5-Hydroxytryptamine

Base Information

• Chemical Name: 5-Hydroxytryptamine
• CAS No.: 50-67-9
• Molecular Formula: C10H12N2O
• Molecular Weight: 176.218
• Hs Code.: 29071400
• European Community (EC) Number: 200-058-9
• UNII: 333DO1RDJY
• DSSTox Substance ID: DTXSID8075330
• Nikkaji Number: J4.107F
• Wikipedia: Serotonin
• Wikidata: Q167934
• NCI Thesaurus Code: C828
• Pharos Ligand ID: MNAP8MWU6R2P
• Metabolomics Workbench ID: 37167
• ChEMBL ID: CHEMBL39
• Mol file: 50-67-9.mol

Synonyms:Indol-5-ol,3-(2-aminoethyl)- (6CI,8CI);3-(2-Aminoethyl)indol-5-ol;3-(b-Aminoethyl)-5-hydroxyindole;5-Hydroxy-3-(b-aminoethyl)indole;Tryptamine, 5-hydroxy-;5-Hydroxytryptamine;

Chemical Property of 5-Hydroxytryptamine

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.63E-07mmHg at 25°C
• Melting Point: 22-23°C(lit.)
• Refractive Index: 1.71
• Boiling Point: 416.089 °C at 760 mmHg
• PKA: 9.8(at 25℃)
• Flash Point: 205.443 °C
• PSA: 62.04000
• Density: 1.288 g/cm³
• LogP: 2.07500
• Storage Temp.: 2-8°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 176.094963011
• Heavy Atom Count: 13
• Complexity: 174

Purity/Quality:

Serotonin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 63-25
• Safety Statements: 36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)C(=CN2)CCN
• Recent ClinicalTrials: Effect of Oral 5-HTP Intake on Urinary 5-HIAA Excretion
• Recent NIPH Clinical Trials: A randomised controlled trial of treatment with SSRI or SNRI for patients with functional (psychogenic) dizziness
• Description: Serotonin 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.
• Uses: neurotransmitter
• Biological Functions: Serotonin (5-hydroxytryptamine, or 5HT) is present in the brain as well as in the periphery. In humans, about 90% of the total serotonin in the body is in enterochromaffin cells in the gastrointestinal tract; the remaining 10% occurs primarily in the platelets and brain. The physiological significance of the vast amounts of serotonin constantly synthesized and metabolized in the periphery still remains an enigma. Brain serotonin has been implicated as a potential neurotransmitter in the mediation of a wide variety of phenomena.
• Clinical Use: Initially, serotonin was thought to be a sleep-promoting neurotransmitter or an “antiwaking” agent. The recognition of the numerous 5-HT receptor subtypes, often with unique anatomical distribution, has required that a more complex role for serotonin be developed. Current studies indicate that conditions for sleep are now met when the serotoninergic system becomes inactive. The serotonin agonists for the 5-HT1 (via the 5-HT1A and 5-HT1B types at the hypothalamic level), 5-HT2, and 5-HT3 receptors cause wakefulness and inhibit sleep. Blockade of the 5-HT2 receptors (e.g., the 5-HT2 antagonist ritanserin) results in increased NREM sleep and inhibition of REM sleep. It has been proposed that the 5-HT1A and 5- HT2 may be involved in sleep by regulation of sleep-promoting substances in the hypothalamus. With the development of newer and more selective ligands for use in studying the numerous serotonin receptor subtypes, a better understanding of the role of serotonin in sleep will evolve.

Technology Process of 5-Hydroxytryptamine

There total 44 articles about 5-Hydroxytryptamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N-Benzyl-2-<5-(benzyloxy)-3-indolyl>-1-ethanamin (147918-24-9) → 3-(2-aminoethyl)-1H-indol-5-ol (50-67-9)

Guidance literature:

With palladium 10% on activated carbon; ammonium formate; In methanol; at 70 ℃; for 0.75h; Inert atmosphere;

DOI:10.1016/j.tet.2016.03.007

Reference yield: 97.0%

L-5-HTP (4350-09-8,4298-20-8) → 3-(2-aminoethyl)-1H-indol-5-ol (50-67-9)

Guidance literature:

With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase; In various solvent(s); at 30 ℃; for 48h;

Reference yield: 73.0%

5-hydroxy-Nb-methoxycarbonyltryptamine (77549-09-8) → 3-(2-aminoethyl)-1H-indol-5-ol (50-67-9)

Guidance literature:

With sodium hydroxide; In methanol; Heating;

upstream raw materials:

2-(5-methoxyindol-3-yl)ethylamine

5-benzyloxytryptamine

5-benzyloxy-3-(2-nitro-ethyl)-indole

[2-(5-benzyloxy-indol-3-yl)-ethyl]-carbamic acid benzyl ester

Downstream raw materials:

(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide

N-p-coumaroylserotonin

N-acetyl-5-hydroxytryptamine

N-methylserotonin

Refernces

• 1、 Cabrera, Ricardo,Filevich, Oscar,García-Acosta, Beatriz,Athilingam, Jegath,Bender, Kevin J.,Poskanzer, Kira E.,Etchenique, Roberto. "A Visible-Light-Sensitive Caged Serotonin". . p. 1036 - 1042. Retrieved 2017.
• 2、 Park, Munyoung,Kang, Kiyoon,Park, Sangkyu,Back, Kyoungwhan. "Conversion of 5-hydroxytryptophan into serotonin by tryptophan decarboxylase in plants, Escherichia coli, and yeast". . p. 2456 - 2458. Retrieved 2008.
• 3、 Torrens-Spence, Michael P.,Lazear, Michael,Von Guggenberg, Renee,Ding, Haizhen,Li, Jianyong. "Investigation of a substrate-specifying residue within Papaver somniferum and Catharanthus roseus aromatic amino acid decarboxylases". . p. 37 - 43. Retrieved 2014.
• 4、 Courtois, Didier,Yvernel, Daniel,Florin, Bruno,Petiard, Vincent. "CONVERSION OF TRYPTAMINE TO SEROTONIN BY CELL SUSPENSION CULTURES OF PEGANUM HARMALA". . p. 3137 - 3142. Retrieved 1988.
• 5、 MacDowell, Karina S.,Munarriz-Cuezva, Eva,Meana, J. Javier,Leza, Juan C.,Ortega, Jorge E.. "Paliperidone Reversion of Maternal Immune Activation-Induced Changes on Brain Serotonin and Kynurenine Pathways". . . Retrieved 2021/06/07.
• 6、 McDonald, Allwin D.,Perkins, Lydia J.,Buller, Andrew R.. "Facile in Vitro Biocatalytic Production of Diverse Tryptamines". . p. 1939 - 1944. Retrieved 2019/07/08.