what substance is this: Dmt wrapped onto 4-position

[Thelema]

if you wrap dmt around onto the 4-position of the indole, what do you call it?

[MeanGreen]

Not sure what you mean by wrapped around, but basically, DMT with a hydroxy group on the 4 position of the ring is Psilocin (4-HO-DMT), with a phosphoryl group it's Psilocybin (4-PO-DMT), with an acetoxy group it's 4-AcO-DMT.

[Thelema]

no, i mean the n attached to 4, or separated by a carbon

[MeanGreen]

I guess that would be 2-(1H-Indol-4-yl)-N,N-dimethylethanamine

 

DMT is 2-(1H-Indol-3-yl)-N,N-dimethylethanamine

[Alchemica]

If  I'm following right, do you mean, my chemistry is getting rusty, the 3,4-fused tricyclic indoles eg 'dehydrodimethyltryptamine'. Could come up with an IUPAC name, I'm getting rusty. Haven't seen that one in the literature, is it stable? There is Dehydrobufotenine: There is a covalent bond formed between the dimethylated nitrogen atom and the indolic 4-position. Problem is, it becomes a quaternary amine. Maybe fused N-methyltryptamine might be more interesting?

 

 

As for names, I'll throw in chemdraw names, 5,5-dimethyl-1,3,4,5-tetrahydro-5l⁴-pyrrolo[4,3,2-de]quinoline for the first and

5-methyl-1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline for the latter

 

http://herbpedia.wikidot.com/dehydrobufotenine

 

I'd be more interested in the non-quaternary forms maybe?

Edited April 26, 2018 by Alchemica

[Thelema]

yeah what is it callled without that annoyin 5-oh

[Alchemica]

Most references I can find to such structures on the 3,4-fused tricyclic indoles, the pyrroloquinolines, of this class go by the class name of 'tetrahydropyrrolo[4,3,2-de]quinolines'. DMT forms the 5,5-dimethyl. Many marine alkaloids are biologically active products and possess the 1,3,4 ,5-tetrahydropyrrolo[4,3,2-de]quinoline core as a common feature [1].

 

Their chemistry is detailed a bit here

 

Fargesine was isolated from the roots and stems of Evodia fargesii [2] Haven't seen a more simple 3,4-fused tricyclic indole of DMT existing in plants?

If this is very 5-HT2AR active? Maybe not? 1) the nature of the nitrogen becomes very different, from aliphatic to aromatic 2) it seems to lack the spacers of carbons needed for ergoline/tryptamine/PEA activity 3) Work with derivatives had indicated that the side  chain probably could not lie in the plane of the aromatic ring

Edited April 29, 2018 by Alchemica