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经验公式(希尔记法):
C21H19Cl2IN4O2
化学文摘社编号:
分子量:
557.21
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
产品名称
AM281, ≥98% (HPLC)
InChI key
AJFFBPZYXRNAIC-UHFFFAOYSA-N
SMILES string
Cc1c(nn(-c2ccc(Cl)cc2Cl)c1-c3ccc(I)cc3)C(=O)NN4CCOCC4
InChI
1S/C21H19Cl2IN4O2/c1-13-19(21(29)26-27-8-10-30-11-9-27)25-28(18-7-4-15(22)12-17(18)23)20(13)14-2-5-16(24)6-3-14/h2-7,12H,8-11H2,1H3,(H,26,29)
assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
white
solubility
DMSO: >6 mg/mL
H2O: insoluble
storage temp.
2-8°C
Quality Level
Gene Information
rat ... Cnr1(25248)
Application
AM281 has been used as a cannabinoid 1 receptor antagonist:
- to study its effects on memory deficit following naloxone-precipitated morphine withdrawal in mice
- to study the role of CB1 receptor system in modulating acetaldehyde-induced effects in rats during the extinction-, relapse-, and conflict-experiments
- to study its effect on scopolamine-induced memory deficit using object recognition paradigm
- to block synthetic cannabinoid (HU210)-induced analgesia in the ventrolateral orbital cortex (VLO) to evaluate the effect of CB1 receptors on the VLO modulation of pain
Biochem/physiol Actions
AM281 is less lipophilic compared to its analog SR 141716A, a cannabinoid receptor antagonist. AM281 may prevent memory deficit post morphine withdrawal by inhibiting cannabinoid receptors in mice.
Potent and selective CB1 cannabinoid receptor antagonist/inverse agonist
Features and Benefits
This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 2 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
存储类别
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Yuwei Wu et al.
Neuroscience letters, 736, 135286-135286 (2020-08-04)
The prefrontal ventrolateral orbital cortex (VLO) is involved in antinociception. It has been found that dopamine receptors, adrenoceptors, serotonin receptors and μ-opioid receptors are involved in this effect through direct/indirect activation of the VLO output neurons. However, the effect of
Golnaz Vaseghi et al.
Basic & clinical pharmacology & toxicology, 111(3), 161-165 (2012-03-21)
Morphine withdrawal leads to the activation of endocannabinoid system and cognitive deficits. The aim of this study was to evaluate the effects of AM281, a cannabinoid antagonist/inverse agonist, on memory deficit following naloxone-precipitated morphine withdrawal in mice. Male mice were
A N Gifford et al.
Neuroscience letters, 238(1-2), 84-86 (1998-02-17)
The SPECT ligand AM 281, a less lipophilic analog of the cannabinoid receptor antagonist SR 141716A, robustly potentiated electrically-evoked release of acetylcholine from superfused hippocampal slices and prevented the inhibition of acetylcholine release by the cannabimimetic drug WIN 55212-2. These
Francisco Molina-Holgado et al.
Molecular and cellular neurosciences, 28(1), 189-194 (2004-12-21)
Cannabinoids (CBs) are neuroprotective in vivo and in vitro, but the mechanisms of their actions are unknown. The aim of this study was to elucidate the signaling pathways that mediate the protective effect of CBs on primary cultured neurons. The
Edgar Alfonso Romero-Sandoval et al.
Molecular pain, 5, 25-25 (2009-05-30)
Cannabinoid receptor type 2 (CBR2) inhibits microglial reactivity through a molecular mechanism yet to be elucidated. We hypothesized that CBR2 activation induces an anti-inflammatory phenotype in microglia by inhibiting extracellular signal-regulated kinase (ERK) pathway, via mitogen-activated protein kinase-phosphatase (MKP) induction.
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