oooooooooohhhh *boohiss* sorry. Ester / Ether not the same thing at all.
Yes, the Ester you were talking about.

Some useful information http://www.jbc.org/content/88/3/659.full.pdf

In Tihkal the synthesis for what Shulgin calls alpha,N-Dimethyltryptamine;


He goes from Indole-3-Acetic acid, to indole-3-acetone;

--->

SYNTHESIS: (from indoleacetone) To a solution of 1.55 g NaOAc in 5 mL acetic anhydride there was added 2.0 g 3-indoleacetic acid and the mixture was heated at 135-140 °C for 18 h. Removal of all volatiles on the rotary evaporator under vacuum produced a pale yellow residue that was the 1-acetylindole-3-acetone. This was dissolved in MeOH to which 0.93 g MeONa was added, and the solution held a reflux several hours. After removal of the solvent under vacuum, the residue was suspended in H2O and extracted with several portions of Et2O. These extracts were pooled, and removal of the solvent under vacuum gave 0.41 g (21%) indole-3-acetone as a white solid, mp 115-117 °C. MS (in m/z): indolemethylene+ 130 (100%); parent ion 173 (16%). IR (in cm-1): 691, 753, 761, 780. 1017, 1110, 1172, and a broad C=O at 1710.

Then from Indole-3-Acetone to the methamphetamine analog of tryptamine, with methylamine. One could always substitute for dimethylamine or ammonia for example;
--->

To 1 g shredded aluminum foil there was added a solution of 20 mg HgCl2 in 15 mL H2O. After 15 min the amalgamated aluminum was drained free of the mercury solution, well washed with fresh H2O, and shaken as dry as possible. There was then added, in sequence, a solution of 1.5 g methylamine hydrochloride in 2 mL H2O, 3 mL of 25% NaOH, 5 mL of IPA, and finally 1 g of indol-3-ylacetone in 20 mL IPA. This was stirred for 1 h, then heated briefly on the steam bath. After cooling, the reaction mixture was filtered and the solids washed with MeOH, the washing and filtrate combined, and stripped of solvent under vacuum. The residue was dissolved in 200 mL H2O, made acidic with HCl, washed with CH2Cl2, treated with aqueous NaOH to a pH of greater than 9 (becomes cloudy), and extracted with 2x50 mL CH2Cl2. Removal of the solvent from the combined extracts gave a light brown oil which distilled at 125-135 °C at 0.4 mm/Hg to give 0.74 g of a viscous oil. This was dissolved in 5 mL IPA, neutralized with concentrated HCl and diluted with anhydrous Et2O to the point of turbidity. After standing, the solids were removed, washed with Et2O and air dried, to yield 0.87 g of a,N-dimethyltryptamine hydrochloride (a,N-DMT) as white crystals. MS (in m/z): C3H8N+ 58 (100%); indolemethylene+ 131-130 (19, 14%); parent ion 188, just above noise level.

Alternately, the indol-3-ylacetone can be catalytically reduced in the presence of methylamine. A solution of 3.3 g indol-3-ylacetone in 100 mL EtOH was hydrogenated over Pd-C catalyst in the presence of an excess of methylamine. After 2 h the catalyst was removed by filtration, the filtrate stripped of solvent under vacuum, the residue dissolved in H2O and made acidic. After washing with Et2O, the aqueous phase was made alkaline, and the solids that formed removed by filtration and recrystallized from a mixture of hexane and THF. The product, a,N-dimethyltryptamine (a,N-DMT), was a tan solid that weighed 2.2 g and had a mp of 93-94 °C. The picrate is brick red from EtOH, and melted at 207-208 °C.

Tihkal
http://www.erowid.org/library/books_online/tihkal/tihkal08.shtml

Also indole-3-acetone (basically indole P2P), is actually quite readily available too.

Nope, LiAlH4 Is too corrosive for my child-like hands and eyes! also sometimes I like to bite my fingernails and I never wear gloves when working with reducing agents ... oops?

Thanks for the info though, This synth seems very useful. recently there was a mimosa hostillis scare, with some vendors (bouncing bear botanicals) being raded. but, now pharalius brachystacy can be used and it contains a whopping 3% alkaloids! (MHRB is ~1%) straight to base method works fine with no defat!

Stainless steel pressure bombs assembled from piping are doable at home, just not the safest things in the world.

Certainly this is a dangerous method, but I can't be the only one to have considered that as the trouble with direct methylation is breaking up the quaternary iodide salt, the use of a bomb containing the easily made alkyl chloride and tryptophan/tryptamine would circumvent this (the former would then be decarboxylated). Why wouldn't that work?

Some people consider the short duration of DMT as an advantage. Plus, if you have a bad trip it isn't that long.

4 years ago on WD i posted results of indole-3-ethanol in very good purity (MP 57C white crystals) by the Erlich method using distillers yeast + h2o + tryptophan + sugar.  it was a 5 day fermentation and i used 1/3 as much water as Erlich because my yeast could live up to 18% alcohol but his only produced 6%.

long story short, the solvent volume and workup is worse than for the Strecker degradation.  i lost some yield trying to extract with petroleum ether.  but then i tried extracting the gum left over with boiling diethyl ether.  on cooling about 1g tryptophol was obtained from maybe 6-7g starting tryptophan.  i believe yields would be higher if i didn't bungle the workup.

i was interested to try the Russian raney nickel reductive amination of tryptophol with the dean-stark apparatus.  http://127.0.0.1/rhodium/Rhodium/chemistry/tryptophol.html  the yeilds in the original ref (thanks Antoncho) were 93% which is worth pursing and the synth is elegant.  i was gonna try with urishibara nickel.  i was most interested to bioassay DET before deciding whether to commit more effort into it.

question- considering that indole-3-acetaldehyde is the actual intermediate in the Russian reference, can we substitute it for the tryptophol and supply hydrogen as gas, or as potassium or ammonium formate?

of course there are other ways to process tryptophol, PBr3 will give bromoethyl-indole.  this will react with dialkylamine at RT over several days (or weeks?).  but tosylation or mesylation is less messy, higher yielding, and the intermediate is (from what i read) 100x or 1000x as reactive toward dialkyamines as bromo-ethyl-indole is.  the pharmaceutical companies mesylate in the patent for Sumatriptan.

i see nothing wrong with obtaining DMT from plants.  the 2% concentration found in certain roots is just begging to be harvested.  if it was 0.2% i would be less sure.  it takes quite an economy of scale to produce synthetic dmt at less than the cost of a plant extraction.  thankfully it's not as ridiculous as synthesizing thc from scratch instead of extracting it- that IMHO is a waste of time and the companies that make their profit that way (at the expense of the sick!) should bee fucking ashamed of themselves.  there is of course no "one right way" to dmt.  it all depends on your own facilities, capabilities, output requirements, and access to feedstock.

there is a possible alternative synth of indole-2-propanone from IAA utilizing Methyl Lithium.  that stuff looks pretty scary to me though so perhaps making your own Ac2O would be preferable.

i was interested to try the Russian raney nickel reductive amination of tryptophol with the dean-stark apparatus.  http://127.0.0.1/rhodium/Rhodium/chemistry/tryptophol.html  the yeilds in the original ref (thanks Antoncho) were 93% which is worth pursing and the synth is elegant.  i was gonna try with urishibara nickel.  i was most interested to bioassay DET before deciding whether to commit more effort into it.

question- considering that indole-3-acetaldehyde is the actual intermediate in the Russian reference, can we substitute it for the tryptophol and supply hydrogen as gas, or as potassium or ammonium formate?

I can't seem to follow this link can anyone help me out with that?  Are you, is he referring to something like Rhodium is talking about here hxxp://parazite.pp.fi/hiveboard/tryptamine/000006702.html ?  "This is the article from J Org Chem USSR, 5, 2158 (1969) mentioned above

General procedure for the preparation of dialkyltryptamines:

Into a flask fitted with a Dean-Stark recieving trap were placed 0.1 moles of tryptophol [2-(3-indolyl)-ethanol], 0.1 moles of a secondary amine [dimethylamine for DMT], 4ml of skeletal nickel suspension in water and 100ml of benzene or xylene [I assume toluene is good too]. The reaction mixture was refluxed, and the condensed water collected for four hours, the hot solution filtered and the catalyst washed repeatedly with benzene or xylene [or toluene] and the mother-liquor concentrated under vacuum. The product was either distilled in vacuo or isolated as the hydrochloride by acidifying with an equivalent of hydrogen chloride solution [they are probably referring to a non-aqueous HCl solution here]. The yields were in the 82-98% range. "

Thank you vesp
I'm a tad coonfused by two contradictory references in degradation to 3-indoleacetaldhyde using hypochlorite
it states that "The reaction is based on that studied by Langheld (6) who showed that
when an a-amino acid is treated with sodium hypochlorite it is converted
into an aldehyde containing one less carbon atom than the original amino
acid."  Yet here https://www.erowid.org/archive/rhodium/chemistry/p2p.strecker.html
which is the reference cited but it shows that that strecker degradation gives 1-(2,3-dihydro-1H-indol-3-yl)propan-2-one.
Maybee I am missing something but would one of you wiser wasps help me figure out whats going on? 

Thank you, wow I feel dumb I read that page like a hundred times and didn't notice that.  In trying to find the answer to said retard question.  Reading in this thread http://127.0.0.1/talk/index.php/topic,448.0.html  in the reference that can be found in reply number 3 posted by java, on page 3 of said reference, it shows the steps the reduction would take and it proceeds though the imine.  How much would this be affected by pictet-spengler ring closure? The following step requires water which I think could provide the H+ needed for it.