It is interesting, where can i get phys-chem properties of substances in the internet? To be more concrete, i wanna to make 5-MeO-DMT from melatonin, formaldehyde and Al/Hg in EtOH. First, I'm interesting of melatonin, 5-MeO-triptamine and 5-MeO-NMT/5-MeO-DMT and these salts solubility information in different solvents (EtOH, acetone, hexane, water, NaOH, HCl). Help, people!

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With best regards,
Dennis Prochko aka Wolf

http://www.chemexper.com/header.html

http://chemfinder.cambridgesoft.com/

might be useful but probably still won't give you exactly what you want.

Unfortunately there doesn't seem to be a way to reductively alkylate tryptamines due to cyclization to beta-carbolines. Use the search engine   .

...short of using NaBH3CN and formaldehyde. That one seems to work.

... with yields around 20%. I don't believe higher yields...

Lilienthal, thank you for your warnings, but AFAIK beta-carbolines will produced when tryptamine is alkilated in presence of acids. What about neutral/basic solutions? Have you or SWIM tried this?

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With best regards,
Dennis Prochko aka Wolf

Lilienthal: In JMC 44(23), 3881 (2001) 5-Cyanotryptamine was reductively alkylated to 5-CN-DMT in 75% yield using that method (the details are on my page, and posted by me in this forum a few months ago).

could someone with a good literature access please find those solubilities for us?

Should bee useful for many a generations of tryptamine-dreaming bees. We know someone has that kind of data in some university library, don't we? Or am i asking too much?


Anyway. Further on. Certainly, HCHO and Al sounds WAY too simple , esp. for tryptamine chemistry. However, no one (to my humble knowledge) ever actually tried doing this.

Moreover, Al/HCHO reductive methylation proceeds at neutral pH and at temp a lil bit above the ambient (guess can do it at  RT and longer time) - seem to bee ideal conditions. HCHO probably should bee added in 2 portions to minimize side-rxns.


Anyway, Dennis, accept my encouragement    in your quest, and i hope someone will help you find out the physical properties you want.



Yours,


Antoncho

I once tried catalytic transfer hydrogenation with Pd/C, formaline, and tryptamine in triethylamine(!) on a 1 mg scale. Independent on the conditions (e.g. neutral solvents instead of TEA) the main product (~ 80%?) was always a beta-carboline! Forget it, don't waste your time. Both, wanted and side product, go through the same intermediate. The only solution seems to be a ring substitution to alter the electronic properties of the ring to inhibit the reaction with the indole-2-position (-CN, -NO2...).

Lili: What about KrZ's 60-70% trials with tryptamines? Are you writing them of as bragging too?

I don't know. Has it been repeated independently? I remember a discussion about some calculation errors.

N,N-Dimethyl-2-[5-[[(trifluoromethyl)sulfonyl]oxy]-1H-indol-3-yl]ethylamine Oxalate (5-MeSO3-DMT)

To a magnetically stirred solution of 18 (0.46 g, 1.5 mmol) and 37% formaldehyde (aqueous, 1.2 mL) in acetonitrile (6 mL) was added NaCNBH3 (0.29 g, 4.5 mmol). The mixture was acidified to pH 5 with acetic acid and stirring continued for 3 h. NaOH (10%, 30 mL) was added, after which the aqueous layer was extracted with CH2Cl2 (3x20 mL). The organic layers were combined and dried over MgSO4. Filtration and removal of the solvent in vacuo gave an oil, which was subjected to column chromatography (SiO2, eluting with CH2Cl2/MeOH (5:1)), affording 193 mg (38%) of a colorless oil. Recrystallization of the oxalate salt from MeOH/ether afforded 164 mg (26%) of white crystals: mp 176-177°C;

Ref: J. Med. Chem. 39, 4717-4726 (1996)