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Author Topic: 6MeO THH  (Read 172 times)

Tungsten.

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6MeO THH
« on: April 26, 2011, 10:01:49 PM »
Can anyone help me with the reaction mechanism of TIHKAL #44 for 6 Methoxy 1,2,3,4 Tetrahydro beta Carboline?

Quote
SYNTHESIS : (from melatonin): To a gently refluxing solution of 1.6 g melatonin in 120 mL dry xylene there was added in small portions 14 g P2O5 over the course of 45 min. The solvent was removed under vacuum, and the residue treated with H2O, then made basic with dilute NaOH, and extracted with Et2O. Removal of the solvent from the pooled extracts and recrystallization of the residue from EtOH gave 1.0 g 6-methoxyharmalan with a mp 205-207 °C.

Attached is the best I could come up with (sorry for the hand drawn picture, I don't have any fancy ChemDraw or anything.)


More importantly, is there a more readily source-able/synthesize-able alternative to P2O5 for this reaction? I'm having trouble finding some phosphorus (and I don't want to have to buy a million matchbooks for one reaction that is more of a curiosity than anything else.) I'm guessing that the usual dehydrating agents like KOH or anhydrous MgSO4 just won't cut it because they aren't soluble in xylene and/or aren't strong enough.

Any help with this little project of mine would be greatly appreciated.  :)
-W

jon

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Re: 6MeO THH
« Reply #1 on: April 26, 2011, 10:13:51 PM »
you should hydrolyse it to 5-methoxy trytamine and convert it to di-isopropyl-5-methoxytryptamine
a very interesting psychedelic and not all that hard to make.
just a thought.
shulgin uses hunig's base di-isopropylethylamine as a proton scavenger i would just use potassium carbonate and add the isopropyl iodide portionwise to prevent quaternization of the tryptamine.
just my .02 grams.

Vesp

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Re: 6MeO THH
« Reply #2 on: April 26, 2011, 11:37:10 PM »
http://en.wikipedia.org/wiki/Pictet%E2%80%93Spengler_reaction

Does this work for what you are trying to accomplish?

Seems like you could just add acetaldehyde to melatonin under acidic conditions and you'd be golden?
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akcom

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Re: 6MeO THH
« Reply #3 on: April 26, 2011, 11:51:38 PM »
looks like the amide is converted to a nitrile and then nucleophilic carbon attacks

jon

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Re: 6MeO THH
« Reply #4 on: April 27, 2011, 12:12:01 AM »
oh i really did'nt look that close acetamide is dehydrated with p4o10 commonly to acetonitrile
the problem with p4o10 is clumping.

p4o10 is a common reagent

Tungsten.

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Re: 6MeO THH
« Reply #5 on: April 27, 2011, 12:51:27 AM »
This is why I love forums! Ask a question and you have a whole bunch of knowledgeable people willing to answer it for you!

Quote from: jon on April 26, 2011, 10:13:51 PM
you should hydrolyse it to 5-methoxy trytamine and convert it to di-isopropyl-5-methoxytryptamine
a very interesting psychedelic and not all that hard to make.
just a thought.
shulgin uses hunig's base di-isopropylethylamine as a proton scavenger i would just use potassium carbonate and add the isopropyl iodide portionwise to prevent quaternization of the tryptamine.
just my .02 grams.

Thanks for the quick reply jon! That does sound very interesting (I just pulled out my copy of TIHKAL to look up the effects) but has 2 main problems: The most important one is that isoproply iodide requires HI which requires Phosphorus (and like I said, I'm having some trouble getting it.) The other thing is that I wanted to combine the 6MeO THH with some smoked DMT because of its MAOI properties.

Plus, I will be doing this with some friends all of whom will be guys (one of which is gay) so the “intense aphrodisiac” effect might not be appreciated. Lol. :D

Quote from: Vesp on April 26, 2011, 11:37:10 PM
http://en.wikipedia.org/wiki/Pictet%E2%80%93Spengler_reaction

Does this work for what you are trying to accomplish?

Seems like you could just add acetaldehyde to melatonin under acidic conditions and you'd be golden?


Time to crank up the aldehyde cell. :)


Side note: Why does the government have to make red phosphorus so damn hard to get?  >:(
-W

Bluebottle

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Re: 6MeO THH
« Reply #6 on: April 27, 2011, 02:15:48 AM »
Re isopropyl iodide: lucas' reagent, and KI in acetone (I forget which that one's called)
"And now we divide both sides by zero..."

jon

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Re: 6MeO THH
« Reply #7 on: April 27, 2011, 02:17:20 AM »
right or you can just reflux it in HBR
and the next reaction is a simple finkelstein reaction


Quote
Why does the government have to make red phosphorus so damn hard to get?  

which government?
the are a lot of governments.

Quote
Plus, I will be doing this with some friends all of whom will be guys (one of which is gay) so the “intense aphrodisiac” effect might not be appreciated. Lol.


i don't know it depends on if your gay friend likes to make roofie coladas.
in that case you may wake up and find that something strange has happened to you.
« Last Edit: April 27, 2011, 02:22:05 AM by jon »

Tungsten.

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Re: 6MeO THH
« Reply #8 on: April 27, 2011, 10:26:53 PM »
I'll have to keep both of those methods in mind. They seem like they are very OTC, now I think I'll have to try out the 5MeO DIT. :)

To answer jon's question:
The government that tries to control the rest of the world's drug policies. You know the one.

And no, he is quite well behaved. :P
-W

jon

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Re: 6MeO THH
« Reply #9 on: April 27, 2011, 11:28:59 PM »
oh yeah i know that government it reminds me of a gigantic phallus trying to dick with everyone's affairs ok now i understand.

Tungsten.

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Re: 6MeO THH
« Reply #10 on: April 28, 2011, 01:58:47 AM »
Quote from: jon on April 27, 2011, 11:28:59 PM
oh yeah i know that government it reminds me of a gigantic phallus trying to dick with everyone's affairs ok now i understand.

Lol :D

Ok, you guys have convinced me that 6MeO DIT is a more worthy pursuit (especially with the cost of melatonin :O .)

I have a question on the hydrolysis. Namely: KOH in EtOH should work just as good as NaOH in ButOH (Rhodium) right?

And for the Isopropyl Iodide: Isoproply Chloride won't work will it? :(

I always feel like a leech on a forum like this. I ask you guys for help, but have nothing to offer in return. Hopefully I can repay your help with a write-up. :)
« Last Edit: April 28, 2011, 03:31:49 AM by Tungsten. »
-W

jon

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Re: 6MeO THH
« Reply #11 on: April 28, 2011, 03:56:28 AM »
no isopropyl iodide it's not hard to boil some ipa in 48% hbr distill it off and react it with potassium iodide.
i looked at that synthesis and it struck me as one of the most practical hallucinogens to make.
he used hunig's base becuase the bulky groups prevent the base from reacting with isopropyl iodide but i don't see why potassium carbonate would'nt work too.
i think with the nitrogenous base in play it prevents quaternization by also tieing up isopropyl iodide but not reacting with it.
but i think a change in strategy just adding the iodide dropwise to prevent qauternization would also work,

atara

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Re: 6MeO THH
« Reply #12 on: April 28, 2011, 07:17:21 AM »
A procedure is described on Rhodium for the hydrolysis of melatonin:

http://www.erowid.org/archive/rhodium/chemistry/mexamine.html

However I'm inclined to doubt it simply because of the way it is written as a set of instructions rather than a report of a synthesis, and the lack of references. The use of isobutanol is kind of confusing as well, though I presume it was chosen for its immiscibility with water despite being rather polar; similar solvents include ethyl acetate, chloroform, dichloromethane, tert-butanol and benzyl alcohol. Ethyl acetate is the primary ingredient in many non-acetone nail polish removers, on a totally unrelated (srsly) note.

One thing mentioned in the link which I think is valuable, though, is the addition of sodium dithionite. Melatonin, as well as other tryptamines, but melatonin in particular, is highly susceptible to oxidation. Sodium dithionite acts as an antioxidant preventing you from losing product. I suspect ascorbic acid could be used to the same effect, and it is rather easier to obtain (it's also known as Vitamin C).

Tungsten.

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Re: 6MeO THH
« Reply #13 on: April 28, 2011, 10:55:54 AM »
Quote from: jon on April 28, 2011, 03:56:28 AM
no isopropyl iodide it's not hard to boil some ipa in 48% hbr distill it off and react it with potassium iodide.
i looked at that synthesis and it struck me as one of the most practical hallucinogens to make.
he used hunig's base becuase the bulky groups prevent the base from reacting with isopropyl iodide but i don't see why potassium carbonate would'nt work too.
i think with the nitrogenous base in play it prevents quaternization by also tieing up isopropyl iodide but not reacting with it.
but i think a change in strategy just adding the iodide dropwise to prevent qauternization would also work,

Damn it. I misspoke I meant to say "Isoproply chloride won't work at the Lucas' reagent in the Finkelstein reaction will it?" I do know enough to realize why Isopropyl Iodide is needed for the reaction with Mexamine. :)

Edit: Please ignore my lack of reading. :P

Quote from: atara on April 28, 2011, 07:17:21 AM
A procedure is described on Rhodium for the hydrolysis of melatonin:

http://www.erowid.org/archive/rhodium/chemistry/mexamine.html

However I'm inclined to doubt it simply because of the way it is written as a set of instructions rather than a report of a synthesis, and the lack of references. The use of isobutanol is kind of confusing as well, though I presume it was chosen for its immiscibility with water despite being rather polar; similar solvents include ethyl acetate, chloroform, dichloromethane, tert-butanol and benzyl alcohol. Ethyl acetate is the primary ingredient in many non-acetone nail polish removers, on a totally unrelated (srsly) note.

One thing mentioned in the link which I think is valuable, though, is the addition of sodium dithionite. Melatonin, as well as other tryptamines, but melatonin in particular, is highly susceptible to oxidation. Sodium dithionite acts as an antioxidant preventing you from losing product. I suspect ascorbic acid could be used to the same effect, and it is rather easier to obtain (it's also known as Vitamin C).

Thanks! I do have some Sodium Dithionite, so I will be using that. :)
« Last Edit: April 28, 2011, 11:55:44 PM by Tungsten. »
-W

atara

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Re: 6MeO THH
« Reply #14 on: April 29, 2011, 07:46:22 AM »
Worth noting: secondary alkyl halides undergo the Finkelstein reaction only with quite a bit of difficulty -- you're better off using plain old HI to make your iPrI.
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