CAS 656820-32-5 Reversine (HCID 210332)

Names & identifiers

Preferred name: Reversine
IUPAC: 6-N-cyclohexyl-2-N-(4-morpholin-4-ylphenyl)-7H-purine-2,6-diamine
English name: REVERSINE
Molecular formula: C21H27N7O
Molecular weight: 393.49

Names & synonyms

Reversine656820-32-52-(4-Morpholinoanilino)-6-cyclohexylaminopurineCHEBI:70723Z499CLJ023DTXSID8041113N(6)-cyclohexyl-N(2)-[4-(morpholin-4-yl)phenyl]-9H-purine-2,6-diamineN(6)-cyclohexyl-N(2)-(4-(morpholin-4-yl)phenyl)-9H-purine-2,6-diamineRefChem:179034DTXCID6021113636-256-0C21H27N7O

Show more names

CS-870Reversine, >96%Reversine, >=98%REVERSINE USP/EP/BPPicropodophyllin (PPP)Reversine, 10 mM in DMSOReversine, Cell-permeable A3 receptor antagonist

N6-cyclohexyl-N2-(4-morpholinophenyl)-7H-purine-2,6-diamineCHEMBL188343N6-cyclohexyl-N2-(4-morpholinophenyl)-9H-purine-2,6-diamineMFCD07784513N~6~-Cyclohexyl-N~2~-(4-Morpholin-4-Ylphenyl)-9h-Purine-2,6-Diamine2vgoUNII-Z499CLJ023Reversine?

Database identifiers

CAS: 656820-32-5
PubChem CID: 210332
DTXSID: DTXSID8041113
ChEMBL: CHEMBL188343
ChEBI: CHEBI:70723
UNII: Z499CLJ023
EC Number: 636-256-0
Nikkaji: J2.006.667I

Properties

Computed structural properties

XLogP: 3.9
Topological polar surface area: 91 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 7
Rotatable bonds: 5
Heavy atoms: 29
Formal charge: 0
Complexity: 503

Physicochemical properties

Melting point: 305 ℃ · 305℃ (decomposition)
Boiling point: 736.4 · 736.4±70.0 °C(Predicted)
Density: 1.343 · 1.343±0.06 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
solubility: 7 mg/mL, · DMSO: 7 mg/mL, soluble
form: solid
pka: 10.51 · 10.51±0.10(Predicted)
color: Off-white
Stability: 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months
InChI: 1S/C21H27N7O/c1-2-4-15(5-3-1)24-20-18-19(23-14-22-18)26-21(27-20)25-16-6-8-17(9-7-16)28-10-12-29-13-11-28/h6-9,14-15H,1-5,10-13H2,(H3,22,23,24,25,26,27)
InChIKey: ZFLJHSQHILSNCM-UHFFFAOYSA-N
SMILES: C1CCC(CC1)Nc2nc(Nc3ccc(cc3)N4CCOCC4)nc5nc[nH]c25
FDA UNII: 499 CLJ023 · Z499CLJ023
UNSPSC Code: 12352200 · 12352200
NACRES: 77 · NA.77
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 264 · P264-P270-P301+P312-P330-P501
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xn
Risk Statements: 22 · 22
WGK Germany: 3 · 3
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 5 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 38 reports by companies from 1 notifications to the ECHA C&L Inventory.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
risk_code: 22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
Storage Class: 11 - Combustible Solids
Hazard statements: H302
Precautionary statements: P264-P270-P301+P312-P330-P501

Chemistry & industry

Applications · 2 items

DescriptionReversine is a 2,6-disubstituted purine derivative that was originally found to induce dedifferentiation of C2C12 culture myoblast cells into stem cell progenitors when used at a concentration of 5 μM for four days. Depending on cell type, reversine promotes either differentiation or dedifferentiation. For example, in NT2 neuronal and HL-60 human promyelocytic leukemia cells, it induces differentiation. It inhibits the Aurora A, B, and C kinases with IC50 values of 98-876 nM and acts as an antagonist at the adenosine A3 receptor with a Ki value of 0.66 μM. Reversine is also used for studies of chromosome segregation. It inhibits the mitotic spindle checkpoint enzyme MPS1 with IC50 values of 6 and 2.8 nM for its kinase domain and full-length version, respectively). Reversine induces autophagy in WRO human follicular thyroid cancer cells and decreases Akt/mTOR signaling.

UsesReversine acts as a potent human A3 adenosine receptor antagonist and pan-aurora A/B/C kinase inhibitor. Used for stem cell differentiation.

Suppliers100 total

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]

阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]

武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]

Additional notes

DefinitionChEBI: A member of the class of purines that is 9H-purine in which the hydrogens at positions 2 and 6 are replaced by a [4-(morpholin-4-yl)phenyl]nitrilo group and a cyclohexylamino group, respectively.