Serotonin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Serotonin
DrugBank Accession Number
DB08839
Background

For temporary relief of nervousness, anxiety, mood swings, joint pains, weakness, drowsiness, itching and lethargy. Not evaluated by the FDA, homeopathic product.

Type
Small Molecule
Groups
Investigational, Nutraceutical
Structure
Thumb
Weight
Average: 176.2151
Monoisotopic: 176.094963016
Chemical Formula
C10H12N2O
Synonyms
  • 3-(2-Aminoethyl)-1H-indol-5-ol
  • 5-HT
  • 5-Hydroxytryptamine
  • Enteramine
  • sérotonine
  • thrombocytin
  • thrombotonin

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USodium-dependent serotonin transporterNot AvailableHumans
U5-hydroxytryptamine receptor 2ANot AvailableHumans
U5-hydroxytryptamine receptor 3ANot AvailableHumans
U5-hydroxytryptamine receptor 3BNot AvailableHumans
USynaptic vesicular amine transporterNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Serotonin is combined with 1,2-Benzodiazepine.
AcenocoumarolThe risk or severity of adverse effects can be increased when Serotonin is combined with Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Serotonin.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Serotonin.
AclidiniumSerotonin may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Serotonin.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Serotonin.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Serotonin.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Serotonin.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Serotonin.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Serotonin hydrochlorideGKN429M9VS153-98-0MDIGAZPGKJFIAH-UHFFFAOYSA-N
International/Other Brands
5-HTP (Natural Factors) / HTP Calm (Natural Balance) / Natural 5-HTP (Healthy Origins) / Seotonin (Apotheca Company) / Super 5-HTP (Action Labs)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as serotonins. These are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Tryptamines and derivatives
Direct Parent
Serotonins
Alternative Parents
Hydroxyindoles / 3-alkylindoles / 2-arylethylamines / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Substituted pyrroles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds
show 2 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 2-arylethylamine / 3-alkylindole / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenols, monoamine molecular messenger, primary amino compound, tryptamines (CHEBI:28790) / Biogenic amines, Indole alkaloids (C00780)
Affected organisms
Not Available

Chemical Identifiers

UNII
333DO1RDJY
CAS number
50-67-9
InChI Key
QZAYGJVTTNCVMB-UHFFFAOYSA-N
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
IUPAC Name
3-(2-aminoethyl)-1H-indol-5-ol
SMILES
NCCC1=CNC2=CC=C(O)C=C12

References

General References
Not Available
Human Metabolome Database
HMDB0000259
KEGG Compound
C00780
ChemSpider
5013
BindingDB
10755
RxNav
1311214
ChEBI
28790
ChEMBL
CHEMBL39
ZINC
ZINC000000057058
PDBe Ligand
SRO
Wikipedia
Serotonin
PDB Entries
2qeh / 2ymd / 3adv / 3brn / 3nk1 / 3q6k / 4dtw / 4due / 4duf / 5mam
show 13 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedDiagnosticBipolar Disorder (BD) / Major Depressive Disorder (MDD)1
4CompletedHealth Services ResearchAsthma / Depression1
4CompletedTreatmentAnxiety Disorders1
4CompletedTreatmentDepression1
4CompletedTreatmentMajor Depressive Disorder (MDD)2
4CompletedTreatmentUrinary Bladder, Overactive1
4Not Yet RecruitingPreventionPostoperative pain / Tibial Plateau Fracture1
4RecruitingOtherObsessive Compulsive Disorder (OCD)1
4RecruitingTreatmentMajor Depressive Disorder (MDD)1
3CompletedTreatmentMajor Depressive Disorder (MDD)7

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.5 mg/mLALOGPS
logP0.56ALOGPS
logP0.48ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.31ChemAxon
pKa (Strongest Basic)10ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area62.04 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity52.35 m3·mol-1ChemAxon
Polarizability19.31 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)GC-MSsplash10-00di-1900000000-461c2a1f67418e6b5d6a
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)GC-MSsplash10-00di-1900000000-2286e87324e9f4a78cb4
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00di-1900000000-927b865023cbba872101
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-00di-1910000000-02c17b4cd3336a8bf9b1
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)GC-MSsplash10-00di-8900000000-4b838943ace80c8b7734
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)GC-MSsplash10-00di-6900000000-a7dd5c569cf4d085d244
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-00di-0900000000-2346e553f96cb980c8fc
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-00di-1900000000-01fbd5196188d4e0f21c
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0002-9800000000-9ce9fb2286c3b7ea7719
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-1900000000-461c2a1f67418e6b5d6a
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-1900000000-2286e87324e9f4a78cb4
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-1900000000-927b865023cbba872101
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-1910000000-02c17b4cd3336a8bf9b1
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-8900000000-4b838943ace80c8b7734
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00di-6900000000-a7dd5c569cf4d085d244
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-0900000000-2346e553f96cb980c8fc
GC-MS Spectrum - GC-MSGC-MSsplash10-00di-1900000000-01fbd5196188d4e0f21c
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0a4i-0900000000-6acaf73bcd452e24b886
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0aor-0900000000-259227b20b82e6362059
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-02e9-5900000000-2f58fbed270523182158
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-0002-9800000000-abcd0769bb17d07b3e38
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-03di-0900000000-bf65d809200ea387ebf5
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-03di-0900000000-8a171ac4fdc0474f7f48
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-03xr-0900000000-a0b7d8a671909c6f4ad1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-014i-1900000000-fa80d05236eabbafd678
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-4900000000-4e2e322d56fc9ee00edd
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-004i-0900000000-c79f0b03a8dc1da0a10a
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-03fr-0900000000-9cb056cd56bae76589d0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-03di-1900000000-d64210214a1b3766ff6e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0900000000-08840bc938c367dacbb2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03yi-0900000000-858936972fd87c0c0b14
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0159-4900000000-a8fc7dff385a4f51b88a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00p0-9400000000-7e4063d2b516ae59df84
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0900000000-bf65d809200ea387ebf5
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0900000000-8a171ac4fdc0474f7f48
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03xr-0900000000-a0b7d8a671909c6f4ad1
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-1900000000-e470cd23466404f9bf5b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-4900000000-d242a2269e10d5bc922e
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-03di-0900000000-a99d60699d7b9ffba28c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0900000000-c79f0b03a8dc1da0a10a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03fr-0900000000-9cb056cd56bae76589d0
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0900000000-77d500913f76964f7f0e
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Henry LK, Field JR, Adkins EM, Parnas ML, Vaughan RA, Zou MF, Newman AH, Blakely RD: Tyr-95 and Ile-172 in transmembrane segments 1 and 3 of human serotonin transporters interact to establish high affinity recognition of antidepressants. J Biol Chem. 2006 Jan 27;281(4):2012-23. Epub 2005 Nov 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Peroutka SJ, Lebovitz RM, Snyder SH: Two distinct central serotonin receptors with different physiological functions. Science. 1981 May 15;212(4496):827-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Voltage-gated potassium channel activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
Gene Name
HTR3A
Uniprot ID
P46098
Uniprot Name
5-hydroxytryptamine receptor 3A
Molecular Weight
55279.835 Da
References
  1. Rusch D, Musset B, Wulf H, Schuster A, Raines DE: Subunit-dependent modulation of the 5-hydroxytryptamine type 3 receptor open-close equilibrium by n-alcohols. J Pharmacol Exp Ther. 2007 Jun;321(3):1069-74. Epub 2007 Mar 7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serotonin-activated cation-selective channel activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
Gene Name
HTR3B
Uniprot ID
O95264
Uniprot Name
5-hydroxytryptamine receptor 3B
Molecular Weight
50291.3 Da
References
  1. Rusch D, Musset B, Wulf H, Schuster A, Raines DE: Subunit-dependent modulation of the 5-hydroxytryptamine type 3 receptor open-close equilibrium by n-alcohols. J Pharmacol Exp Ther. 2007 Jun;321(3):1069-74. Epub 2007 Mar 7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Monoamine transmembrane transporter activity
Specific Function
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
Gene Name
SLC18A2
Uniprot ID
Q05940
Uniprot Name
Synaptic vesicular amine transporter
Molecular Weight
55712.075 Da
References
  1. Gonzalez AM, Walther D, Pazos A, Uhl GR: Synaptic vesicular monoamine transporter expression: distribution and pharmacologic profile. Brain Res Mol Brain Res. 1994 Mar;22(1-4):219-26. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Grundemann D, Koster S, Kiefer N, Breidert T, Engelhardt M, Spitzenberger F, Obermuller N, Schomig E: Transport of monoamine transmitters by the organic cation transporter type 2, OCT2. J Biol Chem. 1998 Nov 20;273(47):30915-20. [Article]

Drug created on February 21, 2013 23:40 / Updated on June 12, 2020 16:52