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Author: Subject: Muscarine and similar....
kazaa81
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thumbup.gif posted on 20-11-2004 at 14:12
Muscarine and similar....


Hallo to all,
I'm searching for muscarine and similar substance infos and synthesis.
Synthesis more than infos....

Thanks at all for help
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solo
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[*] posted on 20-11-2004 at 15:51
Ref: Muscarin Synthesis


STEREOSPECIFIC SYNTHESIS OF (+)-MUSCARINE FROM D-GLUCOSE, SUITABLE FOR PREPARATION OF 5-SUBSTITUTED ANALOGUES
Velimir POPSAVIN, Ostoja BERIC, Ljubica RADIC, Mirjana POPSAVIN, Vera CIRIN-NOVTA and Dusan MILJKOVIC
doi: 10.1135

Collectionof Czechoslovak Chemical Communications 1998, 63(10), 1522-1527



Abstract
A stereospecific synthesis of (+)-muscarine iodide (1) has been achieved starting from D-glucose as a chiral precursor. The key steps of the synthesis involved a stereospecific cyclization of 3,5-di-O-mesyl derivative 3 into the 2,5-anhydride 4, the stereospecific catalytic hydrogenation of unsaturated derivative 6, and the C-4 epimerization of alcohol 12 by Mitsunobu reaction.
Keywords: 2,5-Anhydro sugars; (+)-Muscarine
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Unfortunately I haven't access to this article, but here is one I do have......solo
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An Asymmetric Synthesis of Muscarine, Suitable for the Elaboration of 5- Substituted Analogues
David W. Knight*, Duncan Shaw, Garry Fenton
DOI: 10.1055/s-1994-22835

Synlett 1994, 295-296

Abstract
A total synthesis of (-)-Muscarine 11 has been achieved, starting from (S)-malic acid 4, via the epoxy-ester 5, and proceeding by way of an unusual cyclisation of the homoallylic alcohol 7 which gives the hydroxy-tetrahydrofuran 8a highly stereoselectively

 

[Edited on 21-11-2004 by solo]

Attachment: s-1994-22835.pdf (163kB)
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kazaa81
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[*] posted on 20-11-2004 at 16:22


Thanks for help, solo, but I wasn't access to the file. Due to the inaccesibility to the file and to the relative very recent write of the document, isn't the synthesis of muscarine that I'm searching for, because I don't need compounds of it or analytical uses.
I'm currently seaching for sythesis of muscarine, amanitine and similar compounds...

Thanks at all for help ;) ;)
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chemoleo
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[*] posted on 20-11-2004 at 23:14
muscarine in nutmeg


You do realise you can isolate muscarine from nutmeg (Muskat-nut)? Probably much simpler (and cheaper) than synthesising it.
Hmm... I wonder why you are after it...possibly because of its effect on the brain?
http://www.erowid.org/psychoactives/faqs/natural_highs_faq.s...
Not something I'd try, doesn't seem very pleasant.

LATER edit: ignore this. Nutmeg contains myristicine, not muscarine.

Anyway... Kazaa, I think as a principle it's always appreciated if you say WHY you want something (particularly if it is something as specific as this), and even more so, if some effort is put in yourself.
People put effort into it (i.e. solo here), so it's kinda inpolite to say 'oh I am not really after that' even though it's a perfectly valid response. At least CLARIFY then what you are after!
Ok?

[Edited on 22-11-2004 by chemoleo]
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[*] posted on 21-11-2004 at 15:46


All due respect, chemoleo, but I think you're wrong about nutmeg. Not only does the site you linked to not claim any muscarine content, but the pharmacology is inconsistant with muscarine.

Now, kazaa81: you say you want muscarine, amanitine, or "similar compounds"? Muscarine and amanitine (or amanitin, actually a class of compounds I believe) have no similarities other than the fact that they are toxins found in mushrooms. You're looking for a synthesis of any toxin found in mushrooms? At this point I must note that you have already been given perfectly good syntheses for muscarine. A bit sophisticated in methodology, but the one that solo provided text for also has references to yet more techniques (probably the other does too). Moreover, you should be able to come up with at least a plausible synthesis for the racemic product yourself.

As for other toxins, your best bets are ibotenic acid/muscimol and psylocibin/psylocin. These are occasionally used recreationally. Check Rhodium's site and The Hive (once they return to the land of the living) for possible syntheses.

Note too that muscarine and psylocin have commercially available close pharmaceutical analouges.

Oh, right: monomethylhydrazine (MMH) appears to be the toxic metabolite of the toxins in certain ascomycete species, notably of the genus Gyromitra. It should be within the grasp of many amateurs.
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chemoleo
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[*] posted on 21-11-2004 at 16:56


Oops, I apologise. Wonder where I got that from. I searched 'muscarine and nutmeg' and this link came up... but it's found in shrooms and such which are described on that page too. Somehow I must have remembered incorrectly.
Oh well - that's the result of being awake for the last 36 hours, and working my a** off. My final PhD presentation is on tomorrow, so wish me luck :)

(let's hope I manage to get some sleep :()

Yes it's myristicine I was on about.

[Edited on 22-11-2004 by chemoleo]
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[*] posted on 22-11-2004 at 18:43


If it is general mushroom toxins, you after, there is also the disulfiramlike toxin coprine, fount in some of the deliquescent members of the coprinus genus (ink caps) most notably coprinus atramentarius, the common inky cap.

Just a question, I thought I posted in this thread a while ago, was my post deleted by the mods?

Edit: on the note of monomethylhydrazine, I believe it is something called gyrometrin, wether or not it is actually MMH, as-is I am unsure, but it distills off when cooking the fungi, which are sometimes used as food, although quite toxic, and sometimes causing fatal allergic reactions.

People have suffered MMH poisoning by merely cooking the mushrooms, as the toxin is volatile, and either IS MMH or releases it upon heating into the cooking area:o

[Edited on 23-11-2004 by Reverend Necroticus Rex]




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Vitus_Verdegast
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[*] posted on 9-12-2004 at 12:56
indeed


For muscarine, look into Inocybe species, they are quite common around the globe in temperate regions and many contain good amounts of muscarine.

For myristicin, one could make it with a Duff reaction (formylation w. hexamine) on eugenol, and subjecting the resulting yellow precipitate 5-formyl-eugenol to a Dakin rxn (H2O2/NaOH) to obtain 5-OH-eugenol, followed by methylenation with CH2I2 or your insert your preferred method here. The yields are low however, and the yield-limiting step is of course the formylation.
Details were to be found on the Hive and perhaps also on Rhodium's. Do a search on the latter using the wayback machine.

One could also start from myristicinaldehyde (= the corresponding benzaldehyde) and get that all the way from vanillin via iodination/hydroxylation/methylenation, but it's a byzantine route.

Perhaps extraction from nutmeg oil, or (if you're lucky) parsley seed oil would be preferred?
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wink.gif posted on 21-12-2004 at 23:57
ahah! that's why nutmeg has an intoxicating effect !


wow, thanx for the info.. I didn't know nutmeg had Muscarine just as Clitocybe/ Amanita Muscaria has..
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biggrin.gif posted on 22-12-2004 at 09:35
El ataque de los muertos sin ojos


Quote:

LATER edit: ignore this. Nutmeg contains myristicine, not muscarine
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