Indole-3-methanamine is a derivative of tryptophan metabolism and a biomarker for the intake of barley and cereal foods, with potential applications in anti-tumor and anti-inflammatory treatments.

Synonyms: Indole-3-methanamine

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Quality Control of Indole-3-methanamine Purity: 95% SDS Specification

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Product Details of Indole-3-methanamine

CAS No. :	22259-53-6
Formula :	C₉H₁₀N₂
M.W :	146.19
SMILES Code :	NCC1=CNC2=C1C=CC=C2
Synonyms :	Indole-3-methanamine
MDL No. :	MFCD01631210
InChI Key :	JXYGLMATGAAIBU-UHFFFAOYSA-N
Pubchem ID :	472107

Safety of Indole-3-methanamine

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Application In Synthesis of Indole-3-methanamine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 22259-53-6 ]

[ 22259-53-6 ] Synthesis Path-Downstream 1~35

1
[ 79-03-8 ]
[ 22259-53-6 ]
[ 874892-41-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine; In methanol; at 0 - 20℃; for 4h;	Compound 25 (1.00 g, 6.84 mmol) and Et3N (1.4 mL, 10.26 mmol) were dissolved in MeOH and cooled to 0° C. Propionyl chloride (633 mg, 6.84 mmol) was added dropwise and the reaction was stirred at room temperature for 4 hours. The volatiles were removed and the residue was taken up in CH2Cl2 (40 mL), washed with 10percent citric acid (20 mL), satd. NaHCO3 (20 mL) and brine (20 mL). The organic layer was dried with Na2SO4, filtered and the volatiles were removed to yield 1.33 g of a white, crystalline solid (1.33 g, 96percent yield). An analytical sample was recrystallized from EtOAc/hexanes. m.p.=91-92° C. 1H NMR (CDCl3) delta 8.80 (br s, 1H, NH), 7.62 (d, 1H, ArH, J=7.85 Hz), 7.38 (d, 1H, ArH, J=7.2 Hz), 7.20 (3H, ArH), 5.80 (br s, 1H, NH), 4.60 (d, 2H, ArCH2, J=5.1 Hz), 2.20 (q, 2H, COCH2CH3, J=7.6 Hz),1.14 (t, 3H, COCH2CH3, J=7.6 Hz). 13C NMR (CDCl3) delta 173.6, 136.5, 126.6, 123.3, 122.5, 119.9, 118.8, 112.8, 111.4, 35.2, 29.7, 9.9. IR (KBr) vmax cm-1: 3405, 1891, 1634, 1532, 1097.

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 684 - 692.
[2]Patent: US2007/105907,2007,A1 .Location in patent: Page/Page column Sheet 6/7; 10.

2
[ 75-15-0 ]
[ 100-39-0 ]
[ 22259-53-6 ]
S-benzylbrassinin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 684 - 692.

3
[ 75-15-0 ]
[ 22259-53-6 ]
[ 638-45-9 ]
S-hexylbrassinin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 684 - 692.

4
[ 75-15-0 ]
[ 22259-53-6 ]
[ 106-95-6 ]
S-allylbrassinin [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 684 - 692.

5
[ 22259-53-6 ]
[ 556-61-6 ]
N-(3-indolylmethyl)-N'-methylthiourea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%		The amine was dissolved/suspended in CH2Cl2, cooled to 0° C. and treated with Et3N (2.1-2.2 eq). Methyl isothiocyanate (1.1-1.5 eq) was added about 5 min. later and the reaction was allowed to slowly warm to room temperature while stirring overnight. N-[l-(Indol-3-yl)methyl]-N'-methyl-thiourea (19). The general method was used with 25. The volatiles were removed from the reaction and the crude residue was recrystallized from EtOAc/hexanes to yield a gold, crystalline solid (54percent yield). m.p. 148-150° C. 1H NMR (DMSO-d6) delta 10.9 (br s, 1H, NH), 7.65 (m, 1H, ArH) , 7.36 (m, 2H, ArH), 7.10 (t, 1H, ArH, J=7.2 Hz), 4.75 (br s, 2H, ArCH2), 2.85 (br s, 3H, NHCH3). 13C NMR (DMSO-d6) delta 183.4, 137.1, 124.9, 124.4, 122.1, 119.4, 112.7, 111.9, 40.1 (overlapped with CDCl3), 31.5. IR (KBr) vmax cm-1: 3210, 1565, 1456, 1300, 1089. NP-HPLC (isocratic) r.t.=23.949 min. NP-HPLC (gradient) r.t.=22.493 min.

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 684 - 692.
[2]Patent: US2007/105907,2007,A1 .Location in patent: Page/Page column Sheet 4/7; 9.

6
[ 22259-53-6 ]
[ 18369-83-0 ]
brassitine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With triethylamine; In methanol; at 0 - 20℃; for 6h;	Freshly made 25 (190 mg, 1.3 mnol) and Et3N (271 muL, 1.95 mmol) was dissolved in anhydrous MeOH (10 mL). The flask was cooled to 0° C. and methyl chlorothiolformate (116 muL, 1.36 mmol) was added dropwise followed by stirring at room temperature for 6 hours. A few drops of H2O were added to quench excess reagent and the volatiles were evaporated. The residue was dissolved in EtOAc (35 mL) and washed with 0.5 M HCl (2.x.20 mL), sat. NaHCO3 (20 mL), and brine (15 mL). The organic solution was dried with Na2SO4, filtered and concentrated to afford a crude brownish-orange solid (270 mg). After recrystallization from CH2Cl2/hexanes, beige crystals: 125 mg, 44percent yd. mp 110-111° C. 1H NMR (CDCl3) delta 8.15 (br s, 1H, NH), 7.64 (d, 1H, ArH J=7.9), 7.39 (d, 1H, ArH J=7.1), 7.23 (m, 1H, ArH), 7.18 (m, 1H, ArH), 7.13 (m, 1H, ArH), 5.52 (br s, 1H, CH2NHC), 4.67 (d, 2H, ArCH2, J=5.1), 2.38 (s, 3H, SCH3). 13C NMR (CDCl3) delta 167.6, 136.3, 126.3, 123.3, 122.5, 119.9, 118.7, 112.1, 111.3, 36.9, 12.4. EI-MS m/z (percent) 220 (37, M+), 205 (9), 172 (12, M+-SCH3), 130 (100). NP-HPLC r.t.=9.827 min. RP-HPLC (1/1 CH3CN/H2O+0.1percent TFA) r.t.=9.512 min.

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 684 - 692.
[2]Patent: US2007/105907,2007,A1 .Location in patent: Page/Page column Sheet 5/7; 9-10.

7
[ 75-44-5 ]
[ 22259-53-6 ]
[ 57778-79-7 ]