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SML2417

Sigma-Aldrich

ORG 25543 Hydrochloride

≥95% (HPLC)

Synonym(s):

4-Benzyloxy-3,5-dimethoxy-N-[(1-dimethylaminocyclopentyl)methyl]benzamide hydrochloride, N-[[1-(Dimethylamino)cyclopentyl]methyl]-3,5-dimethoxy-4-(phenylmethoxy)benzamide hydrochloride, ORG 25,543 hydrochloride, ORG 25543 hydrochloride, ORG-25543 hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C24H32N2O4·HCl
CAS Number:
495076-64-7
Molecular Weight:
448.98
MDL number:
MFCD23701926
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥95% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

room temp

InChI

1S/C24H32N2O4.ClH/c1-26(2)24(12-8-9-13-24)17-25-23(27)19-14-20(28-3)22(21(15-19)29-4)30-16-18-10-6-5-7-11-18;/h5-7,10-11,14-15H,8-9,12-13,16-17H2,1-4H3,(H,25,27);1H

InChI key

NIPQJILJYQVZJR-UHFFFAOYSA-N

Biochem/physiol Actions

ORG 25543 is a brain-penetrant (free brain/plasma ratio = 0.53; 35 min post 2 or 20 mg/kg i.v. in mice), high-affinity, potent and selective glycine transporter 2 (GlyT-2; GlyT2) inhibitor (human & mouse pIC50 = 7.9/ GlyT2 vs <4/GlyT1) with great selectivity over a panel of 56 receptor and channel proteins. ORG 25543 is more potent and selective than the brain-impermeable ALX-1393 (GlyT2/GlyT1 pIC50 = 7.1/5.4) and exhibits high in vivo efficacy in a murine diabetic neuropathic pain model (ED50 = 0.07-0.16 mg/kg i.v.; Emin = 0.01 mg/kg). ORG 25543 is practically irreversible due to its tight-binding nature, suboptimal dosage should be applied in vivo to allow low target occupancy only and minimize acute toxicity.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Mingorance-Le Meur et al.
British journal of pharmacology, 170(5), 1053-1063 (2013-08-22)
Available medications for chronic pain provide only partial relief and often cause unacceptable side effects. There is therefore a need for novel molecular targets to develop new therapeutics with improved efficacy and tolerability. Despite encouraging efficacy data in rodents with
Katsuya Morita et al.
The Journal of pharmacology and experimental therapeutics, 326(2), 633-645 (2008-05-02)
Neuropathic pain is refractory against conventional analgesics, and thus novel medicaments are desired for the treatment. Glycinergic neurons are localized in specific brain regions, including the spinal cord, where they play an important role in the regulation of pain signal
M A Gradwell et al.
The Journal of physiology, 595(23), 7185-7202 (2017-09-15)
Spinal parvalbumin-expressing interneurons have been identified as a critical source of inhibition to regulate sensory thresholds by gating mechanical inputs in the dorsal horn. This study assessed the inhibitory regulation of the parvalbumin-expressing interneurons, showing that synaptic and tonic glycinergic
Cristina Romei et al.
Brain research bulletin, 127, 100-110 (2016-10-28)
There is increasing evidence for the neuronal coexistence of classical transmitters. Implications in favor of cotransmission have often been represented by the identification, in the same neuron, of the putative cotransmitters, their synthetic enzymes and/or their vesicular transporters. In contrast
Cristina Romei et al.
Journal of neurochemistry, 119(1), 50-63 (2011-07-28)
Glycine release provoked by ion dysregulations typical of some neuropathological conditions was analyzed in cerebellar synaptosomes selectively pre-labelled with [³H]glycine through GlyT2 transporters and exposed in superfusion to KCl, 4-aminopyridine (4-AP) or veratridine. The overflows caused by relatively low concentrations
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