Under constructionThis 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.thevespiary.org/rhodium/Rhodium/chemistry/dmt.det.html
Direct alkylation of indole grignards:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmt.indole.grignard.html
Reaction with chloroacetaldehyde and reduction with NaBH
4:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmt.chloromethylgramine.html
Acetylation, bromination, dialkylamination, reduction:
https://www.thevespiary.org/rhodium/Rhodium/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/NaCNBH
4 (sodium cyanoborohydride):
https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptamine2dmt.html
Using HCHO/NaBH
4:
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.thevespiary.org/rhodium/Rhodium/chemistry/tryptamine2dmt.html
Starting from tryptophol
Molecule:
tryptophol ("c21ccccc1ncc2CCO")
With chloromethansulfonyl chloride/dimethylamine:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptophol.html
Starting from indoleacetic acid
Molecule:
indoleacetic acid ("c21ccccc1ncc2CC(=O)O")
N,N-Dialkylamide formation, reduction with LAH:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/indoleaceticacid.html
Starting from indoleacetonitrile
Molecule:
indoleacetonitrile ("c21ccccc1ncc2CC#N")
CuCl, dimethylamine, NaBH
4:
Post 351772
(Barium: "Nitriles to tertiary amines", Tryptamine Chemistry)Starting from phenylhydrazine
Molecule:
phenylhydrazine ("c1ccccc1NN")
One step synthesis with 4-dimethylaminobutyraldehyde acetals:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/dmten.html
Two step synthesis with 4-chlorobutanal/dimethylamine:
Post 388588
(Rhodium: "DMT synthesis using 4-chlorobutanal", Tryptamine Chemistry)
Other methodsPost 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)PrecursorsPhenylhydrazine:
https://www.thevespiary.org/rhodium/Rhodium/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.thevespiary.org/rhodium/Rhodium/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 (missing)
(Lego: "An improved method to obtain 3-acylindoles", Tryptamine Chemistry)Tryptamine:
https://www.thevespiary.org/rhodium/Rhodium/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.thevespiary.org/rhodium/Rhodium/chemistry/indoleacetaldehyde.html
Indoleacetic acid:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/iaa.synth.html
Post 324823
(demorol: "indole-3-acetic acid synthesis", Tryptamine Chemistry)Indoleacetonitrile:
https://www.thevespiary.org/rhodium/Rhodium/chemistry/diethylaminoacetonitrile.html
Writeups of synthesis of precursors or/of dialkyltryptaminesDimethylation of tryptamine:
Post 520556
(dimitry: "DMT. NaBH4reduction", Tryptamine Chemistry)Decarboxylation of tryptophan:
Post 507814
(L42L: "novel newbee tryp decarb question session", Tryptamine Chemistry)