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Serotonin

HCID 5202
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
50-67-9
Standard SMILES
NCCc1c[nH]c2ccc(O)cc12
InChIKey
QZAYGJVTTNCVMB-UHFFFAOYSA-N
Molecular formula
C10H12N2O
Average molar mass
176.21 g/mol
Monoisotopic mass
176.09496301

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

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
Formal charge
0
Complexity
174

Experimental & physicochemical properties

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

0.21

0.21

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

Positive

2.35

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Collision Cross Section · 5 items

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]+

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

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
safety_code
36/37-45
hazard_class
IRRITANT
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard statements
H301-H361
Hazard Classifications
Acute Tox. 3 OralRepr. 2
Precautionary statements
P202-P264-P270-P280-P301+P310-P405

Chemistry & industry

Pharmacology

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
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.

Related reactions

30 records
New reaction record
HRID 6746 reaction equation
HRID 6746As reactantuspto-grants-2006_08
HRID 45588 reaction equation
HRID 45588As productuspto-grants-2013_09
HRID 154751 reaction equation
HRID 154751As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 168123 reaction equation
HRID 168123As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 218240 reaction equation
HRID 218240As reactantuspto-grants-2012_06
HRID 327076 reaction equation
HRID 327076As productuspto-grants-1993_12
HRID 347261 reaction equation
HRID 347261As productuspto-grants-2007_02
HRID 365506 reaction equation
HRID 365506As productuspto-grants-2000_10
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Nikkaji
J4.107F

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)
pka
9.8 · 9.8(at 25℃)
form
Solid
color
White to off-white
BRN
143524 · 143524
Stability
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 DataBase Reference
50 · 50-67-9(CAS DataBase Reference)
NCI Dictionary of Cancer Terms
5 · 5-hydroxytryptamine; serotonin
FDA UNII
333 DO1RDJY · 333DO1RDJY
EPA Substance Registry System
Serotonin (50-67-9)
UNSPSC Code
85151701 · 85151701
NACRES
24 · NA.24
Symbol(GHS)
6 · GHS06,GHS08
Signal word
Danger
Hazard statements
301 · H301-H361
Precautionary statements
202 · P202-P264-P270-P280-P301+P310-P405
Hazard Codes
T
Risk Statements
63 · 63-25
Safety Statements
36 · 36/37-45
RIDADR
2811 · UN 2811 6.1 / PGIII
WGK Germany
3 · 3
HazardClass
IRRITANT
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
3 OralRepr · Acute Tox. 3 OralRepr. 2

Usesneurotransmitter

Upstream & downstream products

Downstream products

N-(p-Coumaroyl) SerotoninOleoyl Serotonincinobufotenine

Additional notes

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