BML-190

Names

[ Name ]:
BML-190

[Synonym ]:
2-(1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-1-morpholinoethanone
Indomethacin morpholinamide
Lopac-I-151
BML-190
2-[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-1-(morpholin-4-yl)ethanone
Ethanone (2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-1-(4-morpholinyl)
Tocris-1383
2-Methyl-5-methoxy-3-indolyl-essigsaeure-amid
IMMA
Indomethacin morpholinylamide
Ethanone, 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-1-(4-morpholinyl)-
2-[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-1-(4-morpholinyl)ethanone

Biological Activity

[Description]:

BML-190(IMMA) is a potent and selective CB2 receptor ligand (Ki values are 435 nM and > 2 μM for CB2 and CB1 respectively). IC50 Value: 435 nM(Ki CB2)Target:CB2 receptorin vitro: BML-190 increases the accumulation of cAMP, via forskolin-stimulated mechanism in HEK-293 cells. Alternate studies suggest that BML-190 reduces the toxicity of culture supernatants to SH-SY5Y human neutroblastoma cells. Various research suggests that BML-190 is an essential tool in studying the proliferation of neuroblastoma. BML-190 diminishes LPS-induced NO and IL-6 production in a concentration-dependent manner. BML-190 also inhibits LPS-induced PGE2 production and COX-2 induction. in vivo:

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor

Research Areas >> Cancer

[References]

[1]. Zhang, Qiang; Ma, Peng; Cole, Richard B.; Wang, Guangdi In vitro metabolism of indomethacin morpholinylamide (BML-190), an inverse agonist for the peripheral cannabinoid receptor (CB2) in rat liver microsomes. European Journal of Pharmaceutical Sciences (

[2]. Klegeris, Andis; Bissonnette, Christopher J.; McGeer, Patrick L. Reduction of human monocytic cell neurotoxicity and cytokine secretion by ligands of the cannabinoid-type CB2 receptor. British Journal of Pharmacology (2003), 139(4), 775-786.

[3]. New DC, Wong YH. BML-190 and AM251 act as inverse agonists at the human cannabinoid CB2 receptor: signalling via cAMP and inositol phosphates. FEBS Lett. 2003 Feb 11;536(1-3):157-60.

[Related Small Molecules]

WIN 55212-2 mesylate | AM251 | Taranabant | SR144528 | Bay 59-3074 | Org 27569 | Otenabant | GW842166X | A-836339 | JD-5037 | (±)-SLV319 | Pregnenolone | Anandamide | 2-arachidonoylglycerol | AM1241

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
586.7±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₃H₂₃ClN₂O₄

[ Molecular Weight ]:
426.893

[ Flash Point ]:
308.6±30.1 °C

[ Exact Mass ]:
426.134644

[ PSA ]:
60.77000

[ LogP ]:
2.99

[ Appearance of Characters ]:
solid | off-white

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.625

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: >20mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QD9930000

CHEMICAL NAME :: Morpholine, 4-((2-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolyl) acetyl)-

CAS REGISTRY NUMBER :: 2854-32-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C23-H23-Cl-N2-O4

MOLECULAR WEIGHT :: 426.93

WISWESSER LINE NOTATION :: T56 BNJ BVR DG& C1 GO1 D1V- AT6N DOTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 40 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 114,309,1975

Safety Information

[ WGK Germany ]:
3

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%