BML-190 (Indomethacin morpholinylamide; IMMA)

Alias:
Cat No.:V1520 Purity: ≥98%
BML-190 (formerly IMMA; LM-4131; BML-190; LM4131; BML190; Indomethacin morpholinylamide), is a potent and selective cannabinoid CB2 receptor inverse agonist with potential anti-inflammatory activity.
BML-190 (Indomethacin morpholinylamide; IMMA) Chemical Structure CAS No.: 2854-32-2
Product category: Cannabinoid Receptor
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

BML-190 (formerly IMMA; LM-4131; BML-190; LM4131; BML190; Indomethacin morpholinylamide), is a potent and selective cannabinoid CB2 receptor inverse agonist with potential anti-inflammatory activity. It exhibits 50-fold selectivity over the CB1 receptor and activates the cannabinoid CB2 receptor with a Ki of 435 nM.

Biological Activity I Assay Protocols (From Reference)
Targets
CB2 ( Ki = 435 nM )
ln Vitro

In vitro activity: BML-190 prefers CB2 receptors over CB1 receptors by a factor of 50. BML-190 enhances the forskolin-stimulated cAMP accumulation in HEK-293 cells that express the human CB2 receptor consistently. Cells expressing the CB2 receptor have lower basal levels of inositol phosphate production when exposed to BML-190. BML-190 at 10 μM reduces the accumulation of inositol phosphates by 38%. [1] An aminoalkylindole is BML-190. There are at least 15 metabolic products produced by BML-190. [2] LPS-induced NO and IL-6 production are inhibited by BML-190 in a concentration-dependent manner. Moreover, BML-190 prevents COX-2 induction and PGE2 synthesis brought on by LPS. [3]

ln Vivo

Cell Assay
For 20 to 24 hours, 293/CB2 cells are labeled with [3H]adenine (1 μCi/mL) in MEM containing 1% FBS. After 30 minutes at 37°C, labeled cells are challenged with 50 μM forskolin and the relevant BML-190, and the accumulation of cAMP is measured. Using transfection reagents, 2 × 105 293/CB2 cells are transiently transfected with 16z44 and/or pcDNA3 for IP assays. In order to produce IP, cells are labeled, challenged with BML-190, and assayed. For every data point, triplicates are run, and each ligand is tested in at least three different trials.
Animal Protocol


References

[1]. FEBS Lett . 2003 Feb 11;536(1-3):157-60.

[2]. Eur J Pharm Sci . 2010 Sep 11;41(1):163-72.

[3]. J Cell Biochem . 2001;81(4):715-23.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C23H23CLN2O4
Molecular Weight
426.89
Exact Mass
426.13
Elemental Analysis
C, 64.71; H, 5.43; Cl, 8.30; N, 6.56; O, 14.99
CAS #
2854-32-2
Related CAS #
2854-32-2
Appearance
Solid powder
SMILES
CC1=C(C2=C(N1C(=O)C3=CC=C(C=C3)Cl)C=CC(=C2)OC)CC(=O)N4CCOCC4
InChi Key
BJSDNVVWJYDOLK-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H23ClN2O4/c1-15-19(14-22(27)25-9-11-30-12-10-25)20-13-18(29-2)7-8-21(20)26(15)23(28)16-3-5-17(24)6-4-16/h3-8,13H,9-12,14H2,1-2H3
Chemical Name
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]-1-morpholin-4-ylethanone
Synonyms

BML-190; IMMA; LM-4131; BML 190; LM4131; BML190; LM 4131; Indomethacin Morpholinylamide

HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 22~50 mg/mL (51.5~117.1 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.86 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.3425 mL 11.7126 mL 23.4252 mL
5 mM 0.4685 mL 2.3425 mL 4.6850 mL
10 mM 0.2343 mL 1.1713 mL 2.3425 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Total ion chromatogram (L) and reconstructed ion chromatograms (RICs) for BML-190 and its metabolites. Eur J Pharm Sci . 2010 Sep 11;41(1):163-72.
  • MS/MS spectrum obtained by collision-induced dissociation of the protonated BML-190 at m/z 427 and its proposed fragmentation pathways. Eur J Pharm Sci . 2010 Sep 11;41(1):163-72.
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