4-{ethyl[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}butan-1-ol hydrochloride

• ChemBase ID: 154485
• Molecular Formular: C24H35ClN4O
• Molecular Mass: 431.0139
• Monoisotopic Mass: 430.24993944
• SMILES: CCN(CCCCO)c1c2c(c(n(c2nc(n1)C)c1c(cc(cc1C)C)C)C)C.Cl
• Canonical SMILES: OCCCCN(c1nc(C)nc2c1c(C)c(n2c1c(C)cc(cc1C)C)C)CC.Cl
• InChI: InChI=1S/C24H34N4O.ClH/c1-8-27(11-9-10-12-29)23-21-18(5)19(6)28(24(21)26-20(7)25-23)22-16(3)13-15(2)14-17(22)4;/h13-14,29H,8-12H2,1-7H3;1H
• InChIKey: DKVWSJKPRJIFPC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{ethyl[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino}butan-1-ol hydrochloride
• IUPAC Traditional name: 4-{ethyl[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-yl]amino}butan-1-ol hydrochloride
• Synonyms: 4-(N-Ethyl-n-4-hydroxybutyl)amino-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidine hydrochloride; NIH-3; LWH-63 hydrochloride

Database IDs

• CAS Number: 276890-57-4
• MDL Number: MFCD07784506
• PubChem SID: 162248624; 24724529
• PubChem CID: 16078985

CALCULATED PROPERTIES

• Acid pKa: 15.972545
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 5.4714394
• LogD (pH = 7.4): 5.818559
• Log P: 5.8254
• Molar Refractivity: 133.9869 cm^3
• Polarizability: 46.77247 Å^3
• Polar Surface Area: 54.18 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ~10 mg/mL; H2O: insoluble
• Apperance: light brown solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C24H35ClN4O

DETAILS

Sigma Aldrich - L9167

Biochem/physiol Actions
Non-peptide CRF1 corticotrophin-releasing factor antagonist. Ki = 0.68 nM; blocks ethanol-induced effects as well as CRF effects in mice, suggesting a possible therapeutic target for the treatment of stress-induced alcohol drinking.