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4-Aminopyrazolo[3,4-d]pyrimidine

Names

[ CAS No. ]:
2380-63-4

[ Name ]:
4-Aminopyrazolo[3,4-d]pyrimidine

[Synonym ]:
Methyl 3-piperidinylacetate hydrochloride (1:1)
7-deaza-8-aza-adenine
8-aza-7-deazaadenine
1H-Pyrazolo[3,4-d]pyrimidin-4-amine
1H-pyrazolo[3,4-d]pyrimidin-4-ylamine
EINECS 219-174-6
pyrazolo[3,4-d]pyrimidin-4-amine
Pyrazoloadenine
Aminopurinol
4-aminopyrazolo-(3,4-d)pyrimidine
4-aminopyrazolo[5,4-d]pyrimidine
4-Aminopyrazolopyrimidine
1H-Pyrazolo[3,4-d]pyrimidine-4-ylamine 4-Amino-1H-pyrazolo[3,4-d]pyrimidine
Pyrazolo[3,4-d]pyrimidin-4-amin
4-app
ADENINE ANTIMETABOLITE
MFCD00005688
3-Piperidineacetic acid, methyl ester, hydrochloride (1:1)
4-AMINOPYRAZOLO{3,4-D}PYRIMIDINE
1(H)-4-amine-pyrazolo[3,4-d]pyrimidine
4-Amino pyrazolo[3,4-d]pyrimidine

Biological Activity

[Description]:

Pyrazoloadenine is a potent RET (REarranged during Transfection) lung cancer oncoprotein inhibitor. Pyrazoloadenine shows anticancer activity[1][2].

[Related Catalog]:

Research Areas >> Cancer

[In Vitro]

Pyrazoloadenine inhibits a wide range of protein kinases such as BTK (Bruton’s tyrosine kinase), CDK1/2 (cyclin-dependent kinase 1/2), Src kinase, and RIPK1 (receptor-interacting protein kinase)[1].

Chemical & Physical Properties

[ Density]:
1.612g/cm3

[ Boiling Point ]:
431.1ºC at 760mmHg

[ Melting Point ]:
>325 °C(lit.)

[ Molecular Formula ]:
C5H5N5

[ Molecular Weight ]:
193.671

[ Flash Point ]:
244.4ºC

[ Exact Mass ]:
193.086960

[ PSA ]:
80.48000

[ LogP ]:
0.51630

[ Storage condition ]:
-20°C Freezer

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UR0717000
CHEMICAL NAME :
1H-Pyrazolo(3,4-d)pyrimidine, 4-amino-
CAS REGISTRY NUMBER :
2380-63-4
BEILSTEIN REFERENCE NO. :
0005824
LAST UPDATED :
199701
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C5-H5-N5
MOLECULAR WEIGHT :
135.15
WISWESSER LINE NOTATION :
T56 BMN GN INJ FZ

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 :
141 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ciliary spasm Sense Organs and Special Senses (Eye) - ptosis Behavioral - excitement
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
228 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ciliary spasm Sense Organs and Special Senses (Eye) - ptosis Behavioral - excitement
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
180 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ciliary spasm Sense Organs and Special Senses (Eye) - ptosis Behavioral - excitement
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
181 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD10 - Lethal Dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
15 mg/kg
TOXIC EFFECTS :
Liver - other changes
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
100 mg/kg
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - other changes Gastrointestinal - changes in structure or function of salivary glands Kidney, Ureter, Bladder - urine volume increased
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
22500 mg/kg/9D-I
TOXIC EFFECTS :
Liver - fatty liver degeneration Blood - changes in bone marrow (not otherwise specified) Blood - changes in platelet count

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Rodent - mouse Ascites tumor
DOSE/DURATION :
5 umol/L
REFERENCE :
ECREAL Experimental Cell Research. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.10- 1950- Volume(issue)/page/year: 48,319,1967

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H315-H319-H335

[ Precautionary Statements ]:
P261-P301 + P310-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic;

[ Risk Phrases ]:
R23/24/25;R36/37/38

[ Safety Phrases ]:
S26-S36/37/39-S45-S22

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
UR0717000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Spectroscopic, electronic structure and natural bond analysis of 2-aminopyrimidine and 4-aminopyrazolo[3,4-d]pyrimidine: a comparative study.

Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 96 , 226-41, (2012)

The FTIR and FT-Raman spectra of 2-aminopyrimidine (2-AP) and 4-aminopyrazolo[3,4-d]pyrimidine (4-APP) has been recorded in the region 4000-400 and 3500-100 cm(-1), respectively. The tautomeric stabil...


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Related Compounds