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What did he not-do this time?
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Author Topic: What did he not-do this time?
KrZ
Hive Bee posted 11-16-1999 06:03 PM
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Well, I came up with a good use for all that leftover NaCNBH3 you might have laying around.
"Tryptophan (454g) was suspended in tetralin (1150 ml) containing acetone (12.9 g) and the mixture was heated to reflux for 12 hours with vigorous stirring until no more carbon dioxide was evolved and the reaction mixture became clear. The solvent was removed under vacuum, and the residue was distilled under reduced pressure to give a yellow crystalline solid. (from rhodium). Next 30g of formaldehyde and 120g Tryptophan were disolved in 1800ml of MeOH, to this was slowly added dropwise 50g of NaCNBH3 disolved in 550ml MeOH. Then 14g Glacial Acetic Acid was added dropwise with stirring. The mixture was then stirred for 60 hours. The majority of the MeOH was distilled off (2L collected) to the distillation flask was added 1L of 5% Aq. Ammonia which was extracted with 3x 250ml of DCM. The DCM was washed with a salt solution (not saturated but still pretty strong) then the DCM seperated and dried with a large portion of MgSO4 made by dehydrating epsom salts overnight in the oven at 450C (the rock-solid mass had to be pounded into a powder with a hammer and the small remaining clumps ground in a pestal, quickly so as not to allow H2O uptake from the atmosphere). The DCM was distilled off at atmospheric and then the distillation was continued (~1 torr now) until the dimethyltryptamine was collected. Which was recrystalized from boiling hexane with a few mls of Ethyl Acetate added (these were the 2 hardest things to get!) This afforded 48.8g of DMT, a 35% yield. Not high but it was still a fun adventure. The DMT was immediately mailed 3500 miles away."
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
anonymous
Hive Bee posted 11-17-1999 06:19 PM
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Bright Star,
All you need to do is type your message in a text editor (like notepad), once you are finished select all the text and copy it to the clipboard (ctrl+c), then clik the PGP icon in the tray (near the clock) and select "encrypt and sign clipboard" (or something like that), now pase (ctrl+p) into the message box of hushmail. If everything went well you should have your PGP encrypted message in the box now just address it and send it.
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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