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Name |
Trazodone hydrochloride |
EINECS | 246-855-5 |
CAS No. | 25332-39-2 | Density | N/A |
PSA | 45.78000 | LogP | 3.16660 |
Solubility | Soluble at 25mg/ml in methanol. Also soluble in 0.1M HCl or DMSO. Insoluble in water /n | Melting Point |
223oC |
Formula | C19H23Cl2N5O | Boiling Point | 528.5 °C at 760 mmHg |
Molecular Weight | 408.331 | Flash Point | 273.4 °C |
Transport Information | UN 3249 | Appearance | N/A |
Safety | 22-36-37/39-26 | Risk Codes | 22-40-36/37/38 |
Molecular Structure | Hazard Symbols | Xn,Xi | |
Synonyms |
s-Triazolo[4,3-a]pyridin-3(2H)-one,2-[3-[4-(m-chlorophenyl)-1-piperazinyl]propyl]-, monohydrochloride (8CI);AF1161;Bimaran;Desyrel;KB 831;Mesyrel;Molipaxin;Pragmazone;Thombran;Tombran;Trazolan;Trittico;Trazodone HCL; |
Article Data | 5 |
1-(3-chlorophenyl)piperazine hydrochloride
trazodone hydrochloride
Conditions | Yield |
---|---|
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
trazodone hydrochloride
Conditions | Yield |
---|---|
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
2-(3-chloropropyl)-1,2,4-triazolo<4,3-a>pyridin-3-one
trazodone hydrochloride
Conditions | Yield |
---|---|
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
trazodone hydrochloride
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium carbonate In isopropyl alcohol at 80 - 85℃; for 12h; Reagent/catalyst; | 83% |
2-chloropyridine
trazodone hydrochloride
Conditions | Yield |
---|---|
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
trazodone hydrochloride
Conditions | Yield |
---|---|
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
[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one
trazodone hydrochloride
Conditions | Yield |
---|---|
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
trazodone hydrochloride
Conditions | Yield |
---|---|
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
trazodone hydrochloride
Conditions | Yield |
---|---|
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
trazodone hydrochloride
Conditions | Yield |
---|---|
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 |
The CAS registry number of Trazodone hydrochloride is 25332-39-2. The IUPAC name is 2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one hydrochloride (1:1). Its EINECS registry number is 246-855-5. In addition, the formula is C19H23Cl2N5O and the molecular weight is 408.32482. It is a kind of off-white powder.
Physical properties about this chemical are: (1)ACD/LogP: 1.66; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.67; (4)ACD/LogD (pH 7.4): 1.61; (5)ACD/BCF (pH 5.5): 1.09; (6)ACD/BCF (pH 7.4): 9.68; (7)ACD/KOC (pH 5.5): 19.33; (8)ACD/KOC (pH 7.4): 171.45; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 42.39 Å2 ; (13)Flash Point: 273.4 °C; (14)Enthalpy of Vaporization: 80.34 kJ/mol; (15)Boiling Point: 528.5 °C at 760 mmHg; (16)Vapour Pressure: 2.94E-11 mmHg at 25°C.
Preparation of Trazodone hydrochloride: at first, we should use 2-chloropyridine and hydratehydrazine to prepare pyridinehydrazine. The reaction time is 24 hours by stirring. In this reaction, we should use diethyl ether to extract the product. Then we can use urea and pyridinehydrazine to prepare 1,2,4-triazolo-[4,3-a]pyridine-3(2H)-one. The reaction time is 2 hours by heating at reaction temperature of 155-160 °C. The yield is about 86.5%. At last, trazodone hydrochloride can be prepared by 1,2,4-triazolo-[4,3-a]pyridine-3(2H)-one and 1-(3-chlorophenyl)-4-(3-chloropropyl)piperazinehydrochloride. This reaction will need reagent ethanol and solvent NaOH. The product should be extracted by dichloromethane and dried by Na2SO4. The yield is about 67.5%.
Uses of Trazodone hydrochloride: it is a kind of antidepressants. The effect is similar with tricyclic drugs, but smaller toxicity to the cardiovascular system and no anticholinergic side effects. In addition, it is more applicable to the older or the depression with cardiovascular disease. It can treat the depression, anxiety disorders and schizophrenia in clinical.
When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed and irritating to eyes, respiratory system and skin. You should not breathe dust. Limited evidence of a carcinogenic effect. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: Cl.Clc4cccc(N3CCN(CCCN1/N=C2/C=C\C=C/N2C1=O)CC3)c4
(2)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
(3)InChIKey: OHHDIOKRWWOXMT-UHFFFAOYAR
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | intravenous | > 40mg/kg (40mg/kg) | Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974. | |
dog | LD50 | oral | 500mg/kg (500mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: AGGRESSION | Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974. |
man | TDLo | oral | 667ug/kg (0.667mg/kg) | CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION | American Journal of Psychiatry. Vol. 141, Pg. 1472, 1984. |
man | TDLo | oral | 5714ug/kg/4D- (5.714mg/kg) | BEHAVIORAL: EUPHORIA BEHAVIORAL: EXCITEMENT | British Journal of Psychiatry. Vol. 158, Pg. 275, 1991. |
man | TDLo | oral | 43mg/kg/30D-I (43mg/kg) | BLOOD: AGRANULOCYTOSIS BLOOD: OTHER CHANGES | American Journal of Psychiatry. Vol. 150, Pg. 1563, 1993. |
man | TDLo | oral | 46mg/kg/8D-I (46mg/kg) | BEHAVIORAL: EXCITEMENT CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED | Journal of Clinical Pyschopharmacology. Vol. 6, Pg. 117, 1986. |
monkey | LD50 | intravenous | 25mg/kg (25mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 94, 1981. |
mouse | LD50 | intraperitoneal | 255mg/kg (255mg/kg) | Journal of Pharmaceutical Sciences. Vol. 81, Pg. 99, 1992. | |
mouse | LD50 | intravenous | 91mg/kg (91mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974. |
mouse | LD50 | oral | 584mg/kg (584mg/kg) | Drug Development Research. Vol. 22, Pg. 385, 1991. | |
mouse | LD50 | subcutaneous | > 1500mg/kg (1500mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 967, 1991. | |
rabbit | LD50 | intravenous | 52mg/kg (52mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974. |
rabbit | LD50 | oral | 560mg/kg (560mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974. |
rat | LD50 | intraperitoneal | 178mg/kg (178mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974. |
rat | LD50 | intravenous | 91mg/kg (91mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: CYANOSIS GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974. |
rat | LD50 | oral | 690mg/kg (690mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Modern Problems of Pharmacopsychiatry. Vol. 9, Pg. 76, 1974. |
rat | LD50 | subcutaneous | 2729mg/kg (2729mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 22, Pg. 967, 1991. | |
women | TDLo | oral | 750ug/kg (0.75mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | American Journal of Psychiatry. Vol. 141, Pg. 434, 1984. |
women | TDLo | oral | 80mg/kg (80mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Journal of Analytical Toxicology. Vol. 8, Pg. 91, 1984. |
women | TDLo | oral | 100mg/kg (100mg/kg) | BEHAVIORAL: SLEEP BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION | Clinical Pharmacy. Vol. 4, Pg. 97, 1985. |
women | TDLo | oral | 720mg/kg/34W- (720mg/kg) | LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION | Annals of Internal Medicine. Vol. 118, Pg. 791, 1993. |