Ajulemic acid

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Ajulemic acid
Systematic (IUPAC) name
(6aR,10aR) 3-(1,1-dimethylheptyl)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl- 6H-Dibenzo(b,d)pyran-9-carboxylic acid
Identifiers
CAS number	137945-48-3
ATC code	?
PubChem	3083542
Chemical data
Formula	C25H36O4
Mol. mass	400.551 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Ajulemic acid (IP-751) is a synthetic cannabinoid derivative of the non-psychoactive THC metabolite 11-nor-9-carboxy-THC which shows useful analgesic and anti-inflammatory effects without causing a subjective "high".^[1] It is being developed for the treatment of neuropathic pain and inflammatory conditions such as arthritis.^[2] It does not however share the anti-emetic effects of other cannabinoids but may be useful for treating pain and chronic inflammatory conditions where nausea is not present.^[3] Side effects include dry mouth, tiredness and dizziness. The mechanism of action has not yet been established, but ajulemic acid may activate the CB1 receptor in a different way to psychoactive cannabinoids. ^[4]

[edit] References

1. ^ Burstein SH, Karst M, Schneider U, Zurier RB (2004). "Ajulemic acid: A novel cannabinoid produces analgesia without a "high"". Life Sci. 75 (12): 1513–22. doi:10.1016/j.lfs.2004.04.010. PMID 15240185. 
2. ^ Mitchell VA, Aslan S, Safaei R, Vaughan CW (2005). "Effect of the cannabinoid ajulemic acid on rat models of neuropathic and inflammatory pain". Neurosci. Lett. 382 (3): 231–5. doi:10.1016/j.neulet.2005.03.019. PMID 15925096. 
3. ^ Burstein S (2005). "Ajulemic acid (IP-751): synthesis, proof of principle, toxicity studies, and clinical trials". AAPS J 7 (1): E143–8. doi:10.1208/aapsj070115. PMID 16146336. 
4. ^ Vann RE, Cook CD, Martin BR, Wiley JL (2007). "Cannabimimetic properties of ajulemic acid". J. Pharmacol. Exp. Ther. 320 (2): 678–86. doi:10.1124/jpet.106.111625. PMID 17105826. 

v • d • e Cannabinoids Plant cannabinoids CBD • CBDV • CBN • CBG • CBV • CBL • THC • THC-C4 • THCV Cannabinoid metabolites 11-Hydroxy-THC • 11-nor-9-Carboxy-THC Endogenous cannabinoids Arachidonoyl ethanolamide (Anandamide or AEA) • 2-Arachidonoylglycerol (2-AG) • 2-Arachidonyl glyceryl ether (noladin ether) • Virodhamine • N-arachidonoyl-dopamine (NADA) Synthetic cannabinoid agonists Classical cannabinoids (Dibenzopyrans) A-41988 • Ajulemic acid • AM-087 • AM-411 • AM-855 • AM-905 • AM-906 • AM-919 • AM-938 • AM-4030 • AMG-1 • AMG-3 • AMG-36 • AMG-41 • Dexanabinol (HU-211) • DMHP • Dronabinol • HU-210 • JWH-051 • JWH-133 • JWH-139 • L-759,633 • L-759,656 • Levonantradol • Nabilone • Nabitan • O-806 • O-823 • O-1057 • O-1125 • O-1238 • O-2545 • O-2694 • Parahexyl • THC-O-acetate • THC-O-phosphate Nonclassical cannabinoids CP 47,497 • CP 55,244 • CP 55,940 • HU-308 • 2-Isopropyl-5-methyl-1-(2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene Aminoalkylindoles AM-630 • AM-1241 • JWH-015 • JWH-018 • JWH-073 • JWH-081 • JWH-200 • L-768,242 • Pravadoline • WIN 55,212-2 Aminoalkylpyrroles JWH-030 • JWH-147 • JWH-307 Eicosanoids AM-883 • Arachidonyl-2'-chloroethylamide • Arachidonylcyclopropylamide • Methanandamide • O-585 • O-689 • O-1812 • O-1860 • O-1861 Others BAY 38-7271 • BAY 59-3074 • JWH-171 • O-2220 Endocannabinoid activity enhancers AM-404 • N-arachidonoyl-serotonin • O-1624 • URB-597 • URB-754 Cannabinoid antagonists and inverse agonists AM-251 • AM-281 • AM-630 • BML-190 • JTE-907 • LY-320,135 • NESS-0327 • O-1184 • O-2050 • O-2654 • Rimonabant • SLV-319 • SR-144,528 • Surinabant • Taranabant • VCHSR