I was talking to a friend and suddenly I realized that we talk about alot of different stereoisomers of ketamine, mdma, etc...does DMT have stereoisomers? Is there R and S dmt?

Thanks in advance, chemists.

You need a C-atom that is attached to four different substituents. For example LSD has two of these C-atoms, each marked with a star in this formula:



DMT does not have such an C-atom, making it an molekule that has only one "chiral" form.

I hope you understand this explantion, if not, just ask

''one chiral form''

What about cis-trans or D/L and d-, l- ?

Thank you
Much love

I do understand chirality a little bit, thank you, s far as i understand the cis/trans has to do with double bonds and is not applicable to dmt.. thank you nicita. that is what i thought might have been the case.

dmt contains no stereocenters, thus no epimers nor enantiomers/diastereomers...no isomers.

For scientific rigour, skip the "no isomers" as there are plenty of isomers of C12H16N2 and ten other substitutable positions on the tryptamine molecule besides the sidechain nitrogen. /ends pedantry (for the moment )

we're discussing N,N- DMT, the only possible form is about the terminal amine;
and we're not considering rotatable carbons, we're considering chiral centers.
DMT displays no stereochemistry, any conformations are due to said rotatability
about the alpha and beta carbons...even so, how would you name them?

Yeah, sorry, I already knew I was being excessively pedantic! But it still pays to be absolutely clear about some things.

What would we call the different molecular configurations at the alpha- and beta carbons? I would suggest rotational conformers or rotamers.

https://en.wikipedia.org...Conformational_isomerism

Dmt crystals of different shapes could be the result of different conformational isomers making up the crystal lattice - or maybe not.

Rotatable carbons as benzyme said will always rotate in solution / gaseous phase in which case all possible rotational coformations are equally possible at a given instance. But in a crystal latice there are constrains and fixed conformational isomers can be found. But melt or dissolve the crystal and this effect is lost.

The term conformational isomers is meaningful in larger molecules like proteins or nucleic acids; for dmt, not really.

Yes, especially in solution they are transient at best. There was the Falkenberg paper (Acta Cryst. (1972) B28, 3075) linked to somewhere near here about there being two different crystalline conformations of DMT with very similar favourable energy characteristics but still it isn't anything to do with optical isomers.