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O0257

Sigma-Aldrich

Olvanil

powder

Synonym(s):

(N-Vanillyl)-9-oleamide, N-Vannilyloleoylamide

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About This Item

Empirical Formula (Hill Notation):
C26H43NO3
CAS Number:
58493-49-5
Molecular Weight:
417.62
MDL number:
MFCD00673962
UNSPSC Code:
51111800
PubChem Substance ID:
24897928
NACRES:
NA.77

form

powder

Quality Level

200

color

white to off-white

solubility

H2O: <0.2 mg/mL
DMSO: 20 mg/mL

storage temp.

−20°C

SMILES string

CCCCCCCC\C=C/CCCCCCCC(=O)NCc1ccc(O)c(OC)c1

InChI

1S/C26H43NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26(29)27-22-23-19-20-24(28)25(21-23)30-2/h10-11,19-21,28H,3-9,12-18,22H2,1-2H3,(H,27,29)/b11-10-

InChI key

OPZKBPQVWDSATI-KHPPLWFESA-N

Gene Information

human ... TRPV1(7442)

Application

Olvanil has been used as a vanilloid (VR1) receptors agonist in rat VR1-transfected human embryonic kidney cells (rVR1-HEK) and dorsal root ganglion (DRG) cells to test its effect on calcium levels.

Biochem/physiol Actions

Olvanil is a vanilloid receptor agonist. It is an analog of capsaicin and is non-pungent. It is an orally active analgesic that alleviates pain by desensitizing nociceptors.

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)

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Edmundo Castillo et al.
Biochemical and biophysical research communications, 356(2), 424-430 (2007-03-17)
Capsaicin (Cap) and its analogs (CAPanalogs) have diverse effects in sensory neurons including analgesia, implying they modulate other cellular targets besides the TRPV1 Cap receptor. Since Cap and CAPanalogs are not largely available and their chemical synthesis is cumbersome, they
Vincenzo Micale et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 34(3), 593-606 (2008-06-27)
The endocannabinoid-inactivating enzyme, fatty acid amide hydrolase (FAAH), and the transient receptor potential vanilloid type-1 (TRPV1) channel are new targets for the development of anxiolytic drugs. We studied the effect on anxiety-like behavior in the elevated plus maze of a
M Beltramo et al.
European journal of pharmacology, 364(1), 75-78 (1999-01-27)
The structural similarities between the anandamide transport inhibitor N-(4-hydroxyphenyl)-arachidonylamide (AM404) and the synthetic vanilloid agonist olvanil [(N-vanillyl)-9-oleamide], prompted us to investigate the possibility that olvanil may interfere with anandamide transport. The intracellular accumulation of [3H]anandamide by human astrocytoma cells was
Min-Goo Lee et al.
British journal of pharmacology, 146(4), 596-603 (2005-08-02)
Certain fatty acid amides such as anandamide (AEA) and olvanil are agonists for the transient receptor potential, vanilloid-1 (TRPV1) receptor, but have been found to activate TRPV1-containing C-fibers in some tissues but not others. We used extracellular recording and whole-cell
Yin Duan et al.
Basic & clinical pharmacology & toxicology, 100(2), 91-95 (2007-01-25)
This investigation was conducted to provide further insight into the effects of vanilloid (subtype 1) receptor (VR1) drugs at voltage-gated sodium channels and examine the potential of this interaction to influence release of neurotransmitters from synaptosomes prepared from mammalian brain.
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