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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 none
PubChem 3083542
Chemical data
Formula C 25H36O4  
Mol. mass 400.551 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

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 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. 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. PMID 16146336.   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. PMID 17105826.   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: 4079. doi:10.1002/art.20806.   edit
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