| Identification | Back Directory | [Name]
(R,S)-AM1241 | [CAS]
444912-48-5 | [Synonyms]
(R,S)-AM1241
AM1241
(AM-1241
(R,S)-AM1241 USP/EP/BP
(R,S)-3-(2-Iodo-5-nitrobenzoyl)-1-(1-methyl-2-piperidinylmethyl)-1H-indole
(3-iodo-5-nitrophenyl)-[1-[(1-methylpiperidin-2-yl)methyl]indol-3-yl]methanone
(2-iodo-5-nitrophenyl)-[1-[(1-methylpiperidin-2-yl)methyl]indol-3-yl]methanone
(2-Iodo-5-nitrophenyl)[1-[(1-methyl-2-piperidinyl)methyl]-1H-indol-3-yl]methanone
(2-Iodo-5-nitrophenyl)(1-((1-methylpiperidin-2-yl)methyl)-1H-Indol-3-yl)methanone
Methanone, (2-iodo-5-nitrophenyl)[1-[(1-methyl-2-piperidinyl)methyl]-1H-indol-3-yl]- | [Molecular Formula]
C22H22IN3O3 | [MDL Number]
MFCD11045986 | [MOL File]
444912-48-5.mol | [Molecular Weight]
503.34 |
| Chemical Properties | Back Directory | [Boiling point ]
630.7±55.0 °C(Predicted) | [density ]
1.60±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO: ~18mg/mL at 60°C | [form ]
solid | [pka]
9.73±0.10(Predicted) | [color ]
yellow | [InChI]
1S/C22H22IN3O3/c1-24-11-5-4-6-16(24)13-25-14-19(17-7-2-3-8-21(17)25)22(27)18-12-15(26(28)29)9-10-20(18)23/h2-3,7-10,12,14,16H,4-6,11,13H2,1H3 | [InChIKey]
ZUHIXXCLLBMBDW-UHFFFAOYSA-N | [SMILES]
CN1CCCCC1Cn2cc(C(=O)c3cc(ccc3I)[N+]([O-])=O)c4ccccc24 |
| Hazard Information | Back Directory | [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]
(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. | [Biological Activity]
Potent and selective CB2 receptor agonist (Ki=3.4nM (mouse), Ki=280nM (rat) also in vivo. | [Biochem/physiol Actions]
AM1241 acts as an antinociceptive agent in several animal pain models. It has a potential to delay disease progression in amyotrophic lateral sclerosis (ALS) mouse model. Intrathecal, intravenous or intraperitoneal administration of AM1241 reduces hyperalgesia and allodynia in neuropathic rats. | [target]
CB2 | [References]
[1] B B YAO. In vitro pharmacological characterization of AM1241: a protean agonist at the cannabinoid CB2 receptor?[J]. British Journal of Pharmacology, 2009, 149 2: 145-154. DOI: 10.1038/sj.bjp.0706838
[2] T.PHILIP MALAN JR. . CB2 cannabinoid receptor-mediated peripheral antinociception[J]. PAIN?, 2001, 93 3: Pages 239-245. DOI: 10.1016/s0304-3959(01)00321-9
[3] HAVA KARSENTY AVRAHAM. The cannabinoid CB2 receptor agonist AM1241 enhances neurogenesis in GFAP/Gp120 transgenic mice displaying deficits in neurogenesis[J]. British Journal of Pharmacology, 2013, 171 2: 468-479. DOI: 10.1111/bph.12478
[4] KATHLINE KIM . AM1241, a cannabinoid CB2 receptor selective compound, delays disease progression in a mouse model of amyotrophic lateral sclerosis[J]. European journal of pharmacology, 2006, 542 1: Pages 100-105. DOI: 10.1016/j.ejphar.2006.05.025 |
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