Sciencemadness Discussion Board - What to do with tryptamine?

What to do with tryptamine?

ParanoidAndroid - 22-12-2011 at 14:15

I have a large amount of pure tryptophan and recently came across an exceedingly simple method of making it into tryptamine: basically just reflux it a mixture of xylene and acetone until CO2 stops evolving. A spearmint oil catalyst can be used to speed the reaction but adds a purification step afterward and reduces yield.

My question is: what can I do with the resulting tryptamine? There are a whole slew of interesting substances that are related to tryptamine, but there's very little information on synthesizing those substances using tryptamine as a starting material. Are there any easy ways to do this?

Of particular interest to me are AMT (an MAOI), serotonin (neurotransmitter), and DMT (which is an interesting precursor to other syntheses). The molecular changes aren't complicated; there just isn't a lot of experimental info out there.

Bot0nist - 22-12-2011 at 15:08

Decarboxylate and post a write up with the procedure, yield, and product identification ( melting point, solubility's, etc) before even worrying about methylation.

[Edited on 22-12-2011 by Bot0nist]

Adas - 22-12-2011 at 15:19

Wow, if you really made it, it is a good news! You can make DMT (if it's legal in your country) or DIPrT - this is known to cause auditory hallucinations only.

JibbyDee - 22-12-2011 at 18:19

Very interesting. Have you successfully thermally decarboxylated tryptophan? Tryptamines fascinate me. I'm going to read TIHKAL one of these days, I hear Shulgin did a serious amount of research on tryptamines.

[Edited on 23-12-2011 by JibbyDee]

zoombafu - 22-12-2011 at 19:02

PiHKAL and TiHKAL would probably be your best resources.

[Edited on 23-12-2011 by zoombafu]

Sedit - 22-12-2011 at 21:02

Doubtful, he mostly obtains his typtamines using other starting materials or hard to get reagents. Google is your friend here.

turd - 23-12-2011 at 00:14

Actually Shulgin was eager to develop routes from uncontrollable materials and you will find that he published a route for most of his not ring substituted tryptamines starting with tryptamine or at least gave an outline. Shulgin is a good, humble guy who lets his actions speak.

What he missed was the sodium triacetoxy borohydride (made in-situ) reductive methylation of tryptamine with formaldehyde to DMT. I have heard a few success reports. Yields are low in an amateur setting, but given that it's only two steps from (dirt cheap) tryptophan, overall yield is better than for most OTC routes to phenethylamines.

Original poster: Follow Bot0nist's advice and come back once you have geniune tryptamine. Some successful attempts have been posted on this forum.

DJF90 - 23-12-2011 at 08:46

I dont think alkylation that occurs via an imine will be possible... ever heard of the Pictet-Spengler reaction?

Adas - 23-12-2011 at 08:48

Isn't it possible to methylate tryptamine using simply H2SO4 + methanol?

turd - 23-12-2011 at 09:40

Quote: Originally posted by DJF90

I dont think alkylation that occurs via an imine will be possible... ever heard of the Pictet-Spengler reaction?

Maybe it's not possible in theory, but in practice it is.

Quote:

Isn't it possible to methylate tryptamine using simply H2SO4 + methanol?

Doubtful.

smuv - 23-12-2011 at 10:23

A lot of triptan drugs are methylated by reductive alkylations. I think this is a conditions thing. But yes...pictet-spengler can be a competing reaction.

Edit: haha originally unintelligible.

[Edited on 12-23-2011 by smuv]

DJF90 - 23-12-2011 at 12:52

Thing is, formation of an intermediate imine/iminium cation should react much faster intramolecularly than intermolecularly, although I agree perhaps there are conditions where the Pictet-Spengler cannot occur. I suspect if you can use conditions which would adversely affect the breaking of aromaticity in the intramolecular attack then it may be possible. Perhaps thats why typical Eschweiler-Clarke conditions cannot be employed, as I am sure that reaction proceeds via the P-S pathway.

JibbyDee - 23-12-2011 at 13:03

I was just looking up naturally occuring tryptamines and came across this one:

Norbaeocystin

its psilocybin without the N-methyl groups. The wiki page doesn't say much about it but the wiki page for its mono-N-methylated analogue, baeocystin, states that:

Quote:

Little information exists with regard to human pharmacology, but in the book Magic Mushrooms Around the World, author Jochen Gartz reports being aware of a study in which "10 mg of baeocystin were found to be about as psychoactive as a similar amount of psilocybin."

Heres another interesting one:
5-Bromo-DMT

According to the wiki page, it occurs naturally in some marine invertebrates. I read that in animal studies, there were indications that it had sedative and antidepressant properties. This molecule caught my interest because I remember, in a documentary about LSD, hearing about bromo-LSD which has no psychoactive properties but happens to cure cluster headaches.

Heres a strange one:
Convolutindole A

It also occurs in some marine invertebrates. According to the wiki page, it is an effective anti-nematode (parasitic worm) drug.

[Edited on 23-12-2011 by JibbyDee]

497 - 23-12-2011 at 16:52

Melatonin powder is pretty easy to find too, making all 5-MeO tryptamines available easily. Assymetrically substituted 5-MeO tryptamines should be easy from melatonin too.

smuv - 23-12-2011 at 20:32

Quote: Originally posted by DJF90

imine/iminium cation should react much faster

http://www.scribd.com/doc/48650605/Contemporary-Drug-Synthes... Ch12 many examples w. borohydrides/formalin. You can track down primary refs.

Edit:http://pubs.acs.org/doi/pdf/10.1021/jm00018a016
NaBH3CN in acidic MeOH.

[Edited on 12-24-2011 by smuv]

Methansaeuretier - 25-12-2011 at 06:31

Quote: Originally posted by turd

What he missed was the sodium triacetoxy borohydride (made in-situ) reductive methylation of tryptamine with formaldehyde to DMT. I have heard a few success reports. Yields are low in an amateur setting, but given that it's only two steps from (dirt cheap) tryptophan, overall yield is better than for most OTC routes to phenethylamines.

Really? I heard only of one success report wich was with comercial triacetoxyborohydride and I think a fake as triacetoxy borohydride is extremly sensetive to water and aqueous formaldehyde was used. NaBH(CH3COO)3 or NaBH4/CH3COOH are also able to reduce the indole (see for example "NaBH4 in carboxylic acid media" on Rhodium archive)! You will get a product but I guess no dialkytryptamines.
Can u link any success reports?

Cold alkaline aquesous NaBH4 solution and aq. formaldehyde should work for formylation by simultaneuos titration (and large excess) into an ice cold alcoholic solution of the substrate. Or build imine first before adding NaBH4.

A little cross quoting about reductive alkylation:

Quote:

Eschweiler-Clarke does not work at all. Picted-Spengler would be the main-reaction.

Also Al/Hg does not work very well/ ~20% yields. Source: Tihkal

NaBH(CH3COO)3 or NaBH4/CH3COOH does also not work/leads to extremly low yields or needs special conditions, because it does reduce indole. Source: Rhodium archive - several documents on triacetoxyborohydride and NabH4 in carboxylic acid media are mentioning reduction of indoles with it and some derivates.There are some other reciepes on the in the internet, where this is used to make DMT from tryptamine and aq. Formaldehyde. I think it's pure a fake. Triacetoxyborohydride is very sensitive to water and does reduce indole - no big chance to work under the mentioned conditions (RT, THF, excess CH3COOH as solvent).

BH3*THF or NaBH4/H2SO4 or NaBH4/I2 does also not work. The indole gets also reduced very fast under normal conditions.

NaBH4/MeOH . Does work (!!!), but does reduce aldehydes faster than imines/enamines form. It has to be very cold and a large excess of NaBH4 and aldehyde are neccessary. Does work better for diethylated than for dimethylated tryptamines Source: The Vespiary

H2+Pd/C. Does also work. But needs high pressure of H2. Does sometimes overdo it's job when the catalyst is too strong. Source: Tihkal

Sodium cyaboborohydride does work well but produces side products, esp. beta carbolines. Good workup necessary. Source: Rhodium archive/Vespiary

Untested but very interesting: Zinc borohydride, potassium borohydride and Zn/NaH2PO4

Zinc borohydride because it's known to perfom very well for dialkylations of amines, potassium borohydride because it less active and smoother than NaBH4 and Zn/NaH2PO4 because it's known to alkylate amino acids and alkylamines in high yields. Zn/NaH2PO4 and formaldehyde does also work for dialkylation of tryptophane.... but dimethyltryptophane is very hard to get ripped of CO2 and is extremely toxic. Try it yourself.

[Edited on 25-12-2011 by Methansaeuretier]

[Edited on 25-12-2011 by Methansaeuretier]

[Edited on 25-12-2011 by Methansaeuretier]

turd - 26-12-2011 at 09:51

Quote: Originally posted by Methansaeuretier

Really?

Yes.

Quote:

I heard only of one success report wich was with comercial triacetoxyborohydride and I think a fake as triacetoxy borohydride is extremly sensetive to water and aqueous formaldehyde was used.

I've seen the analytical data and it's unambigous. Though isolated yield was low (~1 g DMT from 5 g tryptamine).

Quote:

NaBH(CH3COO)3 or NaBH4/CH3COOH are also able to reduce the indole (see for example "NaBH4 in carboxylic acid media" on Rhodium archive)!

See Chem. Soc. Rev.,27,395(1998).

Quote:

Can u link any success reports?

No, Private Communication. I will not disclose the author, but post some data in due course.

Vogelzang - 30-12-2011 at 17:17

Here's an interesting Schiff base reduction method.

overload - 6-1-2012 at 11:15

Do an old school DMT synthesis and grow the cool looking crystals DMT forms. Don't vaporize them because its neurotoxic to your 5ht2a and you need those.

Adas - 7-1-2012 at 02:17

Quote: Originally posted by overload

Do an old school DMT synthesis and grow the cool looking crystals DMT forms. Don't vaporize them because its neurotoxic to your 5ht2a and you need those.

DMT is neurotoxic? Really? It occurs naturally in our brains...

GreenD - 7-1-2012 at 11:39

From last I heard, the "spearmint" method of decarboxylation was fake (the "Student").

I attempted myself very crudely with a sticky, nasty mess. My skills by no means constitute incapability of the reaction. However I do believe that a molar ratio of spearmint oil (or molar equivalent of acetophenone) will fully decarboxylate the product... Whether the pictet-spengler occurs, I am again not sure.

I may continue reading up on this in the future.

I'll report anything.

==Making ethyl bromide is quite easy.
==Obtaining diisopropylethylamine is tricky - but some people can get it.

Tryptophan -> DET may be an easy route for a hobbyist.

Bot0nist - 7-1-2012 at 16:10

I don't believe the OP asked anything about ingestion of tryptamine or its methylated variants. I do hope that the original poster has read these threads on decarboxylation of tryptophan right here on SciMad. I also saw some patents on the subject IIRC.

<a href="http://www.sciencemadness.org/talk/viewthread.php?tid=8574#pid97905">L-tryptophan decarboxylation</a>
<a href="http://www.sciencemadness.org/talk/viewthread.php?tid=2255#pid23507">decarboxylation of tryptophan</a>
<a href="http://www.sciencemadness.org/talk/viewthread.php?tid=3544#pid39231">tryptophan decarboxylation</a>
*<a href="http://www.sciencemadness.org/talk/viewthread.php?tid=14147#pid182233">Tryptamine refusing to crystallize</a>

*edit: Sorry turd. I missed that good thread when searching. Thanks.

[Edited on 8-1-2012 by Bot0nist]

12332123 - 7-1-2012 at 16:30

I would just use it to enrich cubensis substrate and get some potent-ass shrooms, but that's just me.

overload - 7-1-2012 at 16:50

Quote: Originally posted by Adas

Quote: Originally posted by overload

Do an old school DMT synthesis and grow the cool looking crystals DMT forms. Don't vaporize them because its neurotoxic to your 5ht2a and you need those.

DMT is neurotoxic? Really? It occurs naturally in our brains...

yes

Edit: On second thought I feel like I should explain the theory ive formed after researching DMT. DMT is a naturally occurring chemical in the brain as well as plants and possibly other places. It is released during life or death situations or near death experiences and has been thought to be the cause of people hallucinating when they die but are resuscitated. It may exist as natures way of saying you need to not let that happen again because it is not a pleasant experience for most people. However.. It's said to produce some euphoria by agonizing 5ht2b receptors and is considered neurotoxic to these receptors along with others. Its associated with the "I'm going to die" state of mind.

[Edited on 8-1-2012 by overload]

mr.crow - 7-1-2012 at 17:00

On a similar note, what can be done with phenylethylamine? You can buy tons of pure PEA hydrochloride from some supplement website. Nothing naughty of course.

turd - 8-1-2012 at 01:04

Quote: Originally posted by Bot0nist

I don't believe the OP asked anything about ingestion of tryptamine or its methylated variants. I do hope that the original poster has read these three threads on decarboxylation of tryptophan right here on SciMad. I also saw some patents on the subject IIRC.

<a href="http://www.sciencemadness.org/talk/viewthread.php?tid=8574#pid97905">L-tryptophan decarboxylation</a>
<a href="http://www.sciencemadness.org/talk/viewthread.php?tid=2255#pid23507">decarboxylation of tryptophan</a>
<a href="http://www.sciencemadness.org/talk/viewthread.php?tid=3544#pid39231">tryptophan decarboxylation</a>

I feel left out

(

)
http://www.sciencemadness.org/talk/viewthread.php?tid=14147#...

@GreenD: Spearmint/caraway oil decarboxylation works great! Also the student workup is a godsend for people without a decent vacuum pump. Try fractionation of the carvone, degassed solvent and inert atmosphere.

Quote:

On a similar note, what can be done with phenylethylamine? You can buy tons of pure PEA hydrochloride from some supplement website. Nothing naughty of course.

Oxidize to benzyl cyanide, one pot Gringard/NaBH4 and reduction to the isopropylamine. Well, some people would consider that naughty.

There is an Iranian article on oxidation of amines to cyanides with TCCA. As with anything out of Iran/India/China to be taken with a grain of salt.

mr.crow - 9-1-2012 at 10:29

I found the paper in the References section "Direct Oxidative Conversion of Alcohols, Amines, Aldehydes, and Benzyl Halides into the Corresponding Nitriles with Trichloroisocyanuric Acid in Aqueous Ammonia"

Its incredible, almost too good to be true. TCCA can oxidize whatever you put into it and turn it into a nitrile at the same time. You could make tons of benzyl cyanide that way. OrgSyn has a good purification procedure

Maybe tryptamine could be turned into indoleacetic acid. Make some plant hormones

GreenD - 12-1-2012 at 06:58

that would be quite the overkill to get iaa...
the wikipedia of IAA has probably the simplest reaction

antibody - 12-1-2012 at 08:51

Would hyrdoboration of the indole double bond not be a competing rxn using Zn(BH4)2 for alkylation or amide reduction?

Bot0nist - 13-2-2012 at 15:47

Quote: Originally posted by ParanoidAndroid

I have a large amount of pure tryptophan and recently came across an exceedingly simple method of making it into tryptamine: basically just reflux it a mixture of xylene and acetone until CO2 stops evolving. A spearmint oil catalyst can be used to speed the reaction but adds a purification step afterward and reduces yield.

My question is: what can I do with the resulting tryptamine? There are a whole slew of interesting substances that are related to tryptamine, but there's very little information on synthesizing those substances using tryptamine as a starting material. Are there any easy ways to do this?

Of particular interest to me are AMT (an MAOI), serotonin (neurotransmitter), and DMT (which is an interesting precursor to other syntheses). The molecular changes aren't complicated; there just isn't a lot of experimental info out there.

Quote: Originally posted by Bot0nist

Decarboxylate and post a write up with the procedure, yield, and product identification ( melting point, solubility's, etc) before even worrying about methylation.

[Edited on 22-12-2011 by Bot0nist]

So, any luck with that decarboxylation android. Waiting for that write up...

[Edited on 14-2-2012 by Bot0nist]

turd - 16-2-2012 at 02:56

Quote: Originally posted by Bot0nist

So, any luck with that decarboxylation android. Waiting for that write up...

The "exceedingly simple method" ParanoidAndroid "came across" and failed to give a reference to (why is it that Newbies always refuse to give references?) is probably fiction. Xylene boils at ~140°C - distinctly lower than the solvents used in verified methods. It'll probably take a long time. But I have not tried it.

bahamuth - 16-2-2012 at 06:19

Quote: Originally posted by turd

Quote: Originally posted by Bot0nist

So, any luck with that decarboxylation android. Waiting for that write up...

It works, but at 40 hours+ at heavy reflux with cyclohexanone as ketone, though I doubt acetone would really be the catalyst of choice due to the way to low bp.

Acetophenone as solvent and catalyst does it nice and clean in less than 2 hours, though I never came up with a good separation of the stuff, so it went down the drain after a month in the fridge...

GreenD - 16-2-2012 at 09:34

Quote: Originally posted by bahamuth

Acetophenone as solvent and catalyst does it nice and clean in less than 2 hours, though I never came up with a good separation of the stuff, so it went down the drain after a month in the fridge...

distill it...?

bahamuth - 16-2-2012 at 11:30

Quote: Originally posted by GreenD

Quote: Originally posted by bahamuth

Acetophenone as solvent and catalyst does it nice and clean in less than 2 hours, though I never came up with a good separation of the stuff, so it went down the drain after a month in the fridge...

distill it...?

At the time I didn't have access to a short path, or a vacuum source below 1 mbar, only one around 14 mbar.

Perhaps the tryptamine would survive the harsh conditions with the acetophenone passing over first, but doubt it.

On a later time I distilled N,N-dipropyltryptamine through a short path with at very low pressure (0.001 - 0.1 mbar) and it worked perfectly, but got greedy and the final product, an oil, got a slight discoloration though before the greedy part the oil was perfectly colorless.

If I were to repeat decarboxylation of tryptophan I would atleast test the intrigueing precipitation of the tryptamine with CO2.

GreenD - 16-2-2012 at 18:47

What would be the source of CO2 - just some dry ice bubbled through a tube?

Nicodem (I think) suggested this; saturate ethanol with fumaric acid. Pour ethanolic solution into acetophenone - decant to get wanted salt?

cgnmxdq9 - 20-4-2012 at 04:57

Quote: Originally posted by GreenD

What would be the source of CO2 - just some dry ice bubbled through a tube?

Nicodem (I think) suggested this; saturate ethanol with fumaric acid. Pour ethanolic solution into acetophenone - decant to get wanted salt?

I did something similar to this to wash the tryptamine (after the allowing the aceophenone to evaporate) using acetone instead.

At the time of its synthesis I did not have anhydrous/reagent grade acetone on hand so I just kind of let it sit around until I did.

Now I have a bunch of tryptamine fumarate lying around that I don't know what to do with.

aMT seems a both a legal (in most places) and interesting option to explore though its synthesis from tryptamine looks like it would be troublesome.

There are also probably ways to get it to do interesting things in vivo but reading papers of tryptamine's neurotoxicity turned me off to this idea.

All in all? Meh.

[Edited on 20-4-2012 by cgnmxdq9]

querjek - 20-4-2012 at 09:27

Would steric hindrance stop the amine from overreacting with isopropyl bromide? ethyl bromide?

GreenD - 20-4-2012 at 11:35

Quote: Originally posted by querjek

Would steric hindrance stop the amine from overreacting with isopropyl bromide? ethyl bromide?

ethyl bromide gives the tertiary compound as the main product.

isopropyl bromide may only give the secondary amine as the major product. The di-isopropyl amine has been made though.

N,N-EthylIsopropyl amine is reportedly active.

rannyfash - 25-4-2012 at 14:03

whenever i have posted questions of this kind i have been attacked, check out my thread http://www.sciencemadness.org/talk/viewthread.php?tid=19194#... , i dont know whether it works though

, im not going to risk getting ass raped for 7 years

http://en.wikipedia.org/wiki/Tryptophol , it mentions "splitting off carbon dioxide and re-placing the amino group with hydroxyl"
i assume its a two stepped enzyme based reaction

chemrox - 25-4-2012 at 15:48

Quote: Originally posted by turd

Actually Shulgin is a good, humble guy who lets his actions speak.

Thanks for this. I know him and this is certainly true.

GreenD - 26-4-2012 at 06:27

Quote: Originally posted by rannyfash

whenever i have posted questions of this kind i have been attacked, check out my thread http://www.sciencemadness.org/talk/viewthread.php?tid=19194#... , i dont know whether it works though

Some people only like to blow shit up on here. Others enjoy introverted analysis. Sometimes the two don't mix. A perfect example is Rosco Bodine.

rannyfash - 26-4-2012 at 12:38

im interested in all parts of chemistry, including blowing things up, i made about 500mg of purified manganese heptoxide, i cannot stress how dangerous and awesome that compound is, i dropped an ant in it :3,

Eddygp - 27-5-2012 at 08:04

Diethyltryptamine?

rannyfash - 31-5-2012 at 08:18

this

turd - 31-5-2012 at 10:43

Please stay in the beginnings forum with these pipe dreams. Generally: Don't cross post.

Vogelzang - 29-7-2012 at 17:14

Try this

http://www.google.com/patents?id=8QwgAAAAEBAJ&pg=PA6&...

Noshtuba - 4-9-2015 at 08:25

I ve tried it using sodium triacetoxyborohydride(not generated in situ). didnt work. vry low yield. i would like to try the zinc borohydride method. but the solvent thats documented is dcm. im afraid tryptamine react with it before it gets methylated? i dont know.

Tryptamine is easily made from tryptophan. i've done it using it acetophenone. the purification is where most people get stuck. Simply extract with acetic acid, wash with dcm, basify, put the whole thing in the freezer overnight then put in the fridge. dirty crystals of T appear out of solution. filter under vacuum. i ve found that ammonia is an excellent recrystallization solvent. Use room temp ammonia to dissolve the crystals, filter the brown impurities, put the solution in the freezer. vacuum filter. gets the job done without vacuum distillation.

zed - 4-9-2015 at 12:05

https://www.erowid.org/archive/rhodium/chemistry/psilocin_sy...

Seems to be an efficient existing synthesis utilizing NaBH4/NaCN. I don't like using NaCN myself, but some times you hafta do things you don't like.

This pathway is reputed to work, and there just ain't very many "easy" pathways available.

In the synthesis of Dimethyl Tryptamines, there always seems to be some unpleasant obstacle.

Noshtuba - 5-9-2015 at 04:46

You d still need the sodium cyanoborohydride though. thats the only pathway i know of which is guaranteed to work. shame it's hard to get

zed - 5-9-2015 at 14:16

Ummm. I've heard that the reagent isn't easy to come by. And, making it involves using HCN. Not fun.

clearly_not_atara - 10-9-2015 at 10:42

Not sure if this is actually a legal (w/r/t the rules) discussion, but since DMT is far more easily extracted, I guess it doesn't count.

IMO you should use methyl oxalate or methyl carbonate or a similar "weak" methylating agent that won't quaternize the tryptamine. Evades all possibility of a Pictet-Spengler. Methyl oxalate is such a good candidate that I'm not sure anything else is worth mention... trimethylsulfonium bromide, maybe.

Pumukli - 11-9-2015 at 02:44

Is methyl-oxalate a methylating agent?
I think it would rather acylate the primary amine yielding tryptamine-oxalyl-amide and methanol.

nlegaux - 11-9-2015 at 10:34

You could perform a Hofmann rearrangement using the tryptamine. It would remove the α-carbon shortening the chain by one, but I am not certain how it would behave with the secondary amine in the heterocyclic ring.

nlegaux

careysub - 12-9-2015 at 09:21

Quote: Originally posted by zed

Ummm. I've heard that the reagent isn't easy to come by. And, making it involves using HCN. Not fun.

It appears that sodium cyanoborohydride can be prepared without ever having free HCN by:
1. making mercury(II) cyanide from mercury(II) oxide and potassium/sodium cyanide*.
then
2. making cyanoborohydride from sodium borohydride and mercury(II) cyanide

Not without its own hazards, and I am not sure that if you have excellent fume handling equipment that it is any safer than HCN.

(*Which can be made in a laboratory crucible using sodium metal and ferrocyanide.)

nlegaux - 12-9-2015 at 16:27

Something else that can be done is a Pictet-Spengler reaction allowing for the creation of interesting heterocycles. All that is required would be the tryptamine, an aldehyde or ketone, and an acid catalyst.

nlegaux

Noshtuba - 14-9-2015 at 02:54

careysub do you know of any sources documenting the procedure with mercury cyanide?

lullu - 14-9-2015 at 04:42

Reductive amination works with plain NaBH4 when done right.
Also there are a lot of better alternatives to NaBH3CN that are easily prepared and that won't reduce your aldehyde and will work at pH 5.
Have a look at substituted pyridine boranes for example.

careysub - 14-9-2015 at 12:07

Quote: Originally posted by Noshtuba

careysub do you know of any sources documenting the procedure with mercury cyanide?

B. Gyori and G. Emri; J. Chem. Soc., Chem. Commun., 1983, 1303.

Referenced here (pg. 7):
http://cora.ucc.ie/bitstream/handle/10468/1656/MyersM_PhD198...

I do not have the original Gyori and Emri article.

Cloner - 15-9-2015 at 07:05

15.1g tryptamine was added to 300 ml shellsol d70 and refluxed with 2.5g spearmint oil. The resulting mixture became beer colored after about 30´. During the operation of the reflux, gas evolved that did precipitate CaOH solution.

However, a wet PH paper held in top of the reflux column did color blue, not red. This is very strange. Could it be NH3? It isn't a good sign at all.

.

Pumukli - 15-9-2015 at 11:14

Tryptamine? Wasn't it tryptophane?

(Cloner, your reaction seems to be a decarboxylation attempt. Am I mistaken?)

Cloner - 16-9-2015 at 09:05

yes, you are of course right.

I started to wonder if it could be tryptamine itself that is slightly volatile...

[Edited on 16-9-2015 by Cloner]