2-(Indol-3-yl)ethylamin
Tryptamine
Grundinformationen
- CAS
61-54-1- Standard-SMILES
NCCc1c[nH]c2ccccc12- InChIKey
APJYDQYYACXCRM-UHFFFAOYSA-N- Summenformel
- C10H12N2
- Durchschnittliche Molmasse
- 160,22 g/mol
- Monoisotopische Masse
- 160,10004839
Überblick
Tryptamine is an aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. It has a role as a mouse metabolite, a plant metabolite and a human metabolite. It is a member of tryptamines, an aminoalkylindole, an indole alkaloid and an aralkylamino compound. It is a conjugate base of a tryptaminium.
Namen und Bezeichner
- Bevorzugter Name
- Tryptamine
- IUPAC
- 2-(1H-indol-3-yl)ethanamine
- Lokaler Name
- 2-(Indol-3-yl)ethylamin
- Englischer Name
- Tryptamine
- Summenformel
- C10H12N2
- Molmasse
- 160.22
Namen und Synonyme
tryptamine61-54-12-(1H-Indol-3-yl)ethanamine3-(2-aminoethyl)indole1H-Indole-3-ethanamine2-(3-Indolyl)ethylamine2-(1H-Indol-3-Yl)Ethan-1-AmineIndole, 3-(2-aminoethyl)-beta-(3-Indolyl)ethylamine422ZU9N5TVCHEBI:16765DTXSID2075340
Weitere Namen anzeigen
L-TRYPTAMINETRIPTAMINETRYPTAMINE CAS 61-54-12-(1H-indol-3-yl)ethan-1-aMine hydrochlorideb mk-2ryptamine
NSC-1652123-[2-Aminoethyl]indoleRefChem:900684DTXCID3042922200-510-5TryptaminIndol-3-ethylamine2-(Indol-3-yl)ethylamine
Datenbank-Bezeichner
- CAS
61-54-1- PubChem CID
- 1150
- DTXSID
DTXSID2075340- ChEMBL
CHEMBL6640- ChEBI
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,6
- Polarare Oberfläche (TPSA)
- 41,8 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 147
Experimentelle und physikochemische Eigenschaften
Drugs
DEA NFLIS-Drug Category -> Tryptamines
Pharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesAngular frequency
LogP
1.55
1.35
Melting Point114 - 119 °C
Physical DescriptionSolid
Collision Cross Section
128.42 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
125.1 Ų [M+H-H2O]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
131.25 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
124.4 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
127.6 Ų [M+H]+
Physikochemische Eigenschaften
- Schmelzpunkt
- 113 · 113-116 °C (lit.)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 1.9% (1 of 52) of reports.
Warning
H315 (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.
Gefahrenhinweise
Regulatory Information
REACH registered substance: 2-(indol-3-yl)ethylamine (EC: 200-510-5)
1H-Indole-3-ethanamine: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (96.2%)
Sicherheitsdaten
- F
- 8-23
- wgk
- 3
- hs_code
- 2933990099
- RTECS-Nr.
- NL4020000
- risk_code
- 20/21/22-36/37/38-41-37/38-22
- hazard_code
- Xi
- safety_code
- 24/25-36/37/39-36-26
- hazard_class
- IRRITANT
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Skin Sens. 1A
Chemie und Industrie
Pharmakologische Informationen
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite PathwaysTryptophan metabolism
Anwendungen
BeschreibungTryptamine 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.
VerwendenTryptamine is a monoamine alkaloid found in plants. Tryptamine is commonly used in the preparation of biologically active compounds such as neurotransmitters and psychedelics.
Darstellung
synthetischeTryptamine, 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.
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