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Demethylation of 3,4,5-trimethoxybenzaldehyde

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Captain_America:
Actually, I think isoproscaline sounds quite interesting.

Yeah moo, I agree, it sounds very interesting, I would however like to taste the sec-butoxy analog, I don't think it has yet been made so I'm working on it.

For instance:

[Escaline: DOSAGE: 40 - 60 mg. DURATION: 8 - 12 h.]
[isoproscaline: DOSAGE: 40 - 80 mg. DURATION: 10 - 16 h.]

[proscaline: DOSAGE: 30 - 60 mg. DURATION: 8 - 12 h.]
[secbutoxy analog would hence probably have the same dosage/duration as proscaline, but it would probably halt at this lenght as receptor won't tolerate further homologation, see for instance the drop in potency with buscaline compared to proscaline (possibly the branched para-[3-penthoxy] would also show some activity, but it's hard to predict).]

Anyways, to the point of the post, this paper might interest you, notice how bromine on para shows increasd activity in sheep just like higher alkyloxy homolgs do, I think this could bee the study that Shulgin comments on in the DESOXY entry in Pihkal*:

Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogs
David E. Nichols, Donald C. Dyer;
J. Med. Chem.; 1977; 20(2); 299-301.



*: A mescaline analogue with a bromo atom in place of the 4-methoxyl group is an analogue of mescaline in exactly the same way that DOB (a very potent am-phetamine) is an analog of TMA-2 (the original trisubstituted amphetamine). This analogue, 3,5-dimethoxy-4-bromoamphetamine, has been found to be a most effective serotonin agonist, and it is a possibility that it could be a most potent phenethylamine. But, as of the present time, it has never been assayed in man.

Disciple:
Captain america couldn't you just pick your base carefully, as their will be a fair bit of difference between the pKa of a phenolic proton and that of an amine's.

Rhodium:
That is inconsequential, as only phenols need to be deprotonated to their corresponding anions for alkylation to proceed, the only requirement is that they are present as their free base.

An alternative to the use of a protection group on the nitrogen is to use the Mitsunobu Reaction: Post 506741 (Rhodium: "O-Methylation of Phenolic Phenethylamine", Chemistry Discourse)

Captain_America:
That is inconsequential, as only phenols need to be deprotonated to their corresponding anions for alkylation to proceed, the only requirement is that they are present as their free base.

Text in red - I know and agree with, but then I don't understand what you meen...

Rhodium:
I said that phenols requires basic conditions to be alkylated, while amines can be alkylated under either neutral or basic conditions (in response to the post by Disciple). The link to the Tyrosine O-alkylation article answers your question.

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