5-MeO-DMT[Merged]

[N3XU5]

so there's gotta be a very simplistic tek for getting 5-MeO-dmt out of a batch of pure N,N. anyone have any ideas? could it possibly be as simple as a standard oxidation to 5-OH-DMT and then just a simple methylation? or would you have to protect the amine prior to oxidation, methylation or both? and if anyone has any teks on this at all please help me out, thanks!

[N3XU5]

revision: would it even be possible to use straight serotonin as the starter? and if so would it be possible simply with methylation of the 5-hydroxy and the 2-amine? i mean looking at the structure 5-meo-dmt is about as close to serotonin as you can get, just missing the 3 methyl groups. I can't find a damn thing on any sort of synthetic 5-meo-dmt synthesis, just extractions from natural n,ndmt and 5-meo-dmt containing plants. Please help?

[jellyfish]

Just logged in to tell you you have no idea what you're talking about. I'd run a column... Why would an oxidation give you 5-OH-DMT from 5-MeO. And why would you protect the amine from methylation when you want it to be methylated. Since you don't seem to know how to purify things, adding a bunch of reagents to your mixture will just make things dirtier.

[DJ Meaty Cheeks]

Just extract it from raw materials like a man.

[N3XU5]

Originally Posted by jellyfish

Just logged in to tell you you have no idea what you're talking about. I'd run a column... Why would an oxidation give you 5-OH-DMT from 5-MeO. And why would you protect the amine from methylation when you want it to be methylated. Since you don't seem to know how to purify things, adding a bunch of reagents to your mixture will just make things dirtier.

first of all i'm talking about n,n-dmt-->5-meo-dmt, not the other way around, that's retarded. and protecting the amine so that during an oxidation to get the methoxy group the amine doesn't oxidize...becaue the amine in N,N-DMT IS ALREADY FUCKING METHYLATED...wouldn't the amine be oxidized as well? so basically protect the amine to oxidize the ring, then unprotect the amine and methylate the oxygen atom. sorry if i was misleading.

secondly, since serotonin's amine group isn't methylated and already has the hydroxy group on the ring, all that it's missing is the methyl group on the oxygen, and the two methyl groups on the amine. so would methylation produce the desired 5-meo without having to utilize n,n-dmt as a starter?

[BungHole]

Play nice kiddies. . .

[Gun Lover]

Originally Posted by N3XU5

secondly, since serotonin's amine group isn't methylated and already has the hydroxy group on the ring, all that it's missing is the methyl group on the oxygen, and the two methyl groups on the amine. so would methylation produce the desired 5-meo without having to utilize n,n-dmt as a starter?

I'm not sure that you're aware of the fact that you'd wind up with the inactive quaternary ammonium salt which is completely inactive.

Once you alkylate an amine once, it is more susceptible to further alkylation to the ammonium species.

A williamson ether synthesis would be how to alkylate the 5-HO, (methinks). Deprotonate to get the phenoxide, react with MeBr/MeCl (which happen to be some of the most toxic chemicals known to man, lol)

Yeah, there's gotta be a better methylating agent, but I'm just a noob.

I can say that starting from serotonin probably isn't the best route, lol.

[N3XU5]

I'm most certainly not trying to say that I know as much as the majority of people on here, i don't. I'm just thinking about different structures and how chemically simple 5-meo-dmt is to serotonin, so i there a methylation that would work a lot better other than the one that involve me poisoning myself? there's gotta be!

[N3XU5]

okay so a little while ago i was talkin about possibly getting the 5-methoxy from N,N as a starter. Fuck that, too hard. So here's my suggestion, starting from melatonin or N-[2-(5-methoxy-1H-indol-3-yl)ethyl] acetamide.
So starting from that my guess is that you first have to do the ketone reduction to the secondary alcohol. So a solution of N-[2-(5-methoxy-1H-indol-3-yl)ethyl] acetamide in absolute ethanol is added Xg. of NaBH4 (under reflux?). Afterwards water is added and the alcohol removed by fractional distillation to yield _____ (need to work on my nomenclature, sorry)

So the secondary alcohol is then dissolved in acetic acid at 28 deg C and KMnO4 is added to form the carbonyl group. this group can then be eliminated. To eliminate the carbonyl a solution of hydrazine dissolved in basic solution with glycol to reduce the carbonyl group from the alkyl chain.

So after this would methylation be able to produce the desired groups on the amine in order to create that sought after product?

If anyone sees potential in this hodge-podge please tell me possible times, conditions, measurements? The hydrazine reaction is supposed to have very good yields buy hydrazine always sketches me out. any ideas welcome!

[Hydroponichronic]

What ketone are you talking about? The only carbonyl group on melatonin is an amide group, which is completely different. If one wanted to make 5-MeO-DMT from melatonin they would start by hydrolyzing the amide in pH~14 solution. From there they'd have 5-MeO-Tryptamine, which could get dimethylated in the same ways they'd normally dimethylate a tryptamine.

[N3XU5]

Originally Posted by Hydroponichronic

What ketone are you talking about? The only carbonyl group on melatonin is an amide group, which is completely different. If one wanted to make 5-MeO-DMT from melatonin they would start by hydrolyzing the amide in pH~14 solution. From there they'd have 5-MeO-Tryptamine, which could get dimethylated in the same ways they'd normally dimethylate a tryptamine.

okay so hydrolyze the amine in basic solution with KOH or whatever doesn't fuckin matter. would it just be a straight Eschweiler-Clarke to the product? And would you happen to know of a less toxic / otc methylating agent than formaldehyde?

[BungHole]

Originally Posted by N3XU5

okay so hydrolyze the amine in basic solution with KOH or whatever doesn't fuckin matter. would it just be a straight Eschweiler-Clarke to the product? And would you happen to know of a less toxic / otc methylating agent than formaldehyde?

Yeah, don't try an Eschweiler-Clarke. The Pictet-Spengler will definitely be a competing reaction. Lots of discussion on this around here. SN2 and eliminate if you're hell bent on methylating the primary amine. I'm sure there's other means of methylating, ones that might even be safe and OTC, but I haven't seen any.

EDIT: I merged your threads. I really think it would help to streamline your questions.

Originally Posted by N3XU5

so there's gotta be a very simplistic tek for getting 5-MeO-dmt out of a batch of pure N,N. anyone have any ideas? could it possibly be as simple as a standard oxidation to 5-OH-DMT and then just a simple methylation? or would you have to protect the amine prior to oxidation, methylation or both? and if anyone has any teks on this at all please help me out, thanks!

Standard oxidation? Not at all. Oxidation of an aromatic ring to get a hydroxy compound is possible, see benzene-->phenol. But I have never heard of it being done on this substrate, and if it was, it would be a very obscure procedure. If anything, you would oxidize the ethylamine chain at the 3-position or the oxidize at the 2-position. This is regardless of N-substitution.

As for methylation, like GL said, quat salt.

[N3XU5]

much appreciated for all the feedback!

also this probably will make me look stoopid...but under any conditions whatsoever reflux etc. would an n,n dimethylation be possible with a solution of methanol and acetic acid? i think it might still produce the co2 needed in the mechanism of the eschweiler-clarke...

[BungHole]

Originally Posted by N3XU5

much appreciated for all the feedback!

also this probably will make me look stoopid...but under any conditions whatsoever reflux etc. would an n,n dimethylation be possible with a solution of methanol and acetic acid? i think it might still produce the co2 needed in the mechanism of the eschweiler-clarke...

Do you mean methylation by S_N2 (methyl iodide, methyl sulfate, etc., not formaldehyde+reduction)? If so, acidic conditions should be avoided, as the ammonium ion cannot act as a nucleophile.

As for CO₂, it isn't "needed." CO₂ is a product. Yes, the donation of an electron and hydrogen atom by the formate ion and subsequent formation of carbon dioxide is inherent to the E-C reaction. But you don't have to create CO₂ to methylate the amine.

I know this is never conducive to internet discussion, but you need to develop a basic understanding of organic chemistry before we can help you. I suppose that using acetic acid replaces formic acid. Acetic acid doesn't act as a reducing agent the way formic acid does though. Also, although there are mechanisms by which alcohols can alkylate amines, the Eschweiler-Clarke is not one of them (atleast I don't think). So methanol will not add the methyl group. I admire your current understanding of organic chemistry, you seem to have a feel for the communication of the field. You need to study mechanism though. These reactions happen for a reason, and you need to realize the reason.

Also, avoid the E-C reactions because it forms a highly toxic MAOI. Before you even get any ideas in your head, realize that it is dangerous. I really should let you figure this out on your own, but I'd rather you not contract Parkinson's.

[Danger]

Dont waste your time... NN pwns the shit out of 5-meo any day of the week.

[N3XU5]

understandably. however i am interested in more applications than just ingestion of the straight 5-methoxy. i read up on shulgin's hypothesis for the 4 position tryptamines that can be made with mushrooms using said 5-methoxy in the substrate. comes out 4-hydroxy-5-methoxytryptamine. what the fuck else could you do? that's where i'm trying to go, not that i would even consider attempting any of this at this point or ever for that matter.

and thank you bunghole. i understand that my knowledge at this point is very splintered however i haven't exactly studied this for years. goin on one year. i took a lot of standard chem in school, no organic chem. so i appreciate all the information you give me to help me understand more. there is a lot to learn and discover.