Author Topic: tryptamine salt  (Read 3270 times)

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meme

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tryptamine salt
« on: February 22, 2002, 11:49:00 AM »
Would trypamine form the triacetate with acetic?  Would an acetyl ionically bond to each H on the NH2, and to the NH?   Thanks in advance.

Solve et Coagula.

terbium

  • Guest
Re: tryptamine salt
« Reply #1 on: February 22, 2002, 11:56:00 AM »
No.

Chromic

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Re: tryptamine salt
« Reply #2 on: February 22, 2002, 10:12:00 PM »
Tryptamine has only one nitrogen with a lone pair of electrons that can be used for sigma bonding. The other nitrogen uses its two extra electrons to form pi bonds in the aromatic indole ring. Plus, there's no places for an ester to form (also called an acetate... but mind you that would be a covalent bond, which is not what you talked about) so... Terbium's answer is right on the money. (just thought I'd add my two cents)  :)

meme

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Re: tryptamine salt
« Reply #3 on: February 27, 2002, 07:48:00 AM »
Thanks, I was thinking that my conceptions were wrong . . .

"I was wrong . . . That changes everything"
-Tool

No barbed wire can cage a bee.

urushibara

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Re: tryptamine salt
« Reply #4 on: February 28, 2002, 02:18:00 AM »
Um 'acetate' don't just mean ester it also means ionically bonded acid ion, like maleate, sulphate, hydrochloride. However, I think that it might only be one acetic acid per tryptamine, because ammonia pulls off one hydrogen when it mixes with water, and amine freebases such as tryptamine (or any other amine freebase) don't do that real well either, that's why they don't mix with water. But they do form OH's in the water when the water is acidic (ie got H+ ions floating around), and many (and tryptamine is probably the same) make salts when the water's removed. Thus meme means does three acetic acid ions ionically bond to Tryptamine. Methinks no. But it probably does make one bond.

When you look at the molecular model that is done for tryptamine (get chime so you can look at the model linked from erowid's TiHKAL) they draw it so that the N is kinda exposed looking. Possibly the reason why DMT doesn't make many solid salts is that to bond ionically it pushes those methyls down, and they're repelled strongly by the hydrogens on the ethyl carbon chain between the amine and the indole, thus not many things can stick ionically. Fumarate and picrate do apparently. Picrate has an ionic oxygen on it which would probably help it bind. This may also be the reason why DMT isn't active by the nose, because it can't do ionic bonding very well.

Or maybe it's just the fact that the methyl brings a pair of three covalently bonded hydrogens really close, which makes bonding difficult without something defusing some of that excess sigma positive (like the oxygen on picrate)

Disclaimer: everything I said I pulled outta my arse  ;D

obia

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Re: tryptamine salt
« Reply #5 on: February 28, 2002, 03:01:00 AM »
dmt makes no solid salts??? hmmm the maleate fumarate oxalate are all solid and nicely crystaline. the hydrochloride is solid but amorphous.
DMT behaves almost exactly like any other tertiary amine.

for what its worth a 1 acetyl (ie an acetyl on the indolic nitrogen- an amide) acetate(a salt formed from the sidechain nitrogen) salt of tryptamine or dmt is formed by treating the free base with acetic anhydride and sodium acetate

urushibara

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Re: tryptamine salt
« Reply #6 on: February 28, 2002, 03:08:00 AM »
really. Where'd you read that? Or did you dream it  ;) ? You don't also happen to know the solubilities of all these little fellas do ya? DMSO and water are the most instresting ones. There's an idea going around on DMT world about dmso and dmt making a variety of insufflation work (spraying it out of a nasal sprayer) solubilities would be rather useful for determining the most appropriate salt to use, to calibrate dosing right, and indeed to ensure dosing is even possible.

Disclaimer: everything I said I pulled outta my arse  ;D

obia

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Re: tryptamine salt
« Reply #7 on: February 28, 2002, 03:56:00 PM »
dmt does dissolve in dmso. afaik it didn't work(no blast off into parallel universes)  via dermal absorbtion. I don't think stick dmso up your nose is a good idea given it causes contact dermatitus.
snorting dmt a la virola and piptadenia snuffs is interesting but doesn't seem to work with pure dmt. there seems to be another component in those snuffs whic activates the dmt (carboline MAOI's???).
if say one wanted to dream about using dmt as a snuff dissolving the maleate or fumarate salt in water would be the way to go. solubility is not the factor really, working out how much the sprayer sprays then working the required concentration/ number of sprays for aroung 50mg is the best strategy

hest

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Re: tryptamine salt
« Reply #8 on: March 01, 2002, 12:18:00 AM »
snorting 50mg of DMT fummerat works nice, not like smoking it but it last for houers.