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AR-M 1000390 hydrochloride

Names

[ CAS No. ]:
209808-47-9

[ Name ]:
AR-M 1000390 hydrochloride

[Synonym ]:
Benzamide, N,N-diethyl-4-(phenyl-4-piperidinylidenemethyl)-, hydrochloride (1:1)
N,N-Diethyl-4-[phenyl(4-piperidinylidene)methyl]benzamide hydrochloride (1:1)
ARM390 Hydrochloride
N,N-Diethyl-4-(phenyl-4-piperidinylidenemethyl)benzamide Hydrochloride
AR-M 1000390 (hydrochloride)

Biological Activity

[Description]:

AR-M 1000390 hydrochloride is an exceptionally selective, potent δ opioid receptor agonist with an EC50 of 7.2±0.9 nM for δ agonist potency.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Opioid Receptor
Signaling Pathways >> Neuronal Signaling >> Opioid Receptor
Research Areas >> Neurological Disease

[Target]

EC50: 7.2±0.9 nM (δ opioid receptor)[1]


[In Vitro]

AR-M 1000390 (Compound 6a) exhibits the binding affinities (IC50) of 0.87±0.23 nM for the δ opioid receptor and extremely high selectivity over the µ receptor (IC50=3800±172 nM) and the κ receptor (IC50=7470±606 nM)[1]. RINm5F cells are treated with AR-M 1000390 (AR-M100390) and Cyclizine for 16-24 h before measurement of intracellular and secreted insulin levels. AR-M 1000390 mediates a dose-dependent decrease in insulin content with a maximal inhibition of ~90% at the highest concentration tested (10 μM)[2].

[In Vivo]

Rats are treated with 5, 100, and 600 μmol/kg of AR-M 1000390 (AR-M100390) for 3 and/or 7 days; another group of rats treated with 600 μmol/kg of compound are allowed to recover for 14 days. AR-M 1000390 (600 μmol/kg) causes vacuolation in the β-cell of the rat pancreas that is associated with depletion of insulin and hyperglycemia after 7 days of dosing. Treatment of rats with 600 μmol/kg of AR-M 1000390 results in vacuolation of the β-cell of the rat pancreas that is similar to that reported for cyclizine and cyproheptadine[2].

[Cell Assay]

RINm5F cells are seeded in 24-well plates and treated with vehicle (DMSO), 10 μM AR-M 1000390 (AR-M100390), and 10 μM Cyclizine in serum-free medium; cells are rinsed with phosphate-buffered saline and stored at -80°C until analysis. RNA is isolated with the RNeasy purification system with DNAse treatment[2].

[Animal admin]

Rats[2] Han Wistar rats (six per treatment group) are treated with vehicle (saline) or 5, 100, and 600 μmol/kg/day of AR-M 1000390 (AR-M100390) for 7 days. A separate group of rats are treated with 600 μmol/kg/day for 7 days followed by a 14-day recovery period. Another group is treated with 600 μmol/kg/day for 3 days. Blood sampling for glucose, lipids, and insulin measurements are taken on days 2, 4, 8, and 22. Blood sampling for AR-M 1000390 concentration measurements are collected on days 4 and 8. The animals are euthanized with CO2 on days 4, 8, and 22 and the pancreas isolated and processed for histopathology, insulin immunohistochemistry, and insulin mRNA analyses[2].

[References]

[1]. Wei ZY, et al. N,N-Diethyl-4-(phenylpiperidin-4-ylidenemethyl)benzamide: a novel, exceptionally selective, potent delta opioid receptor agonist with oral bioavailability and its analogues. J Med Chem. 2000 Oct 19;43(21):3895-905.

[2]. Otieno MA, et al. Mechanistic investigation of N,N-diethyl-4-(phenyl-piperidin-4-ylidenemethyl)-benzamide-inducedinsulin depletion in the rat and RINm5F cells. Toxicol Sci. 2008 Sep;105(1):221-9.


[Related Small Molecules]

PZM-21 | Loperamide hydrochloride | Oliceridine hydrochloride | ADL5859 HCl | JDTic (dihydrochloride) | Naltrindole hydrochloride | LY-2456302 | JTC-801 | Matrine | Met-Enkephalin acetate salt | Cebranopadol | Leu-Enkephalin | DAMGO | Sinomenine HCl | SR17018

Chemical & Physical Properties

[ Molecular Formula ]:
C23H29ClN2O

[ Molecular Weight ]:
384.942

[ Exact Mass ]:
384.196838

[ PSA ]:
32.34000

[ LogP ]:
5.48470

[ Storage condition ]:
2-8℃

Related Compounds