CAS 2380-63-4 1H-Pyrazolo[3,4-d]pyrimidin-4-amine (HCID 75420)

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Basic information

CAS: 2380-63-4
Standard SMILES: Nc1ncnc2[nH]ncc12
InChIKey: LHCPRYRLDOSKHK-UHFFFAOYSA-N
Molecular formula: C5H5N5
Average molar mass: 135.13 g/mol
Monoisotopic mass: 135.05449516

Names & identifiers

Preferred name: 1H-Pyrazolo[3,4-d]pyrimidin-4-amine
IUPAC: 1H-pyrazolo[3,4-d]pyrimidin-4-amine
English name: 4-Aminopyrazolo[3,4-d]pyrimidine
Molecular formula: C5H5N5
Molecular weight: 135.13

Names & synonyms

1H-Pyrazolo[3,4-d]pyrimidin-4-amine2380-63-44-Aminopyrazolo[3,4-d]pyrimidinePyrazoloadenine4-Amino-1H-pyrazolo[3,4-D]pyrimidine4-Aminopyrazolopyrimidine64834-00-02H-Pyrazolo[3,4-d]pyrimidin-4-amine1H-Pyrazolo[3,4-d]pyrimidin-4-ylamine4-Aminopyrazolo(3,4-d)pyrimidine4 APP8-Aza-7-deazaadenine

Show more names

4-appnsc13934-AminopyraAminopurinolTIMTEC-BB SBB004205ADENINE ANTIMETABOLITE

MFCD000056884-Aminopyrazole(3,4-d)pyrimidineNSC 13937-DEAZA-8-AZAADENINE1H-Pyrazolo(3,4-d)pyrimidin-4-amine1H-Pyrazolo(3,4-d)pyrimidine, 4-amino-1H-Pyrazolo[3,4-d]pyrimidine, 4-amino-0356MAT9LX

Database identifiers

CAS: 2380-63-4
PubChem CID: 75420
DTXSID: DTXSID3062362
ChEMBL: CHEMBL388593
UNII: 0356MAT9LX
EC Number: 219-174-6
Nikkaji: J78.787F

Properties

Computed structural properties

XLogP: -0.2
Topological polar surface area: 80.5 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 0
Heavy atoms: 10
Formal charge: 0
Complexity: 127

Physicochemical properties

Melting point: 325 °C · >325 °C(lit.)
Boiling point: 238.81 °C · 238.81°C (rough estimate)
Density: 1.3795 · 1.3795 (rough estimate)
refractive index: 1.7 · 1.7000 (estimate)
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
solubility: soluble in DMSO
pka: 12.12 · 12.12±0.20(Predicted)
form: powder to crystal
color: White to Orange to Green
Water Solubility: Insoluble in water.
BRN: 5824 · 5824
InChI: 1S/C5H5N5/c6-4-3-1-9-10-5(3)8-2-7-4/h1-2H,(H3,6,7,8,9,10)
InChIKey: LHCPRYRLDOSKHK-UHFFFAOYSA-N
SMILES: Nc1ncnc2[nH]ncc12
CAS DataBase Reference: 2380 · 2380-63-4(CAS DataBase Reference)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (97.8%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 22-09-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/31786

Hazard Classes and CategoriesAcute Tox. 3 (97.8%)

Safety data

PPE: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk: 3
tsca: TSCA listed
rtecs: UR0717000
ridadr: UN 2811 6.1/PG 3
hs_code: 29335990
Toxicity: LD50 oral in rat: 141mg/kg
risk_code: 25-36/37/38-23/24/25
Signal word: Danger
Symbol(GHS): GHS06,GHS07
hazard_code: T
safety_code: 26-36/37/39-45-22-36
hazard_class: 6.1
Storage Class: 6.1D - Non-combustible acute toxic Cat.3toxic hazardous materials or hazardous materials causing chronic effects

Chemistry & industry

Uses & manufacturing

General Manufacturing Information1H-Pyrazolo[3,4-d]pyrimidin-4-amine: INACTIVE

Applications · 2 items

Description4-aminopyrazolo[3,4-d]pyrimidine (4-APP), the isomer of adenine with the five-membered ring in the pyrazole configuration, is by far the most potent inhibitor of both enzymatic reactions catalyzed by Stx1. It is also a new type of mTOR inhibitor. The 4-aminopyrazolo[3,4-d]pyrimidines, a well-characterized class of compounds for tyrosine kinase inhibition, were used as a Src inhibitor module that blocks the adenosine binding site[1-2].

Uses4-Amino-1H-pyrazolo[3,4-d]pyrimidine decreases serum cholesterol markedly in rats.