2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one hydrochloride

• ChemBase ID: 73240
• Molecular Formular: C19H23Cl2N5O
• Molecular Mass: 408.32482
• Monoisotopic Mass: 407.12796574
• SMILES: c1ccc(cc1Cl)N1CCN(CC1)CCCn1c(=O)n2c(n1)cccc2.Cl
• Canonical SMILES: Clc1cccc(c1)N1CCN(CC1)CCCn1nc2n(c1=O)cccc2.Cl
• InChI: 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
• InChIKey: OHHDIOKRWWOXMT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one hydrochloride
• IUPAC Traditional name: trazodone hydrochloride
• Synonyms: Bimaran; KB 831; Mesyrel; Molipaxin; Pragmazone; Thombran; Tombran; Trazodone hydrochloride; Trazolan; Trittico; 2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one hydrochloride; Desyrel; Trazodone hydrochloride; 2-(3-(4-(3-Chlorophenyl)-1-piperazinyl)propyl)-s-triazolo(4,3-a)pyridin-3(2H)-one HCl; 2-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one hydrochloride; Trazodone hydrochloride

Database IDs

• CAS Number: 25332-39-2
• EC Number: 246-855-5
• MDL Number: MFCD00079603
• PubChem SID: 24278136; 162038160
• PubChem CID: 62935

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.5380111
• LogD (pH = 7.4): 2.9594436
• Log P: 3.1318567
• Molar Refractivity: 105.8796 cm^3
• Polarizability: 39.210217 Å^3
• Polar Surface Area: 42.39 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble7.4 mg/mL; Chloroform; DMSO: soluble; H2O: insoluble; methanol: soluble25 mg/mL
• Apperance: light yellow powder; White to Off-White Solid
• Melting Point: 223°C; 223-226°C
• Hydrophobicity(logP): 3.85

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: XZ5660000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-40; R:22-36/37/38
• Safety Statements: 22-36; S:25-26-36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Target: Serotonin receptor
• Gene Information: human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2C(3358)

Product Information

• Purity: ≥99% (HPLC); 95%
• Salt Data: hydrochloride

DETAILS

MP Biomedicals - 02191518

Hydrochloride
A serotonin uptake inhibitor.

Selleck Chemicals - S2582

Research Area: Cancer
Biological Activity:
Trazodone hydrochloride (Desyrel) is a hydrochloride salt of trazodone that is a serotonin antagonist and reuptake inhibitor with a Kd of 0.16 μM. Trazodone hydrochloride is a triazolopyridine antidepressant drug. Trazodone is a phenylpiperazine compound. [1][2] Trazodone also has anxiolytic, and hypnotic effects. Trazodone is a psychoactive compound with sedative and anti-depressant properties. Trazodone may also be used for relief of an anxiety disorder (e.g., sleeplessness, tension) and chronic pain. Trazodone behaves as an antagonist at all of the following receptors except 5-HT1A where it acts as a partial agonist similarly to buspirone and tandospirone but with greater intrinsic activity in comparison: 5-HT1A receptor (Kd = 78 nM), 5-HT2A receptor (Ki = 13 nM), 5-HT2C receptor (Ki = 192 nM), α1-adrenergic receptor (Kd = 39 nM), α2-adrenergic receptor (Kd = 405 nM), H1 receptor (Kd = 725 nM). Trazodone acts predominantly as a 5-HT2A receptor antagonist to mediate its therapeutic benefits against anxiety and depression. [3][4] References on Trazodone HCl (Desyrel)[1] http://en.wikipedia.org/wiki/Trazodone, , [2] Psychopharmacology (Berl)., 1992, 109(1-2):2-11[3] J Pharmacol Exp Ther., 1984 Jul, 230(1):94-102[4] Eur J Pharmacol., 1986 Dec 16, 132(2-3):115-21

Sigma Aldrich - T6154

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.

Toronto Research Chemicals - T718500

Antidepressant.

REFERENCES

• Wander TJ et al. Eur J Pharmacol. 1986 Dec 16;132(2-3):115-21.
• Silvestrini, B., et al.: Eur. J. Pharmacol., 12, 231 (1970)
• Brogden, R.N., et al.: Drugs, 21, 401 (1970)
• Gorecki, D., et al.: Anal. Profiles Drug Subs., 16, 693 (1970)