• Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

  • N&PD Moderators: Skorpio

Entactogens of the Future

Ham-milton

Ham-milton

Bluelighter
Joined
Jul 20, 2007
Messages
5,738
I'm sorry if there's another thread by this title, I'm new (well, technically I've been a member for a year or two, but for some reason was never able to post) but a daily reader.

I'm a avid member over at Opiophile, but over time I've been less interested in answering "will snorting vicodin make it stronger" and more interested in the theoretical, SAR-stuff, and the chemistry.

Anyway, a few of us over at the Opiophile have been discussing forming a test group a little, and have been talking about what chems we might consider tasting. We haven't gotten past that yet, but a couple of the chems we've discussed are interesting enough that I thought I'd mention them over here and see what you guys had to say.

One of them is Hydrocotarnine and the other is hydrohydrastinine. These are their chemical structures, but I forget which is which because I'm silly.
http://forum.opiophile.org/attachment.php?attachmentid=1854&stc=1&d=1177354608

http://forum.opiophile.org/attachment.php?attachmentid=1855&stc=1&d=1177354608



Anyway, you can obviously see the relationship to MDMA and the other known entactogens. They're incredibly interesting in my mind, but I can't find much information on human testing.

Apparently they're chemicals lightly watched by the DEA (unknown source) but if they know about them, they do a good job hiding it.

I talked with Nichols, a professor at purdue (? I forget) who published a report in 1994 (again, not entirely sure) that tested some "non-neurotoxic MDMA analogues" one of which had a structure almost exactly like hydrocotarnine.

I believed it substitued in like 80-ish percent of rats trained to discriminate MDMA. That's pretty good, imo.

Does anyone here have any actual knowledge, experience about these chemicals, or has any ideas about them, I'd really appreciate.

This site is a bit more theoretically and technically oriented, and your members are top-notch, so I'd greatly appreciate your assistance.

Hammilton
 
Ham-milton said:
No one? Nothing? Wow... where are members like F&B or msg?
Click to expand...

patience mr Hamilton! :)
On ADD people read the forum infrequently and often do not feel the need to post immediately.
BTW for your info, the links you posted require login and it is impolite to cross reference forums. so it would be appreciated if you either post the contents here, or links that work.
thanks
V
 
Here are the structures if you want them. Hydrocotarnine is a minor constituent of P. somniferum, as well as an oxidative degredation (not a human metabolite) product of noscapine and possibly thebaine. Hydrastinine is found in Hydrastis canadensis L., according to wikipedia. As vector pointed out, the SAR involved in binding and transport for MDMA-like entacteogenic activity does not allow for a tertiary amine. It might be plausible that the entacteogenic activity lies in the N-demethylated metabolites, but this process would be in competition with other primary metabolic processes. Keep in mind the possible pharmacokinetic properties I just listed are purely conjecture.
 

Attachments

  • Entacteogens Future.gif
    Entacteogens Future.gif
    2.5 KB · Views: 116
Last edited:
sorry, no I'm not from Ontario, and apologies for the cross-links.

More importantly, I suppose, does anyone here have any info about these two? I suppose that if and when a shulgin- THIQ book comes out, these two will be ones to get a * or whatever it was that was used for MDMA and 2C-B in their book, next to their name.
 
i doubt anyone has come across these though i would think a synth of hydrohydrastinine would not be too difficult...?

not sure but perhaps it can be finished off without too much difficulty from Piperonyl alcohol?
 
almost guarantee both are very low activity or inactive as releasers as they are tertiary amines. these are cactus quinolines, and are quite widespread if I remember the other trivial names then will post them.

the compounds reported by nichols were methylenedioxy/methyl methoxy amino indans( MDAI and MMAI )and methylenedioxy amino tetralines, with a primary amine one unit further from the benzene ring and a totally carbon containing ring. they did substitute for the MDMA stimulus whatever that was for the rats, however I believe both are very serotinergic rather than dopaminergic or NE. MDAI being almost totally SE specific if I remember right. the n-methyl MDAI might be a little more interesting.
there are some potent DA reuptake inhibitors which contain the ttrahydroisoquinoline structure though the more potent ones have benzyl or similar attached to the nitrogen containing ring.
 
cinnamic acid can be used a precurser to amphetamine, and MDA, I believe. Not that it's an easy route.

I don't know if the MD-analogue would be psychoactive or entactogenic or do anything, but it might be worth a try. the MD-derivitives of vannillin might be interesting, and very easy to synth, but there's nothing available about them.

There are a lot of other chemical 'families' that could be well used to avoid analogue acts. For instance, there are phenethylamines that are active BZD-agonists, and also some that are mu-agonists, as I recall. I doubt they're easily made, however.

As far as hydrocotarnine having any activity (or it's metabolites, anyway), I've tasted it once at around 100mg, I think a little less, and while there was no stimulation there were some obvious serotinergic activity. Not exactly visuals, but not, not visuals either. I'd guess that it'd have to go much higher for anything magical to happen, if it does at all.

I don't doubt that any activity would have to come through metabolites, but unless the dose neccessary was prohibitively high, I don't see a reason not to take the prodrug if it's more easily synthed as I'm sure it is.
 
You must log in or register to reply here.
Top