Olvanil

Names

[ Name ]:
Olvanil

[Synonym ]:
9-Octadecenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-, (9Z)-
N-vanillylamide
oleoyl vanillylamide
TCMDC-124289
N-Vanillyloleamide
Vanillyloleamide
MFCD00673962
(9Z)-N-(4-Hydroxy-3-methoxybenzyl)-9-octadecenamide
N-Vannilyloleoylamide
OLVANIL
(9Z)-N-(4-Hydroxy-3-methoxybenzyl)octadec-9-enamide

Biological Activity

[Description]:

Olvanil (NE-19550)is an agonist of transient receptor potential vanilloid type 1 (TRPV1) channels with an EC50 of 0.7 nM.Analgesic[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel

Research Areas >> Neurological Disease

[Target]

TRPV1:0.7 nM (EC50)

[In Vitro]

Olvanil affects C6 glioma cell proliferation (IC50 value of 5.5 μM)[2]

[In Vivo]

Olvanil is one capsaicin analog, which acts as an agonist at the vanilloid receptor. Olvanil may have causes an anxiogenic-like effect. Doses of 0, 0.2, 1.0 and 5.0 mg/kg Olvanil, respectively, yielded percent open arm entries at 5 min of 25±10.1, 19.3±7.1, 14.9±5.9 and 0±0[3]. Animal Model: Sprague-Dawley rats weighing approximately 200 g[3] Dosage: 0, 0.2, 1.0 and 5.0 mg/kg Administration: Injected intraperitoneally 30 min before the behavioral tests Result: The percent open arm times at 5 min were 12.9±8.1 for the 0 mg/kg dose, 8.9±4.2 for the 0.2 mg/kg dose, 15.2±7.9 for the 1 mg/kg dose and 0±0 for the 5 mg/kg dose. The mean number of entries into the closed arm at 5 min were 1.7±0.3, 3.3±0.8, 2.7±0.3 and 0.25±0.1 for doses of 0, 0.2, 1 and 5 mg/kg, respectively.

[References]

[1]. Giovanni Appendino, et al. Development of the first ultra-potent "capsaicinoid" agonist at transient receptor potential vanilloid type 1 (TRPV1) channels and its therapeutic potential. J Pharmacol Exp Ther. 2005 Feb;312(2):561-70.

[2]. S O Jacobsson, et al. Inhibition of rat C6 glioma cell proliferation by endogenous and synthetic cannabinoids. Relative involvement of cannabinoid and vanilloid receptors.J Pharmacol Exp Ther. 2001 Dec;299(3):951-9.

[3]. John W Kasckow, et al. Effects of the vanilloid agonist olvanil and antagonist capsazepine on rat behaviors. Prog Neuropsychopharmacol Biol Psychiatry. 2004 Mar;28(2):291-5.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
596.1±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₆H₄₃NO₃

[ Molecular Weight ]:
417.62

[ Flash Point ]:
314.3±30.1 °C

[ Exact Mass ]:
417.324280

[ PSA ]:
58.56000

[ LogP ]:
7.69

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.509

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RG2242130

CHEMICAL NAME :: 9-Octadecenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-, (Z)-

CAS REGISTRY NUMBER :: 58493-49-5

BEILSTEIN REFERENCE NO. :: 3466619

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C26-H43-N-O3

MOLECULAR WEIGHT :: 417.70

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 350 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 36,2595,1993

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
RG2242130

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Inhibition by capsaicin and its related vanilloids of compound action potentials in frog sciatic nerves.

Life Sci. 92(6-7) , 368-78, (2013)

Although capsaicin not only activates transient receptor potential vanilloid-1 (TRPV1) channels but also inhibits nerve conduction, the latter action has not yet been fully examined. The purpose of th...

Identification of drug modulators targeting gene-dosage disease CMT1A.

ACS Chem. Biol. 7(7) , 1205-13, (2012)

The structural integrity of myelin formed by Schwann cells in the peripheral nervous system (PNS) is required for proper nerve conduction and is dependent on adequate expression of myelin genes includ...

Activation of recombinant human TRPV1 receptors expressed in SH-SY5Y human neuroblastoma cells increases [Ca(2+)](i), initiates neurotransmitter release and promotes delayed cell death.

J. Neurochem. 102(3) , 801-11, (2007)

The transient receptor potential (TRP) vanilloid receptor subtype 1 (TRPV1) is a ligand-gated, Ca(2+)-permeable ion channel in the TRP superfamily of channels. We report the establishment of the first...