Catalog Number: 1115
Chemical Name: 1-(2,4-Dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-4-morpholinyl-1H-pyrazole-3-carboxamide
Biological Activity
Potent, selective CB1 cannabinoid receptor antagonist/inverse agonist (Ki values are 12 and 4200 nM for CB1 and CB2 receptors respectively). Increases locomotor activity following systemic administration in vivo. Analog of SR141716A (Ki = 14 nM).
Technical Data
  • M.Wt:
    557.22
  • Formula:
    C21H19Cl2IN4O2
  • Solubility:
    Soluble to 75 mM in DMSO with gentle warming
  • Purity:
    >99%
  • Storage:
    Desiccate at +4°C
  • CAS No:
    202463-68-1
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
Licensing Caveats:
Sold with the permission of the University of Connecticut
Background References
  1. Locomotor activity and occupancy of brain cannabinoid CB1 receptors by the antagonist/inverse agonist AM281.
    Cosenza et al.
    Synapse, 2000;38:477
  2. Effect of the cannabinoid receptor SPECT agent, AM 281, on hippocampal acetylcholine release from rat brain slices.
    Gifford et al.
    Neurosci.Lett., 1997;238:84
  3. Imaging the brain marijuana receptor: development of a radioligand that binds to cannabinoid CB1 receptors in vivo.
    Gatley et al.
    J.Neurochem., 1998;70:417
  4. Design and synthesis of the CB1 selective cannabinoid antagonist AM281: a potential human SPECT ligand.
    Lan et al.
    AAPS Pharmsci., 1999;1:E4
Citations:

The citations listed below are publications that use Tocris products. Selected citations for AM 281 include:

26 Citations: Showing 1 - 10
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  1. The synthetic cannabinoid WIN-55,212-55,212 induced-apoptosis in cytotrophoblasts cells by a mechanism dependent on CB1 receptor.
    Authors: Almada
    Toxicology 2017;385:67
  2. Cannabinoid receptor 1 contributes to sprouted innervation in endometrial ectopic growth through mitogen-activated protein kinase activation.
    Authors: Han
    Brain Res 2017;1663:132
  3. Cannabinoid receptor agonist WIN55,212-2 and fatty acid amide hydrolase inhibitor URB597 may protect against cognitive impairment in rats of chronic cerebral hypoperfusion via PI3K/AKT signaling
    Authors: Shao-Hua Su Et al.
    Behavioural Brain Research 2016;313:334
  4. Lack of Hypophagia in CB1 Null Mice is Associated to Decreased Hypothalamic POMC and CART Expression.
    Authors: Lage Et al.
    Mol Pharmacol 2015;18
  5. Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals.
    Authors: Lin Et al.
    Int J Neuropsychopharmacol 2015;16:5555
  6. Selective inhibition of alpha/beta-hydrolase domain 6 attenuates neurodegeneration, alleviates blood brain barrier breakdown, and improves functional recovery in a mouse model of traumatic brain injury.
    Authors: Tchantchou and Zhang
    J Neurotrauma 2013;30:565
  7. Early endogenous activation of CB1 and CB2 receptors after spinal cord injury is a protective response involved in spontaneous recovery.
    Authors: Arévalo-Martín Et al.
    Mol Pharmacol 2012;7:e49057
  8. Increasing 2-arachidonoyl glycerol signaling in the periphery attenuates mechanical hyperalgesia in a model of bone cancer pain.
    Authors: Khasabova Et al.
    Cereb Cortex 2011;64:60
  9. Evidence for a role of endocannabinoids, astrocytes and p38 phosphorylation in the resolution of postoperative pain.
    Authors: Alkaitis Et al.
    PLoS One 2010;5:e10891
  10. Cannabinoid-1 receptor activation induces reactive oxygen species-dependent and -independent mitogen-activated protein kinase activation and cell death in human coronary artery endothelial cells.
    Authors: Rajesh Et al.
    Front Pharmacol 2010;160:688
  11. GPR55 ligands promote receptor coupling to multiple signalling pathways.
    Authors: Henstridge Et al.
    Br J Pharmacol 2010;160:604
  12. Regulation of the hypothalamic-pituitary-adrenal axis circadian rhythm by endocannabinoids is sexually diergic.
    Authors: Atkinson Et al.
    Endocrinology 2010;151:3720
  13. Effects of cannabinoids on caffeine contractures in slow and fast skeletal muscle fibers of the frog.
    Authors: Huerta Et al.
    J Membr Biol 2009;229:91
  14. Analysis of promoter regions regulating basal and interleukin-4-inducible expression of the human CB1 receptor gene in T lymphocytes.
    Authors: Börner Et al.
    Pharmacol Res 2008;73:1013
  15. Endogenous fatty acid ethanolamides suppress nicotine-induced activation of mesolimbic dopamine neurons through nuclear receptors.
    Authors: Melis Et al.
    J Neurosci 2008;28:13985
  16. Pharmacological inhibition of CB1 cannabinoid receptor protects against doxorubicin-induced cardiotoxicity.
    Authors: Mukhopadhyay Et al.
    J Am Coll Cardiol 2007;50:528
  17. N-arachidonoyl-dopamine tunes synaptic transmission onto dopaminergic neurons by activating both cannabinoid and vanilloid receptors.
    Authors: Marinelli Et al.
    Neuropsychopharmacology 2007;32:298
  18. Decreased age-related cardiac dysfunction, myocardial nitrative stress, inflammatory gene expression, and apoptosis in mice lacking fatty acid amide hydrolase.
    Authors: Bátkai Et al.
    Int J Mol Sci 2007;293:H909
  19. Cannabidiol attenuates high glucose-induced endothelial cell inflammatory response and barrier disruption.
    Authors: Rajesh Et al.
    Am J Physiol Heart Circ Physiol 2007;293:H610
  20. CB2-receptor stimulation attenuates TNF-alpha-induced human endothelial cell activation, transendothelial migration of monocytes, and monocyte-endothelial adhesion.
    Authors: Rajesh Et al.
    Am J Physiol Heart Circ Physiol 2007;293:H2210
  21. Tonic enhancement of endocannabinoid-mediated retrograde suppression of inhibition by cholinergic interneuron activity in the striatum.
    Authors: Narushima Et al.
    J Cell Biol 2007;27:496
  22. Endocannabinoids mediate muscarine-induced synaptic depression at the vertebrate neuromuscular junction.
    Authors: Newman Et al.
    Eur J Neurosci 2007;25:1619
  23. Cannabinoid action in the olfactory epithelium.
    Authors: Czesnik Et al.
    Proc Natl Acad Sci U S A 2007;104:2967
  24. Cannabinoid receptor type 2 agonists induce transcription of the mu-opioid receptor gene in Jurkat T cells.
    Authors: Börner Et al.
    J Neurosci 2006;69:1486
  25. BDNF locally potentiates GABAergic presynaptic machineries: target-selective circuit inhibition.
    Authors: Ohba Et al.
    PLoS One 2005;15:291
  26. The FGF receptor uses the endocannabinoid signaling system to couple to an axonal growth response.
    Authors: Williams Et al.
    Br J Pharmacol 2003;160:481
Expand to show all 26 Citations

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