Synthesis of tryptamine

Preparation of tryptamine (3-(2-aminoethyl)indole; 1H-indole-3-ethanamine; 2-(3-indolyl)ethylamine)

3-(2-Nitrovinyl)indole is sparingly soluble in ether, however by using so-called Soxhlet extraction technique, it could be reduced to tryptamine.

Preparation of tryptamine (3-(2-aminoethyl)indole; 1H-indole-3-ethanamine; 2-(3-indolyl)ethylamine)

Preparation of tryptamine (3-(2-aminoethyl)indole; 1H-indole-3-ethanamine; 2-(3-indolyl)ethylamine)

15 g of 3-(2-nitrovinyl)indole is extracted during 8 hours from a Soxhlet thimble into a flask containing 15 g of lithium aluminum hydride dissolved in 300 ml anhydrous ether. The mixture is then treated with 80 ml water, slowly and with cooling, and filtered. The ether solution is separated, dried over sodium sulfate, and saturated with hydrogen chloride. 12.7 g of tryptamine hydrochloride is obtained. After crystallization from methanol-ethyl acetate tryptamine hydrochloride melts at 249-250° C.

E. H. P. Young, J. Chem. Soc, 1958, 3493

IUPAC Name

2-(1H-indol-3-yl)ethanamine

InChI

InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2

InChI Key

APJYDQYYACXCRM-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)C(=CN2)CCN

MeSH Synonyms

3-(2-aminoethyl)indole, tryptamine, tryptamine monohydrochloride, tryptamine sulfate

Depositor-Supplied Synonyms

tryptamine, 2-(1H-Indol-3-yl)ethanamine, 3-(2-aminoethyl)indole, 61-54-1, 1H-Indole-3-ethanamine, 2-(3-Indolyl)ethylamine, Indol-3-ethylamine, Indole, 3-(2-aminoethyl)-, 2-(Indol-3-yl)ethylamine, Tryptamin, 2-(1H-indol-3-yl)ethylamine, 2-Indol-3-ylethylamine, 3-Indoleethylamine, (Amino-2 ethyl)-3 indole [French], BRN 0125513, (Amino-2 ethyl)-3 indole, CHEMBL6640, UNII-422ZU9N5TV, 2-(1H-INDOL-3-YL)-ETHYLAMINE, CHEBI:16765, APJYDQYYACXCRM-UHFFFAOYSA-N, EINECS 200-510-5, 2-(1H-Indol-3-Yl)Ethan-1-Amine, 3-[2-Aminoethyl]indole, 3-Indoleethanamine, 3-indolylethylamine, PubChem9450, (3-Indolyl)ethylamine, Spectrum_000033, ACMC-209mtp, Spectrum2_000873, Spectrum3_001890, Spectrum4_000850, Spectrum5_001296, 2-indol-3-yl-ethylamine, 2-Indol-3-yl-aethylamin, 3-(2-amino)ethyl indole, bmse000207, AC1L1AU8, Lopac-246557, 3-(beta-aminoethyl)-indole, Lopac0_000061, Oprea1_870097, SCHEMBL26725, BSPBio_003400, GTPL125, KBioGR_001459, KBioSS_000393, KSC354A2B, MLS000515794, DivK1c_000862, SPECTRUM1503922, SPBio_000945, .beta.-(3-Indolyl)ethylamine, 193747_ALDRICH, 3-(2-Aminoethyl)-1H-indole, 422ZU9N5TV, AC1Q54C3, CCRIS 8959, SCHEMBL13006684, STOCK1N-28142, CTK2F4020, HMDB00303, HMS502L04, KBio1_000862, KBio2_000393, KBio2_002961, KBio2_005529, KBio3_002903, MolPort-001-002-280, NINDS_000862, [2-(1h-indol-3-yl)ethyl]amine, 2-(1H-indol-3-yl)-ethyl-amine, HMS1922K18, HMS2267B18, 2-(1H-Indol-3-yl)ethanamine #, 343-94-2 (mono-hydrochloride), ACN-F000556, ACT09907, EBD10651, ANW-33851, BBL015353, BDBM50024210, CCG-40088, DNC011705, HTS028111, SBB003963, STK262895, 34685-69-3 (unspecified sulfate), AKOS000119468, ACN-000556, DB08653, FS-3317, MCULE-6402431765, RP22361, RTC-066345, SDCCGMLS-0066798.P001, TRA0076983, VI30132, IDI1_000862, NCGC00014994-01, NCGC00014994-02, NCGC00014994-03, NCGC00014994-04, NCGC00014994-05, NCGC00014994-06, NCGC00014994-07, NCGC00095081-01, NCGC00095081-02, NCGC00095081-03, NCGC00095081-04, NCGC00095081-05, AJ-11665, AK-80344, AM807158, AN-41829, BP-12561, BR-80344, KB-81364, LS-82268, SC-05762, SMR000112268, AB0007015, AB1001199, DB-005731, ST2409261, TC-066345, A8532, FT-0081340, FT-0613523, ST50308344, T0890, V2315, AZ0001-0257, C00398, M-3012, T-8095, T-8100, 2-(3-Indolyl)ethylamine; 3-(2-Aminoethyl)indole, 5-22-10-00045 (Beilstein Handbook Reference), AE-848/30735051, L000946, 3B3-016835, 5E7B376B-5933-446C-9D88-661B5F480122, InChI=1/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H

Removed Synonyms

?Tryptamine, tryptamine sulfate, Tryptamine hydrochloride, Tryptamine monohydrochloride, CID1150, 2-(1H-INDOL-3-YL)ETHANIMINE, C030820, MT4, TSH, TSS

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