AM 251

Cat. No. 1117

AM 251 C22H21Cl2IN4O [183232-66-8]

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Chemical Name: N-(Piperidin-1-yl)-5-(4-iodophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide

Biological Activity

Potent CB1 receptor antagonist (IC50 = 8 nM, Ki = 7.49 nM) that displays 306-fold selectivity over CB2 receptors. Also potent GPR55 agonist (EC50 = 39 nM). Also available in a fluorescent form (Cat. No. 2540).

Technical Data

M.Wt:
555.24
Formula:
C22H21Cl2IN4O
Solubility:
Soluble to 25 mM in ethanol and to 100 mM in DMSO
Purity:
>99 %
Storage:
Store at RT
CAS No:
183232-66-8

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
All Tocris products are intended for laboratory research use only.

Certificate of Analysis / Safety Data Sheet

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Safety Data Sheet: View Safety Data Sheet

Ryberg et al (2007) The orphan receptor GPR55 is a novel cannabinoid receptor. Br.J.Pharmacol. 152 1092. PMID: 17876302.

Pertwee (2005) Inverse agonism and neutral antagonism at cannabinoid CB1 receptors. Life Sci. 76 1307. PMID: 15670612.

Lan et al (1999) Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists. J.Med.Chem. 42 769. PMID: 10052983.

Gatley et al (1997) Binding of the non-classical cannabinoid CP 55,940, and the diarylpyrazole AM251 to rodent brain cannabinoid receptors. Life Sci. 61 191. PMID: 9335234.

Gatley et al (1996) 125I-labeled AM 251: a radioiodinated ligand which binds in vivo to mouse brain cannabinoid CB1 receptors. Eur.J.Pharmacol. 307 331. PMID: 8836622.

If you know of a relevant reference for this product please let us know.

Citations are publications that use Tocris products. Selected citations for AM 251 include:

Malek et al (2015) Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures. Neural Plast 2015 130639. PMID: 26090232.

Zhang et al (2015) Anoctamin Calcium-Activated Chloride Channels May Modulate Inhibitory Transmission in the Cerebellar Cortex. PLoS One 10 e0142160. PMID: 26558388.

Abush and Akirav (2013) Cannabinoids ameliorate impairments induced by chronic stress to synaptic plasticity and short-term memory. Neuropsychopharmacology 38 1521. PMID: 23426383.

Benz et al (2013) Expression and functional relevance of cannabinoid receptor 1 in Hodgkin lymphoma. PLoS One 8 e81675. PMID: 24349109.

Cao et al (2013) Cannabinoid HU210 protects isolated rat stomach against impairment caused by serum of rats with experimental acute pancreatitis. PLoS One 7 e52921. PMID: 23285225.

Chanda et al (2013) Hepatic cannabinoid receptor type 1 mediates alcohol-induced regulation of bile acid enzyme genes expression via CREBH. PLoS One 8 e68845. PMID: 23894352.

Malenczyk et al (2013) CB1 cannabinoid receptors couple to focal adhesion kinase to control insulin release. J Biol Chem 288 32685. PMID: 24089517.

Sreevalsan and Safe (2013) The cannabinoid WIN 55,212-2 decreases specificity protein transcription factors and the oncogenic cap protein eIF4E in colon cancer cells. Mol Cancer Ther 12 2483. PMID: 24030632.

Wargent et al (2013) The cannabinoid δ(9)-tetrahydrocannabivarin (THCV) ameliorates insulin sensitivity in two mouse models of obesity. Nutr Diabetes 3 e68. PMID: 23712280.

Brents et al (2012) Monohydroxylated metabolites of the K2 synthetic cannabinoid JWH-073 retain intermediate to high cannabinoid 1 receptor (CB1R) affinity and exhibit neutral antagonist to partial agonist activity. Biochem Pharmacol 83 952. PMID: 22266354.

Caiati et al (2012) Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses. Sci Rep 2 285. PMID: 22368777.

Ganon-Elazar and Akirav (2012) Cannabinoids prevent the development of behavioral and endocrine alterations in a rat model of intense stress. Neuropsychopharmacology 37 456. PMID: 21918506.

Guida et al (2012) Salvinorin A reduces mechanical allodynia and spinal neuronal hyperexcitability induced by peripheral formalin injection. Mol Pain 8 60. PMID: 22913292.

Laricchiuta et al (2012) CB1 receptor autoradiographic characterization of the individual differences in approach and avoidance motivation. PLoS One 7 e42111. PMID: 22848724.

Liu et al (2012) Betulinic acid targets YY1 and ErbB2 through cannabinoid receptor-dependent disruption of microRNA-27a:ZBTB10 in breast cancer. Mol Cancer Ther 11 1421. PMID: 22553354.

Stern et al (2012) On disruption of fear memory by reconsolidation blockade: evidence from cannabidiol treatment. Neuropsychopharmacology 37 2132. PMID: 22549120.

Tozzi et al (2012) A2A adenosine receptor antagonism enhances synaptic and motor effects of cocaine via CB1 cannabinoid receptor activation. PLoS One 7 e38312. PMID: 22715379.

Tumati et al (2012) Repeated morphine treatment-mediated hyperalgesia, allodynia and spinal glial activation are blocked by co-administration of a selective cannabinoid receptor type-2 agonist. J Neuroimmunol 244 23. PMID: 22285397.

Brents et al (2011) Phase I hydroxylated metabolites of the K2 synthetic cannabinoid JWH-018 retain in vitro and in vivo cannabinoid 1 receptor affinity and activity. PLoS One 6 e21917. PMID: 21755008.

Crespillo et al (2011) Expression of the cannabinoid system in muscle: effects of a high-fat diet and CB1 receptor blockade. Biochem J 433 175. PMID: 20955176.

Li and Burrell (2011) Associative, bidirectional changes in neural signaling utilizing NMDA receptor- and endocannabinoid-dependent mechanisms. Learn Mem 18 545. PMID: 21844187.

Atkinson et al (2010) Regulation of the hypothalamic-pituitary-adrenal axis circadian rhythm by endocannabinoids is sexually diergic. Endocrinology 151 3720. PMID: 20534730.

Buznikov et al (2010) A putative 'pre-nervous' endocannabinoid system in early echinoderm development. Dev Neurosci 32 1. PMID: 19907129.

Curto-Reyes et al (2010) Spinal and peripheral analgesic effects of the CB2 cannabinoid receptor agonist AM1241 in two models of bone cancer-induced pain. Br J Pharmacol 160 561. PMID: 20233215.

Henstridge et al (2010) GPR55 ligands promote receptor coupling to multiple signalling pathways. Br J Pharmacol 160 604. PMID: 20136841.

Jiang et al (2010) The maturation of GABAergic transmission in visual cortex requires endocannabinoid-mediated LTD of inhibitory inputs during a critical period. Neuron 66 248. PMID: 20435001.

Mair et al (2010) Interaction between anandamide and sphingosine-1-phosphate in mediating vasorelaxation in rat coronary artery. Br J Pharmacol 161 176. PMID: 20718749.

Schlosburg et al (2010) Chronic monoacylglycerol lipase blockade causes functional antagonism of the endocannabinoid system. Nat Neurosci 13 1113. PMID: 20729846.

Yuan and Burrell (2010) Endocannabinoid-dependent LTD in a nociceptive synapse requires activation of a presynaptic TRPV-like receptor. J Neurophysiol 104 2766. PMID: 20884761.

Garzón et al (2009) Gz mediates the long-lasting desensitization of brain CB1 receptors and is essential for cross-tolerance with morphine. Mol Pain 5 11. PMID: 19284549.

Mendiguren and Pineda (2009) Effect of the CB(1) receptor antagonists rimonabant and AM251 on the firing rate of dorsal raphe nucleus neurons in rat brain slices. Br J Pharmacol 158 1579. PMID: 19845674.

Tjen-A-Looi et al (2009) Processing cardiovascular information in the vlPAG during electroacupuncture in rats: roles of endocannabinoids and GABA. J Appl Physiol (1985) 106 1793. PMID: 19325030.

Gibson et al (2008) TRPV1 channels mediate long-term depression at synapses on hippocampal interneurons. Neuron 57 746. PMID: 18341994.

Melis et al (2008) Endogenous fatty acid ethanolamides suppress nicotine-induced activation of mesolimbic dopamine neurons through nuclear receptors. J Neurosci 28 13985. PMID: 19091987.

Potenzieri et al (2008) The cannabinoid receptor agonist, WIN 55, 212-2, attenuates tumor-evoked hyperalgesia through peripheral mechanisms. Brain Res 1215 69. PMID: 18486111.

Shen et al (2008) Dichotomous dopaminergic control of striatal synaptic plasticity. Science 321 848. PMID: 18687967.

Crozier et al (2007) Deprivation-induced synaptic depression by distinct mechanisms in different layers of mouse visual cortex. Proc Natl Acad Sci U S A 104 1383. PMID: 17227847.

Czesnik et al (2007) Cannabinoid action in the olfactory epithelium. Proc Natl Acad Sci U S A 104 2967. PMID: 17301239.

Huang et al (2007) Cannabinoids excite hypothalamic melanin-concentrating hormone but inhibit hypocretin/orexin neurons: implications for cannabinoid actions on food intake and cognitive arousal. J Neurosci 27 4870. PMID: 17475795.

Bender et al (2006) Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex. J Neurosci 26 4166. PMID: 16624937.

Cenni et al (2006) Differential effect of cannabinoid agonists and endocannabinoids on histamine release from distinct regions of the rat brain. Eur J Neurosci 24 1633. PMID: 17004927.

Wang et al (2006) Dopaminergic control of corticostriatal long-term synaptic depression in medium spiny neurons is mediated by cholinergic interneurons. Neuron 50 443. PMID: 16675398.

Safo and Regehr (2005) Endocannabinoids control the induction of cerebellar LTD. Neuron 48 647. PMID: 16301180.

Akerman et al (2004) Anandamide acts as a vasodilator of dural blood vessels in vivo by activating TRPV1 receptors. Br J Pharmacol 142 1354. PMID: 15277315.

Chevaleyre and Castillo (2004) Endocannabinoid-mediated metaplasticity in the hippocampus. Neuron 43 871. PMID: 15363397.

Mathison et al (2004) Effects of cannabinoid receptor-2 activation on accelerated gastrointestinal transit in lipopolysaccharide-treated rats. Br J Pharmacol 142 1247. PMID: 15249429.

Melyan et al (2004) Metabotropic regulation of intrinsic excitability by synaptic activation of kainate receptors. J Neurosci 24 4530. PMID: 15140923.

Price et al (2004) Cannabinoid receptor-independent actions of the aminoalkylindole WIN 55,212-2 on trigeminal sensory neurons. Br J Pharmacol 142 257. PMID: 15155534.

Savinainen et al (2003) An optimized approach to study endocannabinoid signaling: evidence against constitutive activity of rat brain adenosine A1 and cannabinoid CB1 receptors. Br J Pharmacol 140 1451. PMID: 14623770.

Savinainen et al (2001) Despite substantial degradation, 2-arachidonoylglycerol is a potent full efficacy agonist mediating CB(1) receptor-dependent G-protein activation in rat cerebellar membranes. Br J Pharmacol 134 664. PMID: 11588122.

Jiang et al Expression and function of cannabinoid receptors CB1 and CB2 and their cognate cannabinoid ligands in murine embryonic stem cells. PLoS One 2 e641. PMID: 17653268.

Lafourcade et al Molecular components and functions of the endocannabinoid system in mouse prefrontal cortex. PLoS One 2 e709. PMID: 17684555.

Do you know of a great paper that uses AM 251 from Tocris? If so please let us know.show all ▼show less ▲

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