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50-67-9

Basic Information
CAS No.: 50-67-9
Name: 1H-Indol-5-ol, 3-(2-aminoethyl)-
Article Data: 43
Cas Database
Molecular Structure:
Molecular Structure of 50-67-9 (1H-Indol-5-ol, 3-(2-aminoethyl)-)
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
Transport Information: N/A
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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;
53157-50-9

N-Cbz-5-hydroxytryptamine

50-67-9

3-(2-aminoethyl)-1H-indol-5-ol

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