5-substituted tryptamines

[fastandbulbous]

^ Not only are they 'stench agents' (take the top off a bottle of 2-mercaptoethanol and tell me it smells nice, I dare you!), but they can form sulphide cross linkages with proteins of your body if you come across a denaturing agent & oxidizer.

Besides if you have an enzyme that's used to dealing with ethers and you give it a thioether to chew on, more often than not the thioether acts as a competetive inhibitor (the 2C-T-x/aleph compounds being a very good example) as it prevents the enzyme taking up the active conformation

 

[retired_chemist]

Interesting that you mention mercaptoethanol.

The basic routes to vinylsulfones all start with either

R-SH + BrCH2CH2OH

or

R-Br + HSCH2CH2OH

-> R-SCH2CH2OH

depending on how you need to put together the puzzle. I did lots of both. According to the literature at least, pure, freshly distilled mercaptoethanol has almost no odor. It's actually the disulfides that stink. I never tested the theory, lol, the basic 1 L bottle from Aldrich was pretty obnoxious.

But compared to some of the thiols I made for use in the bromoethanol route the mercaptoethanol was a veritable petunia. Never met a thiol I liked.

Anyway I'm gettin off topic ...

 

[Hah]

hi,
what are your thoughts on that ?

one possibility is that adding lime and heating causes the formation of dehydrobufotenine a three ring compound where the amino tail ends up joined back to the phenyl ring, this supposedly is active. I am not certain how dehydrobuftenine arises it is quite common in analysis, I think it might be heat and base.

from Tihkal :
O-Methylnordehydrobufotenine, is a rearrangement product of dehydrobufotenine, which may be a natural product or it may be an artifact of analysis.

cheers.

 

[fastandbulbous]

Interesting that you mention mercaptoethanol.

depending on how you need to put together the puzzle. I did lots of both. According to the literature at least, pure, freshly distilled mercaptoethanol has almost no odor. It's actually the disulfides that stink. I never tested the theory, lol, the basic 1 L bottle from Aldrich was pretty obnoxious.

But compared to some of the thiols I made for use in the bromoethanol route the mercaptoethanol was a veritable petunia. Never met a thiol I liked.

Anyway I'm gettin off topic ...

1-bromobutane & NaSH give skunk juice (the small B&W furry animal, not the killer shrubbery from the Netherlands). 1-butanethiol is what gives skunks their fiersome reputation (my lab stunk of the stuff for weeks!)

Mercaptoethanols are internationally monitored reagents as they are one of the possible starting materials for mustard gas

 

[Morninggloryseed]

I think 5-AcO-DMT and some of its N,N-dialkyl homologues are well worth a try. I'd definitely sign up for a shot.

 

[Recept]

I wonder if dehydrobufotenine is even active? Does anyone know if there is any data on the activity of similar types of compounds?

 

[Dondante]

From another thread:

There has been plenty of confusion regarding dehydrobufotenine which is an extraction artifact of bufotenine and which is believed to be psychoactive rather than a violent poison

I'm intrigued by the possibility of psychedelic activity from cyclization products of simple tryptamines. In TIHKAL, O-methyl-nordehydrobufotenine is mentioned under the entry for 5-MEO-NMT. This mention is made in the hard copy only, which adds even more mystery to the question!

Shulgin writes, "A fascinating cyclization product of this "nor-compound" is a cyclic dehydrogenation product where there is a direct coupling of the tryptamine nitrogen to the 4-position of the indole ring. This tricyclic material, O-methyl-nordehydrobufotenine, proved to be of comparable activity to DMT in rat studies, but has not apparently been studied in man."

I've always thought that tryptamines folded up kinda like this anyway, internal salt interaction though, rather than covalent bond.

I attached the structure of dehydrobufotenine.

 

[nuke]

Well, you have LSD with a hydrophilic region in that area, and if that's the gold standard of a serotonergic psychedelic, then that cyclic compound would probably have some other sort of activity.

Though for all we know, it could be metabolized in vivo to something else completely (quaternary amines don't tend to be terribly stable).

 

[Dondante]

Here's another that I'd love to see some data on.

 

[EN21]

If you like those structures, check out that: http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=PubMed&dopt=Citation&list_uids=11558603
Somei et al. found that serotonin derivatives undergo pictet spengler cyclization rather towards the indolic 4 position, forming sth. like dehydrobufotenine, but with an additional carbon between the sidechain nitrogen and the 4- position, than towards the 2- position, forming a carboline.
And all that cool structures are probably in our brains.

 

[nuke]

This experiment established that 5-acetoxy-N:N-dimethyltryptamine (5AcO-DMT: acetyl bufotenine) and 4-methoxy-N:N-dtmethyltryptamine (4MeODMT) have a significantly greater effect than 7-methoxy-N,N-dimethyltryptamine (TMeO-DMT) or 6MeO-DMT. The third experiment demonstrated that 5-methoxy-N-methyl-N-ethyltryptamine (5MeO-MET) has a significantly greater effect than 5AcO-DMT, 4MeO-DMT, 5MeO-DMT and DET. 5AcO-DMT is of particular interest since its lipid solubility characteristics should permit it to cross the blood brain barrier where by the action of tissue esterase it could give rise to 5HO-DMT (bufotenine), a compound which would otherwise not be expected to enter the central nervous system too readily (14)· Accordingly, an attempt was made to establish the dose-response curve for the behavioral effects of this compound· Thus, the effect of several doses of 5-acetoxy-N,N-dimethyltryptamine was investigated, using again a Latin-square experimental design (N = 6:6 animals x 5 dose levels and saline). The conditioned avoidance response failure frequencies were converted first into a percentage of total responses possible in the experlmental period and then into probit units. The resulting regression line was calculated by the method of Finney (20) and is shown in Fig. 1. Analysis of variance shows that there is significant regression. Interestingly, even 5 umoles/kg, the lowest dose given, differed from saline in its behavioral effect at the 0.01 level of significance.

http://www.erowid.org/references/refs_view.php?A=ShowDocPartFrame&ID=5678&DocPartID=5454

 

[Morninggloryseed]

Ahhh, that's the paper I saw that showed 5-MeO-MET is of extreme potency. And if I am reading it correctly, it would seem the acetate ester of bufotenine is certainly worth exploring.

 

[LuxEtVeritas]

of course though the quality of experience imparted by the substance in this class is more important than the quantity or lack thereof needed though potency is always nice

certainly with less material needed the difficulty for some who are using such materials smoked and can not get the appropriate dose fully inhaled potency makes such easier, so if the quality of effect is there than it is a sure winner

certainly of interest to know some feedback on

 

[dorothyperkins]

Sorry, slightly off topic but since retired chemist mentioned DET i thought i'd ask here. Never tried DMT but vaporising DET/DiPT the stuff crystallises again really quickly leaving mouth/throat coated with a solid layer of tryptamine! Its pretty nasty and off putting.

Thought it might not be so bad with DMT because of lower melting point but looking at pihkal there cant be more than 20 deg C difference between the three. Maybe a mixture of the two would depress the melting point enough to circumvent this.

Never heard of anything like this being reported before, or maybe its normal and no-one thinks it worth mentioning?

 

[Morninggloryseed]

of course though the quality of experience imparted by the substance in this class is more important than the quantity or lack thereof needed though potency is always nice

This is true....5-MeO-DET is listed as being a potent psychedelic in that report...but when people try it in psychedelic dosages....terrible side effects are felt (according to TIHKAL). This one is only useful at threshold dosages.

Sorry, slightly off topic but since retired chemist mentioned DET i thought i'd ask here. Never tried DMT but vaporising DET/DiPT the stuff crystallises again really quickly leaving mouth/throat coated with a solid layer of tryptamine! Its pretty nasty and off putting.

Even more off-topic...but you have smoked DiPT? Anything interesting to speak of it? I've only tried it orally.

 

[dorothyperkins]

Not really, MGS, similar to DET, some mental effects but no aural, though i couldnt get much down due the effect i mentioned.

 

[LuxEtVeritas]

maybe a 4-AcO-MET?
If i am correct i'd say 4-AcO-DMT seems to get high marks as a general consenus for perhaps the most 'pleasant' DMT related analogue

 

[egor]

I have a bit of info on 4-aco-met (including a few Tihkal style reports), I'll have to dig it up later tonight

 

[Dondante]

Any chance a mod could cut/paste and give the posts on cyclization products of tryptamines their own thread? There are like 5 or 6 posts starting w/ one on dehydrobufotenine.

Pretty please ... :D

 

[retired_chemist]

Sorry, slightly off topic but since retired chemist mentioned DET i thought i'd ask here. Never tried DMT but vaporising DET/DiPT the stuff crystallises again really quickly leaving mouth/throat coated with a solid layer of tryptamine! Its pretty nasty and off putting.

Thought it might not be so bad with DMT because of lower melting point but looking at pihkal there cant be more than 20 deg C difference between the three. Maybe a mixture of the two would depress the melting point enough to circumvent this.

Never heard of anything like this being reported before, or maybe its normal and no-one thinks it worth mentioning?

Never tried smoking DET hydrochloride, only the base. Unless it is extremely pure, DET base is a light orange oil. Used to saturate a little piece of bud with the oil and smoke that. Tasted like shit, bad aftertaste was pretty much a given.