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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

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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Maria Tóth et al.
Journal of pharmaceutical and biomedical analysis, 41(4), 1354-1359 (2006-05-10)
Tofisopam (1-(3,4-dimethoxyphenyl)-4-methyl-5-ethyl-7,8-dimethoxy-5H-2,3-benzodiazepine) has been shown to be an effective anxiolytic agent in the wide-ranging clinical practice. A high sensitive gas chromatography nitrogen phosphorous detection (GC-NPD) bioanalytical method was developed and validated for the purpose of pharmacokinetic study of tofisopam. A
N P Vanchakova et al.
Bulletin of experimental biology and medicine, 148(2), 343-345 (2009-12-23)
The study demonstrated high anxiolytic activity of tenoten, which was not inferior to the anxiolytic effect of grandaxin. The positive changes persisted after termination of treatment in the tenoten group (but not in grandaxin group). Tenoten can be recommended for
Drug repositioning: identifying and developing new uses for existing drugs.
Ted T Ashburn et al.
Nature reviews. Drug discovery, 3(8), 673-683 (2004-08-03)
Michael D Cameron et al.
Drug metabolism and disposition: the biological fate of chemicals, 35(10), 1894-1902 (2007-07-25)
In vitro studies were conducted to elucidate the metabolic profiles of and the enzymes responsible for the metabolism of (R)- and (S)-tofisopam (1-(3,4-dimethoxyphenyl)-5-ethyl-7,8-dimethoxy-4-methyl-5H-2,3-benzodiazepine). Large differences were observed between the two enantiomers. The major metabolite in incubations of 500 ng/ml (approximately
N Bonnet et al.
Toxicology and applied pharmacology, 221(1), 111-118 (2007-03-27)
The aim of this study was to evaluate the effects of various drugs which present antidepressant properties: selective serotonin-reuptake inhibitors (SSRIs, fluoxetine), serotonin and noradrenaline-reuptake inhibitors (Desipramine) and phosphodiesterase inhibitors (PDE, rolipram and tofisopam) on bone microarchitecture and biomechanical properties.
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