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could a San Pedro produce 2C-B? Options
 
pau
#1 Posted : 6/30/2010 1:49:27 AM

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We've seen threads about dosing or upping the potency of San Pedro with precursor injections, fertilizers, etc etc.

SWIM had a dream: his neighbor accidently dropped a bottle of Bromo-Seltzer over the fence between their properties. This caused the San Pedro to start making 2C-B instead of mescaline.

Anybody have any ideas about how a growing San Pedro could be made to produce 2C-B, short of genetic manipulation (which itself would not be a bad idea)?
WHOA!
 

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Ginkgo
#2 Posted : 6/30/2010 2:29:27 AM

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What an interesting dream! But sadly, it must remain a dream. Firstly, 2C-B and mescaline is not only separated by the bromine at the 4 position compared the oxygen at the same position with mescaline. The position of another oxygen is also a difference, at position 3 for the mescaline and position 2 for 2C-B.

Mescaline is 3,4,5-trimethoxyphenethylamine, while 2C-B is 2,5-dimethoxy-4-bromophenethylamine. Following your dream hypothesis one would end up with 3,5-dimethoxy-4-bromophenethylamine. That's an unknown compound, but I guess it would be psychoactive, although likely with lower potency than 2C-B on par with mescaline.

There's more problems though. It simply will not do to add bromine. The reason mushrooms can produce exotic compounds such as 4-hydroxy-DPT or 4-hydroxy-DIPT by adding DPT or DIPT is that the enzyme that 4-hydroxylates dimethyltryptamine into psilocin (4-hydroxy-dimethyltryptamine) doesn't care too much about its substrate. Next to any tryptamine compound can therefore be 4-hydroxylated by the mushroom.

Cacti doesn't have this 4-hydroxylating enzyme. The biosynthesis of mescaline goes as this:


Now, as you see already in the first step where phenylalanine is hydroxylated into tyrosine, the 4 position is occupied by an oxygen rather than a bromine. At the last step of the biosynthesis this position undergoes another change, by O-methyl transferase the 4 position now carries a methoxy group.

In order for your idea to work, you would have to genetically engineer the cactus to produce a phenylalanine brominating enzyme rather than an phenylalanine hydroxylase. You would also need to disable the last step of the O-methyl transferase, not to mention make sure that all other enzymes at play don't care if their substrate have a huge bromine stuck to it.

That way you would end up with 3,5-dimethoxy-4-bromophenethylamine. However, if the end product rather should be 2C-B (2,5-dimethoxy-4-bromophenethylamine), you would also need to engineer the cactus to hydroxylase and then O-methyl transferase the 2 position instead of the 3 position. Put simply, this is all extremely difficult. It can't be done by adding anything to the cactus.

Nice dream though! Very happy
 
pau
#3 Posted : 6/30/2010 2:57:13 AM

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Thanks for the analysis, E.G! Maybe it would be easier for mushrooms, grown on the propert medium, to make 2C-B!

And, SWIM had a wonderful dream indeed. I did not report his other wonderful dream, in which Kurt Vonnegut accidently dropped a small vial of 2C-B in a creek, and the entire Pacific Ocean turned into ... well, you get the idea.

Anyway, awfully early in the morning for you Norwegian chemists to be at work! Must be midnight sun, no?
WHOA!
 
Ginkgo
#4 Posted : 6/30/2010 3:07:06 AM

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Well, for it to work with mushrooms you would need an even more insane same amount of genetic engineering. 2C-B and psilocin are to vastly different substances! They don't even have the same skeleton, psilocin is a tryptamine while 2C-B is a phenethylamine.

Late it is indeed (or rather early), but I love the night! So quiet and peaceful. There's no midnight sun as far south in the country as I live, but the sun is awake nearly 19 hours a day now! And I am no chemist, just devoted to my entheogens... Pleased
 
soulfood
#5 Posted : 6/30/2010 4:27:03 AM

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... I feel dumber

what?
 
dg
#6 Posted : 6/30/2010 5:41:27 AM
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very well writen reply ther EG!

synthing 2cb would be much easier than growing it in cacti or mushrooms

i have no exp with it but i know its not as hard as some projects
 
burnt
#7 Posted : 6/30/2010 8:44:05 AM

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Most organisms on land do not have enzymes that can incorporate bromine in molecules.

Many organisms in the ocean however do. You'd be much more likely to find a compound like 2cb in the ocean then on land. Although I doubt its a natural compound.
 
Ginkgo
#8 Posted : 6/30/2010 8:56:27 AM

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Yeah, for example 5-bromo-dimethyltryptamine (5-Br-DMT) is found in some marine sponges, including Smenospongia spp. I doubt it's psychedelic though, animal studies suggest sedative effects. Perhaps it's an serotonin antagonist rather than agonist.

But it for sure is a vast number of unidentified substances in marine plants and animals, some of which may be psychedelic. It would be extremely interesting if a phenethylamine with bromine was found in nature!
 
 
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