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Merck
CN

O0257

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
NACRES:
NA.77
PubChem Substance ID:
24897928
UNSPSC Code:
51111800
MDL number:
MFCD00673962
Form:
powder
Quality level:
200

Key Documents

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Product Name

Olvanil, powder

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-

SMILES string

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

InChI key

OPZKBPQVWDSATI-KHPPLWFESA-N

form

powder

color

white to off-white

solubility

H2O: <0.2 mg/mL
DMSO: 20 mg/mL

storage temp.

−20°C

Quality Level

200

Gene Information

human ... TRPV1(7442)

Related Categories

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBW9518
SLBV1845
SLBP4122V
SLBM2190V
SLBL6238V

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Pouya Movahed et al.
British journal of pharmacology, 146(2), 171-179 (2005-07-06)
The endocannabinoid anandamide is an emerging potential signalling molecule in the cardiovascular system. Anandamide causes vasodilatation, bradycardia and hypotension in animals and has been implicated in the pathophysiology of endotoxic, haemorrhagic and cardiogenic shock, but its vascular effects have not
Liu Yang et al.
Biochemical and biophysical research communications, 410(4), 841-845 (2011-06-28)
We examined the effects of TRPV1 agonists olvanil and piperine on glutamatergic spontaneous excitatory transmission in the substantia gelatinosa (SG) neurons of adult rat spinal cord slices with the whole-cell patch-clamp technique. Bath-applied olvanil did not affect the frequency and
Daniel Ursu et al.
European journal of pharmacology, 641(2-3), 114-122 (2010-06-26)
TRPV1 (transient receptor potential vanilloid 1) is a ligand-gated ion channel expressed predominantly in nociceptive primary afferents that plays a key role in pain processing. In vivo activation of TRPV1 receptors by natural agonists like capsaicin is associated with a
J C Jerman et al.
British journal of anaesthesia, 89(6), 882-887 (2002-11-28)
Anandamide, an endogenous lipid, activates both cannabinoid (CB(1)) and vanilloid (VR1) receptors, both of which are co-expressed in rat dorsal root ganglion (DRG) cells. Activation of either receptor results in analgesia but the relative contribution of CB(1) and VR1 in
L Alenmyr et al.
Allergy, 64(5), 807-810 (2009-02-18)
Patients with allergic rhinitis may be abnormally sensitive to stimulation of the ion channel transient receptor potential vanilloid-1 (TRPV1). To examine effects of various TRP ion channel activators on sensory symptoms in allergic rhinitis prior to and during seasonal allergen
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