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15421-84-8

15421-84-8 Structure

15421-84-8 Structure
IdentificationBack Directory
[Name]

7-(DIETHYLAMINO)-5-METHYL-S-TRIAZOLO[1,5-A]PYRIMIDINE
[CAS]

15421-84-8
[Synonyms]

ar12008
TRAPIDIL
Trapymin
Avantrin
rocornal
Trapymine
Trapidil CRS
Trapidil (AR12008)
Trapidil >=98% (HPLC)
5-methyl-7-diaethylamino-s-triazolo(1.5-a)pyrimidin
5-methyl-7-diethylamino-s-triazolo-(1,5-a)-pyrimidine
7-(DIETHYLAMINO)-5-METHYL-S-TRIAZOLO[1,5-A]PYRIMIDINE
5-a)pyrimidin-7-amine,n,n-diethyl-5-methyl-s-triazolo(
7-Diethylamino-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine
7-(Diethylamino)-5-methyl-S-triazolo[1,5-a]pyrimidine ,98%
N,N-Diethyl-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
N,N-Diethyl-5-methyl-[1,2,4]triazolo[5,1-b]pyrimidin-7-amine
[1,2,4]Triazolo[1,5-a]pyrimidin-7-amine,N,N-diethyl-5-methyl-
n,n-diethyl-5-methyl-(1,2,4)triazolo(1,5-a)pyrimidine-7-amine
7-(DIETHYLAMINO)-5-METHYL-S-TRIAZOLO[1,5-A]PYRIMIDINE USP/EP/BP
N,N-Diethyl-4-methyl-1,5,7,9-Tetrazabicyclo[4.3.0]Nona-2,4,6,8-Tetraen-2-Amine
[EINECS(EC#)]

239-434-2
[Molecular Formula]

C10H15N5
[MDL Number]

MFCD00193104
[MOL File]

15421-84-8.mol
[Molecular Weight]

205.26
Chemical PropertiesBack Directory
[Appearance]

White or almost white, crystalline powder
[Melting point ]

98-99.4° (Pfeifer); 102-104° from heptane (Tenor)
[density ]

1.20±0.1 g/cm3(Predicted)
[storage temp. ]

room temp
[solubility ]

H2O: ≥15mg/mL
[form ]

powder
[pka]

pKs = 2.79(at 25℃)
[color ]

white to tan
[InChI]

InChI=1S/C10H15N5/c1-4-14(5-2)9-6-8(3)13-10-11-7-12-15(9)10/h6-7H,4-5H2,1-3H3
[InChIKey]

GSNOZLZNQMLSKJ-UHFFFAOYSA-N
[SMILES]

C12=NC=NN1C(N(CC)CC)=CC(C)=N2
[CAS DataBase Reference]

15421-84-8
Hazard InformationBack Directory
[Chemical Properties]

White or almost white, crystalline powder
[Uses]

Vasodilator;PDGF antagonist
[Originator]

Rocornal,Mochida,Japan,1978
[Definition]

ChEBI:Trapidil is a member of triazolopyrimidines.
[Manufacturing Process]

8.4 g of 5-methyl-7-chloro-s-triazolo-(1,5-a)-pyrimidine were suspended in 30 cc of water and 7.3 g of diethylamine added. After 2 hours heating with stirring, the mixture was concentrated under vacuum. The residue was recrystallized from n-heptane. This process yielded 8.1 g of the 5-methyl-7- diethylamino-s-triazolo-(1,5-a)-pyrimidine having a melting point of 103°C to 104°C. The hydrochloride produced in the usual manner had a melting point of 212°C.
[Therapeutic Function]

Coronary vasodilator
[Biological Activity]

Trapidil is an antiplatelet agent th at acts in part as a phosphodiesterase inhibitor and as a competitive inhibitor of the platelet-derived growth factor (PDGF) receptor. Trapidilwith its vasodilator and NO releasing effect may have some potential to diminish the tissue injury. Trapidil suppresses platelet-derived growth factor (PDGF)-induced vascular smooth muscle cell (VSMC) proliferation by inhibiting Raf-1/extracellular signal-regulated kinase (ERK) via cAMP/protein kinase A (PKA). In addn. to cAMP/PKA activationtrapidil inhibits RhoA/ROCK activation.
[storage]

Store at -20°C, protect from light
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26
[WGK Germany ]

3
[Safety Profile]

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. An experimental teratogen. Other experimental reproductive effects. A coronary vasodilator. When heated to decomposition it emits toxic fumes of NOx. See also MINES.
[Toxicity]

LD50 in mice, rats (mg/kg): 115, 76 i.v.; 380, 235 orally; 155, 100 i.p.; 132, 100 s.c. (Fuller)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Acetic acid-->Phosphorus oxitrichloride-->Ethyl acetoacetate-->Diethylamine-->3-Amino-1,2,4-Triazole
Spectrum DetailBack Directory
[Spectrum Detail]

7-(DIETHYLAMINO)-5-METHYL-S-TRIAZOLO[1,5-A]PYRIMIDINE(15421-84-8)1HNMR
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