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T8200

Sigma-Aldrich

Tofisopam

≥98% (HPLC), solid

Synonym(s):

7,8-Dimethoxy-1-(3,4-dimethoxyphenyl)-5-ethyl-4-methyl-5H-2,3-benzodiazepine, EGYT 341, Seriel

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About This Item

Empirical Formula (Hill Notation):
C22H26N2O4
CAS Number:
22345-47-7
Molecular Weight:
382.45
EC Number:
244-922-3
MDL number:
MFCD00823171
UNSPSC Code:
12352200
PubChem Substance ID:
24724636
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

color

white

solubility

DMSO: ~14 mg/mL
H2O: insoluble

SMILES string

CCC1C(C)=NN=C(c2ccc(OC)c(OC)c2)c3cc(OC)c(OC)cc13

InChI

1S/C22H26N2O4/c1-7-15-13(2)23-24-22(14-8-9-18(25-3)19(10-14)26-4)17-12-21(28-6)20(27-5)11-16(15)17/h8-12,15H,7H2,1-6H3

InChI key

RUJBDQSFYCKFAA-UHFFFAOYSA-N

Application

Tofisopam has been used for studying its biochemical mechanisms of actions using drug repositioning strategies.

Biochem/physiol Actions

Studies have reported that tofisopam functions by blocking PDE4 (phosphodiesterase 4). Furthermore, the S-enantiomer of tofisopam is considered ten times more active than R-enantiomer.
Ligand for the GABAA receptor benzodiazepine modulatory site.

Preparation Note

Tofisopam is soluble in DMSO at approximately 14 mg/ml. However, it is insoluble in water.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H400

Precautionary Statements

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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[Grandaxin in neurological practice].
G M Diukova et al.
Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova, 109(9), 44-48 (2009-11-17)
P Bernard et al.
Current medicinal chemistry, 15(30), 3196-3203 (2008-12-17)
Drug repositioning strategy is an interesting approach for pharmaceutical companies; especially to increase their productivity. SELNERGY(tm) is a reverse docking based-program able to virtually screen thousands of compounds on more than 2000 3D biological targets. This program was successfully applied
S M Leventer et al.
Alimentary pharmacology & therapeutics, 27(2), 197-206 (2007-11-02)
Dextofisopam modulates stimulated activity in animal models of stress, altered bowel motility, and visceral hypersensitivity. To evaluate the effects of dextofisopam in men and women with diarrhoea-predominant or alternating irritable bowel syndrome (IBS) (d-IBS or a-IBS). In this double-blind, placebo-controlled
Mougang Hu et al.
Journal of chromatography. A, 1129(1), 47-53 (2006-07-18)
1-(3,4-Dimethoxyphenyl)-4-methyl-5-ethyl-7,8-dimethoxy-5H-2,3-benzodiazepine (tofisopam) contains one chiral center, so two enantiomeric forms exist. The ring system of tofisopam possesses two sterically stable boat structures, leading to two distinct conformers for each enantiomer. A method was developed for the separation of these enantiomers
Tofisopam inhibits the pharmacokinetics of CYP3A4 substrate midazolam.
Mária Tóth et al.
European journal of clinical pharmacology, 64(1), 93-94 (2007-11-09)
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