Ajulemic acid

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
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	137945-48-3 N
ATC code	None
PubChem	CID 3083542
ChemSpider	21106251 Y
ChEMBL	CHEMBL456341 N
Chemical data
Formula	C25H36O4
Mol. mass	400.551 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C25H36O4/c1-6-7-8-9-12-24(2,3)17-14-20(26)22-18-13-16(23(27)28)10-11-19(18)25(4,5)29-21(22)15-17/h10-11,14-16,18-19,26H,6-9,12-13H2,1-5H3,(H,27,28)/t16?,18-,19-/m1/s1 Y Key:QHGPTMABBHVVQU-VOBHOPKGSA-N Y
N(what is this?)  (verify)

Ajulemic acid (AB-III-56, HU-239, IP-751) is a synthetic cannabinoid derivative of the non-psychoactive THC metabolite 11-nor-9-carboxy-THC that 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. Studies in animals at 100x the dose used in human trials suggest that there is some psychoactivity of ajulemic acid, comparable to that produced by tetrahydrocannabinol,^[4] however there was no difference between ajulemic acid and placebo on the "cannabimimetic" assay when used in humans at therapeutic doses.^[5][6]

References

1. ^ Burstein, S.; Karst, M.; Schneider, U.; Zurier, R. (2004). "Ajulemic acid: A novel cannabinoid produces analgesia without a "high"". Life sciences 75 (12): 1513–1522. doi:10.1016/j.lfs.2004.04.010. PMID 15240185.  edit
2. ^ Mitchell, V.; Aslan, S.; Safaei, R.; Vaughan, C. (2005). "Effect of the cannabinoid ajulemic acid on rat models of neuropathic and inflammatory pain". Neuroscience letters 382 (3): 231–235. doi:10.1016/j.neulet.2005.03.019. PMID 15925096.  edit
3. ^ Burstein, S. (2005). "Ajulemic acid (IP-751): synthesis, proof of principle, toxicity studies, and clinical trials". The AAPS journal 7 (1): E143–E148. doi:10.1208/aapsj070115. PMC 2751505. PMID 16146336. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2751505.  edit
4. ^ Vann, R.; Cook, C.; Martin, B.; Wiley, J. (2007). "Cannabimimetic properties of ajulemic acid". The Journal of pharmacology and experimental therapeutics 320 (2): 678–686. doi:10.1124/jpet.106.111625. PMC 2633725. PMID 17105826. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2633725.  edit
5. ^ Sumariwalla, P.; Gallily, R.; Tchilibon, S.; Fride, E.; Mechoulam, R.; Feldmann, M. (2004). "A novel synthetic, nonpsychoactive cannabinoid acid (HU-320) with antiinflammatory properties in murine collagen-induced arthritis". Arthritis and rheumatism 50 (3): 985–998. doi:10.1002/art.20050. PMID 15022343.  edit
6. ^ Sumariwalla, P. F.; Feldmann, M.; Gallily, R.; Mechoulam, R.; Tchilibon, S.; Fride, E. (2004). "Reply". Arthritis & Rheumatism 50 (12): 4079. doi:10.1002/art.20806.  edit