Back سيروتونين Arabic سيروتونين ARZ Serotonina AST Serotonin Azerbaijani سروتونین AZB Сератанін Byelorussian Сэратанін BE-X-OLD Серотонин Bulgarian সেরোটোনিন Bengali/Bangla Serotonin BS

Serotonin

For other uses, see Serotonin (disambiguation).

Serotonin
Skeletal formula of serotonin
Clinical data
Other names5-HT, 5-Hydroxytryptamine, Enteramine, Thrombocytin, 3-(β-Aminoethyl)-5-hydroxyl solution , Thrombotonin
Physiological data
Source tissuesraphe nuclei, enterochromaffin cells
Target tissuessystem-wide
Receptors5-HT1, 5-HT2, 5-HT3, 5-HT4, 5-HT5, 5-HT6, 5-HT7
AgonistsIndirectly: SSRIs, MAOIs
Precursor5-HTP
BiosynthesisAromatic L-amino acid decarboxylase
MetabolismMAO
Identifiers
  • 3-(2-Aminoethyl)-1H-indol-5-ol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
KEGG
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.054 Edit this at Wikidata
Serotonin
Ball-and-stick model of the serotonin molecule
Ball-and-stick model of the serotonin molecule
Names
IUPAC name
5-Hydroxytryptamine
Preferred IUPAC name
3-(2-Aminoethyl)-1H-indol-5-ol
Other names
5-Hydroxytryptamine, 5-HT, Enteramine; Thrombocytin, 3-(β-Aminoethyl)-5-hydroxyindole, 3-(2-Aminoethyl)indol-5-ol, Thrombotonin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.054 Edit this at Wikidata
KEGG
MeSH Serotonin
UNII
  • 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 checkY
    Key: QZAYGJVTTNCVMB-UHFFFAOYSA-N checkY
  • InChI=1/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
    Key: QZAYGJVTTNCVMB-UHFFFAOYAX
  • C1=CC2=C(C=C1O)C(=CN2)CCN
Properties
C10H12N2O
Molar mass 176.215 g/mol
Appearance White powder
Melting point 167.7 °C (333.9 °F; 440.8 K) 121–122 °C (ligroin)[3]
Boiling point 416 ± 30 °C (at 760 Torr)[1]
slightly soluble
Acidity (pKa) 10.16 in water at 23.5 °C[2]
2.98 D
Hazards
Lethal dose or concentration (LD, LC):
750 mg/kg (subcutaneous, rat),[4] 4500 mg/kg (intraperitoneal, rat),[5] 60 mg/kg (oral, rat)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Serotonin (/ˌsɛrəˈtoʊnɪn, ˌsɪərə-/)[6][7][8], also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and peripheral tissues. It is involved in mood, cognition, reward, learning, memory, and physiological processes such as vomiting and vasoconstriction.[9] In the CNS, serotonin regulates mood, appetite, and sleep.[10][unreliable medical source][11][unreliable medical source]

Most of the body's serotonin—about 90%—is synthesized in the gastrointestinal tract by enterochromaffin cells, where it regulates intestinal movements.[12][13][14] It is also produced in smaller amounts in the brainstem's raphe nuclei, the skin's Merkel cells, pulmonary neuroendocrine cells, and taste receptor cells of the tongue. Once secreted, serotonin is taken up by platelets in the blood, which release it during clotting to promote vasoconstriction and platelet aggregation.[15] Around 8% of the body's serotonin is stored in platelets, and 1–2% is found in the CNS.[16]

Serotonin acts as both a vasoconstrictor and vasodilator depending on concentration and context, influencing hemostasis and blood pressure regulation.[17] It plays a role in stimulating myenteric neurons and enhancing gastrointestinal motility through uptake and release cycles in platelets and surrounding tissue.[18] Biochemically, serotonin is an indoleamine synthesized from tryptophan and metabolized primarily in the liver to 5-hydroxyindoleacetic acid (5-HIAA).

Serotonin is targeted by several classes of antidepressants, including selective serotonin reuptake inhibitors (SSRIs) and serotonin–norepinephrine reuptake inhibitors (SNRIs), which block reabsorption in the synapse to elevate its levels. It is found in nearly all bilateral animals, including insects and worms,[19] and also occurs in fungi and plants.[20] In plants and insect venom, it serves a defensive function by inducing pain.[21] Serotonin released by pathogenic amoebae may cause diarrhea in the human gut,[22] while its presence in seeds and fruits is thought to stimulate digestion and facilitate seed dispersal.[23][failed verification]

  1. ^ Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994–2011 ACD/Labs)
  2. ^ Mazák K, Dóczy V, Kökösi J, Noszál B (April 2009). "Proton speciation and microspeciation of serotonin and 5-hydroxytryptophan". Chemistry & Biodiversity. 6 (4): 578–590. doi:10.1002/cbdv.200800087. PMID 19353542. S2CID 20543931.
  3. ^ Pietra S (1958). "[Indolic derivatives. II. A new way to synthesize serotonin]". Il Farmaco; Edizione Scientifica (in Italian). 13 (1): 75–79. PMID 13524273.
  4. ^ Erspamer V (1952). "Ricerche preliminari sulle indolalchilamine e sulle fenilalchilamine degli estratti di pelle di Anfibio". Ricerca Scientifica. 22: 694–702.
  5. ^ Tammisto T (1967). "Increased toxicity of 5-hydroxytryptamine by ethanol in rats and mice". Annales Medicinae Experimentalis et Biologiae Fenniae. 46 (3): 382–384. PMID 5734241.
  6. ^ Jones D (2003) [1917]. Roach P, Hartmann J, Setter J (eds.). English Pronouncing Dictionary. Cambridge: Cambridge University Press. ISBN 978-3-12-539683-8.
  7. ^ "Serotonin". Dictionary.com Unabridged (Online). n.d.
  8. ^ "Serotonin". Merriam-Webster.com Dictionary. Merriam-Webster.
  9. ^ Young SN (November 2007). "How to increase serotonin in the human brain without drugs". Journal of Psychiatry & Neuroscience. 32 (6): 394–399. PMC 2077351. PMID 18043762.
  10. ^ Sangare A, Dubourget R, Geoffroy H, Gallopin T, Rancillac A (October 2016). "Serotonin differentially modulates excitatory and inhibitory synaptic inputs to putative sleep-promoting neurons of the ventrolateral preoptic nucleus" (PDF). Neuropharmacology. 109: 29–40. doi:10.1016/j.neuropharm.2016.05.015. PMID 27238836.
  11. ^ Rancillac A (November 2016). "Serotonin and sleep-promoting neurons". Oncotarget. 7 (48): 78222–78223. doi:10.18632/oncotarget.13419. PMC 5346632. PMID 27861160.
  12. ^ "Microbes Help Produce Serotonin in Gut". California Institute of Technology. 9 April 2015. Retrieved 3 June 2022.
  13. ^ King MW. "Serotonin". The Medical Biochemistry Page. Indiana University School of Medicine. Retrieved 1 December 2009.
  14. ^ Berger M, Gray JA, Roth BL (2009). "The expanded biology of serotonin". Annual Review of Medicine. 60: 355–366. doi:10.1146/annurev.med.60.042307.110802. PMC 5864293. PMID 19630576.
  15. ^ Schlienger RG, Meier CR (2003). "Effect of selective serotonin reuptake inhibitors on platelet activation: can they prevent acute myocardial infarction?". American Journal of Cardiovascular Drugs. 3 (3): 149–162. doi:10.2165/00129784-200303030-00001. PMID 14727927. S2CID 23986530.
  16. ^ Kling A (2013). 5-HT2A: a serotonin receptor with a possible role in joint diseases (PDF) (Thesis). Umeå Universitet. ISBN 978-91-7459-549-9.
  17. ^ Vanhoutte PM (February 1987). "Serotonin and the vascular wall". International Journal of Cardiology. 14 (2): 189–203. doi:10.1016/0167-5273(87)90008-8. PMID 3818135.
  18. ^ Yano JM, Yu K, Donaldson GP, Shastri GG, Ann P, Ma L, et al. (April 2015). "Indigenous bacteria from the gut microbiota regulate host serotonin biosynthesis". Cell. 161 (2): 264–276. doi:10.1016/j.cell.2015.02.047. PMC 4393509. PMID 25860609.
  19. ^ Huser A, Rohwedder A, Apostolopoulou AA, Widmann A, Pfitzenmaier JE, Maiolo EM, et al. (2012). Zars T (ed.). "The serotonergic central nervous system of the Drosophila larva: anatomy and behavioral function". PLOS ONE. 7 (10): e47518. Bibcode:2012PLoSO...747518H. doi:10.1371/journal.pone.0047518. PMC 3474743. PMID 23082175.
  20. ^ Ramakrishna A, Giridhar P, Ravishankar GA (June 2011). "Phytoserotonin: a review". Plant Signaling & Behavior. 6 (6): 800–809. Bibcode:2011PlSiB...6..800A. doi:10.4161/psb.6.6.15242. PMC 3218476. PMID 21617371.
  21. ^ Erspamer V (1966). "Occurrence of indolealkylamines in nature". 5-Hydroxytryptamine and Related Indolealkylamines. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 132–181. doi:10.1007/978-3-642-85467-5_4. ISBN 978-3-642-85469-9.
  22. ^ Cite error: The named reference pmid6308760 was invoked but never defined (see the help page).
  23. ^ Cite error: The named reference feld was invoked but never defined (see the help page).

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