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T6154

Sigma-Aldrich

Trazodone hydrochloride

≥99% (HPLC), powder

Synonym(s):

2-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C19H22ClN5O · HCl
CAS Number:
25332-39-2
Molecular Weight:
408.32
EC Number:
246-855-5
MDL number:
MFCD00079603
UNSPSC Code:
12352200
PubChem Substance ID:
24278136
NACRES:
NA.77

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

Gene Information

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

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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

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H351

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
J P Feighner
The Journal of clinical psychiatry, 60 Suppl 4, 4-11 (1999-03-23)
The psychopharmacology of depression is a field that has evolved rapidly in just under 5 decades. Early antidepressant medications--tricyclic antidepressants (TCAs) and monoamine oxidase inhibitors (MAOIs)--were discovered through astute clinical observations. These first-generation medications were effective because they enhanced serotonergic
M Pazzagli et al.
European journal of pharmacology, 383(3), 249-257 (1999-12-14)
The effects of the antidepressant drug, trazodone, on the extracellular 5-hydroxytryptamine (5-HT) levels in the frontal cortex of freely moving rats was investigated using microdialysis coupled to a high performance liquid chromatography (HPLC) detection method. Systemic administration of 1.25 and
Andrea Fagiolini et al.
CNS drugs, 26(12), 1033-1049 (2012-11-30)
Trazodone is a triazolopyridine derivative that belongs to the class of serotonin receptor antagonists and reuptake inhibitors (SARIs). The drug is approved and marketed in several countries worldwide for the treatment of major depressive disorder (MDD) in adult patients. In
A Georgotas et al.
Pharmacotherapy, 2(5), 255-265 (1982-09-01)
Trazodone is a new antidepressant agent that was recently introduced in the United States. It has a unique pharmacological profile that is not typical of either tricyclic or monoamine oxidase inhibitor antidepressants. As such it represents a new class of
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