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Merck
CN

SML0520

Sigma-Aldrich

Arvanil

≥98% (HPLC), solution (in ethanol)

Synonym(s):

(5Z,8Z,11Z,14Z)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-5,8,11,14-Eicosatetraenamide, N-Vanillylarachidonamide

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About This Item

Empirical Formula (Hill Notation):
C28H41NO3
CAS Number:
128007-31-8
Molecular Weight:
439.63
MDL number:
MFCD01752675
UNSPSC Code:
12352200
PubChem Substance ID:
329825527

Key Documents

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Assay

≥98% (HPLC)

form

solution (in ethanol)

concentration

50 mg/mL in ethanol

color

colorless to pale yellow

storage temp.

−20°C

SMILES string

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCc1ccc(O)c(OC)c1

InChI

1S/C28H41NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-28(31)29-24-25-21-22-26(30)27(23-25)32-2/h7-8,10-11,13-14,16-17,21-23,30H,3-6,9,12,15,18-20,24H2,1-2H3,(H,29,31)/b8-7-,11-10-,14-13-,17-16-

InChI key

QVLMCRFQGHWOPM-ZKWNWVNESA-N

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Biochem/physiol Actions

Arvanil is an activator of cannabinoid and vanilloid receptors, and a potent inhibitor of anandamide accumulation. Arvanil inhibits growth of astrocytoma xenograft tumors in mice, mimicing the effect of neural precursor cells, that have been shown to kill TRPV1-expressing tumor cells by secreting endovanilloids.
Arvanil is an.activator of cannabinoid and vanilloid receptors; potent inhibitor of anandamide accumulation.

Features and Benefits

This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

Light and air sensitive

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

57.2 °F - closed cup

Flash Point(C)

14.0 °C - closed cup

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
102M4706V
102M4708V

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Sofia Sisay et al.
PloS one, 8(10), e76907-e76907 (2013-10-17)
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). Studies using C57BL/10 and C57BL/6 (Cnr2 (tm1Zim)) CB2 cannabinoid receptor knockout mice have demonstrated
Stephen D Richbart et al.
Journal of medicinal chemistry, 64(3), 1346-1361 (2021-01-29)
Capsaicin displays robust growth-inhibitory activity in multiple human cancers. However, the feasibility of capsaicin as a clinically relevant anticancer drug is hampered by its adverse side effects. This concern has led to extensive research focused on the isolation and synthesis
Anna Zaia Carolina Rodrigues et al.
Molecular and cellular neurosciences, 95, 59-70 (2019-02-15)
Increasing evidence indicates that, first, the sympathetic nervous system interacts extensively with both vasculature and skeletal muscle fibers near neuromuscular junctions (NMJs) and, second, its neurotransmitter, noradrenaline, influences myofiber molecular composition and function and motor innervation. Since sympathomimetic agents have

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