Arvanil

Names

[ Name ]:
Arvanil

[Synonym ]:
(5Z,8Z,11Z,14Z)-N-(4-Hydroxy-3-methoxybenzyl)-5,8,11,14-icosatetraenamide
N-vanillyl-5Z,8Z,11Z,14Z-eicosatetraenamide
5,8,11,14-Eicosatetraenamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-, (5Z,8Z,11Z,14Z)-
ARVANIL
Picrotoxin
(5Z,8Z,11Z,14Z)-N-(4-Hydroxy-3-methoxybenzyl)icosa-5,8,11,14-tetraenamide
N-arachidonoylvanillamine
N-VANILLYLARACHIDONAMIDE
MFCD01752675

Biological Activity

[Description]:

Arvanil is a ligand for vanilloid receptor 1 (VR1) and cannabinoid 1 (CB1). Arvanil can inhibit spasticity, as a potent neuroprotectant[1].

[Related Catalog]:

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

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor

[Target]

VR1, CB1[1]

[References]

[1]. Veldhuis WB, et al. Neuroprotection by the endogenous cannabinoid anandamide and arvanil against in vivo excitotoxicity in the rat: role of vanilloid receptors and lipoxygenases. J Neurosci. 2003;23(10):4127-4133.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
619.4±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₈H₄₁NO₃

[ Molecular Weight ]:
439.63

[ Flash Point ]:
328.4±31.5 °C

[ Exact Mass ]:
439.308655

[ PSA ]:
58.56000

[ LogP ]:
7.00

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.533

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: JX3845000

CHEMICAL NAME :: 5,8,11,14-Eicosatetraenamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-, (all-Z)-

CAS REGISTRY NUMBER :: 128007-31-8

LAST UPDATED :: 199509

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C28-H41-N-O3

MOLECULAR WEIGHT :: 439.70

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 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

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H319

[ Precautionary Statements ]:
P210-P305 + P351 + P338-P370 + P378-P403 + P235

[ RIDADR ]:
UN1170 - class 3 - PG 2 - Ethanol

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Genetic background can result in a marked or minimal effect of gene knockout (GPR55 and CB2 receptor) in experimental autoimmune encephalomyelitis models of multiple sclerosis.

PLoS ONE 8 , e76907, (2013)

Endocannabinoids and some phytocannabinoids bind to CB1 and CB2 cannabinoid receptors, transient receptor potential vanilloid one (TRPV1) receptor and the orphan G protein receptor fifty-five (GPR55)....