BIS(4-METHYL-1-PIPERAZINYLTHIOCARBONYL) DISULFIDE

Names

[ CAS No. ]:
20231-01-0

[ Name ]:
BIS(4-METHYL-1-PIPERAZINYLTHIOCARBONYL) DISULFIDE

[Synonym ]:
Ewp 815
Piperazine,1,1'-(dithiodicarbonothioyl)bis(4-methyl
bis((4-methylpiperazino)thiocarbamoyl)disulfide
MFCD01729803
Bis((4-methyl-1-piperazinyl)thiocarbonyl)disulfide
Bis-<(4-methyl-1-piperazinyl)-thiocarbonyl>disulfid
DISULFIDE,BIS((4-METHYL-1-PIPERAZINYL)THIOCARBONYL)
4-Methylpiperazino-thiuramdisulfide
bis-(4-methyl-piperazine-1-carbothioyl)-disulfane
4,4'-dimethyl-1,1'-(2,3-dithia-butanedithioyl)-bis-piperazine
di-N-methylpiperazinethiuramdisulfide

Biological Activity

[Description]:

EWP 815 is a disulfiram analogue, is a potent inhibitor of Ins(1,4)P2 phosphatase and Ins(1,4,5)P3 5-phosphatase. EWP 815 also inhibits enzyme dopamine β-hydroxylase activity[1][2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphatase

Research Areas >> Others

[Target]

Ins(1,4)P2 phosphatase; Ins(1,4,5)P3 5-phosphatase[1]; dopamine β-hydroxylase[2]

[In Vitro]

EWP 815 inhibits thyrotropin-releasing hormone (TRH; 0.03 mM)-stimulated inositol phospholipid breakdown without affecting basal breakdown rates in prelabelled GH3 cells with IC50s of 83 mM (soluble enzymes) and 71 mM (particulate enzymes), respectively[1]. EWP 815 (30 μM; 1 h) exerts higher inhibition on Ins(1,4)P2 phosphatase rather than Ins(1,4,5)P3 5-phosphatase with the mean [3H]Ins(1,4)P2/mean [3H]InsP recovery ratio of 2.6[1]. EWP 815 (6, 8 μM; 10 min) inhibits dephosphorylation of [3H]Ins(1,4,5)P3 5-phosphatase in particulate and soluble fractions with IC50s of 6 μM and 8 μM, respectively[1]. EWP 815 (3-300 μM; 30 min) suppresses thyrotropin-releasing hormone (TRH)-stimulated (100 nM) inositol phospholipid production by 30% (100 μM) and 1.8% (300 μM), respectively, without affecting Ins(1,4,5)P3 binding[1].

[In Vivo]

EWP 815 (50 mg/kg; i.p.; 30 min before killed) inhibits the enzyme dopamine β-hydroxylase activity in mice[2]. Animal Model: Female mice (20 g)[2] Dosage: 50 mg/kg Administration: Intraperitoneal injection; 30 min before killed Result: Intraperitoneal injection; 30 min before killedInhibited β-hydroxylase of 3H-α-methyldopamine. Reduced the amount of 3H-α-Me-NA by 12%.

[References]

[1]. Fowler CJ, et al. Inhibition of inositol 1,4,5-trisphosphate 5-phosphatase by micromolar concentrations of disulfiram and its analogues. Biochem J. 1993 Feb 1;289 ( Pt 3)(Pt 3):853-9.

[2]. Carlsson A, et al. On the beta-hydroxylation of (+-)-alpha-methyldopamine in vivo. Eur J Pharmacol. 1968 Dec;5(1):85-92.

Chemical & Physical Properties

[ Density]:
1.339g/cm3

[ Boiling Point ]:
450.5ºC at 760 mmHg

[ Melting Point ]:
142ºC

[ Molecular Formula ]:
C₁₂H₂₂N₄S₄

[ Molecular Weight ]:
350.59000

[ Flash Point ]:
226.3ºC

[ Exact Mass ]:
350.07300

[ PSA ]:
127.74000

[ LogP ]:
1.18400

[ Vapour Pressure ]:
2.62E-08mmHg at 25°C

[ Index of Refraction ]:
1.673

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: JO1527500

CHEMICAL NAME :: Disulfide, bis((4-methyl-1-piperazinyl)thiocarbonyl)

CAS REGISTRY NUMBER :: 20231-01-0

BEILSTEIN REFERENCE NO. :: 0893745

LAST UPDATED :: 199709

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C12-H22-N4-S4

MOLECULAR WEIGHT :: 350.62

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ATDAEI Acute Toxicity Data. Journal of the American College of Toxicology, Part B. (Mary Ann Liebert, Inc., 1651 Third Ave., New York, NY 10128) V.1- 1990- Volume(issue)/page/year: 15(Suppl 1),S82,1996

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: APSXAS Acta Pharmaceutica Suecica. (Apotekarsocieteten-Farmacevtiska Foereningen, Box 1136, S-111, 81 Stockholm, Sweden) V.1- 1964- Volume(issue)/page/year: 7,7,1970

Safety Information

[ Safety Phrases ]:
S24/25

[ HS Code ]:
2933599090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933599090

[ Summary ]:
2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%