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
Show more names
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
- Formal charge
- 0
- Complexity
- 174
Experimental & physicochemical properties
Ionization Efficiency
Positive
2.35
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Collision Cross Section
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)]
139.08 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
149.8 Ų [M+Na]+
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
Safety & regulation
GHS classification
GHS Classification
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
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
Applications
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
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A primary amino compound that is the 5-hydroxy derivative of tryptamine.
Related reactions
Linked notes
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