Serotonin

HCID 5202CAS 50-67-9

Basic information

Standard SMILES
NCCc1c[nH]c2ccc(O)cc12
InChIKey
QZAYGJVTTNCVMB-UHFFFAOYSA-N
Molecular formula
C10H12N2O
Average molar mass
176.21 g/mol
Monoisotopic mass
176.094963

Overview

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+).

Names & identifiers

Preferred name
Serotonin
IUPAC
3-(2-aminoethyl)-1H-indol-5-ol
English name
5-Hydroxytryptamine
Molecular formula
C10H12N2O
Molecular weight
176.22

Names & synonyms

serotonin5-HYDROXYTRYPTAMINE50-67-93-(2-Aminoethyl)-1H-indol-5-olEnteramineThrombotoninThrombocytinSerotonine1H-Indol-5-ol, 3-(2-aminoethyl)-Hippophaine3-(beta-Aminoethyl)-5-hydroxyindole333DO1RDJY
Show more names
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

Database identifiers

CAS
50-67-9
PubChem CID
5202
DTXSID
DTXSID8075330
ChEMBL
CHEMBL39
ChEBI
CHEBI:28790
UNII
333DO1RDJY
EC Number
200-058-9
Nikkaji
J4.107F

Properties

Computed structural properties

XLogP
0.2
Topological polar surface area
62 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
13

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesAngular frequency
LogP0.21
Solubility25.5 mg/mL
Physical DescriptionSolid
Ionization Efficiency · 6 items

Positive

2.35

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Physicochemical properties

Melting point
167.5 °C · 167.5 °C
Boiling point
307.83 °C · 307.83°C (rough estimate)
Density
1.1102 · 1.1102 (rough estimate)
refractive index
1.711 · 1.7110 (estimate)
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Safety data

wgk
3
ridadr
UN 2811 6.1 / PGIII
risk_code
63-25
Signal word
Danger
Symbol(GHS)
GHS06,GHS08
hazard_code
T

Chemistry & industry

Pharmacology

Metabolism/MetabolitesSerotonin has known human metabolites that include (2S,3S,4S,5R)-6-[[3-(2-Aminoethyl)-1H-indol-5-yl]oxy]-3,4,5-trihydroxy-2-oxanecarboxylic acid and 3-Ethyl-1H-indol-5-ol.
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
Applications · 2 items

DescriptionSerotonin 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.

Usesneurotransmitter

Upstream & downstream products

Suppliers50 total

湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]

Additional notes

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

Related reactions

30 records

Linked notes

Loading…