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China
Product Name: Olvanil
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58493-49-5

58493-49-5 structure

Name: Olvanil
Chemical Name: (Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]octadec-9-enamide
CAS Number: 58493-49-5
Molecular Formula: C₂₆H₄₃NO₃
Molecular Weight: 417.62
Catalog: Signaling Pathways Membrane Transporter/Ion Channel TRP Channel
Create Date: 2018-02-26 08:00:00
Modify Date: 2024-01-08 17:19:18
Olvanil (NE-19550)is an agonist of transient receptor potential vanilloid type 1 (TRPV1) channels with an EC50 of 0.7 nM.Analgesic[1].

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

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.

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

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

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR	NONH for all modes of transport
RTECS	RG2242130

1196-92-5

112-80-1

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

112-77-6

7149-10-2

~94%

58493-49-5

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

112-80-1

7149-10-2

~81%

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

112-77-6

1196-92-5

~86%

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

112-62-9

7149-10-2

~14%

58493-49-5

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

112-80-1

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

1196-92-5

301-02-0

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

Precursor 6
1196-92-5 112-80-1 112-77-6 7149-10-2
112-62-9 301-02-0
DownStream 0

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