Ecstasy analogues found in cacti

[BilZ0r]

J Psychoactive Drugs. 2008 Jun;40(2):219-22.
Ecstasy analogues found in cacti.
Bruhn JG, El-Seedi HR, Stephanson N, Beck O, Shulgin AT.

Division of Pharmacognosy, Department of Medicinal Chemistry, Uppsala University, Uppsala, Sweden.

Human interest in psychoactive phenethylamines is known from the use of mescaline-containing cacti and designer drugs such as Ecstasy. From the alkaloid composition of cacti we hypothesized that substances resembling Ecstasy might occur naturally. In this article we show that lophophine, homopiperonylamine and lobivine are new minor constituents of two cactus species, Lophophora williamsii (peyote) and Trichocereus pachanoi (San Pedro). This is the first report of putatively psychoactive phenethylamines besides mescaline in these cacti. A search for further biosynthetic analogues may provide new insights into the structure-activity relationships of mescaline. An intriguing question is whether the new natural compounds can be called "designer drugs."

 

[Hammilton]

So homopiperonylamine is a fancy term for MDPEA? and lophophine 2-methoxy-MDPEA?

 

[Jamshyd]

An intriguing question is whether the new natural compounds can be called "designer drugs."

Lol, am I the only person who sees the humour in this?

 

[MurphyClox]

Nope jamshyd, not the only one.

On topic: I wonder to what extend this "minor contents", which are most certainly psychoactive, influence the quality of the trip in comparison to pure mescalin...

And although not related to the thread but touching the same question: Pure psilocybine vs. mushrooms (which contain baeocystine and other)?

- Murphy

 

[Jamshyd]

^ You will find a lot of discussion on the latter if you search PD.l With psychedelics, it is very, very, very, very difficult (if not impossible) to make out any substantial differences (beyond things like duration), because trips are inherently always different even with the same substance.

 

[Hammilton]

certainly psychoactive?

MDPEA is inactive up to at least 300mg- so probably only with an MAOI.

2-Methyl-MDPEA might be active, hard to say though...

what is lobivine though?

 

[Black]

In this article we show that lophophine, homopiperonylamine and lobivine are new minor constituents of two cactus species, Lophophora williamsii (peyote) and Trichocereus pachanoi (San Pedro).

this part is interesting too. i've never heard of lobivine (and havent found any info/structure of it), but in what way are lophophine or mdpea new?

 

[MurphyClox]

Lobivine is "new", i.e. was first mentioned in the cited article. No structure available at SciFinder. Somebody has to get the full ref, I guess, if we want to see the asnwer.

 

[vecktor]

wierdly shulgin is completely aware or should be of the work of bo holmstedt (sp?), who characterised all this stuff in lophophora a long time ago. doesn't seemto be any thing new here.

 

[fastandbulbous]

Well cvonsidering the appearance of various methylenedioxytytrahydroisoquinoline derivatives in peyote and that they are biosynthesised from phenethylamine precursors (as in the methoxylated THIQ compounds), the presence of 3,4-methylenedioxyPEA and 3-methoxy-4,5-methylenedioxyPEA shouldn't come as any great surprise.

By 'ecstacy analogues' I assume they are purely looking at the methylenedioxy ring substituent, because in terms of psychopharmacology the 3-methoxy-4,5-methylenedioxy compounds will be very different to the 3,4-methylenedioxy compounds (well in terms of MMDA vs MDA from personal experience & reports of the activity of lophophine - 3-methoxy-4,5-methylenedioxyPEA being more like mescaline in effect)

 

[BilZ0r]

I don't get to post very often any more, but I just wanted to say that I really miss you guys (FnB esp. Sunderland Rep). I'm actually begging for a job in the UK right now.

I got my first paper published on hallucinogens in the last couple of months. Look at my nick, and think really hard and you might get it.

Seriously though, you still have an ally in somone about to (Cross fingers) get a serious job in a serious neuroscience research intitute in Europe (possibly the best one).

Are you fucking kiddying me, 96k upload limit for PDFs?

PM with you email if you really want the PDF... or better still, PM me with an anonymous way of upload the PDF so everyone can see it.

 

[jackie jones]

I can see similarities in the effects of mda and mescaline.