Found this (yes again) at a desk in the library, looked like there was a stack of journals next to it as well. Amazing the detailed notes ppl leave in the library here.
psychokitty
PimpBee posted 11-16-1999 10:20 PM
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Like I said, you ARE the MAN. It goes without saying that I'm impressed. You're definitely paving the way to success for many of us.
--PK
Slappy
PimpBee posted 11-17-1999 01:23 AM
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I think he not-meant Trptamine, not Tryptophan in the second step.
KrZ
Hive Bee posted 11-17-1999 08:22 AM
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Heh, yes tryptamine indeed. My mistake.
Rhodium
Pimp Master posted 11-17-1999 11:15 AM
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I thought tryptamine cyclized to a beta-carboline on attempted methylation with formaldehyde? But you should know if it was the real stuff you got.
Bright Star
Hive Bee posted 11-17-1999 11:32 AM
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Bra-fuckin-vo.
Anyone know how to paste PGP into Hushmail?
KrZ
Hive Bee posted 11-17-1999 12:22 PM
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J. Med. Chem., 1995, Vol. 38, No. 18 pg 3577. half-way down the page "The general method for dimethylation of indoleethylamines is illustrated below for (S)-N,N-dimethyl-2-[5-[(2-oxo-1,3-oxoazolidin-4-yl)methyl)-1H-indol-3-yl]ethylamine."
KrZ
Hive Bee posted 11-17-1999 12:35 PM
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You should just be able to export your key to a text file, select and paste, and then do the same with any message you might want to send? Is something not working? Works fine on other free-web-mail servers. Why would tryptamine cyclicize? How exactly does that mechanism work?
Rhodium
Pimp Master posted 11-17-1999 03:16 PM
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I don't know the mechanism, but it is called "Pictet-Spengler cyclization". After a formaldehyde molecule has added to the side-chain nitrogen, the other end of it bites the 2-position of indole, water is liberated and you have a betacarboline instead of a tryptamine... It is acid catalyzed and it only takes place in solutions with a pH < 7.
KrZ
Hive Bee posted 11-17-1999 05:30 PM
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I see now, in the notes above they said they used 14g GAA and the freebase of tryptamine. That 14g isn't going to make the reaction mix very acidic. This does occur at pH < 7, but the optimal rate is acheived at lower pH? If so then perhaps cyclization is kept relatively low. No pH testing was done in the notes for this reaction, if only they had kept tabs we could have the answer :-( Even in the sample reaction below they only reported 52% yield, a good sign.
http://orgchem.chem.uconn.edu/namereact/pictetspengler.html (http://orgchem.chem.uconn.edu/namereact/pictetspengler.html)
anonymous
P.S. I hope you have a PC (Win9x/NT)
LaBTop
PimpBee posted 11-18-1999 12:49 PM
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paste : Ctrl+v
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WISDOMwillWIN
Acme
Hive Bee posted 11-18-1999 01:04 PM
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What is the best way to free-base the HCl salt of an amine to be used in the second part? Maybe disolve in aq base, then extract into organic (DCM?) then evaporate? Or can solid NaOH be used, and NaCl salt filtered off?
The Alchemist
Hive Bee posted 02-03-2000 05:55 PM
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Is the 5% Aq. ammonia necessary or can a 10% NaOH soln be substituted for the A/B extraction?
respect...
KrZ
Hive Bee posted 02-03-2000 11:10 PM
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Should be able to, although, thats what SWIM thought about a 2CH extraction once and it didn't work out the same at all :-( Anyways, what concentration is household ammonia? Perchance you could use that.
Jordan Caldwell
NewBee posted 02-05-2000 08:21 PM
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Few questions on this hypothetical synth...
"Tryptophan (454g) was suspended in tetralin (1150 ml) containing acetone (12.9 g)"
What is the point of this step? I don't see you using the resultant yellow crystaline solid... Secondly what is tetralin?
KrZ
Hive Bee posted 02-06-2000 12:00 AM
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that step makes tryptamine.
Lilienthal
Hive Bee posted 02-07-2000 06:26 AM
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Tetralin (1,2,3,4-tetrahydronaphtalin) and decalin (decahydronaphtalin) are widely used solvents and substitutes for turpentine. You can buy them in most drugstores.
It should read: "120 g tryptamine ..." (i.e. the yellow solid), not "120 g tryptophan ...".
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