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| CAS No.: | 61-54-1 |
|---|---|
| Name: | Tryptamine |
| Molecular Structure: | |
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| Formula: | C10H12N2 |
| Molecular Weight: | 160.219 |
| Synonyms: | Indole,3-(2-aminoethyl)- (8CI);2-(1H-Indol-3-yl)ethanamine;2-(3-Indolyl)ethylamine;3-(2-Aminoethyl)-1H-indole;3-(2-Aminoethyl)indole;b-(3-Indolyl)ethylamine; |
| EINECS: | 200-510-5 |
| Density: | 1.158 g/cm3 |
| Melting Point: | 113-116 °C(lit.) |
| Boiling Point: | 378.766 °C at 760 mmHg |
| Flash Point: | 187.672 °C |
| Solubility: | negligible |
| Appearance: | White to orange crystalline powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 20/21/22-36/37/38-41 |
| Safety: | 24/25-36/37/39-26 |
| PSA: | 41.81000 |
| LogP: | 2.36940 |
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; |
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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 %.
![Tryptamine can react with 1H-benzo[d][1,3]oxazine-2,4-dione to get 2-amino-N-(2-indol-3-yl-ethyl)-benzamide.](/UserFilesUpload/Uses of Tryptamine.jpg)
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. |
