Fractalhead

If anyone is still hanging to see that Dateline interview with Strike, I can help you out with a copy. Just PM me with a postal address and I'll send it off ASAP (which is usually pretty slowly for me ?

Yeah it would be interesting (where legal) to try some little experiments with pure DMT to see what kinds of artefacts are formed when it is put through a simulated extraction procedure. I suspect you would get all kinds of funkadelic stuff being formed inc b-carbs

Hi Rev, The merck index states protopine freebase as being: sol in 15 parts chloroform, 900 parts alcohol (presumably ethanol), 1000 parts ether, slightly sol in ethyl acetate, carbon disulphide, benzene, petroleum ether (shellite) and practically insol in water. protopine.HCl: sol in 143 parts water at 13 deg C sol in alcohol Geez the merck index can be vague! Chelerythrine freebase: Has been recrystallised from chloroform+methanol (proportions not specified). Freebase is colourless but quaternary salts are yellow. Aq solutions of freebase and quaternary salts show violet fluorescence (excitation wavelength not specified). The hydrochloride, nitrate and sulfate have been prepared: yellow crystals with poor water solubility. Rev, rather than worry about solvent cost, why don't you make a simple little solvent recovery system and re-use your solvent. You can make a really nifty one out of a large glass jar (preferably pyrex) inwhich you put the solvent containing goodies. You put a slightly smaller jar inside the bigger jar suspended off the bottom by a piece of wire (coat hangers are good) and shape a aluminium foil condenser 'cone' into the top of the big jar, fill the cone (which points down into the small jar) with ice/water and heat the big jar over a steamer. It works just like the old bush survival thing where you dig a hole, fill it with branches and a container and put plastic over the top with a small rock to weigh the plastic down towards the container and catch the transpired water. You might even be able to fashion a larger one out of bigger containers with a bit of imagination. I would try DCM as the non-polar solvent at first. It just seems to be sooo good at dissolving things. Once you get the stuff out, you can play around with other (cheaper, less toxic) solvents for adequate solubility. I doubt you will find any better than DCM tho. Good luck

I'm toying with the idea of putting together something of an ethnobotanical TLC instructional and database page. I thought it might be cool if it could be hosted here with a link off the SAB community page. It would be very simple at first basically with a few pictures and tables with Rf values and detection methods for interesting compounds extracted from the literature. Future expansions might include a section for submission of TLC chromatograms from forum users or even NMR spectra, GC/HPLC retention times, or a downloadable mass spectral library that includes some of the more obscure compounds not found in the NIST libraries etc. Therefore I have several questions: 1. Does this sound like a good idea? 2. Torsten, are you happy to do this? 3. What is the process for submitting a webpage? 4. What is the format you will need? 5. What is a good, easy to use piece of web-authoring software to use in creating the page? [ 01. February 2005, 22:37: Message edited by: Fractalhead ]

Gonzo, I carried out a similar experiment a couple of years ago, and observed the same blue/green oil (soluble in alcohol but not water). Not sure what this stuff is. I tried drinking an alcoholic solution of this stuff (maybe 50 ml) but didn't notice anything special. Need to try more.

I remember noticing a range of effects from eating commercial powdered nutmeg (like masterfoods etc). I have always got some kind of psychoactive effect from eating 30 g or so. There seems to be the toxic effects that cause nausea, dizziness and deep sleep and this seems to happen with just about any nutmeg in a high dose. However, sometimes this effect is overlaid with a distinctly e-like amphetamine type feeling. Only once (n=~7) have i experienced the e feeling with unmistakable open eye phosphene visuals (kaleidoscopic fluorescent colours - very bright). The three classes of effect didn't seem to go hand in hand and suggest differences in chemical makeup and that even allylbenzene devoid material could be called 'active'.

I'm hoping to conduct a HPLC based isolation of himbacine (and co.) in the next 12 months or so for some serious bioassays. Retails for some ridiculous price from Sigma.

When u say 'tested', do you mean bioassay or chemical analysis?

Apparently, Tandy has better (more robust) ones over the counter for about 10 bucks.

OK. I don't know the first thing about law, but my reading of these words below suggests to me that AMT would be covered by these anlalogue laws. Maybe there is a different set of analogue laws by which AMT is not covered? Please explain. I think it is points diii and div that do it: Point iv says that if you replace one of the groups listed in point diii (including a dialklylamine group) with one of the others listed in point diii (including a mono-amine group), you have an analogue. The alpha-methyl group of AMT is also covered by the 'addition' part in point iii. Interestingly, they don't specify mono-alkylamines so I wonder what the go is there?? In any case, it wouldn;t be hard to fuck someone over with legal bullshit like point e: (e) otherwise an homologue, analogue, chemical derivative or substance substantially similar in chemical structure; however obtained, except where the drug analogue is separately specified in this Schedule Exactly how do you define substantially similar in chemical structure? A substance ("drug analogue") which is, in relation to another substance (being a substance specified elsewhere in this Schedule, or a stereoisomer, a structural isomer (with the same constituent groups) or an alkaloid of such a substance): (a) a stereoisomer; or ( a structural isomer having the same constituent groups; or © an alkaloid; or (d) a structural modification obtained in 1 or more of the following ways: (i) by the replacement of up to 2 carbocyclic or heterocyclic ring structures with different carbocyclic or heterocyclic ring structures; (ii) by the addition of hydrogen atoms to 1 or more unsaturated bonds; (iii) by the addition of 1 or more of the following groups, namely alkoxy, cyclic diether, acyl, acyloxy, mono-amino and dialkylamino groups with up to 6 carbon atoms in any alkyl residue; alkyl, alkenyl and alkynyl groups with up to 6 carbon atoms in the group, where the group is attached to oxygen (for example, an ester or an ether group), nitrogen, sulphur or carbon; and halogen, hydroxy, nitro and amino groups; (iv) by the replacement of 1 or more of the groups specified in subparagraph (iii) with another such group or groups; (v) by the conversion of a carboxyl or an ester group into an amide group; or (e) otherwise an homologue, analogue, chemical derivative or substance substantially similar in chemical structure; however obtained, except where the drug analogue is separately specified in this Schedule The minimum trafficable quantity of: (a) that other substance in relation to which the substance is a drug analogue; or ( if there is more than 1 such other substance—that other substance having the least minimum trafficable quantity The minimum commercial quantity, if any, of: (a) that other substance in relation to which the substance is a drug analogue; or ( if there is more than 1 such other substance— that other substance having the least minimum commercial quantity.

I understand that when ergot alkaloids were first identified in morning glory seeds by Hofmann that there was much suspicion by the scientific community that some kind of fungal endophyte or fungal contamination of seed samples must have been responsible for the biosynthesis of the compounds since ergot alkaloids had only been found in fungi at the time. I vaguely remember reading that this controversy had been cleaned up by some kind of study that 'proved' that the compounds were indeed made by the plant. So does anyone know the details of this study? I did a quick search on pubmed and couldn't find anything and i can't remember where i read about the study. I recently attended a seminar in which the speaker said that lysergyl peptide synthetase (lps) enzymes are only known to occur in fungi and bacteria but not plants. These enzymes catalyse the formation of the amide bonds of various lysergic amides in endophytic fungi. Interestingly, a recent knockout experiment showed that ergine production is eliminated in Neotyphodium lolii when the lps1 gene is knocked out suggesting that this enzyme may be responsible for ergine synthesis or a step leading to its synthesis. It would be very interesting to probe Argyreia or Ipomoea genomic DNA for a homologous gene since if some plants do indeed contain lps genes, this would be of great evolutionary significance. Hmmm... I wonder how fussy the lps enzymes are when it comes to substrates?

Cool. So phytochemical studies confirmed that these alkaloids occur in these plants but I guess I'll have to read the refs to find out how they ruled out an endophytic fungus. Interestingly, some convolvulaceous species also contain the lolitrem class alkaloids that occur in A. lolii infected ryegrass. The funny thing is that these alkaloids, while being derived from tryptophan, require a completely different set of genes to the ergoline alkaloids. The independent co-evolution of both alkaloid classes in the plant genome seems unlikely. Perhaps the alkaloids are indeed made by an endosymbiotic fungus? Or perhaps the plants obtained the ability to make these products by some crazy lateral gene transfer process?

Hehe. It was a while ago but i think my original blabberings were about the idea of using a hand-held spectroscope to look at the fluorescence of aqueous alkaloid extracts in order to get a feel for what might (or more readily: what might not be) responsible for the fluorescence. The specroscope basically diffracts the incoming light into a spectrum that you can see on a little 'screen' with a wavelength scale on it. This enables you to get a feel for the wavelengths at which the spectrum peaks. This would allow rapid examinations of solutes without TLC... say during an extraction or chemical reaction... and you wouldn't even need to open the glass vessel containing the solution. This technique would obviously be highly dodgey and only really worth trying for interests sake and pretty colours Handheld spectroscopes are pretty cheap (under $200 for a good one i think). I think the other idea i had was to create a makeshift spectroscope using a prism or diffraction grating to diffract the fluorescence coming out of a solution onto a card with a scale of some sort on it. I vaguely remember suggesting the idea of using a blacklight, a prism and a piece of card with a narrow slit in it as a kind of monochromator. This would allow you to focus a beam of light with a narrow wavelength range onto a solution or TLC plate and check out the ability of certain wavelengths to excite your fluorophores of interest. Also, you can get very tiny (handheld) little USB linking spectrophotometers now that you could hook up to a computer and get absorbance spectra of solutions. I'm not sure if the sensitivity would be high enough, but i think i remember postulating that one of these might be used to obtain absorbance spectra of compounds separated by TLC. This might be useful to obtain extra information with which to ID spots on TLC plates when in the field. Probably more trouble than it is worth since a good Rf value would probably be sufficient reason to bring the sample back to home base for rigorous GC/MS or LC/MS analyses that would provide much better info/labour time ratios. However, the advantages of the little spectrophotometer over MS are portability and affordability. My experience is that the UV/fluorescence thing is most useful when you have a fair idea what you are looking at already and want to obtain estimates of concentration/composition within a limited range of possibilities.

I might have a seed or two to donate aswell...

That is a kick-arse site Rev!

Yeah. give us a call and we'll catch up.

It'll be great to have you DL! It sounds like you're coming with friends. Who else is coming along? You'll be here during peak wildflower season so doing the rounds through wildflower country would be a good option (bring a large capacity memory stick for the DC). The Pinnacles (ie those limestone outcrops) are good value. A lazy day snorkeling around on rottnest island is hard to beat when the weather is on. You'd be crazy not to go down south and see the valley of the giants. The best thing about the west coast is that you don't have to go too far to get away from people. Its pretty easy to find yourself on a completely isolated beach with no other people for miles and miles. I only hope I finish uni before you come over.

Hagakure, where have you come across evidence of negative feedback in secondary metabolism?

Yeah, I wonder what makes them think that GE was involved? So who's going over to get some DNA?

Sounds like a great adventure Torsten! While on the topic of D. hopwoodii... Is there any obvious subjective difference between the effects of nicotine and nor-nicotine? I recently tried smoking a sample of WA D. hopwoodii and felt a really obvious nicotine-type feeling quite indistinguishable from normal tobacco (nicotine). I did notice an absence of some character that was present in the effects of Henrys' material. Henry's seemed to have a deeper, darker and longer lasting feel but this may have been all psychological given that I knew the origins of the different materials. I'm hoping to obtain MS data on this WA stuff soon.

Ed, which edition of Goodman and Gilman is it? which year?

I've done a little bit of chemical analysis (by TLC) on alkaloids from the bark but haven't got seriously into it yet (its somewhere on my very long to do list). I'm definitely interested in finding good aussie sources for this group of compounds and optimising extraction/fractionation procedures to maximise the benefit/damage ratio.

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.)

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

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.