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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

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Certificates of Analysis (COA)

Lot/Batch Number
046M4760V
110M4721
026K47023
026K47022
026K47021

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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
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
[Grandaxin in neurological practice].
G M Diukova et al.
Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova, 109(9), 44-48 (2009-11-17)
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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