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25332-39-2

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25332-39-2 Usage

Description

Trazodone Hydrochloride belongs to the hydrochloride salt form of trazodone with antidepressant and sedative activities, which is primarily used in the treatment of major depression. It serves as a serotonin uptake inhibitor that is effective for patients suffering from major depressive disorders and other subsets of depressive disorders, which is especially helpful for geriatric patients with severe agitation and certain depressive disorders associated with insomnia and anxiety since it has proved that trazodone also has anti-anxiety (anxiolytic) and sleep-inducing (hypnotic) effects. Besides, it is often prescribed as a sedative that is used for the treatment of panic attacks, aggressive behavior, agoraphobia, and cocaine withdrawal in combination with other drugs. Trazodone Hydrochloride is an oral drug that functions by affecting the balance of chemicals (neurotransmitters) within the brain that nerves use to communicate with (stimulate) each other.

References

https://en.wikipedia.org/wiki/Trazodone http://www.medicinenet.com/trazodone/article.htm https://www.drugbank.ca/drugs/DB00656 http://bodyandhealth.canada.com/drug/getdrug/ratio-trazodone https://pubchem.ncbi.nlm.nih.gov/compound/62935#section=Top

Chemical Properties

White to Off-White Solid

Uses

Different sources of media describe the Uses of 25332-39-2 differently. You can refer to the following data:
1. A serotonin uptake inhibitor
2. antihistamine
3. Monoamine reuptake inhibitor; antidepressant.

Definition

ChEBI: A hydrochloride salt prepared from equimolar amounts of trazodone and hydrogen chloride.

Therapeutic Function

Tranquilizer

General Description

Trazodone is a antidepressant drug sold under trade names such as Desyrel? and Oleptro? for treatment of anxiety disorder, depression, and insomnia. Trazadone, a serotonin antagonist and reuptake inhibitor (SARI), also has anti-anxiety and hypnotic effects. This certified Snap-N-Spike? solution is suitable for use in clinical toxicology, forensic analysis, or urine drug testing methods by LC-MS/MS or GC/MS.

Biochem/physiol Actions

Antidepressant that potentiates the activity of serotonin uptake blockers and has full 5-HT2C serotonin receptor agonist activity. It is metabolized to the 5-HT1 serotonin receptor agonist 1-(3-Chlorophenyl)piperazine.

Clinical Use

Tricyclic-related antidepressant

Drug interactions

Potentially hazardous interactions with other drugs Alcohol: increased sedative effects. Antidepressants: avoid concomitant use with MAOIs and moclobemide. Antiepileptics: antagonism of anticonvulsant effect; concentration reduced by carbamazepine. Antimalarials: manufacturer advises avoid concomitant use with artemether and lumefantrine and piperaquine with artenimol. Antivirals: concentration increased by ritonavir; increased risk of ventricular arrhythmias with saquinavir - avoid; concentration possibly increased by telaprevir.

Metabolism

Trazodone is hepatically metabolised via the cytochrome P450 isoenzyme CYP3A4 by n-oxidation and hydroxylation. The metabolite m-chlorophenylpiperazine is active. Trazodone is excreted in the urine almost entirely in the form of its metabolites.

Check Digit Verification of cas no

The CAS Registry Mumber 25332-39-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,3,3 and 2 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 25332-39:
(7*2)+(6*5)+(5*3)+(4*3)+(3*2)+(2*3)+(1*9)=92
92 % 10 = 2
So 25332-39-2 is a valid CAS Registry Number.
InChI:InChI=1/C19H22ClN5O.ClH/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;1H

25332-39-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • USP

  • (1673500)  Trazodone hydrochloride  United States Pharmacopeia (USP) Reference Standard

  • 25332-39-2

  • 1673500-200MG

  • 4,647.24CNY

  • Detail
  • Sigma

  • (T6154)  Trazodone hydrochloride  ≥99% (HPLC), powder

  • 25332-39-2

  • T6154-1G

  • 590.85CNY

  • Detail
  • Sigma

  • (T6154)  Trazodone hydrochloride  ≥99% (HPLC), powder

  • 25332-39-2

  • T6154-5G

  • 1,456.65CNY

  • Detail
  • Cerilliant

  • (T-030)  Trazodone hydrochloride solution  1.0 mg/mL in methanol (as free base), ampule of 1 mL, certified reference material

  • 25332-39-2

  • T-030-1ML

  • 366.21CNY

  • Detail

25332-39-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name trazodone hydrochloride

1.2 Other means of identification

Product number -
Other names BiMaran

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:25332-39-2 SDS

25332-39-2Synthetic route

2-(3-bromopropyl)-1,2,4-triazolo[4,3-a]pyridin-3-(2H)-one

2-(3-bromopropyl)-1,2,4-triazolo[4,3-a]pyridin-3-(2H)-one

1-(3-chlorophenyl)piperazine hydrochloride
13078-15-4

1-(3-chlorophenyl)piperazine hydrochloride

trazodone hydrochloride
25332-39-2

trazodone hydrochloride

Conditions
ConditionsYield
Stage #1: 2-(3-bromopropyl)[1,2,4]triazolo[4,3-a]pyridine-3(2H)-one; 1-(3-chlorophenyl)piperazine hydrochloride With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide for 0.0166667h; Microwave irradiation;
Stage #2: With hydrogenchloride In 1,4-dioxane; acetone Solvent; Reagent/catalyst;
98%
trazodone
19794-93-5

trazodone

trazodone hydrochloride
25332-39-2

trazodone hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 60℃; for 2h; pH=3;93%
With hydrogenchloride In water; acetone at 50℃; pH=3 - 4;90%
With hydrogenchloride In water; acetone pH=3 - 4; Product distribution / selectivity;87%
1-(3-chlorophenyl)piperazine hydrochloride
13078-15-4

1-(3-chlorophenyl)piperazine hydrochloride

2-(3-chloropropyl)-1,2,4-triazolo<4,3-a>pyridin-3-one
19666-40-1

2-(3-chloropropyl)-1,2,4-triazolo<4,3-a>pyridin-3-one

trazodone hydrochloride
25332-39-2

trazodone hydrochloride

Conditions
ConditionsYield
Stage #1: 1-(3-chlorophenyl)piperazine hydrochloride; 2-(3-chloropropyl)-1,2,4-triazolo<4,3-a>pyridin-3-one With tetrabutylammomium bromide; potassium carbonate In acetonitrile for 0.0166667h; Microwave irradiation;
Stage #2: With hydrogenchloride In 1,4-dioxane; acetone Solvent;
90%
1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine hydrochloride
52605-52-4

1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine hydrochloride

1,2,4-triazolo<4,3-a>pyridin-3(2H)-one sodium salt

1,2,4-triazolo<4,3-a>pyridin-3(2H)-one sodium salt

trazodone hydrochloride
25332-39-2

trazodone hydrochloride

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium carbonate In isopropyl alcohol at 80 - 85℃; for 12h; Reagent/catalyst;83%
2-chloropyridine
109-09-1

2-chloropyridine

trazodone hydrochloride
25332-39-2

trazodone hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / 2-ethoxy-ethanol / 0.03 h / Microwave irradiation
2: potassium carbonate; tetrabutylammomium bromide / acetonitrile / Microwave irradiation
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid / 2-ethoxy-ethanol / 0.03 h / Microwave irradiation
2: potassium carbonate; tetrabutylammomium bromide / acetonitrile / 0.02 h / Microwave irradiation
3: potassium carbonate; tetrabutylammomium bromide / acetonitrile / 0.02 h / Microwave irradiation
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid / 2-ethoxy-ethanol / 0.03 h / Microwave irradiation
2: potassium carbonate; tetrabutylammomium bromide / acetonitrile / 0.03 h / Microwave irradiation
3: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 0.02 h / Microwave irradiation
View Scheme
[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one
6969-71-7

[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

trazodone hydrochloride
25332-39-2

trazodone hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate; tetrabutylammomium bromide / acetonitrile / 0.02 h / Microwave irradiation
2: potassium carbonate; tetrabutylammomium bromide / acetonitrile / 0.02 h / Microwave irradiation
View Scheme
1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine hydrochloride
52605-52-4

1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine hydrochloride

[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one
6969-71-7

[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

trazodone hydrochloride
25332-39-2

trazodone hydrochloride

Conditions
ConditionsYield
Stage #1: 1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine hydrochloride; [1,2,4]triazolo[4,3-a]pyridin-3(2H)-one With tetrabutylammomium bromide; potassium carbonate In acetonitrile Microwave irradiation;
Stage #2: With hydrogenchloride In 1,4-dioxane; acetone
2-bromo-pyridine
109-04-6

2-bromo-pyridine

trazodone hydrochloride
25332-39-2

trazodone hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / 2-ethoxy-ethanol / 0.03 h / Microwave irradiation
2: potassium carbonate; tetrabutylammomium bromide / acetonitrile / Microwave irradiation
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid / 2-ethoxy-ethanol / 0.03 h / Microwave irradiation
2: potassium carbonate; tetrabutylammomium bromide / acetonitrile / 0.02 h / Microwave irradiation
3: potassium carbonate; tetrabutylammomium bromide / acetonitrile / 0.02 h / Microwave irradiation
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid / 2-ethoxy-ethanol / 0.03 h / Microwave irradiation
2: potassium carbonate; tetrabutylammomium bromide / acetonitrile / 0.03 h / Microwave irradiation
3: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 0.02 h / Microwave irradiation
View Scheme
pyrid-2-ylhydrazine
4930-98-7

pyrid-2-ylhydrazine

trazodone hydrochloride
25332-39-2

trazodone hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: neat (no solvent) / 0.01 h / Microwave irradiation
2: potassium carbonate; tetrabutylammomium bromide / acetonitrile / Microwave irradiation
View Scheme
Multi-step reaction with 3 steps
1: neat (no solvent) / 0.01 h / Microwave irradiation
2: potassium carbonate; tetrabutylammomium bromide / acetonitrile / 0.02 h / Microwave irradiation
3: potassium carbonate; tetrabutylammomium bromide / acetonitrile / 0.02 h / Microwave irradiation
View Scheme
Multi-step reaction with 3 steps
1: neat (no solvent) / 0.01 h / Microwave irradiation
2: potassium carbonate; tetrabutylammomium bromide / acetonitrile / 0.03 h / Microwave irradiation
3: potassium carbonate; tetrabutylammomium bromide / N,N-dimethyl-formamide / 0.02 h / Microwave irradiation
View Scheme
N-(m-chlorophenyl)piperazine
6640-24-0

N-(m-chlorophenyl)piperazine

trazodone hydrochloride
25332-39-2

trazodone hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / water; 1-methyl-pyrrolidin-2-one / 88 °C / Flow reactor
2: sodium hydroxide / water; acetonitrile / 150 °C / Flow reactor
3: hydrogenchloride / water; acetone / 50 °C / pH 3 - 4
View Scheme
2-(2-methylphenyl)pyridine
10273-89-9

2-(2-methylphenyl)pyridine

trazodone hydrochloride
25332-39-2

trazodone hydrochloride

C31H32N6O

C31H32N6O

Conditions
ConditionsYield
With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 50℃; for 24h; Glovebox; Inert atmosphere;93%
ammonium thiocyanate

ammonium thiocyanate

ammonium molybdate

ammonium molybdate

trazodone hydrochloride
25332-39-2

trazodone hydrochloride

[trazodone(+1H)][Mo(thiocyanato)6]

[trazodone(+1H)][Mo(thiocyanato)6]

Conditions
ConditionsYield
With nitric acid; ascorbic acid In water addn. of soln. of molybdenum (VI) to nitric acid, ammonium thiocyanate and ascorbic acid; standing at 20°C for 15 min; addn. of trazodonehydrochloride; dilution with H2O; standing for 15 min; extn. with CH2Cl2 with shaking for 1 min; filtration, monitoring by UV;
With hydrogenchloride; ascorbic acid In water Kinetics; addn. of soln. of molybdenum (VI) to 4 M HCl, NH4SCN and ascorbic acid; standing at 20°C for 15 min; addn. of trazodone hydrochloride; dilution with H2O; standing for 15 min; extn. with CH2Cl2 with shaking for 1 min; filtration, monitoring by UV;
With sulfuric acid; ascorbic acid In water addn. of soln. of molybdenum (VI) to NH4SCN, H2SO4 and ascorbic acid; standing at 20°C for 15 min; addn. of trazodone hydrochloride; dilution with H2O; standing for 15 min; extn. with CH2Cl2 with shaking for 1 min; filtration, monitoring by UV;
trazodone hydrochloride
25332-39-2

trazodone hydrochloride

trazodone hydrogen iodide

trazodone hydrogen iodide

Conditions
ConditionsYield
With sodium iodide In water
trazodone hydrochloride
25332-39-2

trazodone hydrochloride

A

1-(3-chlorophenyl)-4-(3-(3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)propyl)piperazine 1,4-dioxide

1-(3-chlorophenyl)-4-(3-(3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)propyl)piperazine 1,4-dioxide

B

1-(3-chlorophenyl)-4-(3-(3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)propyl)piperazine 1-oxide

1-(3-chlorophenyl)-4-(3-(3-oxo-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)propyl)piperazine 1-oxide

C

4‐(3‐chlorophenyl)‐1‐(3‐(3‐oxo‐[1,2,4]triazolo[4,3‐a]pyridin‐2(3H)‐yl)propyl)piperazine 1‐oxide
55290-68-1

4‐(3‐chlorophenyl)‐1‐(3‐(3‐oxo‐[1,2,4]triazolo[4,3‐a]pyridin‐2(3H)‐yl)propyl)piperazine 1‐oxide

Conditions
ConditionsYield
With dihydrogen peroxide In water at 20℃; for 24h;
trazodone hydrochloride
25332-39-2

trazodone hydrochloride

A

2-(3-(4-(3,5-dichlorophenyl)piperazin-1-yl)propyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

2-(3-(4-(3,5-dichlorophenyl)piperazin-1-yl)propyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

B

2-(3-((2-((3-chlorophenyl)amino)ethyl)amino)propyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one
220910-12-3

2-(3-((2-((3-chlorophenyl)amino)ethyl)amino)propyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Conditions
ConditionsYield
With hydrogenchloride; water at 70℃; for 24h;
trazodone hydrochloride
25332-39-2

trazodone hydrochloride

A

2-(3-(4-(3-hydroxyphenyl)piperazin-1-yl)propyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

2-(3-(4-(3-hydroxyphenyl)piperazin-1-yl)propyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

B

C38H44Cl2N10O2

C38H44Cl2N10O2

Conditions
ConditionsYield
In water UV-irradiation;
trazodone hydrochloride
25332-39-2

trazodone hydrochloride

C38H44Cl2N10O2

C38H44Cl2N10O2

Conditions
ConditionsYield
Irradiation;

25332-39-2Relevant articles and documents

CONTINUOUS PROCESS FOR THE PREPARATION OF TRAZODONE

-

, (2019/08/29)

The present invention relates to an improved process for the preparation of trazodone. In particular, the present invention relates to a continuous process for the preparation of trazodone. More in particular, the present invention relates to a new method for the preparation of trazodone, said method comprising at least one step consisting of a continuous process performed in a flow reactor.

Preparation method of trazodone hydrochloride

-

Paragraph 0046; 0047, (2016/12/01)

The invention is applicable to the field of chemistry and chemical engineering and provides a preparation method of trazodone hydrochloride. The preparation method comprises the following steps: mixing N-(3-chloro-phenyl)-N'-(3-chloropropyl)-piperazine hydrochloride and 1,2,4-triazolo[4,3-a]pyridin-3(2H)-one in a solvent; adding an alkali, and heating and reflowing; carrying out heat filtering into a reaction system, adding alkali liquid and heating and reflowing again in sequence; crystallizing to obtain trazodone; taking the trazodone to react with hydrochloric acid to obtain the trazodone hydrochloride. According to the preparation method of the trazodone hydrochloride, provided by the invention, the total yield of the product is improved, and the content of an impurity N-(3-chloro-phenyl)-N'-(3-chloropropyl)-piperazine is remarkably reduced, so that the industry limitation requirements can be directly met. The preparation method has simple flow steps so that the production cost is reduced; the process is stable and industrial production can be carried out.

TRAZODONE AND TRAZODONE HYDROCHLORIDE IN PURIFIED FORM

-

Page/Page column 13-16, (2009/04/25)

A process of production of trazodone or trazodone hydrochloride that comprises the steps of: (a) preparing an organic phase comprising trazodone in at least one organic solvent; (b) preparing an aqueous phase comprising at least one basic compound; (c) mixing said aqueous phase with said organic phase; (d) heating at a temperature o at least 40°C for at least 30 minutes; (e) recovering said trazodone; and, optionally, (f) treating said trazodone with hydrochloric acid to obtain trazodone hydrochloride. Trazodone or trazodone hydrochloride comprising less than 15 ppm of alkylating substances, and a pharmaceutical composition comprising said trazodone hydrochloride.

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