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

Soluble to 25 mM in ethanol and to 100 mM in DMSO
>99 %
Store at RT

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

Certificate of Analysis: View current batch
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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:

Shang et al (2016) & #916; 9-Tetrahydrocannabinol Reverses TNFα-induced Increase in Airway Epithelial Cell Permeability through CB 2 Receptors Biochemical Pharmacology. PMID: 27641813.

Bowles et al (2015) A peripheral endocannabinoid mechanism contributes to glucocorticoid-mediated metabolic syndrome. Mol Pharmacol 112 285. PMID: 25535367.

Dincheva et al (2015) FAAH genetic variation enhances fronto-amygdala function in mouse and human. Nat Commun 6 6395. PMID: 25731744.

Krishnan and Chatterjee (2015) Differential immune mechanism to HIV-1 Tat variants and its regulation by AEA [corrected]. PLoS One 5 9887. PMID: 25943894.

Lenkey et al (2015) Tonic endocannabinoid-mediated modulation of GABA release is independent of the CB1 content of axon terminals. Sci Rep 6 6557. PMID: 25891347.

Liu et al (2015) Involvement of GluR2 up-regulation in neuroprotection by electroacupuncture pretreatment via cannabinoid CB1 receptor in mice. Nutr Diabetes 5 9490. PMID: 25830356.

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

Martin et al (2015) Endocannabinoids Mediate Muscarinic Acetylcholine Receptor-Dependent Long-Term Depression in the Adult Medial Prefrontal Cortex. Br J Pharmacol 9 457. PMID: 26648844.

Parvathy and Masocha (2015) Coadministration of indomethacin and minocycline attenuates established paclitaxel-induced neuropathic thermal hyperalgesia: Involvement of cannabinoid CB1 receptors. J Neurosci 5 10541. PMID: 26085115.

Smith et al (2015) The Effects of the Endocannabinoids Anandamide and 2-Arachidonoylglycerol on Human Osteoblast Proliferation and Differentiation. Proc Natl Acad Sci U S A 10 e0136546. PMID: 26414859.

Stanley et al (2015) Cannabidiol causes endothelium-dependent vasorelaxation of human mesenteric arteries via CB1 activation. Front Cell Neurosci 107 568. PMID: 26092099.

Vähätalo et al (2015) Role of the endocannabinoid system in obesity induced by neuropeptide Y overexpression in noradrenergic neurons. Mol Cell Neurosci 5 e151. PMID: 25915740.

Yang et al (2015) Cannabinoid receptor CB2 is involved in tetrahydrocannabinol-induced anti-inflammation against lipopolysaccharide in MG-63 cells. Sci Rep 2015 362126. PMID: 25653478.

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

Zhou et al (2015) Regional effects of endocannabinoid, BDNF and FGF receptor signalling on neuroblast motility and guidance along the rostral migratory stream. Nat Commun 64 32. PMID: 25481343.

Alpár et al (2014) Endocannabinoids modulate cortical development by configuring Slit2/Robo1 signalling. J Neurosci 5 4421. PMID: 25030704.

Hassanzadeh and Rostami (2014) CB1 cannabinoid receptors are involved in neuroleptic-induced enhancement of brain neurotensin. J Neurosci 17 181. PMID: 24847420.

Szabó et al (2014) Presynaptic calcium channel inhibition underlies CB1 cannabinoid receptor-mediated suppression of GABA release. Mediators Inflamm 34 7958. PMID: 24899717.

Tortoriello et al (2014) Miswiring the brain: △9-tetrahydrocannabinol disrupts cortical development by inducing an SCG10/stathmin-2 degradation pathway. Proc Natl Acad Sci U S A 33 668. PMID: 24469251.

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.

Keimpema et al (2013) Diacylglycerol lipase α manipulation reveals developmental roles for intercellular endocannabinoid signaling. Nat Commun 3 2093. PMID: 23806960.

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.

Casarotto et al (2012) Opposing roles for cannabinoid receptor type-1 (CB1) and transient receptor potential vanilloid type-1 channel (TRPV1) on the modulation of panic-like responses in rats. Pain 37 478. PMID: 21937980.

Chanda et al (2012) Activation of cannabinoid receptor type 1 (Cb1r) disrupts hepatic insulin receptor signaling via cyclic AMP-response element-binding protein H (Crebh)-mediated induction of Lipin1 gene. Br J Pharmacol 287 38041. PMID: 22989885.

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.

Gonzalez-Islas et al (2012) Tonic and transient endocannabinoid regulation of AMPAergic miniature postsynaptic currents and homeostatic plasticity in embryonic motor networks. Sci Rep 32 13597. PMID: 23015449.

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.

Niu et al (2012) Effects of gonadal hormones on the peripheral cannabinoid receptor 1 (CB1R) system under a myositis condition in rats. J Pharmacol Exp Ther 153 2283. PMID: 22940464.

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.

Hassanzadeh and Hassanzadeh (2011) The Role of the Endocannabinoids in Suppression of the Hypothalamic-pituitary-adrenal Axis Activity by Doxepin. J Leukoc Biol 14 414. PMID: 23493814.

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

Pan et al (2011) Alterations of endocannabinoid signaling, synaptic plasticity, learning, and memory in monoacylglycerol lipase knock-out mice. J Cell Biol 31 13420. PMID: 21940435.

Acuna-Goycolea et al (2010) Cannabinoids excite circadian clock neurons. J Neurosci 30 10061. PMID: 20668190.

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

Bhaskaran and Smith (2010) Effects of TRPV1 activation on synaptic excitation in the dentate gyrus of a mouse model of temporal lobe epilepsy. Endocrinology 223 529. PMID: 20144892.

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.

Farkas et al (2010) Retrograde endocannabinoid signaling reduces GABAergic synaptic transmission to gonadotropin-releasing hormone neurons. J Biol Chem 151 5818. PMID: 20926585.

Hao et al (2010) The cannabinoid WIN55,212-2 protects against oxidized LDL-induced inflammatory response in murine macrophages. Iran J Basic Med Sci 51 2181. PMID: 20305287.

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

Ho et al (2010) Endocannabinoid modulation of hyperaemia evoked by physiologically relevant stimuli in the rat primary somatosensory cortex. Neuropsychopharmacology 160 736. PMID: 20590576.

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.

Jones et al (2010) Cannabidiol displays antiepileptiform and antiseizure properties in vitro and in vivo. Cereb Cortex 332 569. PMID: 19906779.

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.

Fraga et al (2009) Endogenous cannabinoids induce fever through the activation of CB1 receptors. Neuropsychopharmacology 157 1494. PMID: 19681872.

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.

Ho and Gardiner (2009) Acute hypertension reveals depressor and vasodilator effects of cannabinoids in conscious rats. Br J Pharmacol 156 94. PMID: 19133994.

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.

Meuth et al (2009) The neuroprotective impact of the leak potassium channel TASK1 on stroke development in mice. Exp Neurol 33 42675. PMID: 18930826.

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.

Wallace et al (2009) PKCε regulates behavioral sensitivity, binding and tolerance to the CB1 receptor agonist WIN55,212-2. Iran J Basic Med Sci 34 1733. PMID: 19158669.

Börner et al (2008) Analysis of promoter regions regulating basal and interleukin-4-inducible expression of the human CB1 receptor gene in T lymphocytes. Eur J Pharmacol 73 1013. PMID: 18156315.

Desroches et al (2008) Modulation of the anti-nociceptive effects of 2-arachidonoyl glycerol by peripherally administered FAAH and MGL inhibitors in a neuropathic pain model. Eur J Neurosci 155 913. PMID: 18695638.

Georgieva et al (2008) Unique agonist-bound cannabinoid CB1 receptor conformations indicate agonist specificity in signaling. Br J Pharmacol 581 19. PMID: 18162180.

Giannini et al (2008) Activation of cannabinoid receptors prevents antigen-induced asthma-like reaction in guinea pigs. Br J Pharmacol 12 2381. PMID: 18266975.

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.

Bátkai et al (2007) Endocannabinoids acting at CB1 receptors mediate the cardiac contractile dysfunction in vivo in cirrhotic rats. Br J Pharmacol 293 H1689. PMID: 17557913.

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.

Fortin and Levine (2007) Differential effects of endocannabinoids on glutamatergic and GABAergic inputs to layer 5 pyramidal neurons. J Biol Chem 17 163. PMID: 16467564.

Ghasemi et al (2007) Role of the nitric oxide pathway and the endocannabinoid system in neurogenic relaxation of corpus cavernosum from biliary cirrhotic rats. EMBO J 151 591. PMID: 17486141.

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.

Kelm et al (2007) Calcium release from presynaptic internal stores is required for ethanol to increase spontaneous γ-aminobutyric acid release onto cerebellum Purkinje neurons. PLoS One 323 356. PMID: 17652632.

Rajesh et al (2007) Cannabinoid-2 receptor agonist HU-308 protects against hepatic ischemia/reperfusion injury by attenuating oxidative stress, inflammatory response, and apoptosis. Cardiovasc Res 82 1382. PMID: 17652447.

Saitoh et al (2007) The differential contractile responses to capsaicin and anandamide in muscle strips isolated from the rat urinary bladder. J Neurosci 570 182. PMID: 17586490.

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.

Derbenev et al (2006) Vanilloid-mediated heterosynaptic facilitation of inhibitory synaptic input to neurons of the rat dorsal motor nucleus of the vagus. PLoS One 26 9666. PMID: 16988037.

Jayamanne et al (2006) Actions of the FAAH inhibitor URB597 in neuropathic and inflammatory chronic pain models. J Neurosci 147 281. PMID: 16331291.

Kurihara et al (2006) Effects of peripheral cannabinoid receptor ligands on motility and polarization in neutrophil-like HL60 cells and human neutrophils. Br J Pharmacol 281 12908. PMID: 16513651.

Moezi et al (2006) Anandamide mediates hyperdynamic circulation in cirrhotic rats via CB(1) and VR(1) receptors. J Neurosci 149 898. PMID: 17043671.

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.

Berghuis et al (2005) Endocannabinoids regulate interneuron migration and morphogenesis by transactivating the TrkB receptor. Neurobiol Dis 102 19115. PMID: 16357196.

Gaskari et al (2005) Role of endocannabinoids in the pathogenesis of cirrhotic cardiomyopathy in bile duct-ligated rats. Sci Rep 146 315. PMID: 16025138.

Hoffman et al (2005) Species and strain differences in the expression of a novel glutamate-modulating cannabinoid receptor in the rodent hippocampus. Am J Physiol Heart Circ Physiol 22 2387. PMID: 16262678.

Pacher et al (2005) Hemodynamic profile, responsiveness to anandamide, and baroreflex sensitivity of mice lacking fatty acid amide hydrolase. J Lipid Res 289 H533. PMID: 15821037.

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.

Bátkai et al (2004) Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension. Eur J Pharmacol 110 1996. PMID: 15451779.

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

Galarreta et al (2004) Electrical coupling among irregular-spiking GABAergic interneurons expressing cannabinoid receptors. J Pharmacol Exp Ther 24 9770. PMID: 15525762.

Harkany et al (2004) Endocannabinoid-independent retrograde signaling at inhibitory synapses in layer 2/3 of neocortex: involvement of vesicular glutamate transporter 3. Circulation 24 4978. PMID: 15163690.

Jin et al (2004) Defective adult neurogenesis in CB1 cannabinoid receptor knockout mice. Am J Physiol Heart Circ Physiol 66 204. PMID: 15266010.

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.

Scorticati et al (2004) The inhibitory effect of anandamide on luteinizing hormone-releasing hormone secretion is reversed by estrogen. Mol Pharmacol 101 11891. PMID: 15280536.

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.

Williams et al (2003) The FGF receptor uses the endocannabinoid signaling system to couple to an axonal growth response. J Cell Mol Med 160 481. PMID: 12578907.

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.

Kola et al The orexigenic effect of ghrelin is mediated through central activation of the endogenous cannabinoid system. Br J Pharmacol 3 e1797. PMID: 18335063.

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

Sinnayah et al Feeding induced by cannabinoids is mediated independently of the melanocortin system. Proc Natl Acad Sci U S A 3 e2202. PMID: 18493584.

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