate ethyl ester (CPCCOEt), and DL-threo-β-benzyloxyaspartic acid (TBOA) were purchased from Tocris Bioscience. BAPTA-tetrapotassium was purchased from Life Technologies.

Chen Y., Liu X., Vickstrom C.R., Liu M.J., Zhao L., Viader A., Cravatt B.F, & Liu Q.S. (2016). Neuronal and Astrocytic Monoacylglycerol Lipase Limit the Spread of Endocannabinoid Signaling in the Cerebellum. eNeuro, 3(3), ENEURO.0048-16.2016.

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Pharmacological Modulators of Vascular Signaling

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Chemicals and salts were obtained from Fisher Scientific (Pittsburgh, PA, USA). N-(Piperidin-1-yl)-5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (AM 251), Picrotoxin purchased from Tocris Biosciences (Minneapolis, MN, USA), S-Nitroso-N-acetyl-DL-penicillamine (SNAP), Nω-Nitro-L-arginine methyl ester hydrochloride (L-NAME), 2-(4-Carboxyphenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide (carboxy-PTIO) and 8-(4-Chloorophenylthio)-guanosine 3’, 5’-cyclic monophosphate (8 pCPT-cGMP) were purchased from Sigma-Aldrich (Saint Louis, MO, USA).

Oubraim S., Wang R., Hausknecht K., Kaczocha M., Shen R.Y, & Haj-Dahmane S. (2022). Prenatal ethanol exposure causes anxiety-like phenotype and alters synaptic nitric oxide and endocannabinoid signaling in dorsal raphe nucleus of adult male rats. Translational Psychiatry, 12, 440.

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Neurochemical Modulators for Receptor Study

Cited 1 time

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Unless specified otherwise, all drugs were prepared as concentrated stock solutions and stored at −20 °C before use. Picrotoxin and 6-Cyano-7-nitroquinoxaline-2,3-dione disodium salt hydrate (CNQX) were purchased from Sigma-Aldrich, Inc. (RS)-3-(2-Carboxypiperazin-4-yl) -propyl-1-phosphonic acid ((RS)-CPP), (R)-(+)-[2,3-Dihydro-5-methyl-3-(4-morpholinylmethyl) pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphthalenylmethanone mesylate (WIN55,212-2 mesylate) and N-(Piperidin-1-yl)-5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole -3-carboxamide (AM251) were purchased from Tocris Bioscience. MAGL inhibitor JZL18451 (link) and DAGL inhibitors DO3433 (link) was synthesized in the laboratory of Benjamin Cravatt at the Scripps Research Institute, USA.

Liu X., Chen Y., Vickstrom C.R., Li Y., Viader A., Cravatt B.F, & Liu Q.S. (2016). Coordinated regulation of endocannabinoid-mediated retrograde synaptic suppression in the cerebellum by neuronal and astrocytic monoacylglycerol lipase. Scientific Reports, 6, 35829.

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Pharmacological Modulation of Synaptic Plasticity

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DL-2-amino-5-phosphono-pentanoic acid (D-AP5, 50 μM; Tocris, Ellisville, MO, USA) and 2-Methyl-6-(phenylethynyl) pyridine hydrochloride (MPEP hydrochloride, 10 μM; Tocris) were dissolved directly in the extracellular solution and bath applied. N-(piperidin-1-yl)-5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (AM251, 3 μM; Tocris), picrotoxin (50 μM; Sigma), 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 2-methyloxyethyl 1-methylethyl ester (nimodipine, 1 μM; Tocris) and (2E)-N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-3-[4-(1,1-dimethylethyl)phenyl]-2-propenamide (AMG9810, 1 μM; Tocris) were dissolved in ethanol and then added in the external solution at a final concentration of ethanol of 0.01%–0.1%. N-[2-(4-Chlorophenyl)ethyl]-1,3,4,5-tetrahydro-7,8-dihydroxy-2H-2-benzazepine-2-carbothioamide (capsazepine, 10 μM; Tocris) and (E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methyl-6-nonenamide (capsaicin, 10 μM; Tocris) were dissolved in DMSO and then added in the external solution at a final concentration of DMSO of 0.001 and 0.0025, respectively. Tetrahydrolipstatin (THL, 10 μM; Sigma) was dissolved in DMSO (0.08%) and applied internally via the patch-clamp pipette. DMSO (0.08%), the vehicle used to dilute i-THL, did not preclude the tLTP induced with 10 post-pre pairings (Cui et al., 2015 (link)).

Cui Y., Perez S, & Venance L. (2018). Endocannabinoid-LTP Mediated by CB1 and TRPV1 Receptors Encodes for Limited Occurrences of Coincident Activity in Neocortex. Frontiers in Cellular Neuroscience, 12, 182.

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Investigating Cannabinoid Modulation in Colitis

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All drugs and reagents, unless otherwise stated, were purchased from Sigma-Aldrich (Poznan, Poland). DSS (MW 40,000) was purchased from MP Biomedicals (Solon, OH, USA). N-3-Pyridinyl-4-[[3-[[5-(trifluoromethyl)-2-pyridinyl]oxy]phenyl]methyl]-1-piperidine-carboxamide (PF-3845) was prepared by TriMen Chemicals (Lodz, Poland). N-(Piperidin-1-yl)-5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (AM251), and 6-Iodo-2-methyl-1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl](4-methoxyphenyl) methanone (AM630) were purchased from Tocris Bioscience (Bristol, UK).

Sałaga M., Mokrowiecka A., Zakrzewski P.K., Cygankiewicz A., Leishman E., Sobczak M., Zatorski H., Małecka-Panas E., Kordek R., Storr M., Krajewska W.M., Bradshaw H.B, & Fichna J. (2014). Experimental colitis in mice is attenuated by changes in the levels of endocannabinoid metabolites induced by selective inhibition of fatty acid amide hydrolase (FAAH). Journal of Crohn's & colitis, 8(9), 998-1009.

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Synaptic Transmission Pharmacological Modulation

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S-3,5-Dihydroxyphenylglycine, 2-methyl-6-(phenylethynyl) pyridine hydrochloride (MPEP), (S)-(+)-α-Amino-4-carboxy-2-methylbenzeneacetic acid (LY367385), anisomycin and N-(Piperidin-1-yl)-5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (AM-251) were purchased from Tocris Bioscience. DHPG and MPEP were prepared in ddH₂O. LY367385 was prepared in 1.1eq NaOH solution. AM-251 and anisomycin were prepared in Dimethyl sulfoxide (DMSO). All these drugs have been shown to not have any effect on basal synaptic transmission (30 (link), 74–76 (link)).

Wu P.Y., Ji L., De Sanctis C., Francesconi A., Inglebert Y, & McKinney R.A. (2024). Loss of synaptopodin impairs mGluR5 and protein synthesis–dependent mGluR-LTD at CA3-CA1 synapses. PNAS Nexus, 3(2), pgae062.

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