Catalog Number: 1117
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:
  • Formula:
  • Solubility:
    Soluble to 25 mM in ethanol and to 100 mM in DMSO
  • Purity:
  • Storage:
    Store at RT
  • CAS No:
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.
Additional Information
Other Product-Specific Information:
Background References
  1. The orphan receptor GPR55 is a novel cannabinoid receptor.
    Ryberg et al.
    Br.J.Pharmacol., 2007;152:1092
  2. Inverse agonism and neutral antagonism at cannabinoid CB1 receptors.
    Life Sci., 2005;76:1307
  3. 125I-labeled AM 251: a radioiodinated ligand which binds in vivo to mouse brain cannabinoid CB1 receptors.
    Gatley et al.
    Eur.J.Pharmacol., 1996;307:331
  4. Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists.
    Lan et al.
    J.Med.Chem., 1999;42:769
  5. Binding of the non-classical cannabinoid CP 55,940, and the diarylpyrazole AM251 to rodent brain cannabinoid receptors.
    Gatley et al.
    Life Sci., 1997;61:191

The citations listed below are publications that use Tocris products. Selected citations for AM 251 include:

Showing Results 1 - 10 of 112

  1. & #916; 9-Tetrahydrocannabinol Reverses TNFα-induced Increase in Airway Epithelial Cell Permeability through CB 2 Receptors
    Authors: Shang Et al.
    Biochemical Pharmacology
  2. Endocannabinoids Mediate Muscarinic Acetylcholine Receptor-Dependent Long-Term Depression in the Adult Medial Prefrontal Cortex.
    Authors: Martin Et al.
    Br J Pharmacol
  3. Tonic endocannabinoid-mediated modulation of GABA release is independent of the CB1 content of axon terminals.
    Authors: Lenkey Et al.
    Sci Rep
  4. FAAH genetic variation enhances fronto-amygdala function in mouse and human.
    Authors: Dincheva Et al.
    Nat Commun
  5. Regional effects of endocannabinoid, BDNF and FGF receptor signalling on neuroblast motility and guidance along the rostral migratory stream.
    Authors: Zhou Et al.
    Nat Commun
  6. Role of the endocannabinoid system in obesity induced by neuropeptide Y overexpression in noradrenergic neurons.
    Authors: Vähätalo Et al.
    Mol Cell Neurosci
  7. Differential immune mechanism to HIV-1 Tat variants and its regulation by AEA [corrected].
    Authors: Krishnan and Chatterjee
    PLoS One
  8. Involvement of GluR2 up-regulation in neuroprotection by electroacupuncture pretreatment via cannabinoid CB1 receptor in mice.
    Authors: Liu Et al.
    Nutr Diabetes
  9. Coadministration of indomethacin and minocycline attenuates established paclitaxel-induced neuropathic thermal hyperalgesia: Involvement of cannabinoid CB1 receptors.
    Authors: Parvathy and Masocha
    J Neurosci
  10. Cannabinoid receptor CB2 is involved in tetrahydrocannabinol-induced anti-inflammation against lipopolysaccharide in MG-63 cells.
    Authors: Yang Et al.
    Sci Rep
  11. Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures.
    Authors: Malek Et al.
    Neural Plast
  12. A peripheral endocannabinoid mechanism contributes to glucocorticoid-mediated metabolic syndrome.
    Authors: Bowles Et al.
    Mol Pharmacol
  13. Anoctamin Calcium-Activated Chloride Channels May Modulate Inhibitory Transmission in the Cerebellar Cortex.
    Authors: Zhang Et al.
    PLoS One
  14. The Effects of the Endocannabinoids Anandamide and 2-Arachidonoylglycerol on Human Osteoblast Proliferation and Differentiation.
    Authors: Smith Et al.
    Proc Natl Acad Sci U S A
  15. Cannabidiol causes endothelium-dependent vasorelaxation of human mesenteric arteries via CB1 activation.
    Authors: Stanley Et al.
    Front Cell Neurosci
  16. Endocannabinoids modulate cortical development by configuring Slit2/Robo1 signalling.
    Authors: Alpár Et al.
    J Neurosci
  17. Presynaptic calcium channel inhibition underlies CB1 cannabinoid receptor-mediated suppression of GABA release.
    Authors: Szabó Et al.
    Mediators Inflamm
  18. Miswiring the brain: △9-tetrahydrocannabinol disrupts cortical development by inducing an SCG10/stathmin-2 degradation pathway.
    Authors: Tortoriello Et al.
    Proc Natl Acad Sci U S A
  19. CB1 cannabinoid receptors are involved in neuroleptic-induced enhancement of brain neurotensin.
    Authors: Hassanzadeh and Rostami
    J Neurosci
  20. Expression and functional relevance of cannabinoid receptor 1 in Hodgkin lymphoma.
    Authors: Benz Et al.
    PLoS One
  21. Hepatic cannabinoid receptor type 1 mediates alcohol-induced regulation of bile acid enzyme genes expression via CREBH.
    Authors: Chanda Et al.
    PLoS One
  22. Cannabinoid HU210 protects isolated rat stomach against impairment caused by serum of rats with experimental acute pancreatitis.
    Authors: Cao Et al.
    PLoS One
  23. The cannabinoid δ(9)-tetrahydrocannabivarin (THCV) ameliorates insulin sensitivity in two mouse models of obesity.
    Authors: Wargent Et al.
    Nutr Diabetes
  24. Diacylglycerol lipase α manipulation reveals developmental roles for intercellular endocannabinoid signaling.
    Authors: Keimpema Et al.
    Nat Commun
  25. Cannabinoids ameliorate impairments induced by chronic stress to synaptic plasticity and short-term memory.
    Authors: Abush and Akirav
  26. CB1 cannabinoid receptors couple to focal adhesion kinase to control insulin release.
    Authors: Malenczyk Et al.
    J Biol Chem
  27. The cannabinoid WIN 55,212-2 decreases specificity protein transcription factors and the oncogenic cap protein eIF4E in colon cancer cells.
    Authors: Sreevalsan and Safe
    Mol Cancer Ther
  28. Salvinorin A reduces mechanical allodynia and spinal neuronal hyperexcitability induced by peripheral formalin injection.
    Authors: Guida Et al.
    Mol Pain
  29. 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.
    Authors: Brents Et al.
    Biochem Pharmacol
  30. CB1 receptor autoradiographic characterization of the individual differences in approach and avoidance motivation.
    Authors: Laricchiuta Et al.
    PLoS One
  31. A2A adenosine receptor antagonism enhances synaptic and motor effects of cocaine via CB1 cannabinoid receptor activation.
    Authors: Tozzi Et al.
    PLoS One
  32. 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.
    Authors: Casarotto Et al.
  33. Cannabinoids prevent the development of behavioral and endocrine alterations in a rat model of intense stress.
    Authors: Ganon-Elazar and Akirav
  34. On disruption of fear memory by reconsolidation blockade: evidence from cannabidiol treatment.
    Authors: Stern Et al.
  35. Tonic and transient endocannabinoid regulation of AMPAergic miniature postsynaptic currents and homeostatic plasticity in embryonic motor networks.
    Authors: Gonzalez-Islas Et al.
    Sci Rep
  36. Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses.
    Authors: Caiati Et al.
    Sci Rep
  37. 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.
    Authors: Chanda Et al.
    Br J Pharmacol
  38. Repeated morphine treatment-mediated hyperalgesia, allodynia and spinal glial activation are blocked by co-administration of a selective cannabinoid receptor type-2 agonist.
    Authors: Tumati Et al.
    J Neuroimmunol
  39. Effects of gonadal hormones on the peripheral cannabinoid receptor 1 (CB1R) system under a myositis condition in rats.
    Authors: Niu Et al.
    J Pharmacol Exp Ther
  40. Betulinic acid targets YY1 and ErbB2 through cannabinoid receptor-dependent disruption of microRNA-27a:ZBTB10 in breast cancer.
    Authors: Liu Et al.
    Mol Cancer Ther
  41. Phase I hydroxylated metabolites of the K2 synthetic cannabinoid JWH-018 retain in vitro and in vivo cannabinoid 1 receptor affinity and activity.
    Authors: Brents Et al.
    PLoS One
  42. Expression of the cannabinoid system in muscle: effects of a high-fat diet and CB1 receptor blockade.
    Authors: Crespillo Et al.
    Biochem J
  43. Alterations of endocannabinoid signaling, synaptic plasticity, learning, and memory in monoacylglycerol lipase knock-out mice.
    Authors: Pan Et al.
    J Cell Biol
  44. Associative, bidirectional changes in neural signaling utilizing NMDA receptor- and endocannabinoid-dependent mechanisms.
    Authors: Li and Burrell
    Learn Mem
  45. The Role of the Endocannabinoids in Suppression of the Hypothalamic-pituitary-adrenal Axis Activity by Doxepin.
    Authors: Hassanzadeh and Hassanzadeh
    J Leukoc Biol
  46. The maturation of GABAergic transmission in visual cortex requires endocannabinoid-mediated LTD of inhibitory inputs during a critical period.
    Authors: Jiang Et al.
  47. The cannabinoid WIN55,212-2 protects against oxidized LDL-induced inflammatory response in murine macrophages.
    Authors: Hao Et al.
    Iran J Basic Med Sci
  48. Cannabidiol displays antiepileptiform and antiseizure properties in vitro and in vivo.
    Authors: Jones Et al.
    Cereb Cortex
  49. A putative 'pre-nervous' endocannabinoid system in early echinoderm development.
    Authors: Buznikov Et al.
    Dev Neurosci
  50. Cannabinoids excite circadian clock neurons.
    Authors: Acuna-Goycolea Et al.
    J Neurosci
  51. Effects of TRPV1 activation on synaptic excitation in the dentate gyrus of a mouse model of temporal lobe epilepsy.
    Authors: Bhaskaran and Smith
  52. Interaction between anandamide and sphingosine-1-phosphate in mediating vasorelaxation in rat coronary artery.
    Authors: Mair Et al.
    Br J Pharmacol
  53. Endocannabinoid modulation of hyperaemia evoked by physiologically relevant stimuli in the rat primary somatosensory cortex.
    Authors: Ho Et al.
  54. GPR55 ligands promote receptor coupling to multiple signalling pathways.
    Authors: Henstridge Et al.
    Br J Pharmacol
  55. Spinal and peripheral analgesic effects of the CB2 cannabinoid receptor agonist AM1241 in two models of bone cancer-induced pain.
    Authors: Curto-Reyes Et al.
    Br J Pharmacol
  56. Retrograde endocannabinoid signaling reduces GABAergic synaptic transmission to gonadotropin-releasing hormone neurons.
    Authors: Farkas Et al.
    J Biol Chem
  57. Regulation of the hypothalamic-pituitary-adrenal axis circadian rhythm by endocannabinoids is sexually diergic.
    Authors: Atkinson Et al.
  58. Chronic monoacylglycerol lipase blockade causes functional antagonism of the endocannabinoid system.
    Authors: Schlosburg Et al.
    Nat Neurosci
  59. Endocannabinoid-dependent LTD in a nociceptive synapse requires activation of a presynaptic TRPV-like receptor.
    Authors: Yuan and Burrell
    J Neurophysiol
  60. Gz mediates the long-lasting desensitization of brain CB1 receptors and is essential for cross-tolerance with morphine.
    Authors: Garzón Et al.
    Mol Pain
  61. PKCε regulates behavioral sensitivity, binding and tolerance to the CB1 receptor agonist WIN55,212-2.
    Authors: Wallace Et al.
    Iran J Basic Med Sci
  62. The neuroprotective impact of the leak potassium channel TASK1 on stroke development in mice.
    Authors: Meuth Et al.
    Exp Neurol
  63. Effect of the CB(1) receptor antagonists rimonabant and AM251 on the firing rate of dorsal raphe nucleus neurons in rat brain slices.
    Authors: Mendiguren and Pineda
    Br J Pharmacol
  64. Endogenous cannabinoids induce fever through the activation of CB1 receptors.
    Authors: Fraga Et al.
  65. Acute hypertension reveals depressor and vasodilator effects of cannabinoids in conscious rats.
    Authors: Ho and Gardiner
    Br J Pharmacol
  66. Processing cardiovascular information in the vlPAG during electroacupuncture in rats: roles of endocannabinoids and GABA.
    Authors: Tjen-A-Looi Et al.
    J Appl Physiol (1985)
  67. Analysis of promoter regions regulating basal and interleukin-4-inducible expression of the human CB1 receptor gene in T lymphocytes.
    Authors: Börner Et al.
    Eur J Pharmacol
  68. Unique agonist-bound cannabinoid CB1 receptor conformations indicate agonist specificity in signaling.
    Authors: Georgieva Et al.
    Br J Pharmacol
  69. TRPV1 channels mediate long-term depression at synapses on hippocampal interneurons.
    Authors: Gibson Et al.
  70. Dichotomous dopaminergic control of striatal synaptic plasticity.
    Authors: Shen Et al.
  71. Endogenous fatty acid ethanolamides suppress nicotine-induced activation of mesolimbic dopamine neurons through nuclear receptors.
    Authors: Melis Et al.
    J Neurosci
  72. Modulation of the anti-nociceptive effects of 2-arachidonoyl glycerol by peripherally administered FAAH and MGL inhibitors in a neuropathic pain model.
    Authors: Desroches Et al.
    Eur J Neurosci
  73. Activation of cannabinoid receptors prevents antigen-induced asthma-like reaction in guinea pigs.
    Authors: Giannini Et al.
    Br J Pharmacol
  74. The cannabinoid receptor agonist, WIN 55, 212-2, attenuates tumor-evoked hyperalgesia through peripheral mechanisms.
    Authors: Potenzieri Et al.
    Brain Res
  75. Cannabinoid-2 receptor agonist HU-308 protects against hepatic ischemia/reperfusion injury by attenuating oxidative stress, inflammatory response, and apoptosis.
    Authors: Rajesh Et al.
    Cardiovasc Res
  76. The differential contractile responses to capsaicin and anandamide in muscle strips isolated from the rat urinary bladder.
    Authors: Saitoh Et al.
    J Neurosci
  77. Calcium release from presynaptic internal stores is required for ethanol to increase spontaneous γ-aminobutyric acid release onto cerebellum Purkinje neurons.
    Authors: Kelm Et al.
    PLoS One
  78. Endocannabinoids acting at CB1 receptors mediate the cardiac contractile dysfunction in vivo in cirrhotic rats.
    Authors: Bátkai Et al.
    Br J Pharmacol
  79. Cannabinoids excite hypothalamic melanin-concentrating hormone but inhibit hypocretin/orexin neurons: implications for cannabinoid actions on food intake and cognitive arousal.
    Authors: Huang Et al.
    J Neurosci
  80. Differential effects of endocannabinoids on glutamatergic and GABAergic inputs to layer 5 pyramidal neurons.
    Authors: Fortin and Levine
    J Biol Chem
  81. Role of the nitric oxide pathway and the endocannabinoid system in neurogenic relaxation of corpus cavernosum from biliary cirrhotic rats.
    Authors: Ghasemi Et al.
    EMBO J
  82. Cannabinoid action in the olfactory epithelium.
    Authors: Czesnik Et al.
    Proc Natl Acad Sci U S A
  83. Deprivation-induced synaptic depression by distinct mechanisms in different layers of mouse visual cortex.
    Authors: Crozier Et al.
    Proc Natl Acad Sci U S A
  84. Dopaminergic control of corticostriatal long-term synaptic depression in medium spiny neurons is mediated by cholinergic interneurons.
    Authors: Wang Et al.
  85. Effects of peripheral cannabinoid receptor ligands on motility and polarization in neutrophil-like HL60 cells and human neutrophils.
    Authors: Kurihara Et al.
    Br J Pharmacol
  86. Vanilloid-mediated heterosynaptic facilitation of inhibitory synaptic input to neurons of the rat dorsal motor nucleus of the vagus.
    Authors: Derbenev Et al.
    PLoS One
  87. Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex.
    Authors: Bender Et al.
    J Neurosci
  88. Differential effect of cannabinoid agonists and endocannabinoids on histamine release from distinct regions of the rat brain.
    Authors: Cenni Et al.
    Eur J Neurosci
  89. Anandamide mediates hyperdynamic circulation in cirrhotic rats via CB(1) and VR(1) receptors.
    Authors: Moezi Et al.
    J Neurosci
  90. Actions of the FAAH inhibitor URB597 in neuropathic and inflammatory chronic pain models.
    Authors: Jayamanne Et al.
    J Neurosci
  91. Endocannabinoids control the induction of cerebellar LTD.
    Authors: Safo and Regehr
  92. Hemodynamic profile, responsiveness to anandamide, and baroreflex sensitivity of mice lacking fatty acid amide hydrolase.
    Authors: Pacher Et al.
    J Lipid Res
  93. Species and strain differences in the expression of a novel glutamate-modulating cannabinoid receptor in the rodent hippocampus.
    Authors: Hoffman Et al.
    Am J Physiol Heart Circ Physiol
  94. Role of endocannabinoids in the pathogenesis of cirrhotic cardiomyopathy in bile duct-ligated rats.
    Authors: Gaskari Et al.
    Sci Rep
  95. Endocannabinoids regulate interneuron migration and morphogenesis by transactivating the TrkB receptor.
    Authors: Berghuis Et al.
    Neurobiol Dis
  96. Defective adult neurogenesis in CB1 cannabinoid receptor knockout mice.
    Authors: Jin Et al.
    Am J Physiol Heart Circ Physiol
  97. Endocannabinoid-mediated metaplasticity in the hippocampus.
    Authors: Chevaleyre and Castillo
  98. Electrical coupling among irregular-spiking GABAergic interneurons expressing cannabinoid receptors.
    Authors: Galarreta Et al.
    J Pharmacol Exp Ther
  99. Endocannabinoid-independent retrograde signaling at inhibitory synapses in layer 2/3 of neocortex: involvement of vesicular glutamate transporter 3.
    Authors: Harkany Et al.
  100. Metabotropic regulation of intrinsic excitability by synaptic activation of kainate receptors.
    Authors: Melyan Et al.
    J Neurosci
  101. Cannabinoid receptor-independent actions of the aminoalkylindole WIN 55,212-2 on trigeminal sensory neurons.
    Authors: Price Et al.
    Br J Pharmacol
  102. Anandamide acts as a vasodilator of dural blood vessels in vivo by activating TRPV1 receptors.
    Authors: Akerman Et al.
    Br J Pharmacol
  103. Effects of cannabinoid receptor-2 activation on accelerated gastrointestinal transit in lipopolysaccharide-treated rats.
    Authors: Mathison Et al.
    Br J Pharmacol
  104. Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension.
    Authors: Bátkai Et al.
    Eur J Pharmacol
  105. The inhibitory effect of anandamide on luteinizing hormone-releasing hormone secretion is reversed by estrogen.
    Authors: Scorticati Et al.
    Mol Pharmacol
  106. The FGF receptor uses the endocannabinoid signaling system to couple to an axonal growth response.
    Authors: Williams Et al.
    J Cell Mol Med
  107. An optimized approach to study endocannabinoid signaling: evidence against constitutive activity of rat brain adenosine A1 and cannabinoid CB1 receptors.
    Authors: Savinainen Et al.
    Br J Pharmacol
  108. Despite substantial degradation, 2-arachidonoylglycerol is a potent full efficacy agonist mediating CB(1) receptor-dependent G-protein activation in rat cerebellar membranes.
    Authors: Savinainen Et al.
    Br J Pharmacol
  109. Feeding induced by cannabinoids is mediated independently of the melanocortin system.
    Authors: Sinnayah Et al.
    Proc Natl Acad Sci U S A
  110. The orexigenic effect of ghrelin is mediated through central activation of the endogenous cannabinoid system.
    Authors: Kola Et al.
    Br J Pharmacol
  111. Molecular components and functions of the endocannabinoid system in mouse prefrontal cortex.
    Authors: Lafourcade Et al.
    PLoS One
  112. Expression and function of cannabinoid receptors CB1 and CB2 and their cognate cannabinoid ligands in murine embryonic stem cells.
    Authors: Jiang Et al.
    PLoS One
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