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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H42O3
Molecular Weight 414.6206
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HU-308

SMILES

CCCCCCC(C)(C)C1=CC(OC)=C([C@@H]2C=C(CO)[C@@H]3C[C@H]2C3(C)C)C(OC)=C1

InChI

InChIKey=CFMRIVODIXTERW-BHIFYINESA-N
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-/m1/s1

HIDE SMILES / InChI

Description

HU-308 ([(1R,2R,5R)-2-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl]methanol) is a potent, selective agonist for the CB2 receptor. The synthesis and characterization took place in the laboratory of Prof. Mechoulam at the Hebrew University of Jerusalem in the late 1990s. It has analgesic effects, promotes proliferation of neural stem cells,[3] and protects both liver and blood vessel tissues against oxidative stress via inhibition of TNF-α. In vivo, HU-308 has hypotensive, analgesic, and anti-inflammatory activities in mice that can be reversed by the CB2 receptor antagonist SR 144528 but not the CB1 receptor antagonist rimonabant. Pretreatment of mice with HU-308 decreases the I/R-induced tissue damage, inflammatory cell infiltration, tissue, and serum TNF-α, MIP-1, and MIP-2 levels, tissue lipid peroxidation, and apoptosis. HU-308 increases proliferation of HT29 colon cancer cells and growth of tumors in an HT29 mouse xenograft model. The physiological and toxicological properties of this compound have not been evaluated in humans.

Approval Year

PubMed

PubMed

TitleDatePubMed
HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor.
1999 Dec 7
Subunit-specific modulation of glycine receptors by cannabinoids and N-arachidonyl-glycine.
2008 Oct 15
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Rats were treated with HU-308 (0.3-30 mg/kg i.p.)
Route of Administration: Intraperitoneal
In Vitro Use Guide
Cells were set up 4x103 cells per well of a 96-well plate and were cultured in DMEM medium supplemented with 10% FCS overnight. The medium was replaced for serum-free DMEM medium and cells were incubated for 48h with HU-308 (0.001, 0.01, 0.1, 1 and 10mkM). Cell viability was assayed by Cell Counting Kit-8 (CCK-8).
Name Type Language
HU-308
Common Name English
(+)-HU-308
Common Name English
BICYCLO(3.1.1)HEPT-2-ENE-2-METHANOL, 4-(4-(1,1-DIMETHYLHEPTYL)-2,6-DIMETHOXYPHENYL)-6,6-DIMETHYL-, (1R,4R,5R)-
Systematic Name English
BICYCLO(3.1.1)HEPT-2-ENE-2-METHANOL, 4-(4-(1,1-DIMETHYLHEPTYL)-2,6-DIMETHOXYPHENYL)-6,6-DIMETHYL-, (1R,4R,5R)-REL-(+)-
Systematic Name English
Code System Code Type Description
PUBCHEM
5311172
Created by admin on Tue Oct 22 18:08:18 UTC 2019 , Edited by admin on Tue Oct 22 18:08:18 UTC 2019
PRIMARY
CAS
256934-39-1
Created by admin on Tue Oct 22 18:08:18 UTC 2019 , Edited by admin on Tue Oct 22 18:08:18 UTC 2019
NON-SPECIFIC STEREOCHEMISTRY
CAS
1220887-84-2
Created by admin on Tue Oct 22 18:08:18 UTC 2019 , Edited by admin on Tue Oct 22 18:08:18 UTC 2019
PRIMARY
WIKIPEDIA
HU-308
Created by admin on Tue Oct 22 18:08:18 UTC 2019 , Edited by admin on Tue Oct 22 18:08:18 UTC 2019
PRIMARY