61-49-4

Basic information

• Product Name: 3-(2-Methylaminoethyl)indole
• Synonyms: 3-(2-METHYLAMINOETHYL)INDOLE;NMT;N-OMEGA-METHYLTRYPTAMINE;2-(1H-Indol-3-yl)-N-methylethanamine;3-(2-(methylamino)ethyl)-indol;Dipterine;dl-Methyltryptamine;Indole, 3-(2-(methylamino)ethyl)-
• CAS NO: 61-49-4
• Molecular Formula: C₁₁H₁₄N₂
• Molecular Weight: 174.24
• EINECS: 200-507-9
• Product Categories: Tryptamines;Heterocyclic Compounds;Building Blocks;C11;Chemical Synthesis;Heterocyclic Building Blocks;Indoles
• Mol File: 61-49-4.mol
• Article Data: 27

Chemical Properties

• Melting Point: 87-89 °C(lit.)
• Boiling Point: 295.23°C (rough estimate)
• Flash Point: 157.1 °C
• Appearance: White to off-white/Shiny Crystalline Powder or Flakes
• Density: 0.9649 (rough estimate)
• Vapor Pressure: 0.000114mmHg at 25°C
• Refractive Index: 1.6210 (estimate)
• Storage Temp.: -20°C
• PKA: 17.26±0.30(Predicted)
• CAS DataBase Reference: 3-(2-Methylaminoethyl)indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-Methylaminoethyl)indole(61-49-4)
• EPA Substance Registry System: 3-(2-Methylaminoethyl)indole(61-49-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: NM0450000
• Hazardous Substances Data: 61-49-4(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white shiny cryst. powder or flakes

Uses

Different sources of media describe the Uses of 61-49-4 differently. You can refer to the following data:
1. Reactant for preparation of:? ;Manzamine analogues for the control of neuroinflammation and cerebral infections1? ;Serotonin 4 receptors (5-HT4) receptor agonists2? ;A sulful-containing indole alkaloid, glypetelotine3? ;Selective inhibitors of cyclin dependent kinase (CDK4)4? ;Antagonist of the human tachykinin NK-2 receptor5? ;Inhibitors of the tyrosine-specific protein kinase pp60c-src SH2 Domain6
2. N-Methyltryptamine (NMT) is a naturally-occurring tryptamine which may be derived from L-tryptophan or, indirectly, from serotonin. While substituted NMTs are psychoactive through their effects on monoamine action, NMT appears to be rapidly metabolized by monoamine oxidases. This product is intended for research and forensic applications.[Cayman Chemical]
3. N-Methyltryptamine is an alkylamine, a putative hallucinogen constituent from the root of Mimosa ophthalmocentra. An alkaloid from the leaves of Hammada scoparia.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 49, p. 87, 2001Journal of Medicinal Chemistry, 19, p. 99, 1976 DOI: 10.1021/jm00223a016

InChI:InChI=1/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3/p+1

Synthetic route

methyl 2-(1-H-indol-3-yl)ethylcarbamate (58635-45-3) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 60℃;	95%
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating;	94%
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene for 3h; Inert atmosphere; Reflux;	84%

Nb-formyltryptamine (6502-82-5) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 3.25h; Heating;	90%
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating; Yield given;

ethyl 2-(1H-indole-3-yl)ethylcarbamate (67909-99-3) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating;	89%
With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Inert atmosphere; Reflux;	86%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Reflux;	85%

tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate (103549-24-2) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 24h;	52%

indole (120-72-9) + oxalyl dichloride (79-37-8) + methylamine (74-89-5) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
Stage #1: indole; oxalyl dichloride In tetrahydrofuran at 0 - 20℃; Stage #2: methylamine In tetrahydrofuran at 0 - 20℃; for 2h; Stage #3: With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Reflux;	50%

2-(1H-indol-3-yl)-N-methyl-2-oxoacetamide (2054-72-0) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 7h; Inert atmosphere; Reflux;	42%

2-(1H-indol-3-yl)-N-methyl-2-oxoacetamide (2054-72-0) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + 2,3-dihydro-N-methyltryptamine + 3-(2-Methylamino-ethyl)-2,3-dihydro-1H-indol-3-ol

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran for 48h; Heating;	A 29% B 24% C 36%

methyl 2-(1-H-indol-3-yl)ethylcarbamate (58635-45-3) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + (±)-1,1'-dimethyl-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole (4147-36-8, 4147-37-9, 5545-89-1, 23102-84-3, 85610-66-8) + meso-Chimonanthine (4147-37-9) + N-methyl-2-(6-(1-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-3a-yl)-1H-indol-3-yl)ethanamine

Conditions	Yield
Stage #1: methyl 2-(1-H-indol-3-yl)ethylcarbamate With 2,2,2-trifluoroethanol; bis-[(trifluoroacetoxy)iodo]benzene at -30℃; Stage #2: With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene Heating;	A 9% B 13% C 30% D 23%

tryptamine (61-54-1) + methyl iodide (74-88-4) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

3-(2-bromoethyl)-1H-indole (3389-21-7) + methylamine (74-89-5) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

N-(2-(1H-indol-3-yl)ethyl)-N,4-dimethylbenzenesulfonamide (442531-80-8) + aniline hydrochloride (142-04-1) + aniline (62-53-3) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
With ethanol

L-abrine (526-31-8) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
at 320℃; under 12 Torr;

(2-indol-3-yl-ethyl)-carbamic acid benzyl ester (38750-13-9) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h; Heating;

(+-)-hydroxy-indol-3-yl-acetic acid methylamide → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
With lithium aluminium tetrahydride

tryptamine (61-54-1) + phenyl halide → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / aq. NaOH / CHCl3 / 3 h / 20 °C 2: 89 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 81 percent / DIEA / tetrahydrofuran 2: 79 percent / lithium aluminum hydride / tetrahydrofuran / Heating View Scheme

tryptamine (61-54-1) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / aq. NaOH / CHCl3 / 3 h 2: 89 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: 100 percent / NaOH / H2O; CH2Cl2 / 0 °C 2.1: phenyliodine(III)bis(trifluoroacetate); CF3CH2OH / -30 °C 2.2: 9 percent / Red-Al / toluene / Heating View Scheme
Multi-step reaction with 2 steps 1: Et3N 2: LiAlH4 View Scheme

tryptamine (61-54-1) + N-methyl-isatoic acid-anhydride → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / Et3N / CH2Cl2 / 0 - 20 °C 2: 50 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

tryptamine hydochloride (343-94-2) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH; H2O / CHCl3 / 1 h 2: LiAlH4 / tetrahydrofuran / 24 h / Heating View Scheme

indole-3-acetonitrile (771-51-7) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: LiAlH4; diethyl ether 2: 130 °C 3: LiAlH4 View Scheme

2-(3-indole)-ethanol (526-55-6) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether; phosphorus (III)-bromide View Scheme

phenylhydrazine (100-63-0) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc chloride View Scheme

tryptamine (61-54-1) + chloroformic acid ethyl ester (541-41-3) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
Stage #1: tryptamine; chloroformic acid ethyl ester With sodium hydroxide In water at 20℃; for 3h; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Heating / reflux;

indole (120-72-9) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 0 °C 2: water / 2 h / Cooling with ice 3: lithium aluminium tetrahydride / tetrahydrofuran / 7 h / Inert atmosphere; Reflux View Scheme

indolyl-3-glyoxylyl chloride (22980-09-2) → [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 2 h / Cooling with ice 2: lithium aluminium tetrahydride / tetrahydrofuran / 7 h / Inert atmosphere; Reflux View Scheme

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl N-methyl-N-2-[(1H-indol-3-yl)-ethyl]carbamate (264619-90-1)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;	100%
With triethylamine In tetrahydrofuran at 20℃; for 1.5h; Inert atmosphere;	99%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + 2-fluoro-N-(2-methoxyethyl)-9H-purin-6-amine → N2-[2-(1H-indol-3-yl)ethyl]-N6-(2-methoxyethyl)-N2-methyl-9H-purine-2,6-diamine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 110℃;	100%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + methyl chloroformate (79-22-1) → methyl (2-(1H-indol-3-yl)ethyl)(methyl)carbamate (63637-70-7)

Conditions	Yield
With triethylamine In chloroform at 20℃; for 23h;	99%
With dmap; triethylamine In dichloromethane at 0℃; Inert atmosphere;	68%
With triethylamine Yield given;

2-bromo-thiazole-5-carboxylic acid (54045-76-0) + [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) → N-(2-(1H-indol-3-yl)ethyl)-2-bromo-N-methylthiazole-5-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h;	98%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → N-(2-(1H-indol-3-yl)ethyl)-N-methyl-4-nitrobenzenesulfonamide (1280171-15-4)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	97.5%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + 5,5-diethoxypentanal (79893-96-2) → 1-(4,4-Diethoxy-butyl)-2-methyl-2,3,4,9-tetrahydro-1H-β-carboline (209168-95-6)

Conditions	Yield
In toluene for 2h; Heating;	97%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + Dimethyl 3-(methylthio)-1,2,4-triazine-5,6-dicarboxylate (108005-26-1) → 3-{[2-(1H-Indol-3-yl)-ethyl]-methyl-amino}-[1,2,4]triazine-5,6-dicarboxylic acid dimethyl ester

Conditions	Yield
In methanol Heating;	95%

carbonic acid (E)-4-bromobut-2-en-1-yl methyl ester + [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) → C17H22N2O3 (1241667-72-0)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	95%

5-phenylfuran-2-carbaldehyde (13803-39-9) + [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) → [2-(1H-indol-3-yl)ethyl](methyl)[(5-phenylfuran-2-yl)methyl]amine

Conditions	Yield
Stage #1: 5-phenylfuran-2-carbaldehyde; [2-(1H-indol-3-yl)-ethyl]-methylamine In methanol at 20℃; Molecular sieve; Stage #2: With sodium tetrahydroborate In methanol for 1h; Molecular sieve;	95%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + 2-(4-(benzyloxy)phenyl)acetyl chloride (39188-62-0) → 2-(4-Benzyloxy-phenyl)-N-[2-(1H-indol-3-yl)-ethyl]-N-methyl-acetamide

Conditions	Yield
In dichloromethane for 1h;	94.3%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + tris(3-methylbut-2-enyl)borane (36934-25-5) → trans-2-(1,1-dimethylallyl)-3-(2-methylaminoethyl)indoline

Conditions	Yield
Stage #1: [2-(1H-indol-3-yl)-ethyl]-methylamine; tris(3-methylbut-2-enyl)borane at 120 - 130℃; for 4.5h; Stage #2: With sodium hydroxide In water	94%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → C26H24N2O2 (1227608-19-6)

Conditions	Yield
With sodium carbonate In dichloromethane; water at 20℃; for 0.25h; Inert atmosphere;	92%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + 2-methoxy-1,4-naphthoquinone (2348-82-5) → 2-{[2-(1H-Indol-3-yl)-ethyl]-methyl-amino}-[1,4]naphthoquinone

Conditions	Yield
In ethanol Heating;	91%

formic acid (64-18-6) + [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) → Nb-formyl-Nb-methyltryptamine (54268-27-8)

Conditions	Yield
Stage #1: formic acid With acetic anhydride at 60℃; for 1h; Stage #2: [2-(1H-indol-3-yl)-ethyl]-methylamine In dichloromethane at 20℃; for 1.5h;	90%
With acetic anhydride In diethyl ether

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) → N-methyl-N-(4-carboxybutyryl)-tryptamine (75622-16-1)

Conditions	Yield
In benzene	90%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + S-(3-phenylpropyl) 4-iodobenzenecarbothioate (1178916-17-0) → C18H17IN2O (1178916-52-3)

Conditions	Yield
With potassium phosphate; silver trifluoromethanesulfonate In acetonitrile at 70℃; for 16h;	90%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + p-toluenesulfonyl chloride (98-59-9) → N-(2-(1H-indol-3-yl)ethyl)-N,4-dimethylbenzenesulfonamide (442531-80-8)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;	90%
With dmap; triethylamine In dichloromethane at 0℃; Inert atmosphere;	71%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + methyl ethynyl ketone (1423-60-5) → (E)-4-[(2-(1H-indol-3-yl)ethyl)(methyl)amino]-but-3-en-2-one

Conditions	Yield
In tetrahydrofuran at 20℃; for 5h;	90%

phthalic anhydride (85-44-9) + [2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) → N,N'-bis[2-(1H-indol-3-yl)-ethyl]-N,N'-dimethyl-phthalamide (521949-80-4)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	89%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + 4-methoxy-3-(4-(2,2,2-trichloro-acetyl)piperazin-1-yl)benzene-1-sulfonylchloride (219963-60-7) → N-(2-(1H-indol-3-yl)ethyl)-4-methoxy-N-methyl-3-(4-(2,2,2-trichloroacetyl)piperazin-1-yl)benzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 25℃;	88.5%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + (2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate (99528-65-1) → C19H18N2O2

Conditions	Yield
With potassium tert-butylate In methanol at 5℃; for 3h; Temperature; Reagent/catalyst;	88%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + carbon monoxide (201230-82-2) → 2,9-dihydro-2-methyl-1H-pyrido[3,4-b]indol-1-one (67115-07-5)

Conditions	Yield
With oxygen; copper diacetate; palladium diacetate In toluene at 110℃; under 760.051 Torr; for 24h; Schlenk technique;	88%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + N,N-dimethyl-2-(3-cyano-pyridin-4-yl)etheneamine (67988-51-6) → 4-((E)-2-{[2-(1H-Indol-3-yl)-ethyl]-methyl-amino}-vinyl)-nicotinonitrile (87489-66-5)

Conditions	Yield
With o-toluenesulfonic acid In toluene for 72h; Heating;	87%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) → 2-iodo-N-methyltryptamine

Conditions	Yield
With chloroamine-T; potassium iodide In chloroform for 0.0833333h;	87%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) → 2,3-dihydro-N-methyltryptamine

Conditions	Yield
With triethylsilane; trifluoroacetic acid at 60℃; for 4h;	87%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) + carbon monoxide (201230-82-2) → Strychnocarpine (59156-98-8)

Conditions	Yield
With oxygen; copper diacetate; palladium diacetate In toluene at 110℃; for 6h;	86%
With oxygen; copper diacetate; palladium diacetate In toluene at 80℃; under 760.051 Torr; for 6h; Reagent/catalyst; Solvent; Temperature; Schlenk technique;	86%

[2-(1H-indol-3-yl)-ethyl]-methylamine (61-49-4) → 2-[131I]-iodo-N-methyltryptamine

Conditions	Yield
With sodium hydroxide; [131I]-sodium iodide; chloroamine-T In chloroform for 0.05h;	85.6%

Upstream product

• 6502-82-5 N_b-formyltryptamine 
• 38750-13-9 (2-indol-3-yl-ethyl)-carbamic acid benzyl ester 
• 67909-99-3 ethyl 2-(1H-indole-3-yl)ethylcarbamate 
• 58635-45-3 methyl 2-(1-H-indol-3-yl)ethylcarbamate 
• 61-54-1 tryptamine 
• 541-41-3 chloroformic acid ethyl ester 
• 103549-24-2 tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate 
• 120-72-9 indole 
• 79-37-8 oxalyl dichloride 
• 74-89-5 methylamine 
• 2054-72-0 2-(1H-indol-3-yl)-N-methyl-2-oxoacetamide 
• 22980-09-2 indolyl-3-glyoxylyl chloride 
• 100-63-0 phenylhydrazine 
• 526-55-6 2-(3-indole)-ethanol 

Downstream Products

• 13100-00-0 1,2,3,4-tetrahydro-2-methyl-9H-pyrido[3,4-b]indole 
• 486-91-9 N(b)-Methyl-tetrahydro-harman 
• 61-50-7 N,N-dimethyltryptamine 
• 760957-11-7 2-{[2-(1H-indol-3-yl)-ethyl]-methyl-amino}-1-phenyl-ethanone 
• 760957-18-4 1-(4-chloro-phenyl)-2-{[2-(1H-indol-3-yl)-ethyl]-methyl-amino}-ethanone 
• 760957-20-8 1-(4-bromo-phenyl)-2-{[2-(1H-indol-3-yl)-ethyl]-methyl-amino}-ethanone 
• 16531-06-9 CA₁₉₂ 
• 883561-04-4 CA₂₂₄ 

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