The Vespiary
The Hive => Novel Discourse => Topic started by: neuromodulator on April 17, 2002, 12:14:00 AM
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If you stare at the stucture of delta-9-THC it is not hard to see an allylbenzene functionality just waiting to be aminated. So why not grow some weed, make hash oil and then treat it with PdCl2 and benzoquinone followed by ammonium acetate and sodium cyanoborohydride or with formamide followed by acid hydrolysis. The resulting compound is a substituted phenylethylamine. Has this ever been done yet?
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Shulgin write something about a (army ??) project of puting an amine into the THC molecule, and they just ended up with an inactive molecule.
THC hits the andamid acid receptores, it just a long u-like alken with two carboxylic acid grups at the ends.
When you look at the amphetamines and dopamine or serotonine they are close to each other, usual you'r goal is something who look's like the neurotransmitter witch activate the system you are 'hitting' afther. The only thing you can doo with THC it to modify the propan chain, there are some analogs who are 10-20times stronger than THC and last much longer in the body (up to 48 hours, thats a loong time to bee stoned :)
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Ahem... It's the anandamide receptor (CB1) and anandamide is arachidonic acid ethanolamide. But you are right, the possible binding orientation in the receptor is U-like, with the end of the unsaturated C20-fatty acid tail coming close to the ethanolamide head.
There are several studies about aminated THC analogs, but they didn't yield something interesting, simply because the receptor doesn't need a protonated amine for proper binding (like the serotonin receptors).
The most potent propyl-sidechain modifications are the 1,1-dimethyl-octyl and the 1,2-dimethyl-heptyl variants (which are both incredibly long lasting).
And then there is the yet secret superpotent CB1 agonist "mahanandamide"...
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wonderfull to be reproven by you Lilienthal ;) , coulden't remember tha name of the acid (or how to spell it (as usual))
Thanks
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Wacker doesn't work well on tertiary carbons. You end up with the tertiary alcohol, in stead of the ketone on the alpha-carbon.
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I'd be interested to know exactly which aminated THC compounds they made and tested were. Does anyone know?
If the Wacker is out of the question in this case, then why not use formic acid and 30% H2O2 to form an epoxide and then hydrolyze it with dilute H2SO4 to get the ketone?
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You can't make a ketone out of a tertiary C (= connected to three other C atoms). Not without breaking at least one of the C-C bonds first.
I'm not fat just horizontally disproportionate.
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I'm not trying to make a ketone out of a tertiary carbon. I'm talking about making a ketone out of a secondary carbon. Look at the structure again and you will see that the beta-carbon from the benzene ring is secondary.
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I think a lot of the synthetic work was concentrated on replacing the ring oxygen bridge with nitrogen. from memory there are quite a few '70's papers by a researcher named Razdan.
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