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Merck
CN

T8200

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

Key Documents

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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

Ligand for the GABAA receptor benzodiazepine modulatory site.
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.

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000414970
0000414970
0000105557
0000105555
0000103849

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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)
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
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
Yue Fan et al.
Neuroscience letters, 736, 135262-135262 (2020-07-20)
Spinal cord injury (SCI) is a traumatic condition of the central nervous system (CNS) that can cause paralysis of the limbs. The molecular mechanisms of neural repair following SCI remain unclear and no effective treatment for SCI currently exists, since
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