Name: 5-Hydroxytryptamine
SKU: 50-67-9

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Basic Information

Molecular Structure:
CAS No.:	50-67-9
Name:	5-Hydroxytryptamine
Article Data:	43

Formula:	C₁₀H₁₂N₂O
Molecular Weight:	176.218
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;
EINECS:	200-058-9
Density:	1.288 g/cm³
Melting Point:	22-23°C(lit.)
Boiling Point:	416.089 °C at 760 mmHg
Flash Point:	205.443 °C
Solubility:	0.5 g/100 mL (25 oC)
Appearance:	White powder
Hazard Symbols:	T
Risk Codes:	63-25
Safety:	36/37-45
PSA:	62.04000
LogP:	2.07500

Synthetic route

: 147918-24-9
N-Benzyl-2-<5-(benzyloxy)-3-indolyl>-1-ethanamin

: 50-67-9
3-(2-aminoethyl)-1H-indol-5-ol

Conditions

Conditions	Yield
With palladium 10% on activated carbon; ammonium formate In methanol at 70℃; for 0.75h; Inert atmosphere;	100%

: 4350-09-8
L-5-HTP

: 50-67-9
3-(2-aminoethyl)-1H-indol-5-ol

Conditions

Conditions	Yield
With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase In various solvent(s) at 30℃; for 48h;	97%
With NH4OH-NH4Cl buffer; pyridoxal 5'-phosphate at 30℃; for 0.5h; relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus;
With isopropyl β-D-thiogalactoside; L-tryptophan decarboxylase in recombinant Escherichia coli at 28℃;

: 77549-09-8
5-hydroxy-Nb-methoxycarbonyltryptamine

: 50-67-9
3-(2-aminoethyl)-1H-indol-5-ol

Conditions

Conditions	Yield
With sodium hydroxide In methanol Heating;	73%
With sodium hydroxide In methanol for 4h; Heating;	73%

: 608-07-1
2-(5-methoxyindol-3-yl)ethylamine

: 50-67-9
3-(2-aminoethyl)-1H-indol-5-ol

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at 20℃;	65%
With aluminium trichloride; benzene

: 20776-45-8
5-benzyloxytryptamine

: 50-67-9
3-(2-aminoethyl)-1H-indol-5-ol

Conditions

Conditions	Yield
With methanol; palladium on activated charcoal Hydrogenation;
With palladium on activated charcoal; ethanol; water Hydrogenation;
With methanol; Pd-BaSO4 Hydrogenation;

: 93331-75-0
5-benzyloxy-3-(2-nitro-ethyl)-indole

: 50-67-9
3-(2-aminoethyl)-1H-indol-5-ol

Conditions

Conditions	Yield
With platinum Hydrogenation;
With palladium on activated charcoal Hydrogenation;

: 55895-70-0
[2-(5-benzyloxy-indol-3-yl)-ethyl]-carbamic acid benzyl ester

: 50-67-9
3-(2-aminoethyl)-1H-indol-5-ol

Conditions

Conditions	Yield
With hydrogenchloride; palladium on activated charcoal; ethanol Hydrogenation.und Wasser;

: 61-54-1
tryptamine

: 50-67-9
3-(2-aminoethyl)-1H-indol-5-ol

Conditions

Conditions	Yield
biotransformation by cell cultures of Peganum harmala;
With CYP71P1; NADPH; NADPH-P450 reductase at 30℃; for 0.166667h; pH=7.25; Kinetics; aq. phosphate buffer; Enzymatic reaction;

: 343-94-2
tryptamine hydochloride

A: 15700-23-9
7-Hydroxytryptamine

B: 50-67-9
3-(2-aminoethyl)-1H-indol-5-ol

C: 443-31-2
6-hydroxytryptamine

D: 570-14-9
4-Hydroxytryptamine

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide; ascorbic acid 1.) H2O, 2.) phosphate buffer (pH= 7.2, 0.1 M), 22 deg C, 2.5 min; Multistep reaction. Title compound not separated from byproducts;

...Expand

: 53157-50-9
N-Cbz-5-hydroxytryptamine

: 50-67-9
3-(2-aminoethyl)-1H-indol-5-ol

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol Yield given;

Raw Materials

56-69-9

343-94-2

Downstream Products

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History

Serotonin as originally discovered by Italian Vittorio Erspamer in Rome in 1935 and American scientists in the late 1940s. In 1948, it was isolated and named by Maurice M. Rapport, Arda Green, and Irvine Page of the Cleveland Clinic. It was initially identified as a vasoconstrictor substance in blood serum – hence serotonin, a serum agent affecting vascular tone. Serotonin was later chemically identified as 5-hydroxytryptamine (5-HT) by Rapport, and, as the broad range of physiological roles were elucidated, 5-HT became the preferred name in the pharmacological field.

Specification

The Serotonin, with the CAS registry number 50-67-9, is also known as 5-Hydroxytryptamine. It belongs to the product categories of Tryptamines; Standards - 13C & 2H for GC-Mass Spectrometry. Its EINECS number is 200-058-9. This chemical's molecular formula is C₁₀H₁₂N₂O and molecular weight is 176.21. What's more, its systematic name is 3-(2-Aminoethyl)-1H-indol-5-ol. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Neurotransmitter Agents; (3)Reproductive Effect; (4)Serotonin Agents; (5)Serotonin Receptor Agonists. This chemical is a monoamine neurotransmitter. It is used as a boiler water softener, degreasing detergent, metal corrosion inhibitor or anti-rust agent.

Physical properties of Serotonin are: (1)ACD/LogP: 0.545; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.53; (4)ACD/LogD (pH 7.4): -1.74; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 3; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 62.04 Å²; (13)Index of Refraction: 1.711; (14)Molar Refractivity: 53.495 cm³; (15)Molar Volume: 136.796 cm³; (16)Polarizability: 21.207×10^-24cm³; (17)Surface Tension: 67.0 dyne/cm; (18)Density: 1.288 g/cm³; (19)Flash Point: 205.443 °C; (20)Enthalpy of Vaporization: 69.524 kJ/mol; (21)Boiling Point: 416.089 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by 2-(5-methoxy-indol-3-yl)-ethylamine at the temperature of 20 °C. This reaction will need reagent BBr₃ and solvent CH₂Cl₂. The yield is about 65%.

Serotonin can be prepared by 2-(5-methoxy-indol-3-yl)-ethylamine at the temperature of 20 °C

Uses of Serotonin: it can be used to produce N-Benzyloxycarbonyl-5-hydroxytryptamin at the ambient temperature. It will need reagent Na₂CO₃ and solvent H₂O with the reaction time of 6 hours. The yield is about 84%.

Serotonin can be used to produce N-Benzyloxycarbonyl-5-hydroxytryptamin at the ambient temperature

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc2c(cc1O)c(c[nH]2)CCN
(2)Std. 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
(3)Std. InChIKey: QZAYGJVTTNCVMB-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LDLo	intravenous	5mg/kg (5mg/kg)	CARDIAC: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Farmakologiya i Toksikologiya Vol. 26, Pg. 10, 1963.
guinea pig	LD50	intravenous	12800ug/kg (12.8mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 168, Pg. 373, 1967.
mouse	LD50	intramuscular	750mg/kg (750mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 112, Pg. 319, 1957.
mouse	LD50	intraperitoneal	160mg/kg (160mg/kg)		Indian Journal of Physiology and Pharmacology. Vol. 17, Pg. 31, 1973.
mouse	LD50	intravenous	81mg/kg (81mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Farmakologiya i Toksikologiya Vol. 26, Pg. 10, 1963.
mouse	LD50	oral	60mg/kg (60mg/kg)		Meditsinskii Zhurnal Uzbekistana. Vol. (3), Pg. 61, 1985.
mouse	LD50	subcutaneous	601mg/kg (601mg/kg)	BEHAVIORAL: ATAXIA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Farmakologiya i Toksikologiya Vol. 26, Pg. 10, 1963.
mouse	LD50	unreported	250mg/kg (250mg/kg)		"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(1), Pg. 122, 1982.
rat	LD50	intravenous	30mg/kg (30mg/kg)		Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.
rat	LD50	subcutaneous	285mg/kg (285mg/kg)		Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.

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