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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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Tofisopam inhibits the pharmacokinetics of CYP3A4 substrate midazolam.
Mária Tóth et al.
European journal of clinical pharmacology, 64(1), 93-94 (2007-11-09)
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
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
E J Horváth et al.
Brain research. Molecular brain research, 22(1-4), 211-218 (1994-03-01)
Homophthalazines (2,3-benzodiazepin-derivates, such as tofisopam, nerisopam, girisopam) constitute a drug family with strong anxiolytic and antipsychotic potencies. By autoradiography, all of these drugs showed a specific distribution pattern of binding sites exclusively in brain areas which relate to the striato-pallido-nigral
Ryuji Kato et al.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 123(5), 365-368 (2003-05-30)
Paroxysmal supraventricular tachycardia (PSVT) is a reentrant tachycardia, and the autonomic nervous system influences the paroxysms of PSVT. Tofisopam (Grandaxin) is a derivative of benzodiazepines. It is reported that heart rate variability (HRV) reveals the function of the autonomic nervous
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