O-1918 | CAS# 536697-79-7 | CB1/CB2 endothelial receptor antagonist

MedKoo Cat#: 574825 | Name: O-1918

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Description:

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

O-1918 is a cannabidiol analog that acts as a selective antagonist of abnormal cannabidiol at the non-CB1/CB2 endothelial receptor. O-1918 inhibits the vasorelaxant effects of abnormal cannabidiol and blocks the abnormal cannabidiol-induced activation of the phosphatidylinositol 3-kinase/Akt pathway in human umbilical vein endothelial cells.

Chemical Structure

O-1918

CAS#536697-79-7

Theoretical Analysis

MedKoo Cat#: 574825

Name: O-1918

CAS#: 536697-79-7

Chemical Formula: C19H26O2

Exact Mass: 286.1933

Molecular Weight: 286.42

Elemental Analysis: C, 79.68; H, 9.15; O, 11.17

Price and Availability

Size	Price	Availability
1mg	USD 390.00	2 Weeks
5mg	USD 550.00	2 Weeks
10mg	USD 750.00	2 Weeks
25mg	USD 1,035.00	2 Weeks

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Synonym

O-1918; O 1918; O1918

IUPAC/Chemical Name

1,3-dimethoxy-5-methyl-2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-benzene

InChi Key

ICHJMVMWPKLUKT-JKSUJKDBSA-N

InChi Code

InChI=1S/C19H26O2/c1-12(2)15-8-7-13(3)9-16(15)19-17(20-5)10-14(4)11-18(19)21-6/h9-11,15-16H,1,7-8H2,2-6H3/t15-,16+/m0/s1

SMILES Code

C=C([C@@H]1CCC(C)=C[C@H]1C2=C(OC)C=C(C)C=C2OC)C

Appearance

A solution in methyl acetate

Purity

>95% (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

>3 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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

O-1918 is a cannabidiol analog that acts as a selective antagonist of abnormal cannabidiol at the non-CB1/CB2 endothelial receptor.

In vitro activity:

This study chose to test O-1918 for its potential as an inhibitor of Ca2+ mobilization in these studies, and this study selected a concentration of O-1918 (10 μM) that has been shown to block cannabinoid-dependent effects that are independent of CB1R or CB2R. Simultaneous perfusion with the nonCB1/CB2 receptor antagonist O-1918 (10 μM), attenuated WIN55212-2-promoted increases in [Ca2+]i at both eCa2+ levels (ΔF340/380 O-1918 0.28 ± 0.07, n = 5, p < 0.05, 67% reduction at 0.25 mM; ΔF340/380 O-1918 0.72 ± 0.05, n = 5, p < 0.05, 44% reduction at 2.5 mM, Figure 5B). Reference: Cells. 2022 Sep 21;11(19):2947. https://pubmed.ncbi.nlm.nih.gov/36230909/

In vivo activity:

O-1918 (10 microM), a putative antagonist at a novel endothelial cannabinoid receptor (abnormal-cannabidiol site), markedly reduced the relaxation to oleamide (n=7; P<0.01). It is concluded that oleamide responses in the rat isolated small mesenteric artery are partly dependent on the presence of the endothelium, activation of Ca2+-sensitive K+ channels (KC)) and involve capsaicin-sensitive sensory nerves. Reference: Br J Pharmacol. 2006 Mar;147(5):560-8. https://pubmed.ncbi.nlm.nih.gov/16415907/

	Solvent	mg/mL	mM
Solubility
	DMF	28.6	100.00
	DMSO	28.6	100.00
	Ethanol	28.6	100.00
	Ethanol:PBS (pH 7.2) (1:1)	0.5	1.75

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 286.42 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.

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

Formulation protocol:

1. Pulgar VM, Howlett AC, Eldeeb K. WIN55212-2 Modulates Intracellular Calcium via CB1 Receptor-Dependent and Independent Mechanisms in Neuroblastoma Cells. Cells. 2022 Sep 21;11(19):2947. doi: 10.3390/cells11192947. PMID: 36230909; PMCID: PMC9563019. 2. Lu Q, Yang Y, Zhang H, Chen C, Zhao J, Yang Z, Fan Y, Li L, Feng H, Zhu J, Yi S. Activation of GPR18 by Resolvin D2 Relieves Pain and Improves Bladder Function in Cyclophosphamide-Induced Cystitis Through Inhibiting TRPV1. Drug Des Devel Ther. 2021 Nov 15;15:4687-4699. doi: 10.2147/DDDT.S329507. PMID: 34815664; PMCID: PMC8604640. 3. Hoi PM, Hiley CR. Vasorelaxant effects of oleamide in rat small mesenteric artery indicate action at a novel cannabinoid receptor. Br J Pharmacol. 2006 Mar;147(5):560-8. doi: 10.1038/sj.bjp.0706643. PMID: 16415907; PMCID: PMC1616976.

In vitro protocol:

In vivo protocol:

1. Lu Q, Yang Y, Zhang H, Chen C, Zhao J, Yang Z, Fan Y, Li L, Feng H, Zhu J, Yi S. Activation of GPR18 by Resolvin D2 Relieves Pain and Improves Bladder Function in Cyclophosphamide-Induced Cystitis Through Inhibiting TRPV1. Drug Des Devel Ther. 2021 Nov 15;15:4687-4699. doi: 10.2147/DDDT.S329507. PMID: 34815664; PMCID: PMC8604640. 2. Hoi PM, Hiley CR. Vasorelaxant effects of oleamide in rat small mesenteric artery indicate action at a novel cannabinoid receptor. Br J Pharmacol. 2006 Mar;147(5):560-8. doi: 10.1038/sj.bjp.0706643. PMID: 16415907; PMCID: PMC1616976.

1: Hao JW, Liu TT, Qiu CY, Li XM, Qiao WL, Li Q, Qin QR, Hu WP. Lipid mediator resolvin D2 inhibits ATP currents in rat primary sensory neurons. J Neurochem. 2023 Nov 21. doi: 10.1111/jnc.16009. Epub ahead of print. PMID: 37987505. 2: Pulgar VM, Howlett AC, Eldeeb K. WIN55212-2 Modulates Intracellular Calcium via CB1 Receptor-Dependent and Independent Mechanisms in Neuroblastoma Cells. Cells. 2022 Sep 21;11(19):2947. doi: 10.3390/cells11192947. PMID: 36230909; PMCID: PMC9563019. 3: Bardin M, Pawelzik SC, Lagrange J, Mahdi A, Arnardottir H, Regnault V, Fève B, Lacolley P, Michel JB, Mercier N, Bäck M. The resolvin D2 - GPR18 axis is expressed in human coronary atherosclerosis and transduces atheroprotection in apolipoprotein E deficient mice. Biochem Pharmacol. 2022 Jul;201:115075. doi: 10.1016/j.bcp.2022.115075. Epub 2022 May 4. PMID: 35525326. 4: Kozłowska H, Malinowska B, Baranowska-Kuczko M, Kusaczuk M, Nesterowicz M, Kozłowski M, Müller CE, Kieć-Kononowicz K, Schlicker E. GPR18-Mediated Relaxation of Human Isolated Pulmonary Arteries. Int J Mol Sci. 2022 Jan 26;23(3):1427. doi: 10.3390/ijms23031427. PMID: 35163351; PMCID: PMC8836012. 5: Lu Q, Yang Y, Zhang H, Chen C, Zhao J, Yang Z, Fan Y, Li L, Feng H, Zhu J, Yi S. Activation of GPR18 by Resolvin D2 Relieves Pain and Improves Bladder Function in Cyclophosphamide-Induced Cystitis Through Inhibiting TRPV1. Drug Des Devel Ther. 2021 Nov 15;15:4687-4699. doi: 10.2147/DDDT.S329507. PMID: 34815664; PMCID: PMC8604640. 6: Dort J, Orfi Z, Fabre P, Molina T, Conte TC, Greffard K, Pellerito O, Bilodeau JF, Dumont NA. Resolvin-D2 targets myogenic cells and improves muscle regeneration in Duchenne muscular dystrophy. Nat Commun. 2021 Oct 29;12(1):6264. doi: 10.1038/s41467-021-26516-0. PMID: 34716330; PMCID: PMC8556273. 7: Stott LA, Brighton CA, Brown J, Mould R, Bennett KA, Newman R, Currinn H, Autore F, Higueruelo AP, Tehan BG, MacSweeney C, O'Brien MA, Watson SP. Characterisation of inverse agonism of the orphan-G protein-coupled receptor GPR52 by cannabinoid ligands Cannabidiol and O-1918. Heliyon. 2021 Jun 1;7(6):e07201. doi: 10.1016/j.heliyon.2021.e07201. PMID: 34189291; PMCID: PMC8219759. 8: Kolbe MR, Hohmann T, Hohmann U, Ghadban C, Mackie K, Zöller C, Prell J, Illert J, Strauss C, Dehghani F. THC Reduces Ki67-Immunoreactive Cells Derived from Human Primary Glioblastoma in a GPR55-Dependent Manner. Cancers (Basel). 2021 Mar 3;13(5):1064. doi: 10.3390/cancers13051064. PMID: 33802282; PMCID: PMC7959141. 9: Mazeh AC, Angus JA, Wright CE. Cannabidiol selectively inhibits the contraction of rat small resistance arteries: Possible role for CGRP and voltage-gated calcium channels. Eur J Pharmacol. 2021 Jan 15;891:173767. doi: 10.1016/j.ejphar.2020.173767. Epub 2020 Dec 1. PMID: 33275960. 10: Perna E, Aguilera-Lizarraga J, Florens MV, Jain P, Theofanous SA, Hanning N, De Man JG, Berg M, De Winter B, Alpizar YA, Talavera K, Vanden Berghe P, Wouters M, Boeckxstaens G. Effect of resolvins on sensitisation of TRPV1 and visceral hypersensitivity in IBS. Gut. 2021 Jul;70(7):1275-1286. doi: 10.1136/gutjnl-2020-321530. Epub 2020 Oct 6. PMID: 33023902. 11: Simcocks AC, O'Keefe L, Jenkin KA, Cornall LM, Grinfeld E, Mathai ML, Hryciw DH, McAinch AJ. The Role of Atypical Cannabinoid Ligands O-1602 and O-1918 on Skeletal Muscle Homeostasis with a Focus on Obesity. Int J Mol Sci. 2020 Aug 18;21(16):5922. doi: 10.3390/ijms21165922. PMID: 32824681; PMCID: PMC7460607. 12: Murataeva N, Daily L, Taylor X, Dhopeshwarkar A, Hu SS, Miller S, McHugh D, Oehler O, Li S, Bonanno JA, Mackie K, Straiker A. Evidence for a GPR18 Role in Chemotaxis, Proliferation, and the Course of Wound Closure in the Cornea. Cornea. 2019 Jul;38(7):905-913. doi: 10.1097/ICO.0000000000001934. PMID: 30969262; PMCID: PMC6554050. 13: Simcocks AC, Jenkin KA, O'Keefe L, Samuel CS, Mathai ML, McAinch AJ, Hryciw DH. Atypical cannabinoid ligands O-1602 and O-1918 administered chronically in diet-induced obesity. Endocr Connect. 2019 Mar 1;8(3):203-216. doi: 10.1530/EC-18-0535. PMID: 30707678; PMCID: PMC6391900. 14: Zhou J, Yang H, Lehmann C. Inhibition of GPR 55 improves dysregulated immune response in experimental sepsis. Clin Hemorheol Microcirc. 2018;70(4):553-561. doi: 10.3233/CH-189320. PMID: 30347614. 15: Zuo G, Zhang D, Mu R, Shen H, Li X, Wang Z, Li H, Chen G. Resolvin D2 protects against cerebral ischemia/reperfusion injury in rats. Mol Brain. 2018 Feb 13;11(1):9. doi: 10.1186/s13041-018-0351-1. PMID: 29439730; PMCID: PMC5812187. 16: Matouk AI, Taye A, El-Moselhy MA, Heeba GH, Abdel-Rahman AA. Abnormal cannabidiol confers cardioprotection in diabetic rats independent of glycemic control. Eur J Pharmacol. 2018 Feb 5;820:256-264. doi: 10.1016/j.ejphar.2017.12.039. Epub 2017 Dec 20. PMID: 29274332; PMCID: PMC5767137. 17: Karpińska O, Baranowska-Kuczko M, Malinowska B, Kloza M, Kusaczuk M, Gęgotek A, Golec P, Kasacka I, Kozłowska H. Mechanisms of l-alpha- lysophosphatidylinositol-induced relaxation in human pulmonary arteries. Life Sci. 2018 Jan 1;192:38-45. doi: 10.1016/j.lfs.2017.11.020. Epub 2017 Nov 16. PMID: 29155298. 18: Zong Y, Zhou X, Cheng J, Yu J, Wu J, Jiang C. Cannabinoids Regulate the Diameter of Pericyte-Containing Retinal Capillaries in Rats. Cell Physiol Biochem. 2017;43(5):2088-2101. doi: 10.1159/000484193. Epub 2017 Oct 23. PMID: 29059679. 19: Deyama S, Ishikawa Y, Yoshikawa K, Shimoda K, Ide S, Satoh M, Minami M. Resolvin D1 and D2 Reverse Lipopolysaccharide-Induced Depression-Like Behaviors Through the mTORC1 Signaling Pathway. Int J Neuropsychopharmacol. 2017 Jul 1;20(7):575-584. doi: 10.1093/ijnp/pyx023. PMID: 28419244; PMCID: PMC5492780. 20: Bondarenko AI, Panasiuk O, Okhai I, Montecucco F, Brandt KJ, Mach F. Direct activation of Ca2+ and voltage-gated potassium channels of large conductance by anandamide in endothelial cells does not support the presence of endothelial atypical cannabinoid receptor. Eur J Pharmacol. 2017 Jun 15;805:14-24. doi: 10.1016/j.ejphar.2017.03.038. Epub 2017 Mar 19. PMID: 28327344; PMCID: PMC6520242.

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Description:

Chemical Structure

Theoretical Analysis

Price and Availability

Preparing Stock Solutions

View History

CWP232291

GSK143

KCN1

H 261

W-1-5

JNJ-42165279 hydrochloride

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