A-836339 - CAS 959746-77-1
Catalog number: 959746-77-1
Category: Inhibitor
Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Molecular Formula:
C16H26N2O2S
Molecular Weight:
310.45
COA:
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Targets:
Cannabinoid Receptor
Description:
A-836339 is a synthetic and potent cannabinoid receptor full agonist. It displays a higher affinity for the peripheral CB2 receptor with Ki value of 0.64 nM over the central CB1 receptor with Ki of 270 nM in both human and rat in radioligand binding assays. It also displays analgesic, anti-inflammatory, and anti-hyperalgesic effects in mice at low doses. It exhibits a profile devoid of significant affinity at other G-protein-coupled receptors and ion channels. It has also demonstrated efficacies in the chronic constrain injury (CCI) model of neuropathic pain, skin incision, and capsaicin-induced secondary mechanical hyperalgesia models. It is intended for forensic and research applications. It was suggested to be for human consumption. It was developed by Abbott Laboratories.
Purity:
>99 %
Appearance:
Light yellow to yellow Solid
Synonyms:
N-[3-(2-methoxyethyl)-4,5-dimethyl-1,3-thiazol-2-ylidene]-2,2,3,3-tetramethylcyclopropane-1-carboxamide;CyclopropanecarboxaMide, N-[3-(2-Methoxyethyl)-4,5-diMethyl-2(3H)-thiazolylidene]-2,2,3,3-tetraMethyl-, [N(Z)]-;1-(Tetrahydropyran-4-ylMethyl)-1H-indol-3-yl]-(2,2,3,5-tetraMethylcyclopropyl)Methanone
Solubility:
DMSO: ≥ 12 mg/mL
Storage:
-20°C Freezer
MSDS:
Inquire
Application:
A-836339 displays analgesic, anti-inflammatory, and anti-hyperalgesic effects. It was suggested to be for human consumption.
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Quantity:
Grams to Kilograms
Boiling Point:
388.4±44.0 °C | Condition: Press: 760 Torr
Density:
1.14±0.1 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
InChIKey:
JKGIMVBQKSRTGX-UHFFFAOYSA-N
InChI:
InChI=1S/C16H26N2O2S/c1-10-11(2)21-14(18(10)8-9-20-7)17-13(19)12-15(3,4)16(12,5)6/h12H,8-9H2,1-7H3
Canonical SMILES:
CC1=C(SC(=NC(=O)C2C(C2(C)C)(C)C)N1CCOC)C
Current Developer:
A-836339 was developed by Abbott Laboratories.
1.PET imaging of cannabinoid type 2 receptors with [
Pottier G;Gómez-Vallejo V;Padro D;Boisgard R;Dollé F;Llop J;Winkeler A;Martín A J Cereb Blood Flow Metab. 2017 Mar;37(3):1163-1178. doi: 10.1177/0271678X16685105. Epub 2017 Jan 12.
Cannabinoid type 2 receptors (CB2R) have emerged as promising targets for the diagnosis and therapy of brain pathologies. However, no suitable radiotracers for accurate CB2R mapping have been found to date, limiting the investigation of the CB2 receptor expression using positron emission tomography (PET) imaging. In this work, we report the evaluation of the in vivo expression of CB2R with [;11;C]A-836339 PET after cerebral ischemia and in two rat models of neuroinflammation, first by intrastriatal LPS and then by AMPA injection. PET images and in vitro autoradiography showed a lack of specific [;11;C]A-836339 uptake in these animal models demonstrating the limitation of this radiotracer to image CB2 receptor under neuroinflammatory conditions. Further, using immunohistochemistry, the CB2 receptor displayed a modest expression increase after cerebral ischemia, LPS and AMPA models. Finally, [;18;F]DPA-714-PET and immunohistochemistry demonstrated decreased neuroinflammation by a selective CB2R agonist, JWH133. Taken together, these findings suggest that [;11;C]A-836339 is not a suitable radiotracer to monitor in vivo CB2R expression by using PET imaging. Future studies will have to investigate alternative radiotracers that could provide an accurate binding to CB2 receptors following brain inflammation.
2.Central and peripheral sites of action for CB₂ receptor mediated analgesic activity in chronic inflammatory and neuropathic pain models in rats.
Hsieh GC;Pai M;Chandran P;Hooker BA;Zhu CZ;Salyers AK;Wensink EJ;Zhan C;Carroll WA;Dart MJ;Yao BB;Honore P;Meyer MD Br J Pharmacol. 2011 Jan;162(2):428-40. doi: 10.1111/j.1476-5381.2010.01046.x.
BACKGROUND AND PURPOSE: ;Cannabinoid CB₂ receptor activation by selective agonists has been shown to produce analgesic effects in preclinical models of inflammatory and neuropathic pain. However, mechanisms underlying CB₂-mediated analgesic effects remain largely unknown. The present study was conducted to elucidate the CB₂ receptor expression in 'pain relevant' tissues and the potential sites of action of CB₂ agonism in rats.;EXPERIMENTAL APPROACH: ;Expression of cannabinoid receptor mRNA was evaluated by quantitative RT-PCR in dorsal root ganglia (DRGs), spinal cords, paws and several brain regions of sham, chronic inflammatory pain (CFA) and neuropathic pain (spinal nerve ligation, SNL) rats. The sites of CB₂ mediated antinociception were evaluated in vivo following intra-DRG, intrathecal (i.t.) or intraplantar (i.paw) administration of potent CB₂-selective agonists A-836339 and AM1241.;KEY RESULTS: ;CB₂ receptor gene expression was significantly up-regulated in DRGs (SNL and CFA), spinal cords (SNL) or paws (CFA) ipsilateral to injury under inflammatory and neuropathic pain conditions. Systemic A-836339 and AM1241 produced dose-dependent efficacy in both inflammatory and neuropathic pain models.
3.From Structure-Activity Relationships on Thiazole Derivatives to the In Vivo Evaluation of a New Radiotracer for Cannabinoid Subtype 2 PET Imaging.
Caillé F;Cacheux F;Peyronneau MA;Jego B;Jaumain E;Pottier G;Ullmer C;Grether U;Winkeler A;Dollé F;Damont A;Kuhnast B Mol Pharm. 2017 Nov 6;14(11):4064-4078. doi: 10.1021/acs.molpharmaceut.7b00746. Epub 2017 Oct 18.
Upregulation of the cannabinoid type 2 receptors (CB;2;R) unveils inflammation processes of pathological disorders, such as cancer, pain, or neurodegenerative diseases. Among others, CB;2;R agonist A-836339 has been labeled with carbon-11 for PET imaging of the CB;2;R and displayed promising results in a mouse model of Alzheimer's disease. The aim of the present work was to develop fluorinated analogs of A-836339 for labeling with fluorine-18 to design a new PET tracer for CB;2;R imaging. Seven fluorinated analogs of A-836339 were synthesized in two to three steps and their binding affinities and selectivities for both the human and the mouse CB;2;R were measured as well as their early ADME profiles. Among them, compound 2f (K;ihCB2R; = 0.1 nM, K;ihCB1R;/K;ihCB2R; = 300) displayed high affinity and selectivity for CB;2;R but also promising lipophilicity, kinetic solubility, and membrane permeation properties and was further selected for in vitro metabolism studies. Incubation of 2f with human or rat liver microsomes followed by LC/MS analysis revealed the presence of six different metabolites mainly resulting from oxidation reactions. A tosylated precursor of 2f was synthesized in two steps and radiolabeled with fluorine-18 to afford [;18;F]2f in 15 ± 5% radiochemical yield and a molar activity of 110 ± 30 GBq/μmol.
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CAS 959746-77-1 A-836339

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