444912-48-5

Basic information

• Product Name: (R,S)-AM1241
• Synonyms: (R,S)-AM1241;(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)-1H-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]indol-3-yl]methanone
• CAS NO: 444912-48-5
• Molecular Formula: C22H22IN3O3
• Molecular Weight: 503.34
• Mol File: 444912-48-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 630.709 °C at 760 mmHg
• Flash Point: 335.241 °C
• Appearance: yellow/
• Density: 1.606 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.696
• Solubility: DMSO: ~18mg/mL at 60°C
• PKA: 9.73±0.10(Predicted)
• CAS DataBase Reference: (R,S)-AM1241(CAS DataBase Reference)
• NIST Chemistry Reference: (R,S)-AM1241(444912-48-5)
• EPA Substance Registry System: (R,S)-AM1241(444912-48-5)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37-45
• WGK Germany: 3
• Hazardous Substances Data: 444912-48-5(Hazardous Substances Data)

Usage

Description

(R,S)-AM1241 is a cannabinoid (CB) receptor agonist that is selective for CB2 over CB1. It exhibits neutral antagonist and partial agonist activity, depending on the assay utilized, and acts in a species-dependent manner. In humans, it acts as an agonist at CB2 receptors, while in rats and mice, it acts as an inverse agonist. (R,S)-AM1241 has been found to produce antinociception to thermal stimuli in rats and is neuroprotective, preventing HIV-1 glycoprotein Gp120-induced apoptosis in primary human and murine neural progenitor cells.

Uses

Used in Pain Management:
(R,S)-AM1241 is used as a cannabinoid CB2 agonist for studying its inhibitory effect on bone cancer-induced pain. The antinociceptive actions of (R,S)-AM1241 are blocked by the CB2 receptor-selective antagonist AM630 but not by the CB1 receptor-selective antagonist AM251.
Used in Bone Loss Prevention:
(R,S)-AM1241 is used as a cannabinoid CB2 agonist to study its effect on bone loss, particularly in the context of bone cancer.
Used in Cell Proliferation Studies:
(R,S)-AM1241 is used as a cannabinoid CB2 agonist to study its interaction with 17β-estradiol on proliferation activity in primary human osteoblasts.
Used in Antinociception Research:
(R,S)-AM1241 is used as a cannabinoid CB2 agonist to evaluate the sites of CB2 mediated antinociception in vivo.
Used in Neuroprotection:
(R,S)-AM1241 is used as a neuroprotective agent, preventing HIV-1 glycoprotein Gp120-induced apoptosis in primary human and murine neural progenitor cells and increasing cell survival and differentiation.
Used in Hippocampal Neurogenesis:
(R,S)-AM1241 is used to increase hippocampal neurogenesis and decrease astroand gliogenesis in GFAP/Gp120 transgenic mice when administered at a dose of 10 mg/kg daily for ten days.
Used in Amytrophic Lateral Sclerosis (ALS) Research:
(R,S)-AM1241 is used to delay motor impairment in a murine model of amytrophic lateral sclerosis (ALS).
Used in Pharmaceutical Industry:
(R,S)-AM1241 is used as a compound from the aminkalkylindole family, exerting potent and selective agonist activity for the cannabinoid receptor CB2.

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.

InChI:InChI=1/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

Upstream product

• 907160-87-6 (1-methylpiperidin-2-yl)methyl methanesulfonate 
• 120-72-9 indole 
• 860567-09-5 2-iodo-5-nitrobenzoic acid chloride 

Relevant articles and documents

In vitro pharmacological characterization of AM1241: A protean agonist at the cannabinoid CB2 receptor?

Background and purpose: The CB2 receptor has been proposed as a novel target for the treatment of pain, and CB2 receptor agonists defined in in vitro assays have demonstrated analgesic activity in animal models. Based on its in vivo analgesic efficacy, AM1241 has been classified as a CB2-selective agonist. However, in vitro characterization of AM1241 in functional assays has not been reported. Experimental approach: In this study, AM1241 was characterized across multiple in vitro assays employing heterologous recombinant receptor expression systems to assess its binding potencies at the human CB2 and CB1 receptors and its functional efficacies at the human CB2 receptor. Key results: AM1241 exhibited distinct functional properties depending on the assay conditions employed, a unique profile in contrast to those of the agonist CP 55,940 and the inverse agonist SR144528. AM1241 displayed neutral antagonist activities in FLIPR and cyclase assays. However, when cyclase assays were performed using lower forskolin concentrations for stimulation, AM1241 exhibited partial agonist efficacy. In addition, it behaved as a partial agonist in ERK (or MAP) kinase assays. Conclusions and implications: The unusual phenomenon of inconsistent functional efficacies suggests that AM1241 is a protean agonist at the CB 2 receptor. We postulate that functional efficacies displayed by protean agonists in various assay systems may depend on the levels of receptor constitutive activities exhibited in the assay systems, and therefore, efficacies observed in in vitro assays may not predict in vivo activities.