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 / Safety Data Sheet

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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.

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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.

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.

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.

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.

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.

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.

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.

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Keywords: AM 281, supplier, Potent, selective, CB1, antagonists, inverse, agonists, Cannabinoids, Receptors, AM281, cb1r, Tocris Bioscience, CB1 Receptor Antagonist products

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