Ajulemic acid

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Ajulemic acid
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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 CID 3083542
Chemical data
Formula C25H36O4
Molar mass 400.551 g/mol[[Script error: No such module "String".]]
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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.  More than one of |author2= and |last2= specified (help); More than one of |author3= and |last3= specified (help); More than one of |author4= and |last4= specified (help) 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.  More than one of |author2= and |last2= specified (help); More than one of |author3= and |last3= specified (help); More than one of |author4= and |last4= specified (help) 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 Freely accessible. 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. PMC 2633725 Freely accessible. PMID 17105826.  More than one of |author2= and |last2= specified (help); More than one of |author3= and |last3= specified (help); More than one of |author4= and |last4= specified (help) 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.  More than one of |author2= and |last2= specified (help); More than one of |author3= and |last3= specified (help); More than one of |author4= and |last4= specified (help); More than one of |author5= and |last5= specified (help); More than one of |author6= and |last6= specified (help) 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
it:Acido ajulemico
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