Main Index   Search   Register   Login   Who's Online   FAQ   Links
  2 Online, 0 Active   You are not logged in  
Main Index     The HIVE light edition (TM)
This is a historical archive
The forum is read-only. Private information has been removed. It is not possible to login.


Tryptamine Chemistry  

    Digest: Synthetic routes to dialkyltryptamines   Please login to post  

 
    Lego
(Hive Bee)
07-21-04 16:30
No 519197
User Picture  		      Synthetic routes to dialkyltryptamines
(Rated as: excellent) 		    

Under construction

This digest should cover all synthetic methods leading to dialkyltryptamines, like DMT (dimethyltryptamine), DET (diethyltryptamine) and the like.

Molecule: DMT ("c21ccccc1ncc2CCN(C)C")


Starting from indole
Molecule: indole ("c21ccccc1ncc2")


Reaction with oxalyl chloride, amide formation with a dialkylamine, reduction with LAH: https://www.rhodium.ws/chemistry/dmt.det.html

Direct alkylation of indole grignards: https://www.rhodium.ws/chemistry/dmt.indole.grignard.html

Reaction with chloroacetaldehyde and reduction with NaBH4: https://www.rhodium.ws/chemistry/dmt.chloromethylgramine.html

Acetylation, bromination, dialkylamination, reduction: https://www.rhodium.ws/clandestine/dmt/index.html
Post 451451 (GC_MS: "Reduction of indolyl-3-aminomethylketones", Tryptamine Chemistry)
Post 451545 (Chimimanie: "Thanks", Tryptamine Chemistry)
Post 475429 (Vitus_Verdegast: "Old synthesis of DET via beta-keto-DET", Tryptamine Chemistry)

Starting from tryptamine
Molecule: tryptamine ("c21ccccc1ncc2CCN")


Using HCHO/NaCNBH4 (sodium cyanoborohydride): https://www.rhodium.ws/chemistry/tryptamine2dmt.html

Using HCHO/NaBH4: Post 518988 (Lego: "In defense of HCHO/NaBH4", Tryptamine Chemistry)

Using alkyliodides: Post 126957 (Lilienthal: "Breath of Hoax? / PTC tryptamine alkylation on the test bench", Tryptamine Chemistry)
https://www.rhodium.ws/chemistry/tryptamine2dmt.html


Starting from tryptophol
Molecule: tryptophol ("c21ccccc1ncc2CCO")


With chloromethansulfonyl chloride/dimethylamine: https://www.rhodium.ws/chemistry/tryptophol.html

Starting from indoleacetic acid
Molecule: indoleacetic acid ("c21ccccc1ncc2CC(=O)O")


N,N-Dialkylamide formation, reduction with LAH:
https://www.rhodium.ws/chemistry/indoleaceticacid.html


Starting from indoleacetonitrile
Molecule: indoleacetonitrile ("c21ccccc1ncc2CC#N")


CuCl, dimethylamine, NaBH4: Post 351772 (Barium: "Nitriles to tertiary amines", Tryptamine Chemistry)


Starting from phenylhydrazine
Molecule: phenylhydrazine ("c1ccccc1NN")


One step synthesis with 4-dimethylaminobutyraldehyde acetals: https://www.rhodium.ws/chemistry/dmten.html
Two step synthesis with 4-chlorobutanal/dimethylamine: Post 388588 (Rhodium: "DMT synthesis using 4-chlorobutanal", Tryptamine Chemistry)



[b]Other methods

Post 447677 (Rhodium: "DMT - As easy as ABC", Tryptamine Chemistry)
Post 381563 (Rhodium: "Total synthesis of 5-MeO-DMT (50% overall yield!)", Tryptamine Chemistry)
Post 377548 (Rhodium: "Solid-Phase Synthesis of 5-MeO-DMT (or DMT)", Tryptamine Chemistry)
Post 510951 (Rhodium: "Novel route to dialkyltryptamines", Tryptamine Chemistry)


Precursors
Phenylhydrazine: https://www.rhodium.ws/chemistry/phenylhydrazine.html
4-substituted butanals: Post 388159 (Rhodium: "4-Chlorobutanal", Tryptamine Chemistry)
Post 401468 (Rhodium: "Synthesis of 4-Chlorobutanal and its derivatives", Tryptamine Chemistry)
Post 454558 (Rhodium: "Prep of 4-Chlorobutanol from THF/HCl(aq)", Tryptamine Chemistry)
Post 476152 (Rhodium: "Preparation of 4-halobutanal acetals", Tryptamine Chemistry)
Post 508707 (Rhodium: "4-Aminobutanal Acetals + 5-MeO-Tryptamine", Tryptamine Chemistry)
Post 518714 (Lego: "4-Dialkylaminobutyraldehyde acetals", Tryptamine Chemistry)
Post 456583 (Vaillo: "A new route to 4-(N,N-dimethylamino)butanal", Tryptamine Chemistry)
https://www.rhodium.ws/chemistry/dmten.html
Tryptophol: Post 427106 (Chimimanie: "On tryptophol", Tryptamine Chemistry)
Post 435601 (Rhodium: "Tryptophol from 3-Indoleglyoxyl chloride + NaBH4", Tryptamine Chemistry)
Post 435843 (demorol: "Tryptophol from 3-indoleglyoxylyl chloride + LAH", Tryptamine Chemistry)
Dimethylamine: Post 448644 (Chimimanie: "Dimethylamine from formaline", Tryptamine Chemistry)
Post 513655 (Vitus_Verdegast: "dimethylamine from hydrolysis of DMF", Chemistry Discourse)
3-Acetylindole: Post 448820 (Lego: "An improved method to obtain 3-acylindoles", Tryptamine Chemistry)
Tryptamine: https://www.rhodium.ws/chemistry/tryptamine.html
Post 507814 (L42L: "novel newbee tryp decarb question session", Tryptamine Chemistry)
Post 416740 (Rhodium: "Novel amino acid decarboxylation via the nitrile", Tryptamine Chemistry)
Post 369921 (Cyrax: "Tryptamine from scratch", Tryptamine Chemistry)
Post 300317 (PolytheneSam: "Tryptophan decarboxylation", Tryptamine Chemistry)
Post 361443 (Rhodium: "Cyclohexanol decarboxylation of tryptophan", Tryptamine Chemistry)
Post 211603 (Rhodium: "Another tryptophan decarboxylation", Tryptamine Chemistry)
Indol-3-yl-acetaldehyde: https://www.rhodium.ws/chemistry/indoleacetaldehyde.html
Indoleacetic acid: https://www.rhodium.ws/chemistry/iaa.synth.html
Post 324823 (demorol: "indole-3-acetic acid synthesis", Tryptamine Chemistry)
Indoleacetonitrile: https://www.rhodium.ws/chemistry/diethylaminoacetonitrile.html


Writeups of synthesis of precursors or/of dialkyltryptamines

Dimethylation of tryptamine: Post 520556 (dimitry: "DMT. NaBH4reduction", Tryptamine Chemistry)
Decarboxylation of tryptophan: Post 507814 (L42L: "novel newbee tryp decarb question session", Tryptamine Chemistry)
The tendency is to push it as far as you can 		 
 

   
   

 https://the-hive.archive.erowid.org    the-hive@erowid.org
   
Powered by Aliens v.6.4, (C) 2015, Aleksandr Borodin Computer Services

Links     Erowid     Rhodium

PIHKAL     TIHKAL     Total Synthesis II

Date: 05-13-24, Release: 1.6 (10-04-15), Links: static, unique