4-(4-{3-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]propoxy}phenyl)benzonitrile dihydrochloride

• ChemBase ID: 153850
• Molecular Formular: C22H29Cl2N3O
• Molecular Mass: 422.39116
• Monoisotopic Mass: 421.16876792
• SMILES: CN(C)[C@@H]1CCN(C1)CCCOc1ccc(cc1)c1ccc(cc1)C#N.Cl.Cl
• Canonical SMILES: N#Cc1ccc(cc1)c1ccc(cc1)OCCCN1CC[C@H](C1)N(C)C.Cl.Cl
• InChI: InChI=1S/C22H27N3O.2ClH/c1-24(2)21-12-14-25(17-21)13-3-15-26-22-10-8-20(9-11-22)19-6-4-18(16-23)5-7-19;;/h4-11,21H,3,12-15,17H2,1-2H3;2*1H/t21-;;/m1../s1
• InChIKey: XFPYVTSGYYMTFS-GHVWMZMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(4-{3-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]propoxy}phenyl)benzonitrile dihydrochloride
• IUPAC Traditional name: 4-(4-{3-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]propoxy}phenyl)benzonitrile dihydrochloride
• Synonyms: 4’-[3-[(3(R)-Dimethylamino-1-pyrrolidinyl]propoxy]-[1,1-biphenyl]-4‘-carbonitrile dihydrochloride; A-331440 dihydrochloride

Database IDs

• CAS Number: 392338-13-5(freebase)
• PubChem SID: 162247989; 24724398
• PubChem CID: 16078942

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.31751436
• LogD (pH = 7.4): 1.0834454
• Log P: 3.3643467
• Molar Refractivity: 106.8492 cm^3
• Polarizability: 42.76552 Å^3
• Polar Surface Area: 39.5 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• 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): C22H27N3O · 2HCl

DETAILS

Sigma Aldrich - A7730

Biochem/physiol Actions
A-331440 dihydrochloride is a non-imidazole H3 histamine receptor antagonist. Presynaptic histamine H(3) receptors regulate release of histamine and other neurotransmitters, and histamine H(3) receptor antagonists enhance neurotransmitter release. A-331440 is a histamine H(3) receptor antagonist, which binds potently and selectively to both human and rat histamine H(3) receptors (K(i)=25 nM). Mice on a high-fat diet (45 kcal % lard) prior to 28-day oral b.i.d. dosing for measurement of obesity-related parameters. A-331440 administered at 0.5 mg/kg had no significant effect on weight, whereas 5 mg/kg decreased weight comparably to dexfenfluramine (10 mg/kg). A-331440 administered at 15 mg/kg reduced weight to a level comparable to mice on the low-fat diet. The two higher doses reduced body fat and the highest dose also normalized an insulin tolerance test. Both data shows that the histamine H(3) receptor antagonist, A-331440, has potential as an antiobesity agent.