LOPHOPHINE

[kemist]

This compound was already mentioned here in some threads.

LOPHOPHINE or MMDPEA or 5-MeO MDPEA is naturaly occuring alkaloid in Peyote and San Pedro.

ILPT is very eager to separate this alkaloid from mescaline. He worked more with peruvianus before but recently there were low yields and strange impurities which put him off.
Now parrot found bag of dried Pachanoi chips and ILPT decied to give it a go.
He gonna use 200g semidry STB with calcium hydroxide and pull with limonene. Also, he reserved 50g to try resin route (1st. time ever) if stb wouldn`t yield much.

Anyway, stuff isn`t from reliable vendor and was only found somewhere, so it easily could be bunk. Let`s go back to Lophophine


ILPT cannot find any physical or chemical data on this molecule.

What he really like about LOPHOPHINE is that it has structure of MMDA with only difference of missing one methyl group on the ethylamine end. This make it phenethylamine (like mescaline) not an amphetamine (like mmda)
BUT on the other end it has methylendioxy group on phenyl (like mmda) not three methoxy groups (like mescaline)

So ILPT presuming this molecule must be great, Shulgin wrote that is simmilar to mescaline but ILPT believe this could be more empathogenic and socializing then mescaline and without neurotoxicity and comedowns which methylendioxyamphetamines bringing.



CAN ANYBODY PLEASE GET SOME PHYS/CHEM DATA ABOUT LOPHOPHINE ?

 

[polytrip]

Maybe this is the compound that gives peyote it's XTC-like buzz?

 

[PsilocybeChild]

Erowid Online Books : "PIHKAL" - #95 LOPHOPHINE

Entry #95 LOPHOPHINE from PiHKAL by Alexander & Ann Shulgin.

www.erowid.org

I have been interested in this substance for a long time. I hope it is active.

 

[SnozzleBerry]

I just spent 20 minutes running all of the various names I could find for this compound through Science Direct, PubMed and its extended sections, ISI Web of Knowledge, Science of Synthesis, EBSCOhost and JSTOR (just for shits and giggles). None of these e-journal archives had anything on "homomyristicylamine" or "Homomyristylamine". Searching "3-Methoxy-4,5-methylenedioxyphenethylamine" brought up some results, but none of them seemed at all relevnat, nor did they contain any discussion of the compound within the articles either. I found this through erowid:

2.1.9. Homomyristylamine

3-Methoxy-4,5-methylenedioxyphenethylamine (18, homomyristylamine, lophophine) is of interest both for biosynthetic and for structural analogy reasons, The compound, although not yet detected per se in the peyote cactus, is a logical intermediate in the biosynthesis of several of the methylenedioxy-substituted tetrahydroisoquinolines known to be present, Although supporting evidence has not been sought. (18 ) can theoretically participate in the ring-closure reactions with acetaldehyde to form anhalonine (11) and (after N-methylation) lophophorine (10), Furthermore, (18 ) is the two-carbon analog of the well-established psychotomimetic MMDA (51, Section 3.2.4), The compound has been clinically assayed and is an active psychotomimetic with a threshold level observed at 250 mg (Shulgin, 1976a); thus it has somewhat less than twice the potency of mescaline. Qualitatively it is similar to mescaline in action, with mood elevation progressing into a euphoric state and an enhancement of visual perception, especially in the realm of color. Unlike mescaline, there is little if any nausea and there is no visual distortion.

I'm not sure if it's the search terminology, or if this compound just hasn't been studied; many of the sites also said that it was only theorized to be in peyote, but should logically be there, so I'm guessing there just hasn't been much research on it. Here's another little snippet I found over at lycaeum:

A fourth compound is homomyristicylamine (lophophine, 9) which also has never been observed in the peyote plant, but which presents an obvious theoretical potential as a biosynthetic precursor of the tetrahydroisoquinoline alkaloids such as lophophorine and anhalonine. This compound is active in man at dosage levels of 150 to 200 mg, about twice the potency of mescaline (18 ). The quali- tative description of its action is quite similar to that of mescaline, in that there is a peaceful elevation of mood, the generation of an euphoric state, and the enhancement of visual perception especially in the color sense. There are dis- similarities, particularly in that there is little if any nausea and there is no visual distortion. These latter differences disappear at dosages of 300 mg and there is the generation of eyes-closed imagery similar to that observed with mescaline.

If anyone has any ideas as to other search terms or related ares that may bring up information on this molecule, let me know, I'll gladly see what I can find

 

[kemist]

Erowid Online Books : "PIHKAL" - #95 LOPHOPHINE

Entry #95 LOPHOPHINE from PiHKAL by Alexander & Ann Shulgin.

www.erowid.org

I have been interested in this substance for a long time. I hope it is active.

It must be active. In Shulgin we trust

One batch of cactus, ILPT had was labeled as peruvianus but after first evaporation of salting vinegar solution it didn`t look as clean and solid as from peruvianus, he think it could be san pedro mislabeled.

Anyway he redisolved this reddish gooey oily stuff in little of diluted HCL then filtered and wash the filter with some more hcl.
Then he evaporated HCL. It still looked dirty (very reddish), but it turned to by more hard and crystaly.

ILPT dried it well, powderized it and commence 4 cold anhydrous acetone washes.

Powder lost most of it redness and become off white and little pinkish.
After testing this product was ILPT`s favourite one.It lost all the sedativness and yawning. Fairly psychedelic and quiet emphatic , extremely nic feelings.



Later he took some of this acetone washed hydrochloride and washed it 2 times with cold anhydrous IPA
The powder after was became much whither and more potent by weight, but effects wasn`t as emphatogenic and socializing but more psychedelic.

Ilpt evaporated this IPA wash and retrieve small colourless crystal (almost like sugar). The ammount was tiny so ILPT decided to take it subling. (stupid idea) to feel virtually no effects. Just to remind you ILPT never took any of his extract subling. but always orally. They may not be as active if taken by different route.

Now ILPT gonna do some work and see what is locked inside his San Pedro

If anyone has any ideas as to other search terms or related ares that may bring up information on this molecule, let me know, I'll gladly see what I can find

The IUPAC name should be : 3-Methoxy-4,5-Methylenedioxyphenylethylamine.

 

[SnozzleBerry]

Erowid Online Books : "PIHKAL" - #95 LOPHOPHINE

Entry #95 LOPHOPHINE from PiHKAL by Alexander & Ann Shulgin.

www.erowid.org

If anyone has any ideas as to other search terms or related ares that may bring up information on this molecule, let me know, I'll gladly see what I can find

The IUPAC name should be : 3-Methoxy-4,5-Methylenedioxyphenylethylamine.

Yea, I was using the IUPAC name, but it didn't pull up any exact matches when I put it in quotations. The problem was, when I didn't use quotes it pulled up tons of articles that made no mention of the compound whatsoever. I noticed there were at least two chemical names for it, but neither pulled up any articles and the letter abbreviations didn't fare much better. I dunno what else to search by or if theres another online journal/reference source I should check that I didn't. Lophophine didn't pull up anything either :x mebbe there's just no research on it aside from Sasha?