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OfflineAnnoA
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Misinterpretation of sources
    #2871940 - 07/09/04 08:49 AM (12 years, 8 months ago)

In this thread
http://www.shroomery.org/forums/showflat.php?Cat=&Board=Forum2&Number=2840786
there was a debate whether there are differences among different mushroom strains in their effects .

There are various other chemicals present in a mushroom than the main psychoactive components, psilocybin and psilocin. Which exactly and in what amounts, is the question.

A popular source for a listing of these other chemicals has been for several years a table in the Psilocybe Mushrooms FAQ hosted on Erowid:
http://www.erowid.org/plants/mushrooms/mushrooms_faq.shtml#4
(a mirror of this FAQ is also at the Shroomery)

There is a table that says:
"...These are just the four "biggies". A whole truckload of other indoles are known to exist in Psilocybe mushrooms. Here's a sample of what was found in a batch of Psilocybe baeocystis, excluding the ones mentioned above: "



Indole derivative Amount (ug)

5-Benzyloxy-3-indole acetic acid 2
N,N-Dimethyltryptamine hydrogen-oxalate [aka DMT] 4
Gramine 40
3-Hydroxyethyl indole 2
5-Hydroxy-3-indole acetic acid 2
5-Hydroxyindole 4
3-Hydroxymethylindole 2
5-Hydroxytryptamine creatine sulfate [aka Serotonin] 4
5-Hydroxytryptophane 2
Indole 4
3-Indoleacetamide 2
3-Indole acetic acid 2
3-Indoleacetic acid ethyl ester 2
3-Indoleacetonitrile 2
3-Indolealdehyde 40
3-Indoleacetaldehyde 2
3-Indolecarboxylic acid 4
3-Indolelactic acid 2
gamma-(Indole)-N-butyric acid 4
beta-Indole-3-acrylic acid 2
beta-(Indole-3)-propionic acid 4
Indoxylacetate 2
Indoxylbutyrate 2
Isatin 2
5-Methoxy-2-carboxyindole 2
5-Methoxydimethyltryptamine monooxalate [aka Bufotenine] 4
5-Methoxyindole 4
2-Methylindole 2
3-Methylindole 4
5-Methylindole 4
5-Methyltryptophane 2
N-Methyltryptophane 2
Tryptamine hydrochloride 4
L-Tryptophane 0.8
From: A.Y. Leung, A.H. Smith & A.G. Paul,
"Production of Psilocybin in Psilocybe baeocystis Saprophytic Culture"
J Pharm Sci 54: 1576 (1965)


I was curious in more details about the procedures used, and ordered the whole article this table originated from, from my library.

Here is a scan of the article:



As it turns out, the aforementioned table is NOT a listing of the chemicals found in Psilocybe baeocystis, but merely a list of various chemicals and their chromatography data! The amounts given are not amounts found in P. baeocystis, but the amounts of the chemical in the solution that was prepared to establish the Rf values of various indole derivatives.


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Invisiblewhiterasta
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Re: Misinterpretation of sources [Re: Anno]
    #2871962 - 07/09/04 09:08 AM (12 years, 8 months ago)

IMHO only general outlines for each species will be possible due to the effects environment has on composition. So values for Ps.baeocystis will vary greatly from site to site as with all mushrooms. Baseline info could be gathered using a universal substrate and comparison of local variants. But even this will only provide a range not an exact composition for each species.
WR


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Offlinedebianlinux
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Re: Misinterpretation of sources [Re: Anno]
    #2872037 - 07/09/04 10:09 AM (12 years, 8 months ago)

Quote:

Anno said:
The amounts given are not amounts found in P. baeocystis, but, but the amounts of the chemical in the solution that was prepared to establish the Rf values of various indole derivatives.




you lost me there. maybe it is because i do not know what "Rf values" are? why would there be indoles present in a solution used to determine what indoles are present in a specimen? i guess that if the concentrations are known prior to testing then their presence would not cloud the test. :confused: :confused:


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OfflineAnnoA
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Re: Misinterpretation of sources [Re: debianlinux]
    #2872044 - 07/09/04 10:13 AM (12 years, 8 months ago)

>why would there be indoles present in a solution used to determine what indoles
>are present in a specimen?


The paper disuses thin layer liquid chromatography.
In order to be able to test for unknown substances in a solution(=mushroom extract), you first have to calibrate your testing equipment with solutions of known substances with known concentrations.


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Offlineld50negative1
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Re: Misinterpretation of sources [Re: Anno]
    #2872070 - 07/09/04 10:21 AM (12 years, 8 months ago)

it seems to me they are only testing for psilocybin and psilocin


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Offlinedebianlinux
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Re: Misinterpretation of sources [Re: Anno]
    #2872072 - 07/09/04 10:21 AM (12 years, 8 months ago)

okay, i follow now... seems i was getting on the right track afterall.

Rf = retardation factor... okay... help an ignorant soul out. what is being retarded?


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OfflineAnnoA
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Re: Misinterpretation of sources [Re: debianlinux]
    #2872088 - 07/09/04 10:27 AM (12 years, 8 months ago)

>retardation factor

retardation factor (in planar chromatography), Rf
Ratio of the distance travelled by the centre of the spot to the distance
simultaneously travelled by the mobile phase:
RF = b/a
By definition the RF values are always less than unity. They are usually
given to two decimal places. In order to simplify this presentation the hRF
values may be used: they correspond to the RF values multiplied by 100.
Ideally, RF values are identical to the R values used in column chromatography.

From http://www.iupac.org/goldbook/R05353.pdf

More on TLC:
http://www.chemsoc.org/exemplarchem/entries/2003/hull_pearson/pearson/thin_layer_chromatography.htm


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OfflineBlue_Apocalypse
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Re: Misinterpretation of sources [Re: Anno]
    #2873769 - 07/09/04 06:38 PM (12 years, 8 months ago)

Also I believe you can only qualitatively identify components with TLC, not quantitatively. Basically, you can only tell what is in the mushroom but not how much is there. I suppose you could compare different TLC samples and standards to see which samples have relatively more or less of a substance but it would be a very rough estimate and experimental conditions (ie. temp, solvent, etc..) would need to be kept constant.


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InvisibleHermes_br
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Re: Misinterpretation of sources [Re: Anno]
    #2874383 - 07/09/04 10:50 PM (12 years, 8 months ago)

thank you for getting those papers.' :thumbup:


Does mushrooms have any Gramine at all ?
  • gramine as a vasorelaxing, a 5-HT2a receptor antagonist.

    http://www.ncbi.nlm.nih.gov/entrez/query...itool=iconabstr



    edited...



  • Edited by Hermes_br (07/15/04 09:15 PM)


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    InvisibleHermes_br
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    Re: Misinterpretation of sources [Re: Hermes_br]
        #2878044 - 07/11/04 02:30 PM (12 years, 8 months ago)

    here's a link between: gramine -> ketanserin -> psilocybine

    from: www.maps.org/research/hasler_2004_1.pdf

    " Introduction

    The indolealkylamine psilocybin (PY, 4-phosphoryloxy-N,N-dimethyltryptamine) is the main psychoactive principle of hallucinogenic mushrooms such as Psilocybe cubensis and Psilocybe semilanceata. PY interacts mainly with serotonergic neurotransmission (5-HT1A, 5-HT2A, and 5-HT2C receptor subtypes). Equilibrium dissociation constants (Ki) are 6 nM for the 5-HT2A receptor subtype and 190 nM for the 5-HT1A subpopulation (McKenna et al. 1990). PY and its active metabolite psilocin (PI) have -- in contrast to lysergic acid diethylamide (LSD) -- no affinity for dopamine D2 receptors (Creese 1975). In a receptor-blocking study, we showed that the psychotropic effects of PY could be blocked completely by pretreatment with the 5-HT2A preferential antagonist ketanserin (Vollenweider et al. 1998) suggesting that PY induced effects are mediated primarily via activation of 5-HT2A receptor subtypes. However, some of the psychotropic effects of PY might be due to downstream effects on other neurotransmitter systems."


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    InvisibleZen Peddler
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    Re: Misinterpretation of sources [Re: Anno]
        #2888598 - 07/14/04 06:24 AM (12 years, 8 months ago)

    great post Anno, but ignorance will continue unheeded!


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    OfflineAnnoA
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    Re: Misinterpretation of sources [Re: Anno]
        #2913687 - 07/21/04 09:53 PM (12 years, 8 months ago)

    Updated the images of the article with better scans.


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    Offlineearthe
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    Re: Misinterpretation of sources (tlc quantitative) [Re: Blue_Apocalypse]
        #2913998 - 07/21/04 11:40 PM (12 years, 8 months ago)

    Surprisingly, people do use TLC to do quantitative work, although the accuracy is obviously very limited.

    We have been unable to confirm this with much certainty, but we believe that the [http://www.erowid.org/chemicals/lsd/lsd_history1.shtml] Pharm Chem quantitative work that was done in the 1970s was done with TLC alone!

    One of the methods for doing this is to have several different known concentrations of a given chemical. So lets say an analytical chemist wants to quantify the amount of psilocybin in a given sample. A solution is made from the sample using an appropriate solvent and a measured fraction of this is placed on the TLC plate. Also on the TLC plate several spots of different, known concentration psilocybin are dropped as well. The analyst uses whatever visualization technique, dye, or fixative is appropriate to the plate type, chemical, and solvent and then eyeballs the density of the color, the size of the spot, etc.

    Before they start, they would guesstimate the approximate amount. Lets say they had some mushroom material they suspected contained 10mg of psilocybin. The solution might be 10ml, so that's 1mg per ml. Lets say they were going to deposit .1ml onto the plate, that would be an expected .1mg of psilocybin in the "spot". The analyst would then 'bracket' the spot with one or two below the expected amount and one or two above. So perhaps a spot of .05mg psilocybin, a spot of .1mg psilocybin, a .5mg psilocybin, and a 1.0mg psilocybin. They could then look at the resulting spots and say which one it was most like and then do another plate where they bracketed around that value to try to get closer.

    These are not instructions and the values are used as an example only, I suspect the actual spot volumes would be less than .1ml. But hopefully you get the idea.


    It is easy to get ballpark figures with this and experienced chemists claim they can get very close with a little practice (but one needs the equipment to verify estimates).

    Just thought it might be of interest. Thanks to anno for checking into that source, that table o' misinformation has been around for a while. Great work.

    earth


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    InvisiblePinback
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    Re: Misinterpretation of sources (tlc quantitative) [Re: earthe]
        #2914953 - 07/22/04 07:09 AM (12 years, 8 months ago)

    A better way to do this is by densitometry, i.e. by measuring and integrating the absorbed or fluorescent light of the spots in the TLC plate. There are methods for doing this without the need for (very) expensive equipment, as seen [url=http://www.rsc.org/CFCart/displayarticlefree.cfm?article=8-9"3%24%5D%5E%5CB!8'%5D%5C!(<L%23%5C5%3DP0P%40%5C%3D29%23<%0A]here[/url] or [url=http://www.rhodium.ws/pdf/5-meo-dmt.quant-qual.tlc.analysis.pdf]here[/url].


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