5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine hydrochloride

• ChemBase ID: 122321
• Molecular Formular: C9H9Cl2N5S
• Molecular Mass: 290.17226
• Monoisotopic Mass: 288.99557167
• SMILES: c12c(c(ccc1nsn2)Cl)NC1=NCCN1.Cl
• Canonical SMILES: Clc1ccc2c(c1NC1=NCCN1)nsn2.Cl
• InChI: InChI=1S/C9H8ClN5S.ClH/c10-5-1-2-6-8(15-16-14-6)7(5)13-9-11-3-4-12-9;/h1-2H,3-4H2,(H2,11,12,13);1H
• InChIKey: ZWUKMNZJRDGCTQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine hydrochloride
• IUPAC Traditional name: tizanidine hydrochloride
• Synonyms: 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)benzo[c][1,2,5]thiadiazol-4-amine hydrochloride; AB-021; DS-103-282; Sirdalud; Ternelin; Zanaflex; Tizanidine Hydrochloride; 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine hydrochloride; Tizanidine HCl; 5-Chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine hydrochloride; Tizanidine hydrochloride

Database IDs

• CAS Number: 51322-75-9; 64461-82-1
• MDL Number: MFCD00798231
• PubChem SID: 162216674; 24724634
• PubChem CID: 114869

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.16535637
• LogD (pH = 7.4): 1.6758085
• Log P: 2.024673
• Molar Refractivity: 64.7664 cm^3
• Polarizability: 24.50533 Å^3
• Polar Surface Area: 62.2 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >20 mg/mL; Methanol; Water
• Apperance: Off-White to pale Yellow Solid; white powder
• Melting Point: 281-283°C; 291 - 293°C
• Hydrophobicity(logP): 2.093

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: DK9910000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Target: Adrenergic Receptor

Product Information

• Purity: ≥98% (HPLC); 95%; 98%
• Salt Data: HCl
• Empirical Formula (Hill Notation): C9H9Cl2N5S

DETAILS

Sigma Aldrich - T6950

Biochem/physiol Actions
α2-adrenoceptor agonist.

Toronto Research Chemicals - T449500

An α2-adrenergic agonist; centrally active myotonolytic. A muscle relaxant (skeletal).

REFERENCES

• Turski, L., et al.: Brain Res., 379, 367 (1986)
• Ono, H., et al.: Gen. Pharmacol., 17, 137 (1986)
• Hoogstraten, M.C., et al.: Acta Neurol. Scand., 77, 224 (1988)