(2-iodo-5-nitrophenyl)(1-((1-methylpiperidin-2-yl)methyl)-1H-indol-3-yl)methanone

Base Information Edit

Chemical Name:(2-iodo-5-nitrophenyl)(1-((1-methylpiperidin-2-yl)methyl)-1H-indol-3-yl)methanone
CAS No.:444912-48-5
Molecular Formula:C₂₂H₂₂IN₃O₃
Molecular Weight:503.339
Hs Code.:
European Community (EC) Number:636-937-2
UNII:DLM851L3RD
DSSTox Substance ID:DTXSID301017015
Nikkaji Number:J1.955.911D
Wikipedia:AM-1241
Wikidata:Q4652487
Pharos Ligand ID:9A7TDPVVGR6B
ChEMBL ID:CHEMBL408430
Mol file:444912-48-5.mol

(2-iodo-5-nitrophenyl)(1-((1-methylpiperidin-2-yl)methyl)-1H-indol-3-yl)methanone

Synonyms:AM 1241;AM1241

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Chemical Property of (2-iodo-5-nitrophenyl)(1-((1-methylpiperidin-2-yl)methyl)-1H-indol-3-yl)methanone Edit

Chemical Property:

Vapor Pressure:0mmHg at 25°C
Refractive Index:1.696
Boiling Point:630.709 °C at 760 mmHg
PKA:9.73±0.10(Predicted)
Flash Point:335.241 °C
PSA：71.06000
Density:1.606 g/cm³
LogP:5.33050
Solubility.:DMSO: ~18mg/mL at 60°C
XLogP3:4.7
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:503.07059
Heavy Atom Count:29
Complexity:613

Purity/Quality:

Safty Information:

Pictogram(s): Xn
Hazard Codes:Xn
Statements: 36/37/38-42/43
Safety Statements: 22-26-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Canonical SMILES:CN1CCCCC1CN2C=C(C3=CC=CC=C32)C(=O)C4=C(C=CC(=C4)[N+](=O)[O-])I
Description AM1241 is a cannabinoid (CB) receptor agonist that is selective for CB2 over CB1 with Ki values of 7.1 and 580 nM for human recombinant receptors transfected into HEK and CHO cells, respectively, in a radioligand binding assay. It is considered a protean agonist as it has neutral antagonist and partial agonist activity, depending on the assay utilized. It is also acts in a species-dependent manner in vitro, acting as an agonist at human CB2 receptors (EC50 = 190 nM) but an inverse agonist at rat and mouse CB2 receptors (EC50s = 216 and 463 nM, respectively). AM1241 produces antinociception to thermal stimuli in rat hindpaw. The antinociceptive actions of AM1241 were blocked by the CB2 receptor-selective antagonist AM630 but not by the CB1 receptor-selective antagonist AM251 . AM1241 is neuroprotective, preventing HIV-1 glycoprotein Gp120-induced apoptosis in primary human and murine neural progenitor cells and increasing cell survival and differentiation. It increases hippocampal neurogenesis and decreases astro- and gliogenesis in GFAP/Gp120 transgenic mice when administered at a dose of 10 mg/kg daily for ten days. AM1241 also delays motor impairment in a murine model of amytrophic lateral sclerosis (ALS).
Uses (R,S)-AM1241 has been used as a cannabinoid CB2 agonist: to study its inhibitory effect on bone cancer-induced pain and bone loss to study the effect of its interaction with 17βestradiol on proliferation activity in primary human osteoblasts to evaluate the sites of CB2 mediated antinociception in vivo. (2-Iodo-5-nitrophenyl)[1-[(1-methyl-2-piperidinyl)methyl]-1H-indol-3-yl]methanone is a compound from the aminkalkylindole family which exerts potent and selective agonist activity for the cannabinoid receptor CB2.

Technology Process of (2-iodo-5-nitrophenyl)(1-((1-methylpiperidin-2-yl)methyl)-1H-indol-3-yl)methanone

There total 3 articles about (2-iodo-5-nitrophenyl)(1-((1-methylpiperidin-2-yl)methyl)-1H-indol-3-yl)methanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 120-72-9
indole

: 444912-51-0,444912-48-5,444912-53-2
(2-iodo-5-nitrophenyl)-[1-[(1-methylpiperidin-2-yl)methyl]indol-3-yl]methanone

Guidance literature:: Multi-step reaction with 2 steps

1: EtMgBr; ZnCl₂

2: NaH

With ethylmagnesium bromide; sodium hydride; zinc(II) chloride;
DOI:10.1038/sj.bjp.0706838

Reference yield:

: 860567-09-5
2-iodo-5-nitrobenzoic acid chloride

: 444912-51-0,444912-48-5,444912-53-2
(2-iodo-5-nitrophenyl)-[1-[(1-methylpiperidin-2-yl)methyl]indol-3-yl]methanone

Guidance literature:: Multi-step reaction with 2 steps

1: EtMgBr; ZnCl₂

2: NaH

With ethylmagnesium bromide; sodium hydride; zinc(II) chloride;
DOI:10.1038/sj.bjp.0706838