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Is 2C-B "more synthetic" than LSD? (eye roll)

red22

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Nov 23, 2009
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This discussion came up on The Shroomery. People were alleging the following. LSD is made by isolating the lysergic acid moiety from a naturally-occuring ergoloid. This serves as the base structure. The synthesis indicated in PIHKAL for 2-CB involves building a base phenethylmine from mundane chemicals. I was saying that LSD and 2C-B are on the same level. For one thing, they both have naturally-occurring counterparts that are capable of producing a psychedelic experience: naturally-occuring lysergamides for LSD; and mescaline for 2C-B. Secondly, usually the synthesis of LSD is carried out using toxic and psychicly worthless ergoloids: ergotamine or ergocristine. Those have been found to be the most efficient starting materials. So, as with 2C-B, a batch of LSD can have mundane origins. However, the lysergic acid amides can also be used as a starting material for LSD. Can mescaline be used as the starting material for 2C-B? Moreover, LSD can be made via total synthesis.

My perspective is that LSD and 2C-B are similar in that they both have naturally-occurring counterparts that produce the same effects (relatively speaking) and the syntheses involve similar steps. I think it's unfair to say "2C-B is a man made chemical" as is commonly parroted and a doctor told me that the term "semisynthetic" is bullshit. I believe it's a flexible term and that it can easily be applied to 2C-B.
 
to me, the really interesting thing is that there are many phenethylamine analogs (including 2C-B) with CNS activity of various stripes... some are more visual, some more enactogenic, some just plain speedy. similar efforts with regard to the ergolines has generally failed: there aren't really many (any?) LSD analogs (which are not prodrugs of LSD itself) that have CNS activity equivalent to or greater than the parent compound, LSD. i mean, you can find naturally occurring instances of compounds in the same family: consider LSA in morning glories and HBW seeds, or things like mescaline in psychoactive cacti. but as above, both LSD and 2C-B are ultimately synthetic compounds, neither one is found in nature and neither one is synthesized directly from a natural product.
 
For the record, Hawaiin Baby Woodrose is a type of morning glory and there are a whole bunch of morning glory types that contain lysergamides, all of which are in the following four species: Ipomoea, Turbina, Stictocardia, and Argyreia (arr-guh-rhey-uh) and all of these belong to the tribe, Ipmoeeae. See pages 225, 226, 236, and 238 in the following book: Eckhart Eich. 2008. Solanaceae and Convolvulaceae: Secondary Metabolites: Biosynthesis, Chemotaxonomy, Biological and Economics Significance (a Handbook).
 
For the record, Hawaiin Baby Woodrose is a type of morning glory and there are a whole bunch of morning glory types that contain lysergamides, all of which are in the following four species: Ipomoea, Turbina, Stictocardia, and Argyreia (arr-guh-rhey-uh) and all of these belong to the tribe, Ipmoeeae. See pages 225, 226, 236, and 238 in the following book: Eckhart Eich. 2008. Solanaceae and Convolvulaceae: Secondary Metabolites: Biosynthesis, Chemotaxonomy, Biological and Economics Significance (a Handbook).
Yes this is well known fact. Who is this message aimed at? Because LSD is not found in either of those.
 
to me, the really interesting thing is that there are many phenethylamine analogs (including 2C-B) with CNS activity of various stripes... some are more visual, some more enactogenic, some just plain speedy. similar efforts with regard to the ergolines has generally failed: there aren't really many (any?) LSD analogs (which are not prodrugs of LSD itself) that have CNS activity equivalent to or greater than the parent compound, LSD. i mean, you can find naturally occurring instances of compounds in the same family: consider LSA in morning glories and HBW seeds, or things like mescaline in psychoactive cacti. but as above, both LSD and 2C-B are ultimately synthetic compounds, neither one is found in nature and neither one is synthesized directly from a natural product.

I dont think there has been the same input in ergolines than phenethylamines.
Perhaps because phenethylamines are magnitudes less complex to make than ergolines.

No drug can be more synthetic than another. It's either man made or it's not.
 
Ahh shucks you guys have closed minds....Even Hoffman said 'not yet' when asked if LSD has been found in nature. I, for one, hold out hope 2C-B is found in the ocean. Maybe even 2C-C also...I mean they both feel pretty damn 'natural' to me.
 
I, for one, hold out hope 2C-B is found in the ocean. Maybe even 2C-C also...I mean they both feel pretty damn 'natural' to me.

Ring-brominated tryptamines have been discovered in sea sponges, but not phenethylamines. I wouldn't hold out too long.
...
At best, debate over when things are natural vs. artificial lies outside the scope of this forum and just barely in the scope of PD.

ebola
 
The thing is some drugs are labeled semisynthetic. Is this legitimate? Does 2C-B meet these requirements.

Also, obviously you didn't understand my post about MG seeds. "MG seeds" never refers specifically to Ipomoea tricolor. The term is synonymous with "convolvulaceae seeds." So, the term "MG seeds" covers "Hawaiin Baby Woodrose." There's lots of MG seeds that contain lysergamides. HBWR is of the argyreia species (Argyreia nervosa); and there are several other argyreia species that contain lysergamides (i.e. Argyreia barensii). I took the time to make the post I made above for a reason,.
 
Bloodshed: On our planet, probably not. Who knows what complex organic systems elsewhere produce? Bit of nitpicking here, but yeah :D


I think the only reason why there are so many tryptamines found in nature is because they use DMT, which a lot of organisms have, as the base for their synthesis. Not sure how cacti or morning glories get mescaline or LSA, but the 2Cs don't seem too close to mescaline (both phenethylamines, but as stated, you can't get 2C-B from Mescaline or at least not economically). LSD is a different beast, and it might be found in nature, though I'm sure some crazy ethnobotanist has gotten through the entire family of plants already

(^That's with my limited knowledge of chemistry and biology though.)

That said, this entire debate doesn't really matter as the LSD/2C-B you get is all synthetic and the entire synthetic vs. non-synthetic is a load of bollocks anyway (even psilocybin in mushrooms is synthesized, though not man-made ;))
 
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Sorry. One of the nicknames listed for 2C-B on Erowid is "bromo mescaline." Maybe that's inaccurate and that's what's throwing me off.
 
Look at this. For 2C-B to look like mescaline you'd have to do an awful lot of things, I don't think it's possible for a plant or even humanity today to make that in to 2C-B. Could share a precursor or something, but with evolution in mind it just doesn't seem logical for that to happen. Now look at LSA and LSD, they're quite alike and the synthesis in TiHKAL doesn't have a ton of steps between LSA and LSD. Seems logical, though you'd have to find it in the same family as morning glory (or something phylogenetically close, and yeah I had to look up that last term ;))

There's a good chance the ADDers that are following this thread are cringing at my posts, but still
 
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The thing is some drugs are labeled semisynthetic. Is this legitimate? Does 2C-B meet these requirements.

Also, obviously you didn't understand my post about MG seeds. "MG seeds" never refers specifically to Ipomoea tricolor. The term is synonymous with "convolvulaceae seeds." So, the term "MG seeds" covers "Hawaiin Baby Woodrose." There's lots of MG seeds that contain lysergamides. HBWR is of the argyreia species (Argyreia nervosa); and there are several other argyreia species that contain lysergamides (i.e. Argyreia barensii). I took the time to make the post I made above for a reason,.
So you wanted to list the various types of LSA containing seeds? Okay.

Btw I would call bromomescaline 3,5-dimethoxy 4-bromophenethylamine. Probably a good compound.
 
No drug can be more synthetic than another. It's either man made or it's not.

I am guessing by man-made you mean 'invented by man / not found in nature'. If that's the case, then it would be instructive to mention that even this distinction, while real, means basically nothing. By the way, just to be clear, I quoted you toastmann because you bring up a point I want to expound upon, but I'm not calling you out in a hostile manner. Just to make sure this post doesn't get misunderstood.

By this I mean that some compounds were invented by a chemist either just coming up with a brand new structure in their head, or much more likely by a chemist looking at an existing molecule and modifying the structure in their mind / on paper, and then using their synthetic abilities to make that altered molecule a reality. Other compounds are found in nature, and exist independently of mankind. But there is not any difference between things that were invented and things found in nature besides their source of discovery. They're all just chemicals, and they operate in the body and react to other chemicals based on the same set of physical laws.

There's another distinction that some people make, and that is whether a compound was made by a plant biosynthetically using enzymes or whether it was made in a lab. This relates to an actual sample of a drug, whereas the distinction between 'invented by man' and 'found in nature' is a more theoretical distinction. But this second distinction is just as equally meaningless as far as a drug's function or whether or not it is healthy to use as is the distinction based on invention versus discovery. Some people I have met would take mushrooms, but wouldn't take 4-HO-DMT because it was synthesized in a lab. This is just silly, and I will illustrate the silliness as follows, including both the distinction between invention versus discovery as well as between whether an actual physical sample was synthesized in a lab or in a plant cell, all rolled into one:

There is a compound called N,N-methylethyltryptamine, or MET. This compound was invented, not discovered, and doesn't exist in nature as far as we know. There's another compound called 4-hydroxy-N,N-methylethyltryptamine, abbreviated as 4-HO-MET. As with the unsubstituted MET, 4-HO-MET was also invented, not discovered, and that distinction has held for this compound as well because we have not subsequently discovered it in nature. Since both of these compounds were invented in the mind of Sasha Shulgin, by conceptually modifying the structures of DMT and 4-HO-DMT, they are only created in labs, not in plants, animals, or fungi. So by certain people's measures they're not healthy to use either because they are not found in nature, or because they can only be produced in a lab, or both.

But now things get complicated! It just so happens that if you enrich the substrate upon which psilocybin-containing mushrooms grow with MET, they will take it into their body (mycelium), and here is where it gets interesting. It turns out that the enzymes that take DMT and hydroxylate the 4-position to make 4-HO-DMT, also known as psilocin, are not selective. Those enzymes it turns out will take almost any N,N-disubstituted tryptamine (provided the alkyl substitutions aren't super-long) and stick the hydroxy on the four position, just as the enzymes do to the naturally-occurring, discovered-not-invented compound DMT, turning it into the also naturally-occurring, discovered-not-invented compound 4-HO-DMT.

So in summary, if you take MET and you put it into the stuff magic mushrooms grow on, they will take it and the enzymes that ordinarily take DMT and make 4-HO-DMT will turn the MET into 4-HO-MET.

So the question to the people who make silly distinctions about 'natural' or 'synthetic' things being healthy or not, is what category does the 4-HO-MET that is produced fall into? You have a compound that was invented, not discovered, and is only synthesized in a lab (or better to say 'not found in nature'), that is turned into another compound that was invented, not discovered, and is also not found in nature, by a fungus. So even though both compounds were invented, and neither is found in nature, you can 'hijack' magic mushrooms to take the first compound and make it into the second using a purely biosynthetic, 'natural' process, using enzymes.

So is 4-HO-MET then still 'synthetic'? Obviously the fact that it was invented, not discovered doesn't change, but if you can use a mushroom to perform the 4-substitution, is the resulting compound natural or synthetic?

The whole distinction is goofy. I get that it's based upon earnest beliefs that natural things are safe where man-made things are not, but it isn't that black and white. Surely strychnine, which exists in nature, is not safe. And there's the whole panoply of invented psychedelics that are 'synthetic' but are perfectly safe at ordinary doses. Unfortunately this false dichotomy is very strongly ingrained in the minds of its proponents, and often in my experience no amount of factual information will shift people's views on this matter.

So you wanted to list the various types of LSA containing seeds? Okay.

Btw I would call bromomescaline 3,5-dimethoxy 4-bromophenethylamine. Probably a good compound.

I don't know if there would be enough room there for the bromine. Look up 'steric bulk', as I could be wrong. I'm not an expert here (on steric bulk), chem major or not, but my gut and what training I do have says that either there's simply just not enough room so it couldn't exist, or that it could theoretically exist but that the synthesis would be just too absurdly difficult / that it would be too unfavorable of a product in the reaction, yielding garbage substitutions you don't want and little if any of what you do want.

Maybe there's enough room there for a chlorine? I mean, it would certainly be more likely than bromine, chlorine being smaller, but I still couldn't say for sure if even the 4-chloro version could exist.
 
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