Ajulemic acid

Drugbox
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


width= 180
CAS_number= 137945-48-3
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PubChem= 3083542
DrugBank=
C=25 | H=36 | O=4
molecular_weight = 400.551 g/mol
bioavailability=
metabolism =
elimination_half-life=
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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".cite journal
author=Burstein SH, Karst M, Schneider U, Zurier RB
title=Ajulemic acid: A novel cannabinoid produces analgesia without a "high"
journal=Life Sci.
volume=75
issue=12
pages=1513–22
year=2004
pmid=15240185
doi=10.1016/j.lfs.2004.04.010] It is being developed for the treatment of neuropathic pain and inflammatory conditions such as arthritis.cite journal
author=Mitchell VA, Aslan S, Safaei R, Vaughan CW
title=Effect of the cannabinoid ajulemic acid on rat models of neuropathic and inflammatory pain
journal=Neurosci. Lett.
volume=382
issue=3
pages=231–5
year=2005
pmid=15925096
doi=10.1016/j.neulet.2005.03.019] 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.cite journal
author=Burstein S
title=Ajulemic acid (IP-751): synthesis, proof of principle, toxicity studies, and clinical trials
journal=AAPS J
volume=7
issue=1
pages=E143–8
year=2005
pmid=16146336
doi=10.1208/aapsj070115] 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, [cite journal
author=Vann RE, Cook CD, Martin BR, Wiley JL
title=Cannabimimetic properties of ajulemic acid
journal=J. Pharmacol. Exp. Ther.
volume=320
issue=2
pages=678–86
year=2007
pmid=17105826
doi=10.1124/jpet.106.111625] however there was no difference between ajulemic acid and placebo on the "cannabimimetic" assay when used in humans at therapeutic doses. [cite journal
author= Sumariwalla PF, Gallily R, Tchilibon S, Fride E, Mechoulam R, Feldmann M
title= A novel synthetic, nonpsychoactive cannabinoid acid (HU-320) with anti-inflammatory properties in murine collagen-induced arthritis
journal= Arthritis & Rheumatism
volume=50
issue=3
pages=985-998
year=2004
pmid=15022343
doi=10.1002/art.20050] [cite journal
author= Sumariwalla PF, Feldmann M, Gallily R, Mechoulam R
title= Reply to the Editor
journal= Arthritis & Rheumatism
volume=50
issue=12
pages=4079-4080
year=2004
doi=10.1002/art.20806]

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