Harmaline fluorescence

[John_Barleycorn]

Fractalhead:

Still, your experiment would be worth a shot as it would be extremely unusual if an apolar solvent extracted the alkaloids from non-basified plant material.

Nymphaea lily is one example of an alkaloidal plant that reputedly extracts successfully straight into acetone. However, it is hard to know whether that is because the alkaloids are free-based in the wild, or because the molecule is simply non-polar, protonated or not.

I am wondering at this point whether we are limited to looking at indole-containing substances under blacklight? Sceletium/mesemebrine strikes me as one which could potentially be interesting.

[Fractalhead]

I don't think mesembrine has the long systems of conjugation required for fluorescence. Its got one aryl ring but the rest has no conjugated systems. Certainly looks like it would react with the right detection reagent on tlc - not that it really matters anyway because it is yellow. Nuciferine has a chloroform soluble hydrochloride and it was this property that led to the first successful isolation of nuciferine. I transcribed selected parts of the paper onto the forum some time ago. You should find it if you search for nuciferine and nelumbo nucifera. The guy who isolated it was from a south eastern university from memory.

BTW, this is way off topic, but do you know anything about the 'Ed' Sceletium sp. being tested negative for alkaloids by GC/MS?

[Torsten]

Originally posted by John_Barleycorn:

Sceletium/mesemebrine strikes me as one which could potentially be interesting.

Nope:

Sceletium emarcidum leaf & stem: nil

[Torsten]

Originally posted by Fractalhead:

BTW, this is way off topic, but do you know anything about the 'Ed' Sceletium sp. being tested negative for alkaloids by GC/MS?

This wasn't really for public distribution yet, but as someone obviously couldn't keep their trap shut..... yes.

I was going to ask you for details about your extraction as this result is a little surprising and IMHO unlikely to be right.

[Fractalhead]

SHIT! I'm so sorry! I misunderstood the status of this information. Its just so bizzare. Fuck. I should have just assumed it should have been left to the researcher to bring it up. I'm way out of line here. BIG apologies to all involved parties. I realise I've probably made too much of a contribution already, but if i can help with details of my extraction or repeat it and provide a sample pls let me know.

[John_Barleycorn]

Got myself a blacklight from Jaycar (unspecified wavelength) and had a bit of a play. The results are hard to interpret, so take with a grain of salt. Basically, I found no effect from acidifying a EtOH/H2O solvent. The result which I am describing as "positive" was a mildly fluorescent green in all cases. The soap residue in the bathroom was considerably more fluorescent.

Positive results for:

Melatonin (presumably salt form).

Psilocybe Subs (dried).

Passiflora leaves (one allegedly P. Incarnata; another an unidentified wild vine - perennial, 3-lobed leaves).

Trib Terr (allegedly powdered seeds, sourced from MG via HHH).

Acacia Sophorae phyllodes.

Beer (hoppy and yeasty).

Very minor result for Acacia Suavolens phyllodes.

Negative results for:

Acacia Terminalis feathery leafy thingies.

Indol (sic) Butyric acid (aka striking hormone).

Red wine.

Various reagents: H20, EtOH, vinegar, ammonia water.

Stay tuned for various Acacia barks/roots, Chinese Star Jasmine, and whatever else I can think of. However, it bothers me that I could possibly be fooling myself here. F'rinstance, does anyone know whether chlorophyll is a confounding influence?

[ 11. July 2004, 19:16: Message edited by: John_Barleycorn ]

[Torsten]

John, the effect we were talking about is apparently a LOT stronger than what you suggest. Our fluorescense was often as bright as fluoro paint (or even washing powder )

[Guest electro]

the acid being used here is phosphoric isnt it ?

edit .. no it's formic .. but still it might be worth a shot over the hcl ... *shrug*

if anyone is after some of this, i found some at bunnings in the paint section, 36% (from memory) .. no other listed actives .,.. it was being sold as a rust stripper in the rust kill/metal prep section

[ 12. July 2004, 21:39: Message edited by: electro ]

[devance]

I have a small unit used for ore looking as in stones which can be usable to changed for higher or lower wavelenghts of ultraviolet light. Cubric zirconium glows red while a diamond glows blue at one setting while nothing happens at the other.

Useful for jewlery evalution.

Used for rock hounds to look at stones. flouresecent ores are very valuble to collectors.

But for alkaloid view it gives a option of 2 wavelengths.

[Darklight]

devance:

I have a small unit used for ore looking as in stones which can be usable to changed for higher or lower wavelenghts of ultraviolet light.

Wow! Where can I acquire one of these? And how much did you pay if you don't mind me asking?

[Rev]

drooooool

[devance]

Darklight:

 

Darklight:

I have a small unit used for ore looking as in stones which can be usable to changed for higher or lower wavelenghts of ultraviolet light.

Wow! Where can I acquire one of these? And how much did you pay if you don't mind me asking? I got mine at a flea market for 5 bucks, a oldie but good unit, heres a site I googled

http://www.minershop.com/html/uv_light.html for general info,

ebay or a lapidary shop would have them.

I wouldn't spend alot of money until you know what wavelength is best for your application.

[John_Barleycorn]

My unorthodox EtOH/H20 technique seems to be producing consistent results:

Strong result for Acacia Maidenii bark (old and dry).

Some result for

. Acacia Sophorae bark (old and dry)

. Chinese Star Jasmine root bark (old and dry)

Very minor result for Acacia Suavolens bark (but young and green, nb).

Nil result for

. Acacia Terminalis bark (mature)

. Chinese Star Jasmine leaf

. smoked salmon

. banana

. broccoli

. red cabbage

[Rev]

Ok but what are those results?

colours? relative intensity?

[D-lysergic]

One wonders what a standard tea preparation of Peganum harmala might look like under UV?

We have certainly noted that there is quite an odd blueish yet mysteriously undefinable sheen to a preparation of say 8g or so of crushed seeds boiled lightly in water.

Just a side note, I'm sure you've already checked that the formic acid doesn't glow yellow on its own under UV?

Facinating research guys, keep it up

[Rev]

edit

Edited April 21, 2007 by Rev

[Gunter]

I found this thread very interesting, (I hope bumping it is not too much trouble...

It just so happens that I harvested about 1/2 a kilo of Elaeagnus angustifolia bark from near a river here. For the record betacarbolines are legal here (States) to explore.

Likewise they are all about in flower and have lots of new silvery leaves. My last test of E. angustifolia bark yielded a dilute glow but was not very encouraging.

For me Peganum glows very yellow/green with a slight green, it is fertile Peganum seed (despite the lable saying it isn't) but I have no other info on it...

Black caapi has a very blue glow, while others have been brighter and had more yellow/green tones.

My attempts at getting various tribulus material to glow has not been ideal, just a faint yellow/green thus far.

I'll try to get standardized... sadly a 10 second exposure doesn't seem to pick up the glows in darkness and my digicam doesn't have a 5 minute exposure setting. I have citric acid at my disposal.

I did check some P arundinacea and I got a faint glow that was a bit encouraging, I hear that interesting chemotypes often have a beta-carboline compliment/component while less interesting forms lack it.

[Alice]

ok, about UV tubes:

a normal fluorescent lamp (ie the fluoro tubes used to light up your room) consist of a glass tube filled with mercury vapour. the mercury atoms become excited when a current is passed thru the tube, and emit mainly radiation at 254 and 185 nm. the tube is coated on the inside with a white luminescent film consisting of a calcium halophosphate [(Ca5(PO4)3F1Cl2 or similar] that is doped with Mn2+ and Sb3+. the UV radiation produce by the excited mercury vapours strikes this white luminescent film. The radiation is absorbed by the Sb3+ dopant, and some of the energy is passed on to Mn2+. The Sb3+ emits blue light and the Mn2+ emits yellow light, with the combined emmision appearing white.

A "UV tube" as seen in clubs and in your little hand-held UV gadget is simply a normal fluoro tube minus the while luminescent film coated to the glass. Therefore, these lamps emit UV radiation of 245 and 185 nm. now, my guess is that the purple film that you can see on these UV tubes is probably a substance that has been included to enhance the safety of these lamps. it is probably a substance that selectively absorbs the higher energy 185nm radiation, while allowing the less energetic 254nm UV light to pass thru. thus you still have a source of UV, but the more dangerous 185nm light has been removed so that you can dance under the UV tubes all night and not get totally fried.

Now, i imagine that the lamp you can get in which you can select one of two wavelength (185 or 254nm) is one of these fluoro tubes without the white film and without the purple film. by flicking the switch you are probably altering the current thru the tube, thus selectively producing only one wavelength to the exclusion of the other.

now how can we predict whether or not a compound will have a more pronounced luminescent in acidic, basic, neutral, or freebase or salt form? first a bit of background: (i realise many of you know the following well, this is more for the benefit of non-chemists).

coloured organic compounds appear coloured to our eyes because they absorb a defined quantity of light that correspond in energy to a wavelength that falls within the visible spectrum of light.

non-coloured organic compounds do not absorb light from the visible spectrum, therefore they appear colourless or white to our eyes.

luminescent compound absorb UV light, then re-emit light of a LOWER energy. as visible light is of lower energy than UV light, visible light is what is emitted, so we see a funky colour.

now, whether a compound absorbs UV light or visible light or whatever depends on the electronic configuration of the molecule. conjugation in organic molecules (ie lots of double-single-double-single bonds or aromatic systems) causes the electrons to become delocalised and move around within the molecule more freely. Thus the energy they are required to absorb to produce light may fall in the visible spectrum (visible is lower energy than UV) because the electrons in the molecule are loosly held and dont need much energy to excite. organic compounds with less conjugation have their electrons held in place more tightly, so they require more energy to excite the electrons. so they may absorb UV light, which is of higher energy than visible light.

will a compound will have a more pronounced luminescent in acidic, basic, neutral, solvated, freebase or salt form?

depends entirely on the structure of that particular compound. changing the pH etc affects different compounds in different ways. This is not simply a matter of protonation vs deprotonation. adding or removing a proton from an amine or carboxylic acid can cause drastic changes in the electronic structure of the molecule, depending on what the amine etc is attached to. taking away a proton may just cause a a buildup of charge on the oxygen, but it may also cause a big rearrangement of electrons in the molecule to occur, and the position of double bonds to change. you can also get cyclisation, dimerisation etc etc

all of these changes to the location of electrons/bonds in the molecule affect what wavelength a compound absorbs.

at the start of this thread, it was thought that basifying you plant solution would enhance the luminescence, when in fact the opposite was found to be true for many compounds.

in short: if you're doing a UV test, try acidic, basic, and neutral condition, coz you never know which one a compound may respond to. just imagine if Tort hadn't bothered to squirt in that formic acid coz he assumed it wouldn't do anything....

a good scientist will always challenge the rules. thats what science is all about. well done T

sorry for waffling on a bit folks...

light excites electrons,

chemistry excites me :D

Edited May 17, 2006 by Alice

[teonanacatl]

Interesting post alice

i believe those ones in clubs and the handheld ones from dick smiths are only 364nm

rue ime glows a greeny blue, one of the harmX compounds is yellow the other is blue i believe. one is soluble in acetone the other is not, in an attempt to see if rextallisation could be done from acetone i discovered that the acetone extract was very minor compared to the insoluble in acetone part, one glowed bluey green and the acetone soluble stuff was yellow. im sure thats right, seems to me now like a good way of separating the harmaline from harmine, one being a good maoi and present in caapi greater then the other yeah????

yes uv is good for determining concentration, why did you guys just not use a UV spectro? could have gotten quantitative results.

chlorophyll fluoresces red under UV, its the photosystems releasing the energy when they arnt ready for photosynthesis. You can test the health of the photosystem i or II by using the same idea.

[Gunter]

Is that acetone thing involving freebases or salts?

[teonanacatl]

HCl salt , cant remember if i heated it or not. please do tell if you do it

also i noticed at ayahuasca people tell you dont boil the b-carbolines to hard or they will be destroyed, i can tell you this is not the case with rue at least. I boil for a long time some rue water and it didnt loose its colour, also numerous microwaving for periods of time although all the water evaporated apon addition of water the compound glows again. I wrote a post informing them of this, the fact that you can use a black light to test if b-carbolines were present but i dont believe i ever got a reply.

[Rev]

edit

Edited April 21, 2007 by Rev

[teonanacatl]

that makes sense, might not have as much actives though. like tea i guess, ive been trying to perfect a perfect herbal tea, if i leave the bag in too long it goes bitter, but if just enough its nice.