Olvanil

Modify Date: 2024-01-08 17:19:18

Olvanil Structure
Olvanil structure
Common Name Olvanil
CAS Number 58493-49-5 Molecular Weight 417.62
Density 1.0±0.1 g/cm3 Boiling Point 596.1±50.0 °C at 760 mmHg
Molecular Formula C26H43NO3 Melting Point N/A
MSDS Chinese USA Flash Point 314.3±30.1 °C

 Use of Olvanil


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

 Names

Name (Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]octadec-9-enamide
Synonym More Synonyms

 Olvanil 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
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

 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

~%

Olvanil Structure

Olvanil

CAS#:58493-49-5

Literature: Dang, Hung The; Kang, Gyeoung Jin; Yoo, Eun Sook; Hong, Jongki; Choi, Jae Sue; Kim, Hyung Sik; Chung, Hae Young; Jung, Jee H. Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 4 p. 1520 - 1527

~94%

Olvanil Structure

Olvanil

CAS#:58493-49-5

Literature: Wang, Bo; Yang, Fan; Shan, Yi-Fan; Qiu, Wen-Wei; Tang, Jie Tetrahedron, 2009 , vol. 65, # 27 p. 5409 - 5412

~81%

Olvanil Structure

Olvanil

CAS#:58493-49-5

Literature: Appendino, Giovanni; Minassi, Alberto; Morello, Aniello Schiano; De Petrocellis, Luciano; Di Marzo, Vincenzo Journal of Medicinal Chemistry, 2002 , vol. 45, # 17 p. 3739 - 3745

~86%

Olvanil Structure

Olvanil

CAS#:58493-49-5

Literature: Janusz, John M.; Buckwalter, Brian L.; Young, Patricia A.; LaHann, Thomas R.; Farmer, Ralph W.; et al. Journal of Medicinal Chemistry, 1993 , vol. 36, # 18 p. 2595 - 2604

~14%

Olvanil Structure

Olvanil

CAS#:58493-49-5

Literature: Kobata, Kenji; Yoshikawa, Koichi; Kohashi, Masahiro; Watanabe, Tatsuo Tetrahedron Letters, 1996 , vol. 37, # 16 p. 2789 - 2790

~%

Olvanil Structure

Olvanil

CAS#:58493-49-5

Literature: Janusz, John M.; Buckwalter, Brian L.; Young, Patricia A.; LaHann, Thomas R.; Farmer, Ralph W.; et al. Journal of Medicinal Chemistry, 1993 , vol. 36, # 18 p. 2595 - 2604

~%

Olvanil Structure

Olvanil

CAS#:58493-49-5

Literature: Cho, Yongsung; Kim, Myeong Seop; Kim, Ho Shin; Ann, Jihyae; Lee, Jeewoo; Lee, Jiyoun; Pearce, Larry V.; Pavlyukovets, Vladimir A.; Morgan, Matthew A.; Blumberg, Peter M. Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 16 p. 5227 - 5231

 Articles26

More 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...

 Synonyms

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