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« Carfentanil (Not for pain relief) | Main | Alprazolam/Xanax (Now in 3-D!) »

AM404 (Weed Tylenol?)

Category: Drugs
Posted on: August 17, 2007 8:33 AM, by Molecule of the Day

AM404 is an active metabolite of acetaminophen:

InChI=1/C26H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23-26(29)27-24-21-19-20-22-25(24)28/h6-7,9-10,12-13,15-16,19-22,28H,2-5,8,11,14,17-18,23H2,1H3,(H,27,29)/b7-6-,10-9-,13-12-,16-15-


Acetaminophen is an unusual painkiller - it isn't quite like ibuprofen or other NSAIDs. AM404 is its arachidonic acid conjugate, which has some cannabinoid activity (as well as COX activity).


Anyone who knows anything interesting about cannabinoids in analgesia (please, not people who say "you have to just smoke the plant," I'm much more interested in knowing what's doing the job), I'd love to hear from!

Comments

Seems like that should be para-substituted, not ortho.

Posted by: Strange Painkiller | August 17, 2007 12:26 PM

http://www.mazepath.com/uncleal/ananda.htm
http://www.mazepath.com/uncleal/urb597.gif
happy happy, joy, joy

Rather than administer recreational pharmaceuticals, alter endogenous metabolism and allow the body to accumulate all-natural happiness.

Posted by: Uncle Al | August 17, 2007 12:40 PM

Well, I don't know exactly why cannabinoids seem to be so good as analgesics, but I do know that they excede the opiates in relieving neuropathic pain, rather than noxious pain from heat, chemicals, or whatever. Neuropahic pain is typically treated with things like gabapentin and pregabalin (calcium channel blockers).

And yah, I also think that should be para-substituted if it is indeed a metabolite of acetaminophen.

Posted by: Vince Noir | August 18, 2007 7:32 PM

AM404 is the para-isomer, N-(4-hydroxyphenyl)-arachidonoylamide, which potentiates the activity of endogenous arachidonyl ethanolamide (anandamide) by blocking its re-uptake into presynaptic neurons (anandamide transport inhibitor).

Posted by: tanevala | November 20, 2007 4:35 AM

AM404 is the para-isomer, N-(4-hydroxyphenyl)-arachidonoylamide, which potentiates the activity of endogenous arachidonyl ethanolamide (anandamide) by blocking its re-uptake into presynaptic neurons (anandamide transport inhibitor).

Posted by: tanevala | November 20, 2007 4:36 AM

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