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Two new DOM analogs made and evaluated

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Rhodium:
Synthesis and 5-HT2A Radioligand Receptor Binding Assays of DOMCl and DOMOM, Two Novel 5-HT2A Receptor Ligands
Antje Harms, Ernst Ulmer, Karl-Artur Kovar
Archiv der Pharmazie, Volume 336, Issue 3, 155-158 (2003) (https://www.thevespiary.org/rhodium/Rhodium/pdf/domcl-domom.pdf)
DOI:10.1002/ardp.200390014

Abstract
A synthesis of two new active substances, DOMCl (1-(4-chloromethyl-2,5-dimethoxyphenyl)-2-propanamine (2)  and DOMOM (1-(2,5-dimethoxy-4-methoxymethylphenyl)-2-propanamine (3), was developed. Unexpectedly, the Blanc reaction permitted successful synthesis of 2,5-dimethoxyphenylpropylamine derivatives having a substituted methyl group in position 4 since solvation of the reactant occurs during the reaction. Afterwards, their affinities towards the 5-HT2A receptor were examined in 5-HT2A radioligand receptor binding assays. The study of these substances is of considerable interest because they were predicted, by preliminary molecular modeling studies based on mescalin units, to be potential new hallucinogens that should be added to the list of substances prohibited by law. It was assumed that DOMCl would be 82 times more potent as a hallucinogen than mescalin, and DOMOM would be 94 times more potent. The 5-HT2A radioligand receptor binding studies showed that the affinities of DOMCl and DOMOM for the 5-HT2A receptor are less than expected but are nevertheless 1.6 and 8.7 times higher, respectively, than that of mescalin. Therefore, scheduling these substances as potential drugs of abuse might be considered.

Lilienthal:
Abusing those idiots might be considered  ::)

hypo:
the irony is that practically every compound in this class would have
2-100 mescaline units, wouldn't it? why synth them at all?

Rhodium:
Well, because it is the first examples this far of a -CH2X group in the 4-position where X is something else than C or H...

I'd say it's a very interesting finding (even though the research motivations given above was the stupidest thing I've read in a phenethylamine abstract since Glennon forced newly hatched chickens to ingest 2C-B/MDMA so that he could distinguish entheogens from entactogens by observing the various spasms and odd behavious the poor critters displayed...)

Bandil:
What a nice molecule  8) !

Any idea on how a R-CH2Br version would compare to the chloro version potency wise? My immediate guess would be that it ought to be less potent (with R-CF3 being somewhat more potent).

Anyhow, i would really like to try out this method on some DMA and a bromomethylation ala Post 475109 (Lego: "Amphetamines/PEAs w/o benzaldehyde or nitroethane", Novel Discourse) (bromomethylations are preferred as my current religion does not approve of chloromethylations). Shouldn't be very diffucult.

Regards
Bandil

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