Merck
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T6154

Sigma-Aldrich

Trazodone hydrochloride

≥99% (HPLC), powder

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Synonym(s):
2-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one hydrochloride
Empirical Formula (Hill Notation):
C19H22ClN5O · HCl
CAS Number:
Molecular Weight:
408.32
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥99% (HPLC)

form

powder

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble 23.3 mg/mL
methanol: soluble 25 mg/mL, clear, colorless
0.1 M HCl: soluble 7.4 mg/mL
DMSO: soluble
H2O: soluble, hazy, colorless

originator

Bristol-Myers Squibb

SMILES string

Cl[H].Clc1cccc(c1)N2CCN(CCCN3N=C4C=CC=CN4C3=O)CC2

InChI

1S/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

InChI key

OHHDIOKRWWOXMT-UHFFFAOYSA-N

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This Item
PHR3574H15121673500
Haloperidol powder

Sigma-Aldrich

H1512

Haloperidol

Trazodone hydrochloride United States Pharmacopeia (USP) Reference Standard

USP

1673500

Trazodone hydrochloride

form

powder

form

-

form

powder

form

-

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble 23.3 mg/mL, methanol: soluble 25 mg/mL, clear, colorless, 0.1 M HCl: soluble 7.4 mg/mL, DMSO: soluble, H2O: soluble, hazy, colorless

solubility

-

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.39 mg/mL, 0.1 M HCl: 3 mg/mL, DMSO: soluble, H2O: insoluble, ethanol: soluble

solubility

-

originator

Bristol-Myers Squibb

originator

-

originator

Johnson & Johnson

originator

-

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

-

Gene Information

human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2C(3358), SLC6A4(6532)

Gene Information

-

Gene Information

human ... ABCB1(5243), ADRA1A(148), ADRA2A(150), ADRA2C(152), CHRM1(1128), DRD2(1813), DRD3(1814), DRD4(1815), EBP(10682), HRH1(3269), HTR2A(3356), HTR2C(3358), HTR7(3363), KCNH1(3756), KCNH2(3757), PRNP(5621)
rat ... Adra1a(29412), Adra2a(25083), Chrm1(25229), Chrm2(81645), Drd1a(24316), Drd2(24318), Drd3(29238), Drd4(25432), Hrh1(24448), Htr1a(24473), Htr1b(25075), Htr2a(29595), Htr2c(25187), Oprs1(29336), Slc6a3(24898), Slc6a4(25553)

Gene Information

human ... HTR2A(3356), HTR2C(3358), SLC6A4(6532)

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.

Features and Benefits

This compound is featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Bristol-Myers Squibb. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Trazodone hydrochloride dissolves in methanol at 25 mg/ml to yield a clear, colorless solution. It also dissolves in water at 50 mg/ml, with heating to yield a hazy colorless solution. Furthermore, the product is soluble in DMSO or in 0.1 N HCl (7.4 mg/ml). The solubility in a 45% (w/v) aqueous 2-hydroxpropyl-β-cyclodextrin is 23.3 mg/ml. However, it is practically insoluble in other common organic solvents. For HPLC test, the product can be dissolved at 0.25 mg/ml in 50:50 water:methanol (v/v), as this gives better results of dissolution and peak shape than using the product as a 1 mg/ml solution in water.

Pictograms

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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M Marcoli et al.
The Journal of pharmacology and experimental therapeutics, 285(3), 983-986 (1998-06-17)
The effects of trazodone on the cyclic GMP elevation elicited by N-methyl-D-aspartate in rat cerebellar slices were analyzed. Trazodone inhibited in a concentration-dependent manner (EC50 = 0.82 nM) the cyclic GMP response evoked by 0.1 microM N-methyl-D-aspartate. The inhibition was
Wael Shamseddeen et al.
Journal of child and adolescent psychopharmacology, 22(1), 29-36 (2012-01-19)
In the Treatment of Resistant Depression in Adolescents, study participants who received medication for sleep had a lower response rate. This report sought to clarify this finding. Depressed adolescents who had not responded to a previous adequate serotonin-selective reuptake inhibitor
Letizia Bossini et al.
Expert opinion on pharmacotherapy, 13(12), 1707-1717 (2012-06-21)
Trazodone is an antidepressant belonging to the class of serotonin receptor antagonists and reuptake inhibitors. It is approved by the FDA for the treatment of depression. Insomnia is the most frequent reason for prescription of trazodone. It has also been
Khalil El-Chammas et al.
JAMA pediatrics, 167(3), 250-258 (2013-01-30)
OBJECTIVE To assess the effectiveness of prophylactic headache treatment in children and adolescents. DATA SOURCES PubMed, EMBASE, Cochrane Database of Clinical Trials, and bibliography of retrieved articles through August 11, 2012. STUDY SELECTION Randomized trials of headache treatment among children
Andrew H Westmoreland
Aviation, space, and environmental medicine, 85(1), 71-74 (2014-02-01)
Coronary emergencies at sea requiring air evacuation are not uncommon. On board a Nimitz-class aircraft carrier while in a remote location, an active duty sailor suffered a myocardial infarction. A medical evacuation by helicopter was necessary. Transfer proved difficult due

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