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Trazodone

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Name

Trazodone

EINECS 243-317-1
CAS No. 19794-93-5 Density 1.334 g/cm3
PSA 45.78000 LogP 3.16660
Solubility N/A Melting Point 86-87oC
Formula C19H22ClN5O Boiling Point 528.532 °C at 760 mmHg
Molecular Weight 371.87 Flash Point 273.446 °C
Transport Information N/A Appearance Brown oil
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 19794-93-5 (Trazodone) Hazard Symbols N/A
Synonyms

s-Triazolo[4,3-a]pyridin-3(2H)-one,2-[3-[4-(m-chlorophenyl)-1-piperazinyl]propyl]- (8CI);Trazodon;2-{3-[4-(3-Chlorophenyl)piperazin-1-yl]propyl}[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one;

Article Data 8

Trazodone History

  Trazodone (19794-93-5) was originally discovered and developed in Italy in the 1960s by Angelini research laboratories as a second-generation antidepressant. It was developed according to the mental pain hypothesis, which was postulated from studying patients and which proposes that major depression is associated with a decreased pain threshold.[2] Trazodone was patented and marketed in many countries all over the world. It was approved by the Food and Drug Administration (FDA) at the end of 1981. It is closely related to nefazodone (Serzone).

Trazodone Specification

The Trazodone, with the CAS registry number 19794-93-5, is also known as s-Triazolo(4,3-a)pyridin-3(2H)-one, 2-(3-(4-(m-chlorophenyl)-1-piperazinyl)propyl)-. It belongs to the product categories of Active Pharmaceutical Ingredients; Trazodone; Intermediates & Fine Chemicals; Pharmaceuticals; Serotonin Receptor. Its EINECS registry number is 243-317-1. This chemical's molecular formula is C19H22ClN5O and molecular weight is 371.86388. Its IUPAC name is called 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one.

Physical properties of Trazodone: (1)ACD/LogP: 1.66; (2)ACD/LogD (pH 5.5): 0.67; (3)ACD/LogD (pH 7.4): 1.61; (4)ACD/BCF (pH 5.5): 1.09; (5)ACD/BCF (pH 7.4): 9.68; (6)ACD/KOC (pH 5.5): 19.33; (7)ACD/KOC (pH 7.4): 171.45; (8)#H bond acceptors: 6; (9)#Freely Rotating Bonds: 5; (10)Index of Refraction: 1.67; (11)Molar Refractivity: 104.24 cm3; (12)Molar Volume: 278.8 cm3; (13)Surface Tension: 55 dyne/cm; (14)Density: 1.33 g/cm3; (15)Flash Point: 273.4 °C; (16)Enthalpy of Vaporization: 80.34 kJ/mol; (17)Boiling Point: 528.5 °C at 760 mmHg; (18)Vapour Pressure: 2.94E-11 mmHg at 25°C.

Preparation of Trazodone: This chemical can be perapared as the following steps:

Trazodone can be perapared as these steps

Uses: Trazodone also has anxiolytic, and hypnotic effects. Trazodone has considerably less prominent anticholinergic (dry mouth, constipation, tachycardia) and sexual side effects than most of the tricyclic antidepressants (TCAs).

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1CN(CCN1CCCN2C(=O)N3C=CC=CC3=N2)C4=CC(=CC=C4)Cl
(2)InChI: InChI=1S/C19H22ClN5O/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25/h1-3,5-7,9,15H,4,8,10-14H2
(3)InChIKey: PHLBKPHSAVXXEF-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 475mg/kg (475mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 21, Pg. 401, 1981.
mouse LD50 intraperitoneal 210mg/kg (210mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 21, Pg. 401, 1981.
mouse LD50 intravenous 91mg/kg (91mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 21, Pg. 401, 1981.
mouse LD50 oral 610mg/kg (610mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 21, Pg. 401, 1981.
mouse LD50 subcutaneous > 1gm/kg (1000mg/kg)   Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 21, Pg. 401, 1981.
rat LD50 intramuscular > 1gm/kg (1000mg/kg)   Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 21, Pg. 401, 1981.
rat LD50 intraperitoneal 178mg/kg (178mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 21, Pg. 401, 1981.
rat LD50 intravenous 91mg/kg (91mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 21, Pg. 401, 1981.
rat LD50 oral 690mg/kg (690mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 21, Pg. 401, 1981.
rat LD50 subcutaneous > 1gm/kg (1000mg/kg)   Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 21, Pg. 401, 1981.
women TDLo oral 8mg/kg/4D-I (8mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: EXCITEMENT
International Clinical Psychopharmacology. Vol. 13, Pg. 225, 1998.
women TDLo oral 14mg/kg (14mg/kg) LIVER: "JAUNDICE, CHOLESTATIC" Annals of Internal Medicine. Vol. 99, Pg. 572, 1983.
women TDLo oral 20mg/kg (20mg/kg) BEHAVIORAL: GENERAL ANESTHETIC Psychopathology. Vol. 17(Suppl,

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