(Hive Addict)
05-10-03 05:45
No 432467
(Rated as: good read)
Indole Alkaloids of Acer saccharinum (the Silver Maple), Dictyoloma incanescens, Piptadenia colubrina, and Mimosa hostilis
Irwin J. Pachter, David E. Zacharias, Oscar Ribeiro
J. Org. Chem. 24, 1285-1287 (1959)
Abstract
Gramine was isolated from the leaves of Acer saccharinum L., N,N-dimethyl-5-methoxytryptamine from the bark of
Dictyobma incanescens D.C., bufotenine from the seeds of Piptadenia colubrina Benth., and N,N-dimethyltryptamine from the roots of Mimosa hostilis Benth.
Old and New Alkaloids from Zanthoxylum arborescens
Jonas A. Grina, Matthew R. Ratcliff, Frank R. Stermitz;
J. Org. Chem. 47, 2648-2651 (1982)
Abstract
The new alkaloids (2S,5S)-2,5-dibenzyl-1,4-dimethylpiperaz
Accept No Imitations, There Can Only Bee One; www.the-hive.ws
(Stranger)
05-10-03 09:24
No 432488
In the text they said that Silver Maple contain 0.05% of DMT and Gramine, in the method in the lower part, they only explain the Gramine extraction, is it because the twa are alkaloid so they are extracted the same way or because Silver Maple only contain gramine?
If Silver Maple contain DMT this would be a very good news for Canadian Bees
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(Hive Addict)
05-10-03 19:41
No 432558
needs another carbon on the side chain...
Infinite Radiant Light - THKRA
(Stranger)
05-11-03 07:08
No 432616
This was something that I was thinking about, since gramine is relatively easy to make.
IIRC, reacting gramine with CH3NO2 produces Indole-CH2-CH2-NO2 and (CH3)2NH, which can then be seperated, reacted with CH2O, then with indole to form more gramine (Mannich rxn). Indole-CH2-CH2-NO2 can therefore be made by the following reaction: Indole + CH2O + CH3NO2 --(R2NH)--> Indole-CH2-CH2-NO2 + H2O.
If that nitro group could be reduced, then you would have tryptamine which could be alkylated. The trouble is, the C=C bond in the heterocyclic ring of indole is apparently quite easy to reduce to CH-CH (eg sodium cyanoborohydride will do it in yields over 90% at rt on unsubstituted indole), and might therefore be affected by the conditions necessary to reduce the nitro group. I was wondering about adding HBr accross the double bond, then performing an elimination reaction after the reduction to get tryptamine, but I have no idea if it would work, and even if it did the extra steps (= extra time and effort and lower yield) would mean that it would probably be better to use a totally different method.
"Simplicity is the ultimate sophistication."
(Hive Bee)
05-11-03 08:08
No 432622
Swap the gramine with a cyanide ion, get the indoleacetonitrile.
And then Post 354293 (Rhodium: "This together with what's been posted in Post ...", Tryptamine Chemistry) and Post 351772 (Barium: "Nitriles to tertiary amines", Tryptamine Chemistry)
You will have DMT
(Chief Bee)
05-11-03 11:33
No 432654
Gramine can be used as a starting material for AMT and AET too, see ../rhodium /it-290.
(Moderator)
05-11-03 14:57
No 432688
Nick-J: AFAIK it is not possible to reduce an indole to an indoline with the common hydrides as long as you don't work under stronger acidic conditions like neat acetic acid.
(Stranger)
05-12-03 11:02
No 432827
A bit more reading told me that NaBH3CN in AcOH was used...
So perhaps the nitro group could be removed with a polysulphide. I'll have to try this some time.
First step for me is indole from albumin, I have not had any luck with this so far. It's a pitty the tryptophan can not be isolated from the protein directly
.
"Simplicity is the ultimate sophistication."