O-1602 | CAS#317321-41-8 | GPR55 agonist

MedKoo Cat#: 471154 | Name: O-1602

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Description:

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

O-1602 is an agonist of GPR55. O-1602 has also induced intracellular calcium rise in Hep3B cells in a GPR55-independent manner.

Chemical Structure

O-1602

CAS#317321-41-8

Theoretical Analysis

MedKoo Cat#: 471154

Name: O-1602

CAS#: 317321-41-8

Chemical Formula: C17H22O2

Exact Mass: 258.1620

Molecular Weight: 258.36

Elemental Analysis: C, 79.03; H, 8.58; O, 12.38

Price and Availability

Size	Price	Availability
5mg	USD 450.00	2 Weeks
10mg	USD 650.00	2 Weeks
25mg	USD 1,050.00	2 Weeks

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Related CAS #

No Data

Synonym

O-1602; O 1602; O1602

IUPAC/Chemical Name

5-Methyl-4-((1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-1,3-benzenediol

InChi Key

KDZOUSULXZNDJH-LSDHHAIUSA-N

InChi Code

InChI=1S/C17H22O2/c1-10(2)14-6-5-11(3)7-15(14)17-12(4)8-13(18)9-16(17)19/h7-9,14-15,18-19H,1,5-6H2,2-4H3/t14-,15+/m0/s1

SMILES Code

OC1=CC(C)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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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Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 258.36 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

1: Sun L, Apweiler M, Normann C, Grathwol CW, Hurrle T, Gräßle S, Jung N, Bräse S, Fiebich BL. Anti-Inflammatory Effects of GPR55 Agonists and Antagonists in LPS-Treated BV2 Microglial Cells. Pharmaceuticals (Basel). 2024 May 24;17(6):674. doi: 10.3390/ph17060674. PMID: 38931342; PMCID: PMC11206594. 2: He Y, Shen H, Bi GH, Zhang HY, Soler-Cedeño O, Alton H, Yang Y, Xi ZX. GPR55 is expressed in glutamate neurons and functionally modulates drug taking and seeking in rats and mice. Transl Psychiatry. 2024 Feb 19;14(1):101. doi: 10.1038/s41398-024-02820-3. PMID: 38374108; PMCID: PMC10876975. 3: Xi ZX, He Y, Shen H, Bi GH, Zhang HY, Soler-Cedeno O, Alton H, Yang Y. GPR55 is expressed in glutamate neurons and functionally modulates nicotine taking and seeking in rats and mice. Res Sq [Preprint]. 2023 Oct 3:rs.3.rs-3222344. doi: 10.21203/rs.3.rs-3222344/v1. Update in: Transl Psychiatry. 2024 Feb 19;14(1):101. doi: 10.1038/s41398-024-02820-3. PMID: 37886574; PMCID: PMC10602186. 4: Martínez-Aguilar LM, Ibarra-Sánchez A, Guerrero-Morán DJ, Macías-Silva M, Muñoz-Bello JO, Padilla A, Lizano M, González-Espinosa C. Lysophosphatidylinositol Promotes Chemotaxis and Cytokine Synthesis in Mast Cells with Differential Participation of GPR55 and CB2 Receptors. Int J Mol Sci. 2023 Mar 28;24(7):6316. doi: 10.3390/ijms24076316. PMID: 37047288; PMCID: PMC10094727. 5: Díaz-Barba A, Calvillo-Robledo A, Vázquez-León P, Gallegos-Vieyra E, Quintanar JL, Marichal-Cancino BA. Central GPR55 may prevent nicotine reinforcing actions: a preliminary study. Acta Neurobiol Exp (Wars). 2022;82(3):304-314. doi: 10.55782/ane-2022-029. PMID: 36214713. 6: Sánchez-Zavaleta R, Ávalos-Fuentes JA, González-Hernández AV, Recillas- Morales S, Paz-Bermúdez FJ, Leyva-Gómez G, Cortés H, Florán B. Presynaptic nigral GPR55 receptors stimulate [3 H]-GABA release through [3 H]-cAMP production and PKA activation and promote motor behavior. Synapse. 2022 Sep;76(11-12):e22246. doi: 10.1002/syn.22246. Epub 2022 Jul 23. PMID: 35831708. 7: Wang X, Xiang X, Hu J, Wu Y, Li Y, Jin S, Wu X. Pharmacological Activation of GPR55 Improved Cognitive Impairment Induced by Lipopolysaccharide in Mice. J Mol Neurosci. 2022 Aug;72(8):1656-1669. doi: 10.1007/s12031-022-02020-y. Epub 2022 May 20. PMID: 35596056. 8: Shen SY, Yu R, Li W, Liang LF, Han QQ, Huang HJ, Li B, Xu SF, Wu GC, Zhang YQ, Yu J. The neuroprotective effects of GPR55 against hippocampal neuroinflammation and impaired adult neurogenesis in CSDS mice. Neurobiol Dis. 2022 Jul;169:105743. doi: 10.1016/j.nbd.2022.105743. Epub 2022 Apr 28. PMID: 35490927. 9: Xiang X, Wang X, Wu Y, Hu J, Li Y, Jin S, Wu X. Activation of GPR55 attenuates cognitive impairment, oxidative stress, neuroinflammation, and synaptic dysfunction in a streptozotocin-induced Alzheimer's mouse model. Pharmacol Biochem Behav. 2022 Mar;214:173340. doi: 10.1016/j.pbb.2022.173340. Epub 2022 Jan 25. PMID: 35090841. 10: Lee SJ, Im DS. GPR55 Antagonist CID16020046 Protects against Atherosclerosis Development in Mice by Inhibiting Monocyte Adhesion and Mac-1 Expression. Int J Mol Sci. 2021 Dec 3;22(23):13084. doi: 10.3390/ijms222313084. PMID: 34884889; PMCID: PMC8658038. 11: Xiang X, Wang X, Jin S, Hu J, Wu Y, Li Y, Wu X. Activation of GPR55 attenuates cognitive impairment and neurotoxicity in a mouse model of Alzheimer's disease induced by Aβ1-42 through inhibiting RhoA/ROCK2 pathway. Prog Neuropsychopharmacol Biol Psychiatry. 2022 Jan 10;112:110423. doi: 10.1016/j.pnpbp.2021.110423. Epub 2021 Aug 13. PMID: 34363866. 12: Kang S, Lee AY, Park SY, Liu KH, Im DS. O-1602 Promotes Hepatic Steatosis through GPR55 and PI3 Kinase/Akt/SREBP-1c Signaling in Mice. Int J Mol Sci. 2021 Mar 17;22(6):3091. doi: 10.3390/ijms22063091. PMID: 33803038; PMCID: PMC8003045. 13: 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. 14: Orrego-González E, Londoño-Tobón L, Ardila-González J, Polania-Tovar D, Valencia-Cárdenas A, Velez-Van Meerbeke A. Cannabinoid Effects on Experimental Colorectal Cancer Models Reduce Aberrant Crypt Foci (ACF) and Tumor Volume: A Systematic Review. Evid Based Complement Alternat Med. 2020 Jul 20;2020:2371527. doi: 10.1155/2020/2371527. PMID: 32765628; PMCID: PMC7387981. 15: Wróbel A, Serefko A, Szopa A, Ulrich D, Poleszak E, Rechberger T. O-1602, an Agonist of Atypical Cannabinoid Receptors GPR55, Reverses the Symptoms of Depression and Detrusor Overactivity in Rats Subjected to Corticosterone Treatment. Front Pharmacol. 2020 Jul 8;11:1002. doi: 10.3389/fphar.2020.01002. PMID: 32733244; PMCID: PMC7360849. 16: Wróbel A, Zapała Ł, Zapała P, Piecha T, Radziszewski P. The effect of O-1602, a GPR55 agonist, on the cyclophosphamide-induced rat hemorrhagic cystitis. Eur J Pharmacol. 2020 Sep 5;882:173321. doi: 10.1016/j.ejphar.2020.173321. Epub 2020 Jun 29. PMID: 32615180. 17: Wróbel A, Serefko A, Szopa A, Poleszak E. Stimulation of atypical cannabinoid receptor GPR55 abolishes the symptoms of detrusor overactivity in spontaneously hypertensive rats. Eur J Pharm Sci. 2020 Jul 1;150:105329. doi: 10.1016/j.ejps.2020.105329. Epub 2020 Apr 29. PMID: 32360768. 18: Wróbel A, Szopa A, Serefko A, Poleszak E. A Novel Alternative in the Treatment of Detrusor Overactivity? In Vivo Activity of O-1602, the Newly Synthesized Agonist of GPR55 and GPR18 Cannabinoid Receptors. Molecules. 2020 Mar 18;25(6):1384. doi: 10.3390/molecules25061384. PMID: 32197469; PMCID: PMC7144400. 19: McCloskey AG, Miskelly MG, Moore CBT, Nesbit MA, Christie KA, Owolabi AI, Flatt PR, McKillop AM. CRISPR/Cas9 gene editing demonstrates metabolic importance of GPR55 in the modulation of GIP release and pancreatic beta cell function. Peptides. 2020 Mar;125:170251. doi: 10.1016/j.peptides.2019.170251. Epub 2020 Jan 7. PMID: 31923454. 20: Wei D, Wang H, Yang J, Dai Z, Yang R, Meng S, Li Y, Lin X. Effects of O-1602 and CBD on TNBS-induced colonic disturbances. Neurogastroenterol Motil. 2020 Mar;32(3):e13756. doi: 10.1111/nmo.13756. Epub 2019 Dec 4. PMID: 31802588.