3-(2-nitroethyl)indole
tryptamine
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol under 760.051 Torr; for 24h; | 98% |
With sodium hypophosphite monohydrate; 5%-palladium/activated carbon; hypophosphorous acid In 2-methyltetrahydrofuran; water for 7h; Sonication; chemoselective reaction; | 94% |
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 15h; | 86.94% |
Conditions | Yield |
---|---|
With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase In various solvent(s) at 30℃; for 48h; | 98% |
cyclohexenone In various solvent(s) at 154℃; for 1.5h; | 92.3% |
With L-amino acid decarboxylase from Micrococcus percitreus AJ 1065; NH4OH-NH4Cl buffer; pyridoxal 5'-phosphate In water at 30℃; for 0.5h; Product distribution; study of the inhibition of the enzyme by various amino acids and amines, inhibition of L-dopa in different buffer solutions; |
tert-butyl 4-(2-aminophenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate
tryptamine
Conditions | Yield |
---|---|
Stage #1: tert-butyl 4-(2-aminophenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate With trifluoroacetic acid In dichloromethane at 0 - 25℃; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In water pH=> 7; Inert atmosphere; Saturated solution; | 98% |
With trifluoroacetic acid In dichloromethane at 0 - 25℃; for 2h; Inert atmosphere; | 98% |
N-tosyl tryptamine
tryptamine
Conditions | Yield |
---|---|
With pyrrolidine; samarium diiodide; water In tetrahydrofuran at 20℃; Inert atmosphere; | 94% |
(2-indol-3-yl-ethyl)-carbamic acid benzyl ester
tryptamine
Conditions | Yield |
---|---|
With hydrogen; palladium In ethanol; ethyl acetate under 22502.3 Torr; | 94% |
Conditions | Yield |
---|---|
Stage #1: indole; L-serin With engineered tryptophan synthase In methanol; aq. phosphate buffer at 75℃; for 12h; pH=8.0; Enzymatic reaction; Stage #2: With pyridoxal 5'-phosphate; Ruminococcus gnavus L-tryptophan decarboxylase In methanol; aq. phosphate buffer at 37℃; pH=8.0; Enzymatic reaction; | 92% |
3-[(E)-2-nitroeth-1-enyl]-1H-indole
tryptamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 7h; Reflux; | 89% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 6h; Inert atmosphere; | 83.5% |
With lithium aluminium tetrahydride; diethyl ether |
tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate
tryptamine
Conditions | Yield |
---|---|
In various solvent(s) at 150℃; for 1h; microwave irradiation; | 88% |
With 1,1,1,3',3',3'-hexafluoro-propanol at 150℃; for 1h; Microwave irradiation; | 88% |
With 1,1,1,3',3',3'-hexafluoro-propanol at 150℃; for 1h; Microwave irradiation; | 88% |
Conditions | Yield |
---|---|
With sodium hydroxide In water; ethylene glycol | 82% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran Reflux; | 81% |
With lithium aluminium tetrahydride | |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; |
Conditions | Yield |
---|---|
With ammonium bromide; ethylenediamine at 80℃; for 5h; Microwave irradiation; Inert atmosphere; neat (no solvent); | 81% |
With recombinant Arabidopsis thaliana histone deacetylase 14 In aq. buffer at 30℃; pH=8; Reagent/catalyst; Enzymatic reaction; |
4-(4,8-Dimethoxy-naphthalen-1-ylmethyl)-N-[2-(1H-indol-3-yl)-ethyl]-benzenesulfonamide
tryptamine
Conditions | Yield |
---|---|
With ammonia borane In ethanol Irradiation; | 78% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 12h; Inert atmosphere; | 75% |
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; | 74% |
With lithium aluminium tetrahydride; diethyl ether |
3-(2-azidoethyl)-1H-indole
tryptamine
Conditions | Yield |
---|---|
Stage #1: 3-(2-azidoethyl)-1H-indole With formic acid; tris(2,2'-bipyridyl)ruthenium dichloride; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; N-ethyl-N,N-diisopropylamine In methanol; N,N-dimethyl-formamide at 25℃; for 24h; Irradiation; Stage #2: With di-tert-butyl dicarbonate; triethylamine In methanol; N,N-dimethyl-formamide at 25℃; for 12h; | 72% |
tryptamine
Conditions | Yield |
---|---|
With hydrogenchloride; iron In methanol; water for 0.5h; Heating; | 71% |
Conditions | Yield |
---|---|
In diphenylether for 10h; Heating; | 63% |
With Catharanthus roseus tryptophan decarboxylase In aq. phosphate buffer at 25℃; pH=7.5; Kinetics; Reagent/catalyst; Enzymatic reaction; |
2-(2,3-dihydro-2-oxo-3-indolyl)ethylamine
tryptamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; | 62% |
4-chloro-1-hydroxy-1-butanesulfonate sodium
phenylhydrazine hydrochloride
tryptamine
Conditions | Yield |
---|---|
With disodium hydrogenphosphate In ethanol at 70℃; for 6h; | 61% |
With disodium hydrogenphosphate In ethanol at 70℃; for 6h; |
(3-Indolyl)acetaldehyd-dimethylhydrazon
tryptamine
Conditions | Yield |
---|---|
With hydrogen; rhenium; nickel In methanol under 760 Torr; for 12h; Ambient temperature; | 52% |
indole-3-acetonitrile
A
tryptamine
B
1-(3-methyl-1H-indole)-1,2,3,4-tetrahydro-β-carboline
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol for 96h; | A 38% B 31% |
indole-3-acetonitrile
A
tryptamine
B
3-(2-aminoethyl)-2,3-dihydro-1H-indole
Conditions | Yield |
---|---|
With ammonia; nickel at 100℃; under 66195.7 Torr; Hydrogenation; |
Conditions | Yield |
---|---|
With ammonia; water |
Conditions | Yield |
---|---|
With zinc(II) chloride |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride | |
With lithium aluminium tetrahydride In tetrahydrofuran Heating; | |
With lithium aluminium tetrahydride In 1,4-dioxane for 34h; Heating; | 0.90 g |
With lithium aluminium tetrahydride In 1,4-dioxane for 50h; Heating; |
Conditions | Yield |
---|---|
With hydrogenchloride for 24h; Heating; |
(E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxy-3-methoxyphenyl)acrylamide
A
tryptamine
B
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
Conditions | Yield |
---|---|
In sodium hydroxide |
2-[1-(phenylsulfonyl)-1H-indol-3-yl]ethanamines
tryptamine
Conditions | Yield |
---|---|
With sodium hydroxide for 2h; Heating; Yield given; |
(E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)acrylamide
A
tryptamine
B
p-Coumaric Acid
Conditions | Yield |
---|---|
In sodium hydroxide |
Conditions | Yield |
---|---|
Stage #1: tryptamine; phenyl isocyanate In dichloromethane at 60℃; Stage #2: With isatoic anhydride-N-(CH2)3-C8F17 In dichloromethane at 60℃; for 2.5h; | 100% |
In dichloromethane at 60℃; for 5h; Inert atmosphere; Sealed reaction vessel; | 98% |
tryptamine
benzyl chloroformate
(2-indol-3-yl-ethyl)-carbamic acid benzyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 1h; | 100% |
With N-ethyl-N,N-diisopropylamine In chloroform at 0 - 20℃; for 1h; | 100% |
With sodium hydroxide In tetrahydrofuran | 97% |
tryptamine
chloroacetyl chloride
2-chloro-N-<2-(indol-3-yl)ethyl>acetamide
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane Ambient temperature; | 100% |
In dichloromethane | 100% |
With triethylamine In tetrahydrofuran at 20℃; for 6h; Cooling with ice; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 2h; | 100% |
With triethylamine In dichloromethane at 0 - 20℃; | 99% |
With triethylamine In dichloromethane at 0 - 20℃; for 2h; | 99% |
tryptamine
4-Phenylbutyric acid
N-(2-(1H-indol-3-yl)ethyl)-4-phenylbutanamide
Conditions | Yield |
---|---|
With Trimethyl borate In acetonitrile at 80℃; for 15h; | 100% |
With tris(2,2,2-trifluoroethyl) borate In acetonitrile at 80℃; for 15h; | 70% |
at 180℃; |
Conditions | Yield |
---|---|
for 24h; Reflux; | 100% |
for 6h; Reflux; | 100% |
With triethylamine In methanol at 100℃; for 16h; Inert atmosphere; | 97% |
tryptamine
chloroformic acid ethyl ester
ethyl 2-(1H-indole-3-yl)ethylcarbamate
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane Ambient temperature; | 100% |
With triethylamine In dichloromethane at 0℃; Inert atmosphere; | 99.4% |
With sodium hydroxide In chloroform for 3h; | 95% |
Conditions | Yield |
---|---|
In toluene at 20℃; for 12h; | 100% |
In methanol at 25℃; for 16h; | 70% |
With molecular sives 4A In dichloromethane Ambient temperature; |
tryptamine
propynoic acid methyl ester
(E)-3-[2-(1H-Indol-3-yl)-ethylamino]-acrylic acid methyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran for 5h; Ambient temperature; | 100% |
tryptamine
ethyl acrylate
3-<<2-(1H-indol-3-yl)ethyl>amino>propanoic acid ethyl ester
Conditions | Yield |
---|---|
In ethanol for 1h; Reflux; | 100% |
In ethanol at 0℃; for 24h; | 83% |
In tetrahydrofuran at 20℃; for 12h; | 83% |
In ethanol at 0 - 20℃; | 80% |
In ethanol |
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane; water at 0℃; | 100% |
With triethylamine | 100% |
With sodium hydroxide In ethyl acetate at 25℃; for 0.5h; | 95% |
tryptamine
di-tert-butyl dicarbonate
tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane for 1h; | 100% |
With guanidine hydrochloride In ethanol at 35 - 40℃; for 0.05h; | 100% |
With amberlyst-15 In ethanol at 20℃; for 2h; chemoselective reaction; | 100% |
tryptamine
3,6-diiodopyridazine
[2-(1H-indol-3-yl)-ethyl]-(6-iodo-pyridazin-3-yl)-amine
Conditions | Yield |
---|---|
In iso-butanol for 96h; Heating; | 100% |
Conditions | Yield |
---|---|
In methanol at 20℃; | 100% |
tryptamine
2-Nitrobenzenesulfonyl chloride
N-(2-(1H-indol-3-yl)ethyl)-2-nitrobenzenesulfonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 1.5h; | 100% |
With triethylamine In dichloromethane at 0 - 20℃; for 1h; | 97% |
With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h; Inert atmosphere; | 97% |
tryptamine
3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride
N-(2-(1H-indol-3-yl)ethyl)-3,5-bis(trifluoromethyl)benzamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; Inert atmosphere; | 100% |
With triethylamine In dichloromethane at 22℃; for 16h; |
Conditions | Yield |
---|---|
Stage #1: tryptamine; 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester With acetic acid at 100℃; for 4.5h; Stage #2: With hydrogenchloride In 1,4-dioxane at 20℃; | 100% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 120℃; for 18h; | 100% |
tryptamine
3-Cyanobenzaldehyde
3-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indol-1-yl)benzonitrile
Conditions | Yield |
---|---|
With trifluoroacetic acid In 1,1-dichloroethane Reflux; | 100% |
With trifluoroacetic acid In dichloromethane at 20℃; for 24h; Pictet-Spengler Synthesis; | 18% |
Conditions | Yield |
---|---|
With trifluoroacetic acid In 1,1-dichloroethane Reflux; | 100% |
tryptamine
Boc-Trp-OH
(S)-Nα-tert-butoxycarbonyl-N-[2-(3-indolyl)ethyl]tryptophanamide
Conditions | Yield |
---|---|
Stage #1: Boc-Trp-OH With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.5h; Inert atmosphere; Stage #2: tryptamine In dichloromethane at 20℃; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In dichloromethane at 0℃; for 12h; | 100% |
tryptamine
2-Methylbutyraldehyde
N-(2-(1H-indol-3-yl)ethyl)-2-methylbutan-1-amine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 2-methyltetrahydrofuran at 18℃; for 2h; Solvent; Green chemistry; | 100% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere; | 100% |
tryptamine
pyrrol-2-yl trichloromethyl ketone
N-(2-(1H-indol-3-yl)ethyl)-1H-pyrrole-2-carboxamide
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 50℃; for 3h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; | 100% |
In dichloromethane at 20℃; for 6h; | 95% |
Conditions | Yield |
---|---|
In ethanol at 85℃; | 100% |
In ethanol at 85 - 90℃; for 4h; Schlenk technique; | 91% |
With acetic acid In dichloromethane at 20℃; Inert atmosphere; Schlenk technique; | 59% |
In ethanol Reflux; | |
In ethanol at 80 - 85℃; for 4h; Inert atmosphere; |
Conditions | Yield |
---|---|
In methanol at 20℃; | 100% |
Conditions | Yield |
---|---|
In methanol at 20℃; | 100% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 3h; | 99% |
With sodium hydroxide In acetone at -30℃; | 95% |
In dichloromethane | 82% |
The Tryptamine, with the CAS registry number 61-54-1, is also known as 2-Indol-3-yl-aethylamin. It belongs to the product categories of Drug Intermediates; Indole; Indoles; Tryptamines; Amines; Heterocycles; Non-Chiral Heterocyclic Compounds. Its EINECS registry number is 200-510-5. This chemical's molecular formula is C10H12N2 and molecular weight is 160.22. What's more, both its IUPAC name and systematic name are the same which is called 2-(1H-Indol-3-yl)ethanamine. It should be stored in a dry and sealed place at 4 °C. Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It is found in trace amounts in the brains of mammals and is believed to play a role as a neuromodulator or neurotransmitter.
Physical properties about Tryptamine are: (1)ACD/LogP: 1.542; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.53; (4)ACD/LogD (pH 7.4): -0.81; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 2; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 41.81 Å2; (13)Index of Refraction: 1.669; (14)Molar Refractivity: 51.613 cm3; (15)Molar Volume: 138.366 cm3; (16)Polarizability: 20.461×10-24cm3; (17)Surface Tension: 54.728 dyne/cm; (18)Density: 1.158 g/cm3; (19)Flash Point: 187.672 °C; (20)Enthalpy of Vaporization: 62.67 kJ/mol; (21)Boiling Point: 378.766 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.
Uses of Tryptamine: it is used to produce other chemicals. For example, it can react with 1H-benzo[d][1,3]oxazine-2,4-dione to get 2-amino-N-(2-indol-3-yl-ethyl)-benzamide. This reaction needs solvent acetonitrile at ambient temperature. The reaction time is 3 hours. The yield is 92.7 %.
When you are dealing with this chemical, you should be very careful. This chemical may cause inflammation to the skin or other mucous membranes. It is harmful by inhalation, in contact with skin and if swallowed. In addition, it is irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. You must avoid contacting with skin and eyes. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1) SMILES: c1ccc2c(c1)c(c[nH]2)CCN
(2) 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
(3) InChIKey: APJYDQYYACXCRM-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 100mg/kg (100mg/kg) | European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 9, Pg. 453, 1974. | |
mouse | LD50 | subcutaneous | 500mg/kg (500mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Dissertationes Pharmaceuticae et Pharmacologicae. Vol. 22, Pg. 313, 1970. |
rat | LD50 | intraperitoneal | 223mg/kg (223mg/kg) | Journal of Pharmaceutical Sciences. Vol. 66, Pg. 1692, 1977. |
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