AM 281

Cat. No. 1115

AM 281 C21H19Cl2IN4O2 [202463-68-1]

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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).

Licensing Information

Sold with the permission of the University of Connecticut

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.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

Certificate of Analysis / Product Datasheet
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Cosenza et al (2000) Locomotor activity and occupancy of brain cannabinoid CB1 receptors by the antagonist/inverse agonist AM281. Synapse 38 477. PMID: 11044895.

Lan et al (1999) Design and synthesis of the CB1 selective cannabinoid antagonist AM281: a potential human SPECT ligand. AAPS Pharmsci. 1 E4. PMID: 11741201.

Gatley et al (1998) Imaging the brain marijuana receptor: development of a radioligand that binds to cannabinoid CB1 receptors in vivo. J.Neurochem. 70 417. PMID: 9422389.

Gifford et al (1997) Effect of the cannabinoid receptor SPECT agent, AM 281, on hippocampal acetylcholine release from rat brain slices. Neurosci.Lett. 238 84. PMID: 9464661.

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 281 include:

Shao-Hua Su et al (2016) 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 Behavioural Brain Research 313 334. PMID: 27424778.

Lage et al (2015) Lack of Hypophagia in CB1 Null Mice is Associated to Decreased Hypothalamic POMC and CART Expression. Mol Pharmacol 18. PMID: 25655433.

Lin et al (2015) Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals. Int J Neuropsychopharmacol 16 5555. PMID: 25768340.

Tchantchou and Zhang (2013) 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. J Neurotrauma 30 565. PMID: 23151067.

Arévalo-Martín et al (2012) Early endogenous activation of CB1 and CB2 receptors after spinal cord injury is a protective response involved in spontaneous recovery. Mol Pharmacol 7 e49057. PMID: 23152849.

Khasabova et al (2011) Increasing 2-arachidonoyl glycerol signaling in the periphery attenuates mechanical hyperalgesia in a model of bone cancer pain. Cereb Cortex 64 60. PMID: 21440630.

Alkaitis et al (2010) Evidence for a role of endocannabinoids, astrocytes and p38 phosphorylation in the resolution of postoperative pain. PLoS One 5 e10891. PMID: 20531936.

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

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

Rajesh et al (2010) 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. Front Pharmacol 160 688. PMID: 20590572.

Huerta et al (2009) Effects of cannabinoids on caffeine contractures in slow and fast skeletal muscle fibers of the frog. J Membr Biol 229 91. PMID: 19506935.

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

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.

Bátkai et al (2007) Decreased age-related cardiac dysfunction, myocardial nitrative stress, inflammatory gene expression, and apoptosis in mice lacking fatty acid amide hydrolase. Int J Mol Sci 293 H909. PMID: 17434980.

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

Marinelli et al (2007) N-arachidonoyl-dopamine tunes synaptic transmission onto dopaminergic neurons by activating both cannabinoid and vanilloid receptors. Neuropsychopharmacology 32 298. PMID: 16760924.

Mukhopadhyay et al (2007) Pharmacological inhibition of CB1 cannabinoid receptor protects against doxorubicin-induced cardiotoxicity. J Am Coll Cardiol 50 528. PMID: 17678736.

Narushima et al (2007) Tonic enhancement of endocannabinoid-mediated retrograde suppression of inhibition by cholinergic interneuron activity in the striatum. J Cell Biol 27 496. PMID: 17234582.

Newman et al (2007) Endocannabinoids mediate muscarine-induced synaptic depression at the vertebrate neuromuscular junction. Eur J Neurosci 25 1619. PMID: 17408433.

Rajesh et al (2007) Cannabidiol attenuates high glucose-induced endothelial cell inflammatory response and barrier disruption. Am J Physiol Heart Circ Physiol 293 H610. PMID: 17384130.

Rajesh et al (2007) CB2-receptor stimulation attenuates TNF-alpha-induced human endothelial cell activation, transendothelial migration of monocytes, and monocyte-endothelial adhesion. Am J Physiol Heart Circ Physiol 293 H2210. PMID: 17660390.

Börner et al (2006) Cannabinoid receptor type 2 agonists induce transcription of the mu-opioid receptor gene in Jurkat T cells. J Neurosci 69 1486. PMID: 16434616.

Ohba et al (2005) BDNF locally potentiates GABAergic presynaptic machineries: target-selective circuit inhibition. PLoS One 15 291. PMID: 15238431.

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

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