5-(2-{2,8-dimethyl-1H,2H,3H,4H,5H-pyrido[4,3-b]indol-5-yl}ethyl)-2-methylpyridine hydrate dihydrochloride

• ChemBase ID: 154400
• Molecular Formular: C21H29Cl2N3O
• Molecular Mass: 410.38046
• Monoisotopic Mass: 409.16876792
• SMILES: Cc1ccc2c(c1)c1c(n2CCc2ccc(nc2)C)CCN(C1)C.O.Cl.Cl
• Canonical SMILES: CN1CCc2c(C1)c1cc(C)ccc1n2CCc1ccc(nc1)C.O.Cl.Cl
• InChI: InChI=1S/C21H25N3.2ClH.H2O/c1-15-4-7-20-18(12-15)19-14-23(3)10-9-21(19)24(20)11-8-17-6-5-16(2)22-13-17;;;/h4-7,12-13H,8-11,14H2,1-3H3;2*1H;1H2
• InChIKey: QQHQMWVYYVVAOV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(2-{2,8-dimethyl-1H,2H,3H,4H,5H-pyrido[4,3-b]indol-5-yl}ethyl)-2-methylpyridine hydrate dihydrochloride
• IUPAC Traditional name: latrepirdine hydrate dihydrochloride
• Synonyms: 2,8-Dimethyl-5-[2-(6-methyl-3-pyridinyl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole dihydrochloride hydrate; Dimebolin dihydrochloride hydrate; Dimeboline dihydrochloride hydrate; Dimebone dihydrochloride hydrate; Dimebon dihydrochloride hydrate

Database IDs

• CAS Number: 97657-92-6(anhydrous)
• MDL Number: MFCD17215933
• PubChem SID: 162248539
• PubChem CID: 71311856

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.8634037
• LogD (pH = 7.4): 3.081123
• Log P: 3.4085224
• Molar Refractivity: 100.7248 cm^3
• Polarizability: 39.457382 Å^3
• Polar Surface Area: 21.06 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥10 mg/mL
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/38
• Safety Statements: 26-36/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C21H25N3 · 2HCl · xH2O

DETAILS

Sigma Aldrich - D6196

Biochem/physiol Actions
Mechanism of neuroprotection and cognition enhancement is not certain, but Dimebon blocks both cholinesterase and the NMDA receptor simultaneously and also appears to block the action of neurotoxic β-amyloid proteins and inhibit L-type calcium channels, and may exert a neuroprotective effect by blocking a novel target that involves mitochondrial pores.