CAS 452-06-2 2-Aminopurine (HCID 9955)

Overview

2-aminopurine is the parent compound of the 2-aminopurines, comprising a purine core carrying an amino substituent at the 2-position. It has a role as an antimetabolite. It is a member of 2-aminopurines and a nucleobase analogue.

Names & identifiers

Preferred name: 2-Aminopurine
IUPAC: 7H-purin-2-amine
English name: 2-Aminopurine
Molecular formula: C5H5N5
Molecular weight: 135.13

Names & synonyms

2-aminopurine452-06-29H-Purin-2-amine1H-PURIN-2-AMINEPurine, 2-amino-IsoadenineDTXSID40196416NSC-24129O14B3U97FWCHEBI:479072SQ-224512 Aminopurine

Show more names

sq22451SQ 22,4514-purinamineiso-Adenine2-Aminoperin2-amino-purin4-aminopurine

RefChem:85407DTXCID50118907207-197-47H-purin-2-amine191236-69-82-APAminopurineSQ 22451

Database identifiers

CAS: 452-06-2
PubChem CID: 9955
DTXSID: DTXSID40196416
ChEMBL: CHEMBL388594
ChEBI: CHEBI:479072
UNII: O14B3U97FW
EC Number: 207-197-4
Nikkaji: J823K

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

Experimental & physicochemical properties

Solubility>20.3 [ug/mL] (The mean of the results at pH 7.4)

Physicochemical properties

Melting point: 280 · 280-282 °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.: 2 · 2-8°C
solubility: Aqueous Acid (Slightly), Methanol (Slightly, Heated)
form: Amorphous Powder
pka: 8.02 · 8.02±0.20(Predicted)
color: Light beige
biological source: synthetic
Stability: Hygroscopic
InChI: 1S/C5H5N5/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H3,6,7,8,9,10)
InChIKey: MWBWWFOAEOYUST-UHFFFAOYSA-N
SMILES: Nc1ncc2[nH]cnc2n1
CAS DataBase Reference: 452 · 452-06-2(CAS DataBase Reference)
FDA UNII: 14 B3U97FW · O14B3U97FW
NIST Chemistry Reference: 2 · Purine, 2-amino-(452-06-2)
UNSPSC Code: 41116107 · 41116107
NACRES: 51 · NA.51
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 301 · P301+P312+P330
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xn
Risk Statements: 22 · 22-36/37/38-20/21/22
Safety Statements: 22 · 22-36-26
WGK Germany: 3 · 3
RTECS: 7475000 · UO7475000
HS Code: 29349990 · 29349990
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 Oral · Acute Tox. 4 Oral
Toxicity: 100 mg/PLATE · mmo-sat 100 mg/PLATE MUREAV 111,283,83

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
rtecs: UO7475000
hs_code: 29349990
Toxicity: mmo-sat 100 mg/PLATE MUREAV 111,283,83
risk_code: 22-36/37/38-20/21/22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 22-36-26
Storage Class: 11 - Combustible Solids
Hazard statements: H302
Hazard Classifications: Acute Tox. 4 Oral
Precautionary statements: P301+P312+P330

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationDrugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)

Applications · 3 items

UsesA probe of structural dynamics and charge transfer in DNA .

Uses2-Aminopurine has been used to inhibit eukaryotic initiation factor-2α (eIF2α)-phosphorylation of osteoarthritis (OA) chondrocytes.

UsesA probe of structural dynamicas and charge transfer in DNA