GW 842166X
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 529301

CAS#: 666260-75-9

Description: GW 842166X is a cannabinoid receptor 2 (CB2) agonist potentially for the treatment of inflammatory pain.


Chemical Structure

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GW 842166X
CAS# 666260-75-9

Theoretical Analysis

MedKoo Cat#: 529301
Name: GW 842166X
CAS#: 666260-75-9
Chemical Formula: C18H17Cl2F3N4O2
Exact Mass: 448.07
Molecular Weight: 449.250
Elemental Analysis: C, 48.12; H, 3.81; Cl, 15.78; F, 12.69; N, 12.47; O, 7.12

Price and Availability

Size Price Availability Quantity
5mg USD 285 2 Weeks
10mg USD 450 2 Weeks
25mg USD 850 2 Weeks
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Synonym: GW-842166X; 842166X; 842166; GW-842166; GW842166X; GW842166; GW 842166X; GW 842166

IUPAC/Chemical Name: 2-((2,4-dichlorophenyl)amino)-N-((tetrahydro-2H-pyran-4-yl)methyl)-4-(trifluoromethyl)pyrimidine-5-carboxamide

InChi Key: TWQYWUXBZHPIIV-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H17Cl2F3N4O2/c19-11-1-2-14(13(20)7-11)26-17-25-9-12(15(27-17)18(21,22)23)16(28)24-8-10-3-5-29-6-4-10/h1-2,7,9-10H,3-6,8H2,(H,24,28)(H,25,26,27)

SMILES Code: O=C(C1=CN=C(NC2=CC=C(Cl)C=C2Cl)N=C1C(F)(F)F)NCC3CCOCC3

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).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Biological target: GW842166X is a potent and selective cannabinoid receptor 2 (CB2) agonist with IC50 values of 63 and 91 nM for human and rat CB2, respectively.
In vitro activity: TBD
In vivo activity: The selective CB2 agonist GW842166x exerted neuroprotective effects against 6-hydroxydopamine (6-OHDA)-induced loss of dopaminergic terminals and dopamine release in the striatum, which were blocked by the CB2 antagonist AM630. 6-OHDA-treated mice exhibited anxiogenic- and depressive-like behaviors in the open-field, sucrose preference, novelty-suppressed feeding, marble burying, and forced swim tests but did not show significant changes in the elevated plus-maze and light-dark box test. GW842166x treatments ameliorated 6-OHDA-induced anxiogenic- and depressive-like behaviors, but the effects were blocked by CB2 antagonism, suggesting a CB2-dependent mechanism. Reference: Biomedicines. 2022 Jul 22;10(8):1776. https://pubmed.ncbi.nlm.nih.gov/35892676/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 20.0 44.52
DMF:PBS (pH 7.2) (1:3) 0.3 0.56
DMSO 37.8 84.07
Ethanol 0.3 0.67

Preparing Stock Solutions

The following data is based on the product molecular weight 449.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Liu X, Yu H, Chen B, Friedman V, Mu L, Kelly TJ, Ruiz-Pérez G, Zhao L, Bai X, Hillard CJ, Liu QS. CB2 Agonist GW842166x Protected against 6-OHDA-Induced Anxiogenic- and Depressive-Related Behaviors in Mice. Biomedicines. 2022 Jul 22;10(8):1776. doi: 10.3390/biomedicines10081776. PMID: 35892676; PMCID: PMC9329798. 2. Yu H, Liu X, Chen B, Vickstrom CR, Friedman V, Kelly TJ, Bai X, Zhao L, Hillard CJ, Liu QS. The Neuroprotective Effects of the CB2 Agonist GW842166x in the 6-OHDA Mouse Model of Parkinson's Disease. Cells. 2021 Dec 16;10(12):3548. doi: 10.3390/cells10123548. PMID: 34944056; PMCID: PMC8700250.
In vitro protocol: TBD
In vivo protocol: 1. Liu X, Yu H, Chen B, Friedman V, Mu L, Kelly TJ, Ruiz-Pérez G, Zhao L, Bai X, Hillard CJ, Liu QS. CB2 Agonist GW842166x Protected against 6-OHDA-Induced Anxiogenic- and Depressive-Related Behaviors in Mice. Biomedicines. 2022 Jul 22;10(8):1776. doi: 10.3390/biomedicines10081776. PMID: 35892676; PMCID: PMC9329798. 2. Yu H, Liu X, Chen B, Vickstrom CR, Friedman V, Kelly TJ, Bai X, Zhao L, Hillard CJ, Liu QS. The Neuroprotective Effects of the CB2 Agonist GW842166x in the 6-OHDA Mouse Model of Parkinson's Disease. Cells. 2021 Dec 16;10(12):3548. doi: 10.3390/cells10123548. PMID: 34944056; PMCID: PMC8700250.

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1: Chen JJ, Han S, Cao Y, Chen JZ. The agonist binding mechanism of human CB2 receptor studied by molecular dynamics simulation, free energy calculation and 3D-QSAR studies. Yao Xue Xue Bao. 2013 Sep;48(9):1436-49. PubMed PMID: 24358778.

2: Petrov RR, Ferrini ME, Jaffar Z, Thompson CM, Roberts K, Diaz P. Design and evaluation of a novel fluorescent CB2 ligand as probe for receptor visualization in immune cells. Bioorg Med Chem Lett. 2011 Oct 1;21(19):5859-62. doi: 10.1016/j.bmcl.2011.07.099. PubMed PMID: 21855337; PubMed Central PMCID: PMC3171627.

3: Ostenfeld T, Price J, Albanese M, Bullman J, Guillard F, Meyer I, Leeson R, Costantin C, Ziviani L, Nocini PF, Milleri S. A randomized, controlled study to investigate the analgesic efficacy of single doses of the cannabinoid receptor-2 agonist GW842166, ibuprofen or placebo in patients with acute pain following third molar tooth extraction. Clin J Pain. 2011 Oct;27(8):668-76. doi: 10.1097/AJP.0b013e318219799a. PubMed PMID: 21540741.

4: Giblin GM, O'Shaughnessy CT, Naylor A, Mitchell WL, Eatherton AJ, Slingsby BP, Rawlings DA, Goldsmith P, Brown AJ, Haslam CP, Clayton NM, Wilson AW, Chessell IP, Wittington AR, Green R. Discovery of 2-[(2,4-dichlorophenyl)amino]-N-[(tetrahydro- 2H-pyran-4-yl)methyl]-4-(trifluoromethyl)- 5-pyrimidinecarboxamide, a selective CB2 receptor agonist for the treatment of inflammatory pain. J Med Chem. 2007 May 31;50(11):2597-600. PubMed PMID: 17477516.