Art. -Nr.: HY-13288

Org 27569

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Org 27569 is a potent CB1 receptor allosteric modulator, which increases agonist binding, yet blocks agonist-induced CB1 signaling.

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Reinheit: 99.75%
CAS. Nr.: 868273-06-7
Formel: C₂₄H₂₈ClN₃O
Molecular Weight:409.95

Speicherung:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 2 years , -20°C, 1 year

Org 27569 Chemical Structure

CAS. Nr.: 868273-06-7

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Use of MCE Products

Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biologische Aktivität
- Beschreibung
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Protokoll
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

Org 27569 is a potent CB1 receptor allosteric modulator, which increases agonist binding, yet blocks agonist-induced CB1 signaling.

Alle Cannabinoid Receptor Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
CHO	EC₅₀	83 nM Compound: 1; Org27569	Positive allosteric modulator activity at human CB1R expressed in CHO cells assessed as enhanced binding of [3H]CP55,940 after 60 mins by liquid scintillation spectrometric analysis Positive allosteric modulator activity at human CB1R expressed in CHO cells assessed as enhanced binding of [3H]CP55,940 after 60 mins by liquid scintillation spectrometric analysis	[PMID: 26529344]
CHO-K1	EC₅₀	324 nM Compound: 1; Org27569	Negative allosteric modulator activity at human CB1R expressed in CHO-K1 cells assessed as effect on CP55,940-induced inhibition of forskolin-induced cAMP accumulation preincubated for 30 mins followed by CP55,940 addition measured for 30 mins by HitHunte Negative allosteric modulator activity at human CB1R expressed in CHO-K1 cells assessed as effect on CP55,940-induced inhibition of forskolin-induced cAMP accumulation preincubated for 30 mins followed by CP55,940 addition measured for 30 mins by HitHunte	[PMID: 26529344]
CHO-K1	EC₅₀	9.05 nM Compound: 1; Org27569	Negative allosteric modulator activity at human CB1R expressed in CHO-K1 cells assessed as inhibition of CP55,940-induced beta-arrestin recruitment preincubated for 30 mins followed by CP55,940 addition measured for 90 mins by PathHunter assay Negative allosteric modulator activity at human CB1R expressed in CHO-K1 cells assessed as inhibition of CP55,940-induced beta-arrestin recruitment preincubated for 30 mins followed by CP55,940 addition measured for 90 mins by PathHunter assay	[PMID: 26529344]
CHO-K1	IC₅₀	2 nM Compound: Org27569	Negative allosteric modulation of human CB1 receptor expressed in CHO-K1 cells assessed as inhibition of CP55940 induced beta arrestin recruitment preincubated for 30 mins followed by addition of CP55940 for 90 mins by chemiluminescence assay Negative allosteric modulation of human CB1 receptor expressed in CHO-K1 cells assessed as inhibition of CP55940 induced beta arrestin recruitment preincubated for 30 mins followed by addition of CP55940 for 90 mins by chemiluminescence assay	[PMID: 27542310]
HEK293	EC₅₀	0.14 μM Compound: 1, Org 27569	Allosteric modulation of human recombinant CB1 receptor expressed in HEK293 cells assessed as stimulation of [3H]CP55940 binding Allosteric modulation of human recombinant CB1 receptor expressed in HEK293 cells assessed as stimulation of [3H]CP55940 binding	[PMID: 22571451]
HEK293	EC₅₀	0.64 μM Compound: 1, ORG27569	Activity at hemagglutinin-tagged human CB1 receptor expressed in HEK293 cells assessed as effect on forskolin-induced cAMP accumulation after 15 mins in presence of CP55,940 by cAMP BRET assay Activity at hemagglutinin-tagged human CB1 receptor expressed in HEK293 cells assessed as effect on forskolin-induced cAMP accumulation after 15 mins in presence of CP55,940 by cAMP BRET assay	[PMID: 26203658]
HEK293	EC₅₀	10.59 μM Compound: 1, ORG27569	Activity at hemagglutinin-tagged human CB1 receptor expressed in HEK293 cells assessed as effect on forskolin-induced cAMP accumulation after 5 mins in presence of CP55,940 by cAMP BRET assay Activity at hemagglutinin-tagged human CB1 receptor expressed in HEK293 cells assessed as effect on forskolin-induced cAMP accumulation after 5 mins in presence of CP55,940 by cAMP BRET assay	[PMID: 26203658]
HEK293	EC₅₀	2.09 μM Compound: 1, ORG27569	Activity at hemagglutinin-tagged human CB1 receptor expressed in HEK293 cells assessed as effect on forskolin-induced cAMP accumulation after 10 mins in presence of CP55,940 by cAMP BRET assay Activity at hemagglutinin-tagged human CB1 receptor expressed in HEK293 cells assessed as effect on forskolin-induced cAMP accumulation after 10 mins in presence of CP55,940 by cAMP BRET assay	[PMID: 26203658]
HEK293	EC₅₀	2.24 μM Compound: 1, ORG27569	Activity at hemagglutinin-tagged human CB1 receptor expressed in HEK293 cells assessed as effect on forskolin-induced cAMP accumulation in presence of CP55,940 by cAMP BRET assay Activity at hemagglutinin-tagged human CB1 receptor expressed in HEK293 cells assessed as effect on forskolin-induced cAMP accumulation in presence of CP55,940 by cAMP BRET assay	[PMID: 26203658]
HEK293	IC₅₀	>10 μM Compound: 1, Org 27569	Allosteric modulation of human recombinant CB2 receptor expressed in HEK293 cells assessed as inhibition of [3H]CP55940 binding Allosteric modulation of human recombinant CB2 receptor expressed in HEK293 cells assessed as inhibition of [3H]CP55940 binding	[PMID: 22571451]

In Vitro

Org 27569 enhances agonist (CP55940) binding, promotes agonist binding to CB1 yet inhibits agonist-induced G protein activation and blocks the agonist-induced conformational changes in TM6. Org 27569 inhibits agonist-induced TM6 movement in CB1 detected by a fluorescent probe on site 342^[2]. Org 27569 produces a significant, but saturable, increase in the level of specific [³H]CP 55,940 binding. Org 27569 (1 μM) inhibits electrically evoked contractions of the mouse vas deferens with the pEC₅₀ and E_max being 8.66±0.11 and 77% (95% confidence limits, 70.6-82.7), respectively^[4]. In hCB1R cells, Org 27569 (1 and 10 μM) behaves as a weak inverse agonist producing a small but significant decrease in basal [³⁵S]GTPγS binding. Org 27569 is less effective as an inhibitor of WIN55212-mediated inhibition of forskolin-stimulated cAMP production. Org 27569 induces a small but significant level of ERK1/2 phosphorylation with an E_max of 19% and pEC₅₀ value of 8.55±0.99^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

ORG 27569 (3.2 and 5.6 mg/kg, i.p.) significantly attenuates cocaine associated cue-induced reinstatement, cocaine priming-induced reinstatement, methamphetamine associated cue-induced reinstatement and methamphetamine priming-induced reinstatement in rat^[1]. Org27569 (30 mg/kg, i.p.) produces CB1-independent hypophagic effects and does not affect the discriminative stimulus effects of anandamide (AEA). Org27569 (100 μg intracerebroventricularly) does not affect the pharmacologic effects of systemically administered CP55,940 compared with vehicle^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Chemical Information

CAS. Nr. 868273-06-7
Appearance Solid
Molecular Weight 409.95
Formel C₂₄H₂₈ClN₃O
Color Off-white to pink
SMILES

ClC1=CC=C(C2=C1)NC(C(NCCC3=CC=C(C=C3)N4CCCCC4)=O)=C2CC
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	2 years
	-20°C	1 year

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : ≥ 52.2 mg/mL (127.33 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

* "≥" means soluble, but saturation unknown.

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

2.4393 mL

12.1966 mL

24.3932 mL

5 mM

0.4879 mL

2.4393 mL

4.8786 mL

10 mM

0.2439 mL

1.2197 mL

2.4393 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: 2.5 mg/mL (6.10 mM); Suspended solution; Need ultrasonic

This protocol yields a suspended solution of 2.5 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)

Solubility: 2.5 mg/mL (6.10 mM); Suspended solution; Need ultrasonic

This protocol yields a suspended solution of 2.5 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 2.5 mg/mL (6.10 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Protokoll

Kinase Assay^[4]

Binding assays are performed with the CB1 receptor agonist [³H]CP 55,940 (0.7 nM) and the CB1 receptor antagonist [³H]SR 141716A (1.2 nM), 1 mg/mL BSA and 50 mM Tris buffer containing 0.1 mM EDTA and 0.5 mM MgCl₂, pH 7.4, in a total assay volume of 500 μL. Binding is initiated by the addition of mouse brain membranes (30 μg). Assays are carried out at 37°C for 60 min before termination by addition of ice-cold wash buffer (50 mM Tris buffer and 1 mg/mL BSA) and vacuum filtration using a 24-well sampling manifold and Whatman GF/B glass-fiber filters that have been soaked in wash buffer at 4°C for 24 h. Each reaction tube is washed five times with a 4-mL aliquot of buffer. The filters are oven-dried for 60 min and then placed in 5 mL of scintillation fluid, and radioactivity is quantitated by liquid scintillation spectrometry. Specific binding is defined as the difference between the binding that occurs in the presence and absence of 1 μM concentrations of the corresponding unlabeled ligand and is 70 to 80% of the total binding.

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Administration^[3]

Following a 1-week acclimation period, CB1 (+/+) and (−/−) mice are food-deprived, given an intraperitoneal injection of Org27569 (30 mg/kg), rimonabant (10 mg/kg; positive control), or vehicle at 23 h, and placed in a plastic cage with access to water. A premeasured amount (2.3-2.6 g) of sweet cereal or standard chow is placed in the test cage from 24 to 26h. All mice receive each treatment condition in a counterbalanced design, with at least 96 h between test days.

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (276 KB)
SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Jing L, et al. Effects of the cannabinoid CB? receptor allosteric modulator ORG 27569 on reinstatement of cocaine- and methamphetamine-seeking behavior in rats. Drug Alcohol Depend. 2014 Oct 1;143:251-6. [Content Brief]

[2]. Fay JF, et al. A key agonist-induced conformational change in the cannabinoid receptor CB1 is blocked by the allosteric ligand Org 27569. J Biol Chem. 2012 Jul 30. [Content Brief]

[3]. Gamage TF, et al. In-vivo pharmacological evaluation of the CB1-receptor allosteric modulator Org-27569. Behav Pharmacol. 2014 Apr;25(2):182-5. [Content Brief]

[4]. Price MR, et al. Allosteric modulation of the cannabinoid CB1 receptor. Mol Pharmacol. 2005 Nov;68(5):1484-95. [Content Brief]

[5]. Baillie GL, et al. CB(1) receptor allosteric modulators display both agonist and signaling pathway specificity. Mol Pharmacol. 2013 Feb;83(2):322-38. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	2.4393 mL	12.1966 mL	24.3932 mL	60.9830 mL
	5 mM	0.4879 mL	2.4393 mL	4.8786 mL	12.1966 mL
	10 mM	0.2439 mL	1.2197 mL	2.4393 mL	6.0983 mL
	15 mM	0.1626 mL	0.8131 mL	1.6262 mL	4.0655 mL
	20 mM	0.1220 mL	0.6098 mL	1.2197 mL	3.0492 mL
	25 mM	0.0976 mL	0.4879 mL	0.9757 mL	2.4393 mL
	30 mM	0.0813 mL	0.4066 mL	0.8131 mL	2.0328 mL
	40 mM	0.0610 mL	0.3049 mL	0.6098 mL	1.5246 mL
	50 mM	0.0488 mL	0.2439 mL	0.4879 mL	1.2197 mL
	60 mM	0.0407 mL	0.2033 mL	0.4066 mL	1.0164 mL
	80 mM	0.0305 mL	0.1525 mL	0.3049 mL	0.7623 mL
	100 mM	0.0244 mL	0.1220 mL	0.2439 mL	0.6098 mL

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Org 27569

GPCR/G Protein Compound Library

Neuronal Signaling Compound Library

Pain-Related Compound Library

Membrane Protein-targeted Compound Library

Membrane Receptor-targeted Compound Library

Allosteric Modulators (AMs) Compound Library

Bioactive Compound Library Max

MCE Bioactive Compound Library

Bioactive Compound Library

High-Throughput Bioactive Compound Library

Lactylation Compound Library

Alle Cannabinoid Receptor Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Lösungsmittel & Löslichkeit

Protokoll

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Org 27569

GPCR/G Protein Compound Library

Neuronal Signaling Compound Library

Pain-Related Compound Library

Membrane Protein-targeted Compound Library

Membrane Receptor-targeted Compound Library

Allosteric Modulators (AMs) Compound Library

Bioactive Compound Library Max

MCE Bioactive Compound Library

Bioactive Compound Library

High-Throughput Bioactive Compound Library

Lactylation Compound Library

Alle Cannabinoid Receptor Isoform-spezifische Produkte anzeigen

Biologische Aktivität

Chemical Information

Lösungsmittel & Löslichkeit

Protokoll

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

Org 27569 Related Classifications

HY-13288 Related Classifications