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SML2166

Sigma-Aldrich

KML29

≥98% (HPLC)

Synonyme(s) :

1,1,1,3,3,3-Hexafluoropropan-2-yl 4-(dibenzo[d][1,3]dioxol-5-yl(hydroxy)methyl)piperidine-1-carboxylate, 4-[bis(1,3-Benzodioxol-5-yl)hydroxymethyl]-1-piperidinecarboxylic acid 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ester, KML 29, KML-29

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About This Item

Formule empirique (notation de Hill):
C24H21F6NO7
Numéro CAS:
1380424-42-9
Poids moléculaire :
549.42
Numéro MDL:
MFCD22987957
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

InChI

1S/C24H21F6NO7/c25-23(26,27)20(24(28,29)30)38-21(32)31-7-5-13(6-8-31)22(33,14-1-3-16-18(9-14)36-11-34-16)15-2-4-17-19(10-15)37-12-35-17/h1-4,9-10,13,20,33H,5-8,11-12H2

Clé InChI

SXHQLPHDBLTFPM-UHFFFAOYSA-N

Actions biochimiques/physiologiques

KML29, an O-hexafluoroisopropyl (HFIP) carbamate analogue of JZL184. is a potent and orally active monoacylglycerol lipase (monoglyceride lipase; MAGL; MGLL; MGL) inhibitor (IC50 = 5.9/15/43 nM against human/mouse/rat MAGL) that targets MAGL active site with greatly improved selectivity (rat/mouse ABHD6 IC50 = 1.60/4.87; no inhibitory activity against human/rat/mouse fatty acid amide hydrolase (FAAH) up to 50 μM). KML29 in vivo treatment results in a selective upregulation of 2-arachidonoyl glycerol (2-AG), but not N-arachidonoyl-ethanolamine (AEA) in mice (brain Emax ∼20 mg/kg p.o. or i.p.; peripheral Emax ∼1 mg/kg p.o.) and rats (brain Emax ∼40 mg/kg i.p.). KML29 reduces inflammatory and neuropathic nociceptive behaviour in animal studies without cannabimimetic side effects seen with dual FAAH & MAGL inhibition, chronic administration, however, leads to CB1 receptor desensitization as observed with other MAGL inhibitors.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Molly S Crowe et al.
British journal of pharmacology, 174(23), 4523-4539 (2017-10-01)
Gabapentin is commonly prescribed for nerve pain but may also cause dizziness, sedation and gait disturbances. Similarly, inhibition of the endogenous cannabinoid enzyme monoacylglycerol lipase (MAGL) has antinociceptive and anti-inflammatory properties but also induces sedation in mice at high doses.
Andreu Viader et al.
eLife, 5, e12345-e12345 (2016-01-19)
Metabolic specialization among major brain cell types is central to nervous system function and determined in large part by the cellular distribution of enzymes. Serine hydrolases are a diverse enzyme class that plays fundamental roles in CNS metabolism and signaling.
Sally Miller et al.
Investigative ophthalmology & visual science, 57(7), 3287-3296 (2016-06-23)
Cannabinoids, such as Δ9-THC, act through an endogenous signaling system in the vertebrate eye that reduces IOP via CB1 receptors. Endogenous cannabinoid (eCB) ligand, 2-arachidonoyl glycerol (2-AG), likewise activates CB1 and is metabolized by monoacylglycerol lipase (MAGL). We investigated ocular
B M Ignatowska-Jankowska et al.
British journal of pharmacology, 171(6), 1392-1407 (2013-07-16)
Since monoacylglycerol lipase (MAGL) has been firmly established as the predominant catabolic enzyme of the endocannabinoid 2-arachidonoylglycerol (2-AG), a great need has emerged for the development of highly selective MAGL inhibitors. Here, we tested the in vivo effects of one
Maria Morena et al.
Neuropharmacology, 111, 59-69 (2016-08-25)
Systemic activation of cannabinoid receptors often induces biphasic effects on emotional memory and anxiety depending on the levels of emotional arousal associated to the experimental context. The basolateral nucleus of the amygdala (BLA) represents a crucial structure for the ability
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