Onternabez

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

MedKoo CAT#: 531958

CAS#: 256934-39-1

Description: Onternabez, also known as HU-308, is a potent, selective agonist for the peripheral CB2 (cannabinoid 2) receptor. The Ki for CB1 is >10 µM, while the Ki for CB2 is approximately 20 nM.


Chemical Structure

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Onternabez
CAS# 256934-39-1

Theoretical Analysis

MedKoo Cat#: 531958
Name: Onternabez
CAS#: 256934-39-1
Chemical Formula: C27H42O3
Exact Mass: 414.31
Molecular Weight: 414.630
Elemental Analysis: C, 78.21; H, 10.21; O, 11.58

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Onternabez; Onternabezum; HU-308; HU 308; HU308;

IUPAC/Chemical Name: [(1R,2S,5R)-2-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl]methanol

InChi Key: CFMRIVODIXTERW-FDFHNCONSA-N

InChi Code: InChI=1S/C27H42O3/c1-8-9-10-11-12-26(2,3)19-14-23(29-6)25(24(15-19)30-7)20-13-18(17-28)21-16-22(20)27(21,4)5/h13-15,20-22,28H,8-12,16-17H2,1-7H3/t20-,21-,22+/m0/s1

SMILES Code: OCC1=C[C@H](C2=C(OC)C=C(C(CCCCCC)(C)C)C=C2OC)[C@@]3([H])C[C@]1([H])C3(C)C

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 414.63 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Zhang B, Zheng F, Liu A, Li Z, Zheng F, Liu Q, Yang L, Chen K, Wang Y, Zhang Z, He Q, Zhan J. Activation of CB2 receptor inhibits pyroptosis and subsequently ameliorates cecal ligation and puncture-induced sepsis. Int Immunopharmacol. 2021 Aug 5;99:108038. doi: 10.1016/j.intimp.2021.108038. Epub ahead of print. PMID: 34364304.

2: Tucci MA, Pride Y, Strickland S, Marocho SMS, Jackson RJ, Jefferson JR, Chade AR, Grill RJ, Grayson BE. Delayed Systemic Treatment with Cannabinoid Receptor 2 Agonist Mitigates Spinal Cord Injury-Induced Osteoporosis More Than Acute Treatment Directly after Injury. Neurotrauma Rep. 2021 Jun 22;2(1):270-284. doi: 10.1089/neur.2020.0059. PMID: 34223557; PMCID: PMC8244511.

3: Aly E, Masocha W. Targeting the endocannabinoid system for management of HIV- associated neuropathic pain: A systematic review. IBRO Neurosci Rep. 2021 Jan 25;10:109-118. doi: 10.1016/j.ibneur.2021.01.004. PMID: 34179865; PMCID: PMC8211923.

4: Sultana S, Burkovskiy I, Zhou J, Kelly MM, Lehmann C. Effect of Cannabinoid 2 Receptor Modulation on the Peripheral Immune Response in Central Nervous System Injury-Induced Immunodeficiency Syndrome. Cannabis Cannabinoid Res. 2021 Aug;6(4):327-339. doi: 10.1089/can.2020.0130. Epub 2021 Mar 3. PMID: 33998888.

5: Karan AA, Spivak YS, Gerasimov KA, Suleymanova EM, Volobueva MN, Kvichansky AA, Vinogradova LV, Bolshakov AP. CB2 receptors modulate seizure-induced expression of pro-inflammatory cytokines in the hippocampus but not neocortex. Mol Neurobiol. 2021 Aug;58(8):4028-4037. doi: 10.1007/s12035-021-02395-w. Epub 2021 Apr 27. PMID: 33907944.

6: Song S, Kong X, Borlongan C, Sava V, Sanchez-Ramos J. Granulocyte Colony- Stimulating Factor Enhances Brain Repair Following Traumatic Brain Injury Without Requiring Activation of Cannabinoid Receptors. Cannabis Cannabinoid Res. 2021 Feb 12;6(1):48-57. doi: 10.1089/can.2019.0090. PMID: 33614952; PMCID: PMC7891202.

7: Sarott RC, Viray AEG, Pfaff P, Sadybekov A, Rajic G, Katritch V, Carreira EM, Frank JA. Optical Control of Cannabinoid Receptor 2-Mediated Ca2+ Release Enabled by Synthesis of Photoswitchable Probes. J Am Chem Soc. 2021 Jan 20;143(2):736-743. doi: 10.1021/jacs.0c08926. Epub 2021 Jan 5. PMID: 33399457.

8: Hirono M, Yanagawa Y. Endocannabinoids regulate cerebellar GABAergic transmission in a synapse type-dependent manner. J Neurosci Res. 2021 Mar;99(3):898-913. doi: 10.1002/jnr.24765. Epub 2020 Dec 3. PMID: 33271631.

9: Mensching L, Rading S, Nikolaev V, Karsak M. Monitoring Cannabinoid CB2 -Receptor Mediated cAMP Dynamics by FRET-Based Live Cell Imaging. Int J Mol Sci. 2020 Oct 23;21(21):7880. doi: 10.3390/ijms21217880. PMID: 33114208; PMCID: PMC7660676.

10: Ossola CA, Rodas JA, Balcarcel NB, Astrauskas JI, Elverdin JC, Fernández- Solari J. Signs of alveolar bone damage in early stages of periodontitis and its prevention by stimulation of cannabinoid receptor 2. Model in rats. Acta Odontol Latinoam. 2020 Sep 1;33(2):143-152. English. PMID: 32920617.

11: González-Naranjo P, Pérez C, Girón R, Sánchez-Robles EM, Martín-Fontelles MI, Carrillo-López N, Martín-Vírgala J, Naves M, Campillo NE, Páez JA. New cannabinoid receptor antagonists as pharmacological tool. Bioorg Med Chem. 2020 Oct 1;28(19):115672. doi: 10.1016/j.bmc.2020.115672. Epub 2020 Jul 29. PMID: 32912440.

12: Abidi AH, Alghamdi SS, Dabbous MK, Tipton DA, Mustafa SM, Moore BM. Cannabinoid type-2 receptor agonist, inverse agonist, and anandamide regulation of inflammatory responses in IL-1β stimulated primary human periodontal ligament fibroblasts. J Periodontal Res. 2020 Oct;55(5):762-783. doi: 10.1111/jre.12765. Epub 2020 Jun 20. PMID: 32562275.

13: Fede C, Pirri C, Petrelli L, Guidolin D, Fan C, De Caro R, Stecco C. Sensitivity of the Fasciae to the Endocannabinoid System: Production of Hyaluronan-Rich Vesicles and Potential Peripheral Effects of Cannabinoids in Fascial Tissue. Int J Mol Sci. 2020 Apr 22;21(8):2936. doi: 10.3390/ijms21082936. PMID: 32331297; PMCID: PMC7216169.

14: Ghanbari MM, Joneidi M, Kiani B, Babaie J, Sayyah M. Cannabinoid receptors and the proconvulsant effect of toxoplasmosis in mice. Microb Pathog. 2020 Jul;144:104204. doi: 10.1016/j.micpath.2020.104204. Epub 2020 Apr 18. PMID: 32315753.

15: Saroz Y, Kho DT, Glass M, Graham ES, Grimsey NL. Cannabinoid Receptor 2 (CB2) Signals via G-alpha-s and Induces IL-6 and IL-10 Cytokine Secretion in Human Primary Leukocytes. ACS Pharmacol Transl Sci. 2019 Oct 1;2(6):414-428. doi: 10.1021/acsptsci.9b00049. PMID: 32259074; PMCID: PMC7088898.

16: Liu AP, Yuan QH, Zhang B, Yang L, He QW, Chen K, Liu QS, Li Z, Zhan J. Cannabinoid receptor 2 activation alleviates septic lung injury by promoting autophagy via inhibition of inflammatory mediator release. Cell Signal. 2020 May;69:109556. doi: 10.1016/j.cellsig.2020.109556. Epub 2020 Feb 4. Erratum in: Cell Signal. 2020 Aug;72:109600. PMID: 32027949.

17: Hua T, Li X, Wu L, Iliopoulos-Tsoutsouvas C, Wang Y, Wu M, Shen L, Brust CA, Nikas SP, Song F, Song X, Yuan S, Sun Q, Wu Y, Jiang S, Grim TW, Benchama O, Stahl EL, Zvonok N, Zhao S, Bohn LM, Makriyannis A, Liu ZJ. Activation and Signaling Mechanism Revealed by Cannabinoid Receptor-Gi Complex Structures. Cell. 2020 Feb 20;180(4):655-665.e18. doi: 10.1016/j.cell.2020.01.008. Epub 2020 Jan 30. PMID: 32004463; PMCID: PMC7898353.

18: Westphal MV, Sarott RC, Zirwes EA, Osterwald A, Guba W, Ullmer C, Grether U, Carreira EM. Highly Selective, Amine-Derived Cannabinoid Receptor 2 Probes. Chemistry. 2020 Jan 27;26(6):1380-1387. doi: 10.1002/chem.201904584. Epub 2020 Jan 21. PMID: 31961047.

19: Xu A, Yang Y, Shao Y, Wu M, Sun Y. Activation of cannabinoid receptor type 2-induced osteogenic differentiation involves autophagy induction and p62-mediated Nrf2 deactivation. Cell Commun Signal. 2020 Jan 15;18(1):9. doi: 10.1186/s12964-020-0512-6. PMID: 31941496; PMCID: PMC6964093.

20: Berger G, Arora N, Burkovskiy I, Xia Y, Chinnadurai A, Westhofen R, Hagn G, Cox A, Kelly M, Zhou J, Lehmann C. Experimental Cannabinoid 2 Receptor Activation by Phyto-Derived and Synthetic Cannabinoid Ligands in LPS-Induced Interstitial Cystitis in Mice. Molecules. 2019 Nov 21;24(23):4239. doi: 10.3390/molecules24234239. PMID: 31766439; PMCID: PMC6930590.