Biocatalytic allylbenzene/amphetamine conversion

[Fractalhead]

Ok, there has been much discussion on the forums about how if you rub certain allylbenzene containing essential oils onto the body and do some vigorous exercise, you get effects that are hypothetically attributable to the body converting the allylbenzenes into the corresponding amphetamines. Indeed, I have experienced effects from eating nutmeg powder that match with descriptions in the literature of MMDA effects.

The question I want to raise in this thread is just what is the pool of DIRECT evidence that this conversion 'actually' takes place.

In the MMDA section of PIHKAL, Shulgin mentions that "It has been reported that the passage of this oil through the liver of a rabbit will generate MMDA in that animal."

Does anyone have any further details on that experiment? Furthermore, has an amphetamine derivative ever been detected in human urine after ingestion or application of an allylbenzene? This would surely be a simple experiment and it would seem surprising if it had not been carried out somewhere.

What about an in vitro conversion using a liver homogenate? I vaguely remember someone mentioning an experiment being carried out where the oil was passed through a column containing immobilised liver enzymes or something and coming out the bottom fully converted.

Please, if anyone has anything to add, i'm burning with curiosity

[Guest electro]

heh u could probably test that theory by using one of those "pro" e test kits /.... th eoned that differentiate between mmda mdma mdea mda etc aswell as between speed and mdx..

apply some oil to the test chemical, observe colour change.

eat a whole bunch of it (where legal), wait until effects are felt (if any) then use urine as the next test sample... if it does get converted so late, with a large dose "some" bio produced amphetamine should be filtered out without being broken down into something else .

You may have to remove the water from the urine (mmm evap urine .. i cant believe i am even thinking this ! LOL) .... then use the concentrated salts as the test material to actually get a positive result (If there will indeed even be one).

Failing this one may have to actually take a real drug test and see if one gets a positive (as they test for metabolites of drugs rather than drugs themselves generally)

[theobromos]

I would be surprised if a pill test did not show the presence of lots of colourful compounds in your urine, there are lots of substituted phenethylamines produced by the body.

[Torsten]

Originally posted by Fractalhead:

The question I want to raise in this thread is just what is the pool of DIRECT evidence that this conversion 'actually' takes place.

The only direct evidence is the paper covering the liver experiment. I don't have it but have read sections of it. You should not have any problems sourcing this. If in doubt maybe check the ref section of Sasha's book or ask him.

Furthermore, has an amphetamine derivative ever been detected in human urine after ingestion or application of an allylbenzene? This would surely be a simple experiment and it would seem surprising if it had not been carried out somewhere.

Not a lot of any original drug makes it out through the urine unchanged. most get metabolised. so what you should be looking for are the metabolites. problems is that some of these amphetamin metabolites may be the same as the allylbenzene metabolites. But that in itself would be an interesting find.

What about an in vitro conversion using a liver homogenate?

Seems to me that the trend is for easy drug manufacture, not complicated.

[theobromos]

Rabbit liver cells will also destroy MDMA as well as create it:

Kumagai Y, Schmitz DA, Cho AK. "Aromatic hydroxylation of methylenedioxybenzene (MDB) and methylenedioxymethamphetamine (MDMA) by rabbit liver microsomes." Xenobiotica (1992) 22(4): 395-403.

Kumagai Y, Wickham KA, Schmitz DA, Cho AK. "Metabolism of methylenedioxyphenyl compounds by rabbit liver preparations. Participation of different cytochrome P450 isozymes in the demethylenation reaction." Biochem Pharmacol 1991 Aug 8;42(5):1061-7.

Fukuto JM, Kumagai Y, Cho AK. "Determination of the mechanism of demethylenation of (methylenedioxy)phenyl compounds by cytochrome P450 using deuterium isotope effects." J Med Chem 1991 Sep;34(9):2871-6.

And if you ask Sasha perhaps you could also ask if he is ever going to repair the reference section of PIHKAL. I had a hell of a time trying to follow up all those fucked-up references that would shame any respectable scientist.

The point of references is not to fill out a few pages of print, references exist so that other researchers can check on your interpretation of the original data. Very necessary as most scientists are unable to see out of their boxes. I have seen quite a few mistakes in science generally. I have also seen things that I would assume are mistakes in Sasha's work. If I could have checked his references easily I would have been able to draw his attention to his errors.

Bad enough to lack any indication of which reference refers to which assertions in the text but to have incomplete references is unforgivable (murple seems to have learned this bad habit from his aquaintance).

Torsten, what do you mean by "not a lot"? MDMA itself can be found unchanged in the urine of consumers by most normal analytical methods.

[Fractalhead]

Here's an interesting article. I wonder if anyone has tried eating these...

Biochim Biophys Acta. 1971 Aug 19;244(2):322-8. Related Articles, Links

Urinary excretion of tertiary amino methoxy methylenedioxy propiophenones as metabolites of myristicin in the rat and guinea pig.

Oswald EO, Fishbein L, Corbett BJ, Walker MP.

I've got a few more references to put up including the one in which amphetamine derivatives were reported...

[Rev]

"not a lot' still satisfies the test as Zero content would be the control

Piss in a jar and GCMS?

but where would you get the refernce for MMDA? I dont think this is a common drug is it?

[Fractalhead]

There could well be relative Rf data for MMDA somewhere. However, Rf data for the hypothetical safrole metabolites is definitely available so this might be a better option. Mass spectral data would be even more useful so it might be worth sending urine samples off to a trusted lab (although you might have to convince them that you were only on safrole

[ 04. August 2004, 17:39: Message edited by: Fractalhead ]

[Rev]

Any idea on cost?

less than $100, more than $100?

[Fractalhead]

I haven't really shopped around so I'm not really the person to ask but off the top of my head, you are looking at a minimum order of around $400. For that you might get 5-10 samples analysed if you're lucky. There may be better deals around but that kind of figure is fairly standard in my understanding.

[Fractalhead]

Here's another ref:

Braun, U., Kalbhen, D.A. 1973, Pharmacology. 9(5):312-6 'Evidence for the biogenic formation of amphetamine derivatives from components of nutmeg.

(Haven't got the abstract or full text for this one yet.)