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

Identification

Name
Serotonin
Accession Number
DB08839
Type
Small Molecule
Groups
Investigational, Nutraceutical
Description

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

Structure
Thumb
Synonyms
  • 3-(2-Aminoethyl)-1H-indol-5-ol
  • 5-HT
  • 5-Hydroxytryptamine
  • Enteramine
  • sérotonine
  • thrombocytin
  • thrombotonin
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
UNII
333DO1RDJY
CAS number
50-67-9
Weight
Average: 176.2151
Monoisotopic: 176.094963016
Chemical Formula
C10H12N2O
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USodium-dependent serotonin transporterNot AvailableHuman
U5-hydroxytryptamine receptor 2ANot AvailableHuman
U5-hydroxytryptamine receptor 3ANot AvailableHuman
U5-hydroxytryptamine receptor 3BNot AvailableHuman
USynaptic vesicular amine transporterNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when Serotonin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Serotonin is combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Serotonin.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Serotonin is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when 3,4-Methylenedioxyamphetamine is combined with Serotonin.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Serotonin.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Serotonin is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Serotonin.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Serotonin is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Serotonin.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0000259
KEGG Compound
C00780
ChemSpider
5013
BindingDB
10755
ChEBI
28790
ChEMBL
CHEMBL39
HET
SRO
Wikipedia
Serotonin
PDB Entries
2qeh / 2ymd / 3adv / 3brn / 3nk1 / 3q6k / 4dtw / 4due / 4duf / 5mam
show 7 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentDepressive Disorder and Anxiety Disorders / Depressive Disorders1
2Not Yet RecruitingTreatmentCrohn's Disease (CD) / Remission / Tiredness / Ulcerative Colitis (UC)1
3CompletedTreatmentDepression / Major Depressive Disorder (MDD)1
Not AvailableCompletedNot AvailableMajor Depressive Disorder (MDD)1

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

Taxonomy

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
Serotonin / 3-alkylindole / Hydroxyindole / Indole / 2-arylethylamine / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Substituted pyrrole / Benzenoid / Pyrrole
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)

Targets

Kind
Protein
Organism
Human
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. [PubMed:16272152]
Kind
Protein
Organism
Human
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. [PubMed:7221567]
Kind
Protein
Organism
Human
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. [PubMed:17360702]
Kind
Protein
Organism
Human
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. [PubMed:17360702]
Kind
Protein
Organism
Human
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. [PubMed:7912402]

Transporters

Kind
Protein
Organism
Human
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. [PubMed:9812985]

Drug created on February 21, 2013 16:40 / Updated on November 02, 2018 09:13