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R2028

Sigma-Aldrich

RHC 80267

≥98% (HPLC), solid

Synonym(s):

1,6-bis(Cyclohexyloximinocarbonylamino)hexane, U 57908

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About This Item

Empirical Formula (Hill Notation):
C20H34N4O4
CAS Number:
83654-05-1
Molecular Weight:
394.51
MDL number:
MFCD00210844
UNSPSC Code:
41106300
PubChem Substance ID:
329824011
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: 9 mg/mL

SMILES string

O=C(NCCCCCCNC(=O)O\N=C1/CCCCC1)O\N=C2/CCCCC2

InChI

1S/C20H34N4O4/c25-19(27-23-17-11-5-3-6-12-17)21-15-9-1-2-10-16-22-20(26)28-24-18-13-7-4-8-14-18/h1-16H2,(H,21,25)(H,22,26)

InChI key

RXSVYGIGWRDVQC-UHFFFAOYSA-N

Biochem/physiol Actions

RHC 80267 is a diacylglycerol (DAG) lipase inhibitor and an important second messenger in signal transduction pathways. RHC 80267 is generated by the hydrolysis of phosphatidylinositol (PI) and bPC by phospholipase C (PLC). DAG mediates the actions of a large number of hormones and cytokines by activating protein kinase C (PKC). A sustained elevation in intracellular DAG may cause neoplastic transformation.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Sharleen Yuan et al.
Journal of neurophysiology, 104(5), 2766-2777 (2010-10-05)
Recent studies have found that some forms of endocannabinoid-dependent synaptic plasticity in the hippocampus are mediated through activation of transient potential receptor vanilloid (TRPV) receptors instead of cannabinoid receptors CB1 or CB2. The potential role for synaptic localization of TRPV
Takahiro Shimizu et al.
European journal of pharmacology, 499(1-2), 99-105 (2004-09-15)
Recently, we reported that intracerebroventricularly (i.c.v.) administered arginine-vasopressin evokes the release of noradrenaline and adrenaline from adrenal medulla by brain thromboxane A2-mediated mechanisms in rats. These results suggest the involvement of brain arachidonic acid in the vasopressin-induced activation of the
Donna L Pedicord et al.
Biochemical and biophysical research communications, 411(4), 809-814 (2011-07-27)
Diacylglycerol lipase α is the key enzyme in the formation of the most prevalent endocannabinoid, 2-arachidonoylglycerol in the brain. In this study we identified the catalytic triad of diacylglycerol lipase α, consisting of serine 472, aspartate 524 and histidine 650.
Rogier Min et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 30(7), 2710-2715 (2010-02-19)
Endocannabinoids control hippocampal inhibitory synaptic transmission through activation of presynaptic CB(1) receptors. During depolarization-induced suppression of inhibition (DSI), endocannabinoids are synthesized upon postsynaptic depolarization. The endocannabinoid 2-arachidonoylglycerol (2-AG) may mediate hippocampal DSI. Currently, the best studied pathway for biosynthesis of
Philippe Ghisdal et al.
European journal of pharmacology, 517(1-2), 97-102 (2005-06-17)
The diacylglycerol lipase inhibitor 1,6-bis(cyclohexyloximinocarbonylamino) hexane (RHC-80267) was tested for its effect on acetylcholine-evoked relaxation in rat mesenteric artery. In artery contracted with either noradrenaline or KCl, RHC-80267 (0.1-10 muM) potentiated the relaxation evoked by acetylcholine. The effect of RHC-80267
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