MedKoo Cat#: 562627 | Name: Virodhamine trifluoroacetate

Description:

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

Virodhamine trifluoroacetate is an endogenous cannabinoid receptor mixed agonist/antagonist. It acts by being a full agonist at GPR55 and CB2 and partial agonist/antagonist at CB1.

Chemical Structure

Virodhamine trifluoroacetate
Virodhamine trifluoroacetate
CAS#1415264-56-0

Theoretical Analysis

MedKoo Cat#: 562627

Name: Virodhamine trifluoroacetate

CAS#: 1415264-56-0

Chemical Formula: C24H38F3NO4

Exact Mass: 461.2753

Molecular Weight: 461.56

Elemental Analysis: C, 62.45; H, 8.30; F, 12.35; N, 3.03; O, 13.86

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Virodhamine trifluoroacetate; Virodhamine trifluoroacetate salt; Virodhamine-trifluoroacetate;
IUPAC/Chemical Name
O-(2-Aminoethyl)-5Z,8Z,11Z,14Z-eicosatetraenoate trifluoroacetate
InChi Key
APQWCQIPZHJFAU-XVSDJDOKSA-N
InChi Code
InChI=1S/C22H37NO2.C2HF3O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23;3-2(4,5)1(6)7/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3;(H,6,7)/b7-6-,10-9-,13-12-,16-15-;
SMILES Code
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(OCCN)=O.O=C(O)C(F)(F)F
Appearance
Solid powder
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 461.56 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: Hillard CJ, Huang H, Vogt CD, Rodrigues BE, Neumann TS, Sem DS, Schroeder F, Cunningham CW. Endocannabinoid Transport Proteins: Discovery of Tools to Study Sterol Carrier Protein-2. Methods Enzymol. 2017;593:99-121. doi: 10.1016/bs.mie.2017.06.017. Epub 2017 Jul 17. PubMed PMID: 28750817. 2: Pertwee RG. Endocannabinoids and Their Pharmacological Actions. Handb Exp Pharmacol. 2015;231:1-37. doi: 10.1007/978-3-319-20825-1_1. Review. PubMed PMID: 26408156. 3: Hind WH, Tufarelli C, Neophytou M, Anderson SI, England TJ, O'Sullivan SE. Endocannabinoids modulate human blood-brain barrier permeability in vitro. Br J Pharmacol. 2015 Jun;172(12):3015-27. doi: 10.1111/bph.13106. Epub 2015 Apr 10. PubMed PMID: 25651941; PubMed Central PMCID: PMC4459020. 4: Brantl SA, Khandoga AL, Siess W. Activation of platelets by the endocannabinoids 2-arachidonoylglycerol and virodhamine is mediated by their conversion to arachidonic acid and thromboxane A2, not by activation of cannabinoid receptors. Platelets. 2014;25(6):465-6. doi: 10.3109/09537104.2013.835040. Epub 2013 Oct 8. Review. PubMed PMID: 24102401. 5: Brantl SA, Khandoga AL, Siess W. Mechanism of platelet activation induced by endocannabinoids in blood and plasma. Platelets. 2014;25(3):151-61. doi: 10.3109/09537104.2013.803530. Epub 2013 Jun 21. PubMed PMID: 23789792. 6: Dudášová A, Keir SD, Parsons ME, Molleman A, Page CP. The effects of cannabidiol on the antigen-induced contraction of airways smooth muscle in the guinea-pig. Pulm Pharmacol Ther. 2013 Jun;26(3):373-9. doi: 10.1016/j.pupt.2013.02.002. Epub 2013 Feb 18. PubMed PMID: 23428645. 7: Hayase T. Working memory- and anxiety-related behavioral effects of repeated nicotine as a stressor: the role of cannabinoid receptors. BMC Neurosci. 2013 Feb 9;14:20. doi: 10.1186/1471-2202-14-20. PubMed PMID: 23394117; PubMed Central PMCID: PMC3599339. 8: Rogers TJ. The molecular basis for neuroimmune receptor signaling. J Neuroimmune Pharmacol. 2012 Dec;7(4):722-4. doi: 10.1007/s11481-012-9398-4. Epub 2012 Aug 31. PubMed PMID: 22935971; PubMed Central PMCID: PMC4011130. 9: Ottria R, Casati S, Ciuffreda P. Optimized synthesis and characterization of N-acylethanolamines and O-acylethanolamines, important family of lipid-signalling molecules. Chem Phys Lipids. 2012 Oct;165(7):705-11. doi: 10.1016/j.chemphyslip.2012.06.010. Epub 2012 Jul 28. PubMed PMID: 22850591. 10: Sharir H, Console-Bram L, Mundy C, Popoff SN, Kapur A, Abood ME. The endocannabinoids anandamide and virodhamine modulate the activity of the candidate cannabinoid receptor GPR55. J Neuroimmune Pharmacol. 2012 Dec;7(4):856-65. doi: 10.1007/s11481-012-9351-6. Epub 2012 Mar 28. PubMed PMID: 22454039; PubMed Central PMCID: PMC3669693. 11: Günther J, Schulte K, Wenzel D, Malinowska B, Schlicker E. Prostaglandins of the E series inhibit monoamine release via EP3 receptors: proof with the competitive EP3 receptor antagonist L-826,266. Naunyn Schmiedebergs Arch Pharmacol. 2010 Jan;381(1):21-31. doi: 10.1007/s00210-009-0478-9. Epub 2009 Dec 10. PubMed PMID: 20012265. 12: O'Sullivan SE, Kendall DA. Cannabinoid activation of peroxisome proliferator-activated receptors: potential for modulation of inflammatory disease. Immunobiology. 2010 Aug;215(8):611-6. doi: 10.1016/j.imbio.2009.09.007. Epub 2009 Oct 14. Review. PubMed PMID: 19833407. 13: Reichenbach V, Ros J, Jiménez W. [Endogenous cannabinoids in liver disease: Many darts for a single target]. Gastroenterol Hepatol. 2010 Apr;33(4):323-9. doi: 10.1016/j.gastrohep.2009.06.010. Epub 2009 Sep 16. Review. Spanish. PubMed PMID: 19758727. 14: Ozalp A, Barroso B. Simultaneous quantitative analysis of N-acylethanolamides in clinical samples. Anal Biochem. 2009 Dec 1;395(1):68-76. doi: 10.1016/j.ab.2009.08.005. Epub 2009 Aug 8. PubMed PMID: 19665986. 15: Malinowska B, Lupinski S, Godlewski G, Baranowska U, Schlicker E. Role of endocannabinoids in cardiovascular shock. J Physiol Pharmacol. 2008 Dec;59 Suppl 8:91-107. Review. PubMed PMID: 19258666. 16: Gkoumassi E, Dekkers BG, Dröge MJ, Elzinga CR, Hasenbosch RE, Meurs H, Nelemans SA, Schmidt M, Zaagsma J. (Endo)cannabinoids mediate different Ca2+ entry mechanisms in human bronchial epithelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2009 Jul;380(1):67-77. doi: 10.1007/s00210-009-0406-z. Epub 2009 Mar 3. PubMed PMID: 19255745. 17: Brusberg M, Arvidsson S, Kang D, Larsson H, Lindström E, Martinez V. CB1 receptors mediate the analgesic effects of cannabinoids on colorectal distension-induced visceral pain in rodents. J Neurosci. 2009 Feb 4;29(5):1554-64. doi: 10.1523/JNEUROSCI.5166-08.2009. PubMed PMID: 19193902. 18: Thomas A, Hopfgartner G, Giroud C, Staub C. Quantitative and qualitative profiling of endocannabinoids in human plasma using a triple quadrupole linear ion trap mass spectrometer with liquid chromatography. Rapid Commun Mass Spectrom. 2009 Mar;23(5):629-38. doi: 10.1002/rcm.3918. PubMed PMID: 19170046. 19: Hayase T. Nicotine (NC)-induced "depressive" behavioral symptoms and effects of antidepressants including cannabinoids (CBs). J Toxicol Sci. 2008 Dec;33(5):555-64. PubMed PMID: 19043277. 20: Kozłowska H, Baranowska M, Schlicker E, Kozłowski M, Laudañski J, Malinowska B. Virodhamine relaxes the human pulmonary artery through the endothelial cannabinoid receptor and indirectly through a COX product. Br J Pharmacol. 2008 Dec;155(7):1034-42. doi: 10.1038/bjp.2008.371. Epub 2008 Sep 22. PubMed PMID: 18806815; PubMed Central PMCID: PMC2597267.