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All 11 posts   Subject: DMT. NaBH4reduction   Please login to post   Down

 
    dimitry
(Stranger)
07-21-04 07:53
No 520556
      DMT. NaBH4reduction     

Hi,bees!
SWIM methylated tryptamine and 5meotryptamine with NaBH4 and CH2O aq.
There is description of synthesis:
The 0.8g tryptamine was dissolved in 20ml MeOH and cooled in refregerator(t minus 10C)1-2hours. Flask got from refregerator and dropped 1/10 part of 37% CH2O aq(on 1mole tryptamine take 4moles FORMALDEHYDE),shaked 1 minute and added a few (on the knife top)powder NaBH4(1g borhydride on 1g tryptamine approximatly)and vigorously shaked. When sodium borhydride was dissolved next part of 37% CH2O aq dropped and so on until all CH2O and NaBH4 was conducted to reaction(40min-1.5hours need).The temperature was keep about 5-20C(cooled in refregerator if need). The reaction mix allowed stand at room temperature some hours. Rm was diluted  water, MeOH disstilled and product extracted CHCl3. Solvent removed in water bath, specific smell oil(weight 0.9g) yielded.  Smoke 50mg its oil produce intense open/close eye visuals, time distortion, empathy and other strong effects. Duration up to 15min. Can anyone repit its synthesis and determine how much Dmt consist in that oil?
Sorry, my english is poor.
 
 
 
 
    java
(Hive Bee)
07-23-04 17:43
No 521141
User Picture 
      DMT Sodium Borohydride Reduction.....     

Read this , you may find your answer here,

https://www.rhodium.ws/chemistry/tryptamine2dmt.html

Just hold on to the thread...that keeps us going
http://www.chiapaslink.ukgateway.net/
 
 
 
 
    ChemMang
(Hive Bee)
07-27-04 19:55
No 522045
      50mg DMT inhaled doesn't produce effects above     

Your product is not pure N,N DMT Freebase.  (I assume you smoked the freebase because u described it as an oil and with the freebase form of dimethylated tryptamine being hygroscopic it frequently yeilds an oil when extracted or synthesized when the utmost precautions to purity are taking place you'll get white too whiteish pink crunchy radial needles tis worth a slow recrystallization for larger much purer crystals...indole oil is rank...back to the point:)

I don't believe your product is very pure unless you were trying to smoke 50mg of the hydrochloride or fumarate salt which you'd have a hard time doing and at most achieve muted affects of DMT which you described above sounds like 10mg inhaled.  A good 30-50mg dosage of PURE DMT freebase inhaled immediately will bring about from the time it hits your lungs  damn near you begin to trip and with time exponentially the intensity and ferocity of your experience as well as diminishing of your ego increase to the point of otherworldy ALIENNESS.  You will know when its pure some people have a higher tolerance taking up to 75-100mg to breakthrough so to speak but to achieve visuals that are incredibly intricate and astounding can be had with one good lungful (15-20mg) of N,N DMT freebase that is PURE.  My friend I suggest you clean up your product.  I hope my information has been of aid to you.  Peace

'A Helpful Bee, is a Friend Indeed'
 
 
 
 
    Lilienthal
(Moderator)
07-27-04 20:07
No 522048
User Picture 
      It stands: as long as nobody can provide some...     

It stands: as long as nobody can provide some meaningfull analytical data (at least TLC) I don't believe that DMT can be obtained as the main product in such a reaction. I'm sure that the main product will always be the cyclized tetrahydro-beta-carboline. I must have posted that about hundred times on this board...
 
 
 
 
    armageddon
(Hive Bee)
09-01-04 19:08
No 528906
User Picture 
      strange     

Hmm...

As stated by Dimitry in the first post of this thread:
"Smoke 50mg its oil produce intense open/close eye visuals, time distortion, empathy and other strong effects. Duration up to 15min."

and further said by ChemMang:
"which you described above sounds like 10mg inhaled.  A good 30-50mg dosage of PURE DMT freebase inhaled immediately will bring about from the time it hits your lungs  damn near you begin to trip and with time exponentially the intensity and ferocity of your experience as well as diminishing of your ego increase to the point of otherworldy ALIENNESS.  You will know when its pure some people have a higher tolerance taking up to 75-100mg to breakthrough so to speak but to achieve visuals that are incredibly intricate and astounding can be had with one good lungful (15-20mg) of N,N DMT freebase that is PURE."

...then beta-carbolines maybe have psychedelic properties, too? Maybe 1/5th the potency of DMT? wink

Or how would you explain the effects described above? (just wondering)

Greetz A

Pleased to meet you hope you get my name.
But whats puzzlin you is the nature of my game!
 
 
 
 
    indole_amine
(Stranger)
09-17-04 16:37
No 531805
      Tetrahydro-beta-carbolines - active or not?     

Tetrahydro-beta-carbolines, Potential Neuroactive Alkaloids, in Chocolate and Cocoa

(Tomas Herraiz; J. Agric. Food Chem. 2000, 48 (10)(4900-4904))

Abstract
Tetrahydro-beta-carbolines (THbCs), potential neuroactive alkaloids, were found in chocolate and cocoa. 6-Hydroxy-1-methyl-1,2,3,4-tetrahydro-b-carboline (6OHMTHbC), 1,2,3,4-tetrahydro-b-carboline-3-carboxylic acid (THbCA), 1-methyl-1,2,3,4-tetrahydro-b-carboline-3-carboxylic acid (MTbCA) in both diastereoisomers (1S,3S and 1R,3S), and 1-methyl-1,2,3,4-tetrahydro-b-carboline (MTHbC), besides serotonin and tryptamine biogenic amines, were identified and quantified in dark chocolate, milk chocolate, cocoa, and chocolate-containing cereals by RP-HPLC-fluorescence and HPLC-MS. For each THC, the concentration ranges were determined: 6OHMTbHC (0.16-3.92 g/g), THbCA (0.01-0.85 g/g), 1S,3S-MTbCA (0.35-2 g/g), 1R,3S-MTbCA (0.14-0.88 g/g), and MTbHC (nd-0.21 g/g). The highest content was generally found in chocolates and cocoas, but cereals containing chocolate also showed an appreciable amount of THbCs. The possible biological implications of this novel group of alkaloids in chocolate are discussed.








Identification and Occurrence of Tryptamine- and Tryptophan-Derived Tetrahydro--carbolines in Commercial Sausages

[i](Tomas Herraiz, Ekaterini Papavergou; . Agric. Food Chem. 2004, 52(9), (2652-2658))

Abstract
The identification and occurrence of tetrahydro--carbolines were studied in different kinds of commercial sausages including cooked, fresh, dry-fermented, and ripened sausages, such as salamis and Spanish chorizo, salchichon, fuet, and morcilla, both smoked and unsmoked(...)





smile

indole_amine
 
 
 
 
    dimitry
(Stranger)
09-22-04 18:58
No 532728
      again about dmt reduction     

Hi,bees!
I accumulated several questions and answers for you. So then:
don't believe your product is very pure unless you were trying to smoke 50mg of the hydrochloride or fumarate salt which you'd have a hard time doing and at most achieve muted... .[blue]
I don't believe my product is very pure too, but i hoped to obtain 50% dmt in my final product. I made this syntesis several years ago, but i have recent report your colleagues which contain optimistic results. Do you saw that post:Post 500899 (koalaa: "Successful synthesis, reduced yields.", Tryptamine Chemistry)?(But i dont undestand why authors added formalin and borohydryd so quikly: 2-7 minuts. May be 30-60min will give better results.).This reaction may have optimal conditions for receipt dmt.
[blue]affects of DMT which you described above sounds like 10mg inhaled

I am not very eloquent,for english especially.
I'm sure that the main product will always be the cyclized tetrahydro-beta-carbolineI must have posted that about hundred times on this board...   
Do You have investigations of kinetic that reaction? Speed of reaction ciclisation much more then speed of reduction aldimine?
 
 
 
 
    Sunlight
(Pioneer Researcher)
11-10-04 19:40
No 540888
      An old test     

I remeber that I tried that rxn with 5-MeO-T and formaldehyde years ago. When I mixed the tryptamine and formaldehyde in methanol, immediatly appeared brown solids that could not be dissolved again. I commented it in the Hive. Unless the tryptamine was very impure (and I doubt it), it seemed it cyclized or polimerized.
 
 
 
 
    Nicodem
(Hive Bee)
11-10-04 21:43
No 540910
User Picture 
      Tempering the cyclisation-somehow?     

It sounds quite reasonable that a Pictet-Spengler cyclisation happens on such a reactive substrate. Lilienthal is strongly promoting such a view and I think the majority of other bees is also of this opinion. Some experimental results seam to confirm it but others seam to oppose it or claim at least a partial success. But with all the pro et contra, I have not seen much discussion on altering the conditions in such a way to prevent the cyclisation from occurring (unless I if should have UTFSE more). In such a cyclisation it seams that the pH is of utmost importance for its kinetic rate. Obviously it will happen very fast in an acidic environment and quite fast in a neutral or slightly basic conditions even according to Sunlight’s experience. Lego already wrote a good post on the subject: Post 518988 (Lego: "In defense of HCHO/NaBH4", Tryptamine Chemistry). I don’t know what would happen in relatively basic conditions, but anyway I agree with Dimitry in his request of kinetic investigations, since the conflicting results might also arise from small details like the time between adding HCHO and NaBH4, temperature, water content and who knows what.

I had this following thought buzzing in my head since I first read the paper on DMA chloromethylation in Post 486635 (Rhodium: "Two new DOM analogs made and evaluated", Serious Chemistry) where the authors comment their choice of chlorobenzene as the most suitable solvent in a, for me at least, completely not understandable way. See Post 487878 (Nicodem: "The SOLVENT!", Novel Discourse).

My interpretation was and the question is: The Pictet-Spengler works best in polar solvents, like acetic acid for example, so could it bee that the non-polar and inert chlorobenzene somehow prevents it? Was this the reason they used it?

So let’s suppose this is the reasoning for using chlorobenzene, besides its inertness to HCHO/HCl, off course. Is there any way to use this inhibition of the cyclisation reaction also on the even much more reactive tryptamine(s) while somehow performing the reductive amination so that its rate does not suffer? If I had enough tryptamine and other chemicals to play with, together with some TLC plates, this is what I would like to try. I would dissolve the tryptamine in toluene (as there is no need for the more inert chlorobenzene here), then I would ad some TBAB or other suitable PTC catalyst, an excess of paraformaldehyde at about 10°C, and once all is dissolved (if?) I would add the NaBH4.
The major problems are:
a.) That I don’t think the reduction would work well with Bu4NBH4 in such a non-polar solvent, so it might just happen that both reaction rates would equally slow down yielding again the same improper ratio of tetrahydro-beta-carboline to DMT. Apparently, when heathing and removing water the cyclisation readily happens also in benzene (see Post 446193 (Vitus_Verdegast: "Pictet-Spengler", Tryptamine Chemistry)), but those are already harsh conditions.
b.) That in such conditions all the HCHO would be reduced to methanol instead of the imine being reduced faster.

I would appreciate very much any thought on this ‘cause my knowledge of borohydride reductive aminations is very limited.

“The real drug-problem is that we need more and better drugs.” – J. Ott
 
 
 
 
    PolytheneSam
(Master Searcher)
11-10-04 21:55
No 540911
User Picture 
      Post 506399     

Post 506399 (PolytheneSam: "Reductive methylation", Tryptamine Chemistry)

http://www.geocities.com/dritte123/PSPF.html
 
 
 
 
    Lilienthal
(Moderator)
11-10-04 23:13
No 540931
User Picture 
      There is a post from me about using NaBH4,...     

There is a post from me about using NaBH4, paraformaldehyde, and triethylamine, resulting in high amounts of cyclized product. I can't remember the solvent - MeOH?
 
 

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