A-836339

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 530627

CAS#: 959746-77-1

Description: A-836339 is a drug developed by Abbott Laboratories that acts as a potent cannabinoid receptor full agonist. It is selective for CB2, with Ki values of 0.64 nM at CB2 vs 270 nM at the psychoactive CB1 receptor, but while it exhibits selective analgesic, anti-inflammatory and anti-hyperalgesic effects at low doses, its high efficacy at both targets results in typical cannabis-like effects appearing at higher doses, despite its low binding affinity for CB1.


Price and Availability

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A-836339 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 530627
Name: A-836339
CAS#: 959746-77-1
Chemical Formula: C16H26N2O2S
Exact Mass: 310.1715
Molecular Weight: 310.456
Elemental Analysis: C, 61.90; H, 8.44; N, 9.02; O, 10.31; S, 10.33


Synonym: A-836339; A 836339; A836339; A-836,339; A 836,339; A836,339;

IUPAC/Chemical Name: (Z)-N-(3-(2-methoxyethyl)-4,5-dimethylthiazol-2(3H)-ylidene)-2,2,3,3-tetramethylcyclopropane-1-carboxamide

InChi Key: JKGIMVBQKSRTGX-VKAVYKQESA-N

InChi Code: 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/b17-14-

SMILES Code: CC1=C(C)N(CCOC)/C(S1)=N/C(C2C(C)(C)C2(C)C)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Pottier G, Gómez-Vallejo V, Padro D, Boisgard R, Dollé F, Llop J, Winkeler A, Martín A. PET imaging of cannabinoid type 2 receptors with [(11)C]A-836339 did not evidence changes following neuroinflammation in rats. J Cereb Blood Flow Metab. 2017 Mar;37(3):1163-1178. doi: 10.1177/0271678X16685105. Epub 2017 Jan 12. PubMed PMID: 28079433; PubMed Central PMCID: PMC5363492.

2: Moldovan RP, Teodoro R, Gao Y, Deuther-Conrad W, Kranz M, Wang Y, Kuwabara H, Nakano M, Valentine H, Fischer S, Pomper MG, Wong DF, Dannals RF, Brust P, Horti AG. Development of a High-Affinity PET Radioligand for Imaging Cannabinoid Subtype 2 Receptor. J Med Chem. 2016 Sep 8;59(17):7840-55. doi: 10.1021/acs.jmedchem.6b00554. Epub 2016 Aug 23. PubMed PMID: 27500461.

3: Leung K. 2,2,3,3-Tetramethylcyclopropanecarboxylic acid [3-(2-[(11)C]methoxyethyl)-4,5-dimethyl-3H-thiazol-(2Z)-ylidene]amide. 2010 Dec 6 [updated 2011 Jan 27]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK51676/ PubMed PMID: 21290620.

4: 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. Central and peripheral sites of action for CB₂ receptor mediated analgesic activity in chronic inflammatory and neuropathic pain models in rats. Br J Pharmacol. 2011 Jan;162(2):428-40. doi: 10.1111/j.1476-5381.2010.01046.x. PubMed PMID: 20880025; PubMed Central PMCID: PMC3031063.

5: Horti AG, Gao Y, Ravert HT, Finley P, Valentine H, Wong DF, Endres CJ, Savonenko AV, Dannals RF. Synthesis and biodistribution of [11C]A-836339, a new potential radioligand for PET imaging of cannabinoid type 2 receptors (CB2). Bioorg Med Chem. 2010 Jul 15;18(14):5202-7. doi: 10.1016/j.bmc.2010.05.058. Epub 2010 May 25. PubMed PMID: 20554448; PubMed Central PMCID: PMC2903661.

6: McGaraughty S, Chu KL, Dart MJ, Yao BB, Meyer MD. A CB(2) receptor agonist, A-836339, modulates wide dynamic range neuronal activity in neuropathic rats: contributions of spinal and peripheral CB(2) receptors. Neuroscience. 2009 Feb 18;158(4):1652-61. doi: 10.1016/j.neuroscience.2008.11.015. Epub 2008 Nov 14. PubMed PMID: 19063946.

7: Yao BB, Hsieh G, Daza AV, Fan Y, Grayson GK, Garrison TR, El Kouhen O, Hooker BA, Pai M, Wensink EJ, Salyers AK, Chandran P, Zhu CZ, Zhong C, Ryther K, Gallagher ME, Chin CL, Tovcimak AE, Hradil VP, Fox GB, Dart MJ, Honore P, Meyer MD. Characterization of a cannabinoid CB2 receptor-selective agonist, A-836339 [2,2,3,3-tetramethyl-cyclopropanecarboxylic acid [3-(2-methoxy-ethyl)-4,5-dimethyl-3H-thiazol-(2Z)-ylidene]-amide], using in vitro pharmacological assays, in vivo pain models, and pharmacological magnetic resonance imaging. J Pharmacol Exp Ther. 2009 Jan;328(1):141-51. doi: 10.1124/jpet.108.145011. Epub 2008 Oct 17. PubMed PMID: 18931146.