2-(Indol-3-yl)ethylamin
L-TRYPTAMINE · TRIPTAMINE · 1H-INDOLE-3-ETHANAMINE · TRYPTAMINE CAS 61-54-1 · 2-(1H-INDOL-3-YL)ETHANAMINE · 2-(1H-indol-3-yl)ethan-1-aMine hydrochloride · Tryptamin · 3-(2-AMINOETHYL)INDOLE
Identifikatoren & physikalische Daten
| CAS No. | 61-54-1 |
|---|---|
| Summenformel | C10H12N2 |
| Durchschnittliche Molmasse | 160,22 g/mol |
| Monoisotopische Masse | 160,10004838 g/mol |
| SMILES | NCCc1c[nH]c2ccccc12 |
| InChIKey | APJYDQYYACXCRM-UHFFFAOYSA-N |
| PubChem CID | 1150 |
| ChEMBL | CHEMBL6640 |
| ChEBI | CHEBI:16765 |
| EC No. | 200-510-5 |
| DTXSID | DTXSID2075340 |
| Lokaler Name | 2-(Indol-3-yl)ethylamin |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 41,8 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 147 |
| Arzneimittel | DEA NFLIS-Drug Category -> TryptaminesPharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Angular frequency |
| LogP (Verteilungskoeffizient) | 1.55 |
| Schmelzpunkt | 114 - 119 °C113-116 °C (lit.) |
| Physical Description | Solid |
| Collision Cross Section | 128.42 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]131.55 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]137.97 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]124.4 Ų [M+H-H2O]+ [CCS Type: TW127.6 Ų [M+H]+ |
| Siedepunkt | 137 °C/0.15 mmHg (lit.) |
| Dichte | 0.9787 (rough estimate) |
| Brechungsindex | 1.6210 (estimate) |
| Flammpunkt | 185 °C |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | water: soluble1g/L at 20°Cnegligible |
| pKa (Säurekonstante) | 10.2(at 25℃) |
| Aggregatzustand | crystalline |
| Farbe | white |
| pH | 11.07 (10g/l, H2O, 24.7℃) |
| Merck | 14,9796 |
| BRN | 125513 |
| Hauptanwendungen | cleaning productscosmeticsfood and beveragespersonal care |
| InChI | 1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2 |
| InChIKey | APJYDQYYACXCRM-UHFFFAOYSA-N |
| SMILES | NCCc1c[nH]c2ccccc12 |
| CAS Datenbank | 61-54-1(CAS DataBase Reference) |
| NIST chemische Informationen | 1H-Indole-3-ethanamine(61-54-1) |
| EPA chemische Informationen | Tryptamine (61-54-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 1.9% (1 of 52) of reports.WarningH315 (96.2%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 52 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 29-09-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/128031H-Indole-3-ethanamine: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (96.2%) |
| F | 8-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29339990 |
| RTECS-Nr. | NL4020000 |
| R-Sätze (R) | 20/21/22-36/37/38-41-37/38-22 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 24/25-36/37/39-36-26 |
| Gefahrenklasse | IRRITANTAcute Tox. 4 OralEye Dam. 1Skin Sens. 1A |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Tryptamine is an indole alkaloid and intermediate in the biosynthesis of serotonin and the phytohormone melatonin in plants. It increases the levels of the terpenoid indole alkaloids ajmalicine, strictosidine, and catharanthine in cultures of C. roseus. Tryptamine is also a product of tryptophan metabolism in mammals. Tryptamine derivatives have been synthetically produced as hallucinogenic drugs of abuse that act on the serotonergic system.
Verwenden
Tryptamine is a monoamine alkaloid found in plants. Tryptamine is commonly used in the preparation of biologically active compounds such as neurotransmitters and psychedelics.
Herstellung & Synthese
synthetische
Tryptamine, a monoamine alkaloid containing an indole ring structure is derived by the decarboxylation of amino acid tryptophan.The synthesis of tryptamines is typically conducted following a classic route starting with a Mannich reaction of an indole heterocycle, followed by quaternization of the amine, nucleophilic substitution with highly toxic cyanide and final reduction.