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Entactogens/Entheogens of the Future.

methylenedioxybenzyl piperidine

a bit earlier someone mentioned this as a possible entactogen, I am certain that 2-(3,4-methylenedioxybenzyl) piperidine 2-MDPip is a known substance, it is so obvious and easily synthesised.
doing a search didn't turn up the piperidine but did turn up the related pyrrolidines which indicate that they are analgesic to an extent and are central stimulants. some substitution patterns showed effects on blood pressure. nowhere in the patent did it mention the test rats bouncing around with glow sticks but that doesn't mean that the substance isn't a potential empathogen.
patent
http://v3.espacenet.com/textdoc?DB=EPODOC&IDX=US4279918&F=0

I haven't got the time right now but it would be interesting to see what other patents the applicants have filed.

V
 
Great link...I had a sneaking suspicion after examining the structures of endomorphin 1 & 2 that N-methyl-ring substituted 2-benzylpyrrolidines would have analgesic effects given then Tyr-Pro motif, but had been unable to find any synthetic compounds matching the description.
 
I'm sure the following compound gets a big fat zero for realistic entactogenic potential but if entactogenic effects stemmed directly from artistic design of molecules this would be a winner. Two methlenedioxy's and an aminoindan.

I call it the ninja. =D
 

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Why not just replace the methylenedioxy ring with a furan ring? I think people have noted that with the O on the 3, it's almost the same as a methylenedioxy (to the monkeys anyway). Benzaldehyde, nitroalkene (or I prefer nitroalcohol) then off you go...
 
^Just realised you were talking about the usefull compounds above. Good point in which case, I shall stop posting useless but cool looking chemicals :)
 
haribo1 said:
Why not just replace the methylenedioxy ring with a furan ring? I think people have noted that with the O on the 3, it's almost the same as a methylenedioxy (to the monkeys anyway). Benzaldehyde, nitroalkene (or I prefer nitroalcohol) then off you go...
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which molecule are we talking about? I'm confused...more than usual:)
 
Serious discussion: 2-(3,4-methylenedioxybenzyl) piperidine 2-MDPip etc mentioned by yourself.

Unserious discussion: My crazy Three-point Di-methylenedioxy-aminoindan. Looks cool but is probably rubbish.
 
Reminisant B said:
Serious discussion: 2-(3,4-methylenedioxybenzyl) piperidine 2-MDPip etc mentioned by yourself.

Unserious discussion: My crazy Three-point Di-methylenedioxy-aminoindan. Looks cool but is probably rubbish.
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ok i was confused as to how the benzaldehyde nitroalkene or nitroalcohol has anything to do with making 2(-34MD)pip by any of the common sensible routes and I still cannot see how. the morpholine could be made from the nitro alcohol, and the fencamfamine analog from the nitroalkene. hence my confusion

the crazy aminoindan does look very cool indeed just from a nicely symetrical molecule perspective, I have no idea how it would be made or if it could be made, I suspect not.

I do think that the 2-(dihydrobenzofuranylmethyl) piperidine could be interesting.
 
Yeah 2-(dihydrobenzofuranylmethyl) piperidine looks cool.

Has anyone made 2,3-Dihydro-benzofuran-2-ylamine, 2-aminoindan but with Oxygen incorporated like a benzofuran?
 
Reminisant B said:
Yeah 2-(dihydrobenzofuranylmethyl) piperidine looks cool.

Has anyone made 2,3-Dihydro-benzofuran-2-ylamine, 2-aminoindan but with Oxygen incorporated like a benzofuran?
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pretty sure these or something very similar are known, for some reason I think that they are anticoagulants a bit lik heparin or warfarin.
 
vecktor said:
pretty sure these or something very similar are known, for some reason I think that they are anticoagulants a bit lik heparin or warfarin.
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EEK! Definately stay away fromt those then.
 
Reduce the N-propyl to NH2 and the alpha-propyl to alpha-methyl or alpha-ethyl and I would bet it would be active, probably a-MT or a-ET-like.
 
Reminisant B said:
Do you think the followng compound would display warfarin like properties?

In rats in apparently induces dopamine release, not sure if that would translate as levo-dopa type release or amphetamine release.

http://www.ingentaconnect.com/content/els/00142999/2001/00000421/00000003/art01040
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fI may have been somewhat hasty WRT to anticoagulants from what remember at it was a very long time ago, a 5 or six membered ring containing oxygen and but not neccesarily either a keto group (to make a lactone) or an amino group next to the ring oxygen is required for anticoagulant activity.
feel free to jump in to correct me!
 
Reminisant B said:
Do you think the followng compound would display warfarin like properties?

In rats in apparently induces dopamine release, not sure if that would translate as levo-dopa type release or amphetamine release.

http://www.ingentaconnect.com/content/els/00142999/2001/00000421/00000003/art01040
Click to expand...
this compound is called BPAP. there is only limited literature on it, it is classified as a catecholaminergic tone increaser whatever that means. I think PPAP the phenyl analog has been used medicinally, it (ppap) is widely used in research as a non maoi selegine type substance.
there are some issues with benzofuran drugs which have a side chain coming out of the furan ring, there have been several with serious liver toxicity, I cannot remeber off the top of my head which ones, I will edit ths post when remember. whether BPAP is toxic due to the liver opening the furan ring in the same way I do not know.
there is certain interest in BPAP amongst life extension and nootropics groups, it seems to be fairly unselective between 5-HT DA and NE.
the benzothiophene is also known
 
morninggloryseed said:
Reduce the N-propyl to NH2 and the alpha-propyl to alpha-methyl or alpha-ethyl and I would bet it would be active, probably a-MT or a-ET-like.
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the benzofuran isosteres of the tryptamines have already been investigated, they are considerably less active than the parent compounds, something like less than 1/10th, I believe they have been discussed on this forum.
I wouldn't expect the benzofuran isostere of AMT or AET to be very active.
 
All of the N-desmonomethyl 3, 4,-mono and 3,4-di-methyl methamphetamines are expected to be active as stand alone alpha-methyl-phenylethylamines, where amine is an anagram of mania and where I know that comment is beyond random.

That word comment is a test of the Emergency World Word Inventing Militia.
Had this been an actual emergency, you would not have been overtly informed nor would you have been capable of taking much preventive action at that point anyway. wElcOmE.

N-alpha-methyl-N-cyclotetramethylene-yl-3,4-MDO-Ph-1-ethanamine.
 
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