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25332-39-2 molecular structure
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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 and InChIs

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

Cite this record

CBID:73240 http://www.chembase.cn/molecule-73240.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
25332-39-2
EC Number
246-855-5
MDL Number
MFCD00079603
PubChem SID
162038160
24278136
PubChem CID
62935

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 1.5380111  LogD (pH = 7.4) 2.9594436 
Log P 3.1318567  Molar Refractivity 105.8796 cm3
Polarizability 39.210217 Å3 Polar Surface Area 42.39 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.1 M HCl: soluble7.4 mg/mL expand Show data source
Chloroform expand Show data source
DMSO: soluble expand Show data source
H2O: insoluble expand Show data source
methanol: soluble25 mg/mL expand Show data source
Apperance
light yellow powder expand Show data source
White to Off-White Solid expand Show data source
Melting Point
223°C expand Show data source
223-226°C expand Show data source
Hydrophobicity(logP)
3.85 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
XZ5660000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-40 expand Show data source
R:22-36/37/38 expand Show data source
Safety Statements
22-36 expand Show data source
S:25-26-36/37/39 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H351 expand Show data source
GHS Precautionary statements
P281 expand Show data source
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 expand Show data source
Target
Serotonin receptor expand Show data source
Gene Information
human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2C(3358) expand Show data source
Purity
≥99% (HPLC) expand Show data source
95% expand Show data source
Salt Data
hydrochloride expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02191518 external link
Hydrochloride
A serotonin uptake inhibitor.
Selleck Chemicals - S2582 external link
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 external link
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.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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