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Description: Potent and selective CB1 inverse agonist
Chemical Name: 1-(2,4-Dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-4-morpholinyl-1H-pyrazole-3-carboxamide
Purity: ≥99% (HPLC)
Biological Activity for AM 281
AM 281 is a 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 for AM 281
| M. Wt | 557.22 |
| Formula | C21H19Cl2IN4O2 |
| Storage | Desiccate at +4°C |
| Purity | ≥99% (HPLC) |
| CAS Number | 202463-68-1 |
| PubChem ID | 4302962 |
| InChI Key | AJFFBPZYXRNAIC-UHFFFAOYSA-N |
| Smiles | CC1=C(N(N=C1C(=O)NN1CCOCC1)C1=C(Cl)C=C(Cl)C=C1)C1=CC=C(I)C=C1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Product Datasheets for AM 281
References for AM 281
References are publications that support the biological activity of the product.
Cosenza et al (2000) Locomotor activity and occupancy of brain cannabinoid CB1 receptors by the antagonist/inverse agonist AM281. Synapse 38 477 PMID: 11044895
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
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
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
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Keywords: AM 281, AM 281 supplier, Potent, selective, CB1, antagonists, inverse, agonists, Cannabinoids, Receptors, AM281, cb1r, 1115, Tocris Bioscience
40 Citations for AM 281
Citations are publications that use Tocris products. Selected citations for AM 281 include:
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
Lecca et al (2011) Effects of drugs of abuse on putative rostromedial tegmental neurons, inhibitory afferents to midbrain DA cells. Neuropsychopharmacology 36 589 PMID: 21048703
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
Al-Hayani and Davies (2000) Cannabinoid receptor mediated inhibition of excitatory synaptic transmission in the rat hippocampal slice is developmentally regulated. Br J Pharmacol 131 663 PMID: 11030713
Melis et al (2004) Prefrontal cortex stimulation induces 2-arachidonoyl-glycerol-mediated suppression of excitation in DA neurons. J Neurosci 24 10707 PMID: 15564588
Baker (2004) The cannabinomimetic arachidonyl-2-chloroethylamide (ACEA) acts on capsaicin-sensitive TRPV1 receptors but not cannabinoid receptors in rat joints. Br J Pharmacol 142 1361 PMID: 15277316
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
Ford et al (2002) Evidence of a novel site mediating anandamide-induced negative inotropic and coronary vasodilatator responses in rat isolated hearts. Br J Pharmacol 135 1191 PMID: 11877326
Hohmann et al (2019) On the influence of cannabinoids on cell morphology and motility of glioblastoma cells. PLoS One 14 e0212037 PMID: 30753211
Hohmann et al (2019) Synthetic Cannabinoids Influence the Invasion of Glioblastoma Cell Lines in a Cell- and Receptor-Dependent Manner. Cancers (Basel) 11 PMID: 30709059
Uhelski et al (2013) The non-selective cannabinoid receptor agonist WIN 55,212-2 attenuates responses of C-fiber nociceptors in a murine model of cancer pain. Neuroscience 247 84 PMID: 23673278
Zhang et al (2010) Cannabinoid CB1 receptor facilitation of substance P release in the rat spinal cord, measured as neurokinin 1 receptor internalization. Eur J Neurosci 31 225 PMID: 20074214
Burdyga et al (2010) Expression of cannabinoid CB1 receptors by vagal afferent neurons: kinetics and role in influencing neurochemical phenotype. Am J Physiol Gastrointest Liver Physiol 299 G63 PMID: 20430875
Ohba et al (2005) BDNF locally potentiates GABAergic presynaptic machineries: target-selective circuit inhibition. PLoS One 15 291 PMID: 15238431
Han (2017) Cannabinoid receptor 1 contributes to sprouted innervation in endometrial ectopic growth through mitogen-activated protein kinase activation. Brain Res 1663 132 PMID: 28322749
Almada (2017) The synthetic cannabinoid WIN-55,212-55,212 induced-apoptosis in cytotrophoblasts cells by a mechanism dependent on CB1 receptor. Toxicology 385 67 PMID: 28495606
Musella (2017) A novel crosstalk within the endocannabinoid system controls GABA transmission in the striatum. Sci Rep 7 7363 PMID: 28779174
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
Small-Howard et al (2005) Anti-inflammatory potential of CB1-mediated cAMP elevation in mast cells. Biochem J 388 465 PMID: 15669919
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
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
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
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
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
Hashimotodani et al (2007) Presynaptic monoacylglycerol lipase activity determines basal endocannabinoid tone and terminates retrograde endocannabinoid signaling in the hippocampus. J Neurosci 27 1211 PMID: 17267577
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
Newman et al (2007) Endocannabinoids mediate muscarine-induced synaptic depression at the vertebrate neuromuscular junction. Eur J Neurosci 25 1619 PMID: 17408433
Czesnik et al (2007) Cannabinoid action in the olfactory epithelium. Proc Natl Acad Sci U S A 104 2967 PMID: 17301239
Mukhopadhyay et al (2007) Pharmacological inhibition of CB1 cannabinoid receptor protects against doxorubicin-induced cardiotoxicity. J Am Coll Cardiol 50 528 PMID: 17678736
Marinelli et al (2007) N-arachidonoyl-DA tunes synaptic transmission onto DArgic neurons by activating both cannabinoid and vanilloid receptors. Neuropsychopharmacology 32 298 PMID: 16760924
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 DA neurons through nuclear receptors. J Neurosci 28 13985 PMID: 19091987
Aherne et al (2018) Coordination of ENT2-dependent adenosine transport and signaling dampens mucosal inflammation. JCI Insight 3 PMID: 30333323
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
Lin et al (2015) Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals. Int J Neuropsychopharmacol 16 5555 PMID: 25768340
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
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