overunity33
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Type of UV for ergo alkaloid identification?
What would be the best wavelength light for ergo alkaloid identification? Specifically LSA and LSH. An UV Led should work fine correct?
[Edited on 30-9-2010 by overunity33]
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DDTea
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This quote is from the website http://researchlsd.blogspot.com/ .
| Quote: | | LSD absorption is maximal at 320 nm, and LSD fluorescence is maximal at 435 nm. These values are somewhat flexible depending on the spectrophotometer,
with some authors reporting LSD absorption at 325 nm, and LSD fluorescence at 445 nm. |
The way to answer this question on your own in the future is to look up the UV-Vis and Fluorescence spectra of your compound of interest. In this
case, I'm using a similar compound with well-described physical properties. It's a pretty good match, mostly. If you want to be super-precise,
though, you could ask yourself how the slightly different moieties (in this case, the R groups on the amide) would affect the lambda-max value for
absorption/emission. It probably wouldn't make much of a difference though, especially if you're just going to use a UV Led. Something like ~350 nm
should work fine.
"In the end the proud scientist or philosopher who cannot be bothered to make his thought accessible has no choice but to retire to the heights in
which dwell the Great Misunderstood and the Great Ignored, there to rail in Olympic superiority at the folly of mankind." - Reginald Kapp.
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Picene
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UV leds are typically a little short for any sort of visual identification. Try visualizing a TLC plate with one sometime. Anything white-ish will
glow just as brightly as the compound you are looking for.
There is a stain that will detect the presence of microscopic quantities of many indole alkaloids, including ergot derivatives. Treatment of an indole
alkaloid with a solution of 4-dimethylaminobenzaldehyde (p-DMAB) and concentrated hydrochloric acid gives a strong blue color.
In the lab this mixture is usually used as a developer for TLC plates. Law enforcement uses this mixture to detect the presence of LSD in solutions,
with postive results being obtained with quantities as low as 6 micrograms.
Obviously the reagent's sensitivity will vary depending on the indole alkaloid being tested (steric hindrance of the alpha carbon can block access by
the p-DMAB). It will work beautifully with LSA, however.
Here is a link with a list of color tests used by the law enforcement. Many of these tests/reagents are specific to certain functional groups, and
can be adapted to assess all kinds of plants and chemicals. Great fun for an amateur chemist.
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DDTea
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LSD is actually a very strongly fluorescent compound, which means that the detection limits by fluorescence are extremely low. I quote again:
| Quote: | | As little as 0.001 microgram of LSD, or 1/100,000 of a dose, can be analyzed [by absorption and fluorescence], thus LSD detected by spectroscopic
methods has better sensitivity than LSD detection by coloration with Van Urk reagent. |
I'm always partial to spectroscopic tests over wet test 
"In the end the proud scientist or philosopher who cannot be bothered to make his thought accessible has no choice but to retire to the heights in
which dwell the Great Misunderstood and the Great Ignored, there to rail in Olympic superiority at the folly of mankind." - Reginald Kapp.
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Picene
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I agree, DDTea, spec is awesome, but I think both methods have advantages and disadvantages.
The disadvantages of spec are portability and cost. You aren't going to measure that sort of absorbance without a spectrophotometer and a tungsten
lamp. Even used that sort of setup is going to set you back several hundred bucks. (thousands new!).
Ergot alkaloids can be visualized at much higher concentrations with simple visual fluorescence, but again, you need a shortwave UV source. Most UV
leds emit in the 380-395 range, which just wont cut it. He'd need to buy a lamp.
Wet tests are not as precise by a long shot, but they are great for portability (30 dollars worth of chemicals and a handful of eppendorf tubes in a
shaving kit!), and as tools to monitor reaction progress using TLC or to quick test something eluting from a column.
In short, I will keep my bottles and my gemini both, thank you much!
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peach
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Black lights are used for chromatography visualization. They emit a broadband spectrum so they're going to make pretty much anything that's UV active
light up. Keeping in mind that a number of organics are sensitive to UV, high intensity illumination is the opposite of what you're after.
LED's and lasers emit incredibly tight bands by comparison, so you could miss a compound if you happen to be using a wavelength at which it doesn't
absorb well.
Fine line width and tunable lines are used in high performance chromatography where the UV spectrum has already been checked, to find a suitable
number to use.
It's somewhat ironic, to me, that a lot of the chemicals they're using in that PDF have the words VERY TOXIC in bold immediately
after them, where as the chemical they're trying to find is one the least toxic drugs known to man. 
Toxicity is in the mind of the beholder, it seems.
[Edited on 6-10-2010 by peach]
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DDTea
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peach: The big problem is that LSD and related compounds absorb ~330 nm while UV LED's tend to emit only between 380-400nm. SOME can make it down to
350nm, but those are uncommon. There are ways to cause a bathochromic shift in absorption maxima, such as by doing the measurement in a particularly
polar solvent (which stabilizes the usually more-polarized excited state)--however, I doubt that would cause a 50nm shift! It might be possible to
add some kind of fluorophore, but then we could be pushing the limits of "street chemistry," so to speak.
Better options might be tungsten lamps or Xe lamps. In any case, at the concentrations (<0.01 μg) of interest by absorption/fluorescence,
LSA's would easily overpower other fluorescent molecules. Fluorescence would be ~450nm, which is easily visible to the naked eye (no need for a
fluorimeter, unless you want to be super ANALytical). A possible disadvantage, though, is that exposure to UV can destroy the molecule.
[Edited on 10-6-10 by DDTea]
"In the end the proud scientist or philosopher who cannot be bothered to make his thought accessible has no choice but to retire to the heights in
which dwell the Great Misunderstood and the Great Ignored, there to rail in Olympic superiority at the folly of mankind." - Reginald Kapp.
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peach
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That'd be why I didn't suggest an LED.
You're making this way more complicated than it needs to be. There are numerous bulb type lamps available that are used as standard in organic
chemistry labs for illuminating plates and columns for fluorescence.
The number you're discussing is the peak absorption, but there is quite a wide band of absorption for both LSD and billions of other organics. Even
Quantum Dots have quite a wide absorption band, and they re-emit in diode like line widths.
Shine a mid / deep UV lamp on it, and it'll glow bluey violet, since it's re-emitting not far above the absorption.
This is like all the guys who think they need a microgram balance to make LSD, because the doses are measured in micrograms. That is an indicator of a
very big gap in their scientific ability.
They tune high performance chromotography to somewhere around the peak absorption of the substance they're after because they're dealing with
absolutely minute quantities of it, well below what you'd be working with in a preparative gravity column.
I'm not an LSD genius & neither am I making it, but I have spoken to people who've made kilos of the stuff. And are now in jail.
I think Hofmann was correct in calling it his problem child, but for the reasons a lot of people seem to miss. He called it that because he was so
upset about people chewing through it as a recreational drug. He didn't like Owsley, and Owsley didn't like Timothy Leary constantly turning up with
all his friends to make a mess.
Something that has long baffled me is why so many people who like LSD and believe in health and curing people, and making the world a better place,
focus so strongly, if not solely, on LSD as opposed to the other uses of the lysergides. I've eaten some of them and they seem to make far better
headache curers than Ibuprofen or Paracetamol, minus the tripping. And then there's AIDs and cancer, and many other things that are just as worthy of
attention. Yet they never seem to bother. And I can't get prescriptions of the lysergides because it's been floored by the LSD guys.
I feel Albert's pain, quite literally if he had a near constant headache.
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DDTea
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Once again, my dyslexia has kicked my ass and I've misread a post! I missed the part about "...lasers and LED's."
Here's the link to the absorption/fluorescence spectrum of LSD I'm referring to:
So yes, something between ~280-350 nm would be ideal. I think we're on the same page now.
"In the end the proud scientist or philosopher who cannot be bothered to make his thought accessible has no choice but to retire to the heights in
which dwell the Great Misunderstood and the Great Ignored, there to rail in Olympic superiority at the folly of mankind." - Reginald Kapp.
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Picene
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@Peach,
Hydergine (ergoloid mesylates) is, I think, one of the coolest things to come from his line of research.
It is a powerful oxygen radical scavenger, such that when admistered intravenously during stroke it can delay significant brain damage by several
precious minutes.
It also serves a function post traumatic brain injury, regulating synaptic transmission in a way that dramatically speeds recovery.
There is even some evidence that it is useful as a nootropic by these same properties.
It is presently unregulated (FDA and DEA) in the US, not sure what its availability in your home country is. It isn't useful as an LSD precursor
because the 9,10 double bond is already saturated, so converting it to the amide gives a non psychoactive compound.
It still functions as a vasodilator though. I would be curious to know what it's effectiveness as a headache treatment is (I don't get them).
All that from simple 9,10 dihydroergotamine. Who would have though?
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DDTea
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Picene:
Vasodilators are a bad idea for things like cluster headaches and migraines--it can agitate them a lot more. Anyone who's done a nitration knows
what I mean Generally, vasoconstrictors are used.
I used to take ergotamine tartrate for migraines (Ergomar, sublingual). It works really well if you catch your migraine before it actually
starts (that's the thing: these drugs are preventives more than abortives, so they're great for people who get sensory disturbances before pain).
I've heard of preventive lysergides like Sansert, although that particular one has fallen out of favor with doctors. However, in my humble opinion,
the newer triptan drugs work a lot better (i.e.: totally eliminating a full-blown migraine within 1 minute, literally). They just cost about
$40/pill... However, nothing's a silver bullet, and doctors generally try a lot of different medicines *before* they go down the ergotamine route.
[Edited on 10-6-10 by DDTea]
"In the end the proud scientist or philosopher who cannot be bothered to make his thought accessible has no choice but to retire to the heights in
which dwell the Great Misunderstood and the Great Ignored, there to rail in Olympic superiority at the folly of mankind." - Reginald Kapp.
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peach
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It is remarkable how such minute changes to something can produce such dramatic effects in what it does to people's minds. Whether that's psilocybin /
cin versus serotonin, or the colour of the backing on the price tag bars at the supermarket.
I have noticed a common theme from all the people talking about LSD, including Albert H himself, that they feel like children again, awake and alive
to the world. I'm sure part of that is the psychotropic effects, but Albert mentioned how the feeling remained for some time after. Again, possibly
memory based causes.
But something I was considering is that it has to be removed from the synapses by our bodies. It's possible that in doing so, the body upregulates the
esterases / vesicle production / mobilities and other such factors to clear the LSD out of the way. Once the LSD is gone, it'll take time for those to
drop back down to where they were before. During which time, they will be free to also accelerate the process for normal neurotransmitters.
That may be part of the feeling of being awake and sensitive to the world again, that the synapses are actually transmitting slightly quicker than
they were beforehand, due to upregulation.
Other drugs, like the phenethylamines, can do the opposite and leave people feeling depressed, so it's not hard to imagine that there may be some
semi-persistent, biochemical change in the brain after the LSD is gone as well.
I will have to look into the Hydergine. I know quite a few people use the sore back problem just because they really like getting super high, but I
did genuinely find lysergides far, far more effective than anything else I've tried, and I have tried countless things over the years (different
sleeping patterns, changing my diet until I only drank water and ate full grains, no sugar, no concentrates, no caffeine, no smoking, no alcohol,
buying special light bulbs for the house, excising until I was being sick and wrecking tendons, yoga, hanging upside down in the garage for half an
hour a day, rubbing the points on my skull that help stimulate blood flow and many more things I've forgotten).
There is already a fairly well visited page on the web all about lysergides and cluster headaches. I do think it has real world potential for that.
Ergot the fungus is of coarse a vasoconstrictor, which is what creates the gangrene problem. Part of the reason Sandoz was looking at it in the first
place, if not the prime reason, was that it was being used in the middle ages during childbirth, as it causes an increase in abdominal muscle tension
and the vasoconstriction helps prevent blood loss. The ergotline content of the various strains varies, significantly, and can even drop off within
the same strain if it's cloned too often from the original plate. Feeding people uncontrolled amounts of fungus with unknown quantities of the things
in it was obviously not a predictable way to help.
So Arthur Stoll isolated Ergotamin in 1917, and happened to work at Sandoz, where Hofmann would produce LSD a few decades later.
The lysergides have since been used for treating headaches, but the original Ergotamin product was sold as Gynergen. Gyn generally tends to relate to
a childbirth. Gynecology -> Gynaika (greek) -> Related to women.
It is quite normal for drugs to be rebranded for different uses after they initially come out.
@DDTea, you're correct about the *before* part, and it may even be an *instead of* I suspect for where I am. I have not heard from a single person
first hand, ever, who has been prescribed ergotamine based medicines in the UK in my life time. I don't know how much those things cost to buy from
the companies, but I'm guessing the US may be at an advantage as you're footing the bill directly for them, rather than the overburdened tax budget
the NHS runs on. Paracetamol and Ibuprofen are dirt cheap in big bucket quantities. Ergot, from all the papers I've read about culturing it in the
60's and 70's, is not that simple and not a constant producer. The genetics need controlling for a start, to get a consistency and yield out of it
that are suitable for pharmaceutical production.
And the total synthesis is nothing easy either. Involving anhydrous solvents, very expensive reagents, ten or more stages and a 1% yield being
typical.
There is someone I know who's working on this (legally) as a kind of carry over from Hofmann's original intention, not for making lots of drugs. He
has produced a computer modeled synthesis that could produce it at a few thousand dollars a kilo, which could make it a potential competitor with the
Ibuprofens and Asprins on the price point; a key factor whether you pay for it directly or the NHS does.
[Edited on 6-10-2010 by peach]
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