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3-(2-Methylaminoethyl)indole

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Name

3-(2-Methylaminoethyl)indole

EINECS 200-507-9
CAS No. 61-49-4 Density 1.088 g/cm3
PSA 27.82000 LogP 2.32070
Solubility N/A Melting Point 87-89 °C(lit.)
Formula C11H14N2 Boiling Point 336.2 °C at 760 mmHg
Molecular Weight 174.246 Flash Point 157.1 °C
Transport Information N/A Appearance white to off-white shiny cryst. powder or flakes
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 61-49-4 (3-(2-Methylaminoethyl)indole) Hazard Symbols N/A
Synonyms

Indole,3-[2-(methylamino)ethyl]- (6CI,7CI,8CI);3-(2-Methylaminoethyl)indole;3-[2-(Methylamino)ethyl]-1H-indole;Dipterine;Methyltryptamine;Monomethyltryptamine;N-Methyl-1H-indole-3-ethanamine;N-Methyltryptamine;N-Monomethyltryptamine;N10-Methyltryptamine;Nb-Methyltryptamine;Nw-Methyltryptamine;[2-(1H-Indol-3-yl)ethyl]methylamine;

Article Data 42

3-(2-Methylaminoethyl)indole Synthetic route

58635-45-3

methyl 2-(1-H-indol-3-yl)ethylcarbamate

61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
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%
6502-82-5

Nb-formyltryptamine

61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
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;
67909-99-3

ethyl 2-(1H-indole-3-yl)ethylcarbamate

61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
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%
103549-24-2

tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate

61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 25℃; for 24h;52%
120-72-9

indole

79-37-8

oxalyl dichloride

74-89-5

methylamine

61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
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%
2054-72-0

2-(1H-indol-3-yl)-N-methyl-2-oxoacetamide

61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 7h; Inert atmosphere; Reflux;42%
2054-72-0

2-(1H-indol-3-yl)-N-methyl-2-oxoacetamide

A

61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

B

2,3-dihydro-N-methyltryptamine

C

3-(2-Methylamino-ethyl)-2,3-dihydro-1H-indol-3-ol

Conditions
ConditionsYield
With dimethylsulfide borane complex In tetrahydrofuran for 48h; Heating;A 29%
B 24%
C 36%
58635-45-3

methyl 2-(1-H-indol-3-yl)ethylcarbamate

A

61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

4147-36-8, 4147-37-9, 5545-89-1, 23102-84-3, 85610-66-8

(±)-1,1'-dimethyl-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole

C

4147-37-9

meso-Chimonanthine

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
ConditionsYield
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%
61-54-1

tryptamine

74-88-4

methyl iodide

61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

3389-21-7

3-(2-bromoethyl)-1H-indole

74-89-5

methylamine

61-49-4

[2-(1H-indol-3-yl)-ethyl]-methylamine

3-(2-Methylaminoethyl)indole Specification

The CAS register number of 3-(2-Methylaminoethyl)indole is 61-49-4. It also can be called as N(omega)-Methyltryptamine and the IUPAC name about this chemical is 2-(1H-indol-3-yl)-N-methylethanamine. The molecular formula about this chemical is C11H14N2 and the molecular weight is 174.24. It belongs to the following product categories, such as Tryptamines; Heterocyclic Compounds and so on. When you are using it, please avoid contact with skin and eyes.

Physical properties about 3-(2-Methylaminoethyl)indole are: (1)ACD/LogP: 1.52; (2)ACD/LogD (pH 5.5): -1.58; (3)ACD/LogD (pH 7.4): -1.42; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 8.17Å2; (12)Index of Refraction: 1.621; (13)Molar Refractivity: 56.3 cm3; (14)Molar Volume: 160 cm3; (15)Polarizability: 22.32x10-24cm3; (16)Surface Tension: 45.2 dyne/cm; (17)Enthalpy of Vaporization: 57.93 kJ/mol; (18)Boiling Point: 336.2 °C at 760 mmHg; (19)Vapour Pressure: 0.000114 mmHg at 25°C.

Preparation: this chemical can be prepared by N-(2-indol-3-yl-ethyl)-formamide. This reaction will need reagent LiAlH4.

Uses of 3-(2-Methylaminoethyl)indole: it can be used to produce 2-iodo-N-methyltryptamine. This reaction will need reagent aq. chloramine-T, KI and solvent CHCl3 with reaction time of 5 min. The yield is about 87%.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cccc2c1c(cn2)CCNC
(2)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
(3)InChIKey: NCIKQJBVUNUXLW-UHFFFAOYAC
(4)Std. InChI: InChI=1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3
(5)Std. InChIKey: NCIKQJBVUNUXLW-UHFFFAOYSA-N

The toxicity data is as follows: 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 158mg/kg (158mg/kg) BEHAVIORAL: EXCITEMENT Journal of Toxicology and Environmental Health. Vol. 1, Pg. 515, 1976.
 

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