The Hive > Serious Chemistry

Two new DOM analogs made and evaluated

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GC_MS:
What a coincidence... I discussed this class of substances (DOMCl, DOMBr, DOMI) with a colleague, even not that long ago  :) .

Concerning the comment on putting this substance on the Lists, it should be noted that these articles usually have to pass reviewers. I wouldn't be surprised if there has been a fervent puritan reviewer pressing to add this comment. Note that this article has been written by ppl from the pharmaceutical industry. Ever seen a pharmacist not on drugs?  ;D  Anyway, it still is possible they added the comment themselves, but as been noted, it sounds rediculous.

Also, it rather suprises me that the amine doesn't condense with formaldehyde. I guess I should give it a try...

Bandil, don't forget about iodomethylation  ;) .

moo:
In theory the halomethyl group could alkylate eg. DNA when ingested and have carcinogenic properties, couldn't it? I don't really know - what do you think?

Rhodium:
I would personally not ingest something which could stick an ugly halomethyl group right into my serotonin receptors. I'd definitely settle for DOMOM...

Osmium:
> I would personally not ingest something which could stick an
> ugly halomethyl group right into my serotonin receptors.

So the molecule goes into the receptor, but will it come out again voluntarily or firmly implant itself onto the nitrogen it will meet there?

Lego:
Moreover, the resulting benzyl halide 2 (DOMCl) is reactive and unstable against bases. Therefore it is essential to perform the synthesis in one step
--- End quote ---

Aha, this compound will never bee ingested as a hallucinogen. If it does not survive the in-vitro conditions it will not even survive the in-vivo conditions. It is unstable against bases so if it is taken orally it might not bee hydrolysed in the acidic stomach but from there it will not bee absorbed. In the more basic areas of the intestinum where basic drugs are absorbed it will react with any base to form some pharmacological crap. This more a carcinogen than a hallucinogen.

To a solution of NaOCH3, prepared by addition of sodium metal (0.2 g, 8.7 mmol) and methanol (30 mL), was added 2 HCl (1.5 g, 5.4 mmol).
[...]
Yield 0.8 g (24 %)
--- End quote ---


5.4 mmol hydrochloride are added to 8.7 mmol NaOCH3. The methoxide will first react with the ammonium group forming MeOH and R-NH2. 2.7 mmol NaOCH3 are left which is only half the amount of the amphetamine.
Does anybee understands this?  ::)


Another strange point in this article is that the authors do not mention whether the compounds are agonists or antagonists at the 5HT2 receptor. This makes a big difference, a ligand is not necessarily a drug.

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