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MedKoo Cat#: 540033 | Name: Arvanil
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Arvanil is a CB1 and TRPV1 agonist. It increases lung tidal volume, diaphragm activity, mean arterial blood pressure and inhibits lymphocyte proliferation.

Chemical Structure

Arvanil
CAS#128007-31-8

Theoretical Analysis

MedKoo Cat#: 540033

Name: Arvanil

CAS#: 128007-31-8

Chemical Formula: C28H41NO3

Exact Mass: 439.3086

Molecular Weight: 439.64

Elemental Analysis: C, 76.50; H, 9.40; N, 3.19; O, 10.92

Price and Availability

Size Price Availability Quantity
10mg USD 285.00 2 Weeks
50mg USD 750.00 2 Weeks
100mg USD 1,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Arvanil; RT-011322; B-6699; I14-44667; RT011322; B6699; I1444667; RT 011322; B 6699; I14 44667; N-Vanillylarachidonamide
IUPAC/Chemical Name
(5Z,8Z,11Z,14Z)-N-(4-hydroxy-3-methoxybenzyl)icosa-5,8,11,14-tetraenamide
InChi Key
QVLMCRFQGHWOPM-ZKWNWVNESA-N
InChi Code
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-
SMILES Code
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(NCC1=CC=C(O)C(OC)=C1)=O
Appearance
A solution in ethanol
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 439.64 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kopczyńska B. Midcervical vagotomy precludes respiratory response to novel anti-inflammatory and anti-tumour drug arvanil in rats. Eur J Pharmacol. 2010 Sep 15;643(1):101-6. doi: 10.1016/j.ejphar.2010.06.012. Epub 2010 Jun 18. PubMed PMID: 20599930. 2: Sancho R, de la Vega L, Appendino G, Di Marzo V, Macho A, Munoz E. The CB1/VR1 agonist arvanil induces apoptosis through an FADD/caspase-8-dependent pathway. Br J Pharmacol. 2003 Nov;140(6):1035-44. Epub 2003 Oct 6. PubMed PMID: 14530215; PubMed Central PMCID: PMC1574119. 3: Malfitano AM, Matarese G, Pisanti S, Grimaldi C, Laezza C, Bisogno T, Di Marzo V, Lechler RI, Bifulco M. Arvanil inhibits T lymphocyte activation and ameliorates autoimmune encephalomyelitis. J Neuroimmunol. 2006 Feb;171(1-2):110-9. Epub 2005 Oct 18. PubMed PMID: 16239036. 4: de Lago E, Urbani P, Ramos JA, Di Marzo V, Fernández-Ruiz J. Arvanil, a hybrid endocannabinoid and vanilloid compound, behaves as an antihyperkinetic agent in a rat model of Huntington's disease. Brain Res. 2005 Jul 19;1050(1-2):210-6. PubMed PMID: 15975564. 5: Di Marzo V, Griffin G, De Petrocellis L, Brandi I, Bisogno T, Williams W, Grier MC, Kulasegram S, Mahadevan A, Razdan RK, Martin BR. A structure/activity relationship study on arvanil, an endocannabinoid and vanilloid hybrid. J Pharmacol Exp Ther. 2002 Mar;300(3):984-91. PubMed PMID: 11861807. 6: Lo YK, Chiang HT, Wu SN. Effect of arvanil (N-arachidonoyl-vanillyl-amine), a nonpungent anandamide-capsaicin hybrid, on ion currents in NG108-15 neuronal cells. Biochem Pharmacol. 2003 Feb 15;65(4):581-91. PubMed PMID: 12566085. 7: Kopczyńska B. Role of VR1 and CB1 receptors in modelling of cardio-respiratory response to arvanil, an endocannabinoid and vanilloid hybrid, in rats. Life Sci. 2008 Jul 18;83(3-4):85-91. doi: 10.1016/j.lfs.2008.04.023. Epub 2008 May 11. PubMed PMID: 18572197. 8: Malfitano AM, Toruner GA, Gazzerro P, Laezza C, Husain S, Eletto D, Orlando P, De Petrocellis L, Terskiy A, Schwalb M, Vitale E, Bifulco M. Arvanil and anandamide up-regulate CD36 expression in human peripheral blood mononuclear cells. Immunol Lett. 2007 Apr 15;109(2):145-54. Epub 2007 Mar 5. PubMed PMID: 17360047. 9: Sharkey KA, Cristino L, Oland LD, Van Sickle MD, Starowicz K, Pittman QJ, Guglielmotti V, Davison JS, Di Marzo V. Arvanil, anandamide and N-arachidonoyl-dopamine (NADA) inhibit emesis through cannabinoid CB1 and vanilloid TRPV1 receptors in the ferret. Eur J Neurosci. 2007 May;25(9):2773-82. Epub 2007 Apr 25. PubMed PMID: 17459108. 10: Brooks JW, Pryce G, Bisogno T, Jaggar SI, Hankey DJ, Brown P, Bridges D, Ledent C, Bifulco M, Rice AS, Di Marzo V, Baker D. Arvanil-induced inhibition of spasticity and persistent pain: evidence for therapeutic sites of action different from the vanilloid VR1 receptor and cannabinoid CB(1)/CB(2) receptors. Eur J Pharmacol. 2002 Mar 29;439(1-3):83-92. PubMed PMID: 11937096. 11: Veldhuis WB, van der Stelt M, Wadman MW, van Zadelhoff G, Maccarrone M, Fezza F, Veldink GA, Vliegenthart JF, Bär PR, Nicolay K, Di Marzo V. Neuroprotection by the endogenous cannabinoid anandamide and arvanil against in vivo excitotoxicity in the rat: role of vanilloid receptors and lipoxygenases. J Neurosci. 2003 May 15;23(10):4127-33. PubMed PMID: 12764100. 12: Visintin C, Aliev AE, Riddall D, Baker D, Okuyama M, Hoi PM, Hiley R, Selwood DL. Membrane receptor probes: solid-phase synthesis of biotin-Asp-PEG-arvanil derivatives. Org Lett. 2005 Apr 28;7(9):1699-702. PubMed PMID: 15844884. 13: Di Marzo V, Breivogel C, Bisogno T, Melck D, Patrick G, Tao Q, Szallasi A, Razdan RK, Martin BR. Neurobehavioral activity in mice of N-vanillyl-arachidonyl-amide. Eur J Pharmacol. 2000 Oct 20;406(3):363-74. PubMed PMID: 11040343. 14: Di Marzo V, Bisogno T, De Petrocellis L, Brandi I, Jefferson RG, Winckler RL, Davis JB, Dasse O, Mahadevan A, Razdan RK, Martin BR. Highly selective CB(1) cannabinoid receptor ligands and novel CB(1)/VR(1) vanilloid receptor "hybrid" ligands. Biochem Biophys Res Commun. 2001 Feb 23;281(2):444-51. PubMed PMID: 11181068. 15: Ross RA, Gibson TM, Brockie HC, Leslie M, Pashmi G, Craib SJ, Di Marzo V, Pertwee RG. Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens. Br J Pharmacol. 2001 Feb;132(3):631-40. PubMed PMID: 11159715; PubMed Central PMCID: PMC1572597. 16: Barrière DA, Mallet C, Blomgren A, Simonsen C, Daulhac L, Libert F, Chapuy E, Etienne M, Högestätt ED, Zygmunt PM, Eschalier A. Fatty acid amide hydrolase-dependent generation of antinociceptive drug metabolites acting on TRPV1 in the brain. PLoS One. 2013 Aug 5;8(8):e70690. doi: 10.1371/journal.pone.0070690. Print 2013. PubMed PMID: 23940628; PubMed Central PMCID: PMC3734263. 17: Márquez N, De Petrocellis L, Caballero FJ, Macho A, Schiano-Moriello A, Minassi A, Appendino G, Muñoz E, Di Marzo V. Iodinated N-acylvanillamines: potential "multiple-target" anti-inflammatory agents acting via the inhibition of t-cell activation and antagonism at vanilloid TRPV1 channels. Mol Pharmacol. 2006 Apr;69(4):1373-82. Epub 2006 Jan 4. PubMed PMID: 16394182. 18: Stock K, Kumar J, Synowitz M, Petrosino S, Imperatore R, Smith ES, Wend P, Purfürst B, Nuber UA, Gurok U, Matyash V, Wälzlein JH, Chirasani SR, Dittmar G, Cravatt BF, Momma S, Lewin GR, Ligresti A, De Petrocellis L, Cristino L, Di Marzo V, Kettenmann H, Glass R. Neural precursor cells induce cell death of high-grade astrocytomas through stimulation of TRPV1. Nat Med. 2012 Aug;18(8):1232-8. doi: 10.1038/nm.2827. Epub 2012 Jul 22. PubMed PMID: 22820645; PubMed Central PMCID: PMC3480991. 19: Hurley JD, Akers AT, Friedman JR, Nolan NA, Brown KC, Dasgupta P. Non-pungent long chain capsaicin-analogs arvanil and olvanil display better anti-invasive activity than capsaicin in human small cell lung cancers. Cell Adh Migr. 2017 Jan 2;11(1):80-97. doi: 10.1080/19336918.2016.1187368. Epub 2016 May 19. PubMed PMID: 27196129; PubMed Central PMCID: PMC5308228. 20: Ursu D, Knopp K, Beattie RE, Liu B, Sher E. Pungency of TRPV1 agonists is directly correlated with kinetics of receptor activation and lipophilicity. Eur J Pharmacol. 2010 Sep 1;641(2-3):114-22. doi: 10.1016/j.ejphar.2010.05.029. Epub 2010 Jun 8. PubMed PMID: 20576527.