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3-(2-Aminoethyl)indol-5-ol

Serotonin

HCID 5202
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Grundinformationen

CAS
50-67-9
Standard-SMILES
NCCc1c[nH]c2ccc(O)cc12
InChIKey
QZAYGJVTTNCVMB-UHFFFAOYSA-N
Summenformel
C10H12N2O
Durchschnittliche Molmasse
176,21 g/mol
Monoisotopische Masse
176,09496301

Überblick

Serotonin is a primary amino compound that is the 5-hydroxy derivative of tryptamine. It has a role as a neurotransmitter, a mouse metabolite and a human metabolite. It is a monoamine molecular messenger, a member of tryptamines, a member of phenols, a primary amino compound and a member of hydroxyindoles. It is functionally related to a tryptamine. It is a conjugate base of a serotonin(1+).

Namen und Bezeichner

Bevorzugter Name
Serotonin
IUPAC
3-(2-aminoethyl)-1H-indol-5-ol
Lokaler Name
3-(2-Aminoethyl)indol-5-ol
Englischer Name
5-Hydroxytryptamine
Summenformel
C10H12N2O
Molmasse
176.22

Namen und Synonyme

serotonin5-HYDROXYTRYPTAMINE50-67-93-(2-Aminoethyl)-1H-indol-5-olEnteramineThrombotoninThrombocytinSerotonine1H-Indol-5-ol, 3-(2-aminoethyl)-Hippophaine3-(beta-Aminoethyl)-5-hydroxyindole333DO1RDJY
Weitere Namen anzeigen
3-(2-aminoethyl)-1H-indol-5-ol hydrochloride5-htaSEROTONIN BASE5-Hydroxytryptamine,freebaseantemoquaantemovissubstanzds
DTXSID8075330CHEBI:287903-(2-Aminoethyl)-1H-indol-5-oSerotonin (Human)5 HydroxytryptamineSerotonin 1543RefChem:6493DTXCID4040765

Datenbank-Bezeichner

CAS
50-67-9
PubChem CID
5202
DTXSID
DTXSID8075330
ChEMBL
CHEMBL39

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,2
Polarare Oberfläche (TPSA)
62 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
2
Schwere Atome
13
Formalladung
0
Komplexität
174

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesAngular frequency
LogP · 2 Einträge

0.21

0.21

Solubility25.5 mg/mL
Physical DescriptionSolid
Ionization Efficiency · 6 Einträge

Positive

2.35

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Collision Cross Section · 5 Einträge

150.8 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

146.9 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

135.85 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

127.98 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

150.9 Ų [M+H]+

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 · 4 Einträge

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 67 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Sicherheitsdaten

wgk
3
ridadr
UN 2811 6.1 / PGIII
risk_code
63-25
hazard_code
T
safety_code
36/37-45
hazard_class
IRRITANT
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
Acute Tox. 3 OralRepr. 2

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesSerotonin has known human metabolites that include 3-Ethyl-1H-indol-5-ol and (2S,3S,4S,5R)-6-[[3-(2-Aminoethyl)-1H-indol-5-yl]oxy]-3,4,5-trihydroxy-2-oxanecarboxylic acid.
MeSH Pharmacological ClassificationEndogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS.
Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite Pathways3-Methylthiofentanyl Action Pathway
Anwendungen · 2 Einträge

BeschreibungSerotonin is the baby boomer of neurotransmitters: It was identified in the late 1940s, its adolescence was troubled and turbulent, it made the drug scene in the 1960s, and it nearly died of an overdose in the early 1970s. At one point, the remark was made that serotonin doesn't do anything. On reaching its middle years, serotonin has matured and become an important topic of study, a household name, and more complicated than ever. Serotonin has been associated with, among other things, anxiety, depression, schizophrenia, drug abuse, sleep, dreaming, hallucinogenic activity, headache, cardiovascular disorders, and appetite control, and it is now dabbling in acupuncture and transcendental meditation. Serotonin was independently identified in the late 1940s by two groups of investigators: In the United States, it was called serotonin, whereas in Italy, it was called enteramine. Its total synthesis in the early 1950s confirmed that both substances were 5-hydroxytryptamine (5-HT ). Serotonin (5-HT ) was detected in numerous plant and animal species and, in the mid-1950s, was identified in the central nervous system (CNS) of animals. A neurotransmitter role was subsequently proposed for this substance. Later, 5-HT was implicated in a variety of central and peripheral physiologic actions. It seemed to be involved in vasoconstriction and vasodilation, regulation of body temperature, sleep, and hormonal regulation, and evidence suggested that it might be involved in depression. The structural similarity between 5-HT and the then recently discovered hallucinogenic agent (+)-lysergic acid diethylamide (LSD) intrigued investigators. This observation led to speculation that 5-HT might be involved in the mechanism of action of psychoactive substances and that it might play a seminal role in various mental disorders.

Zugehörige Reaktionen

30
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 6746
HRID 6746als Eduktuspto-grants-2006_08
Reaktionsgleichung von HRID 45588
HRID 45588als Produktuspto-grants-2013_09
Reaktionsgleichung von HRID 154751
HRID 154751als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 168123
HRID 168123als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
Reaktionsgleichung von HRID 218240
HRID 218240als Eduktuspto-grants-2012_06
Reaktionsgleichung von HRID 327076
HRID 327076als Produktuspto-grants-1993_12
Reaktionsgleichung von HRID 347261
HRID 347261als Produktuspto-grants-2007_02
Reaktionsgleichung von HRID 365506
HRID 365506als Produktuspto-grants-2000_10
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ChEBI
CHEBI:28790
UNII
333DO1RDJY
EC Number
200-058-9
Nikkaji
J4.107F

Physikochemische Eigenschaften

Schmelzpunkt
167.5 °C · 167.5 °C
Siedepunkt
307.83 °C · 307.83°C (rough estimate)
Dichte
1.1102 · 1.1102 (rough estimate)
Brechungsindex
1.711 · 1.7110 (estimate)
storage temp.
2 · 2-8°C
Löslichkeit
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka
9.8 · 9.8(at 25℃)
Aggregatzustand
Solid
Farbe
White to off-white
BRN
143524 · 143524
Stabilität
Hygroscopic
InChI
InChI=1S/C10H12N2O/c11-4-3-7-6-12-10-2-1-8(13)5-9(7)10/h1-2,5-6,12-13H,3-4,11H2
InChIKey
QZAYGJVTTNCVMB-UHFFFAOYSA-N
SMILES
N1C2=C(C=C(O)C=C2)C(CCN)=C1
CAS Datenbank
50 · 50-67-9(CAS DataBase Reference)
EPA chemische Informationen
Serotonin (50-67-9)

Verwendenneurotransmitter

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

N-(p-Coumaroyl) SerotoninOleoyl Serotonincinobufotenine

Ergänzende Hinweise

DefinitionChEBI: A primary amino compound that is the 5-hydroxy derivative of tryptamine.