2-hydroxypropane-1,2,3-tricarboxylic acid 2-[2-(diethylamino)ethoxy]ethyl 1-phenylcyclopentane-1-carboxylate

• ChemBase ID: 134259
• Molecular Formular: C26H39NO10
• Molecular Mass: 525.58856
• Monoisotopic Mass: 525.25739645
• SMILES: CCN(CC)CCOCCOC(=O)C1(CCCC1)c1ccccc1.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
• Canonical SMILES: OC(=O)C(CC(=O)O)(CC(=O)O)O.CCN(CCOCCOC(=O)C1(CCCC1)c1ccccc1)CC
• InChI: InChI=1S/C20H31NO3.C6H8O7/c1-3-21(4-2)14-15-23-16-17-24-19(22)20(12-8-9-13-20)18-10-6-5-7-11-18;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-7,10-11H,3-4,8-9,12-17H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
• InChIKey: AKJDEXBCRLOVTH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxypropane-1,2,3-tricarboxylic acid 2-[2-(diethylamino)ethoxy]ethyl 1-phenylcyclopentane-1-carboxylate
• IUPAC Traditional name: citro; pentoxyverine
• Synonyms: 1-Phenylcyclopentanecarboxylic acid 2-(2-diethylaminoethoxy)ethyl ester citrate salt; Carbetapentane citrate salt; 1-phenyl-Cyclopentanecarboxylic Acid 2-[2-(Diethylamino)ethoxy]ethyl Ester Citrate; 1-Phenylcyclopentane-1-carboxylic Acid Diethylaminoethoxyethyl Ester Citrate; 2-(Diethylaminoethoxy)ethyl 1-Phenyl-1-cyclopentanecarboxylate Citrate; Atussil Citrate; Carbetapentane Citrate; Pentoxiverine Citrate; Pentoxyverine Citrate

Database IDs

• CAS Number: 23142-01-0
• EC Number: 245-449-5
• MDL Number: MFCD00055697
• PubChem SID: 24277965; 162228536
• PubChem CID: 90010

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.606898
• LogD (pH = 7.4): 1.961526
• Log P: 3.9665852
• Molar Refractivity: 97.1698 cm^3
• Polarizability: 38.364464 Å^3
• Polar Surface Area: 38.77 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 84-86°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: GY3500000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... OPRL1(4987), OPRS1(10280)

DETAILS

Sigma Aldrich - C4662

Biochem/physiol Actions
High affinity σ1 agonist; ORL1 antagonist; antitussive.

Toronto Research Chemicals - P276600

An over-the-counter cough suppressant.

REFERENCES

• Deisemann, H., et al.: J. Cardiovas. Pharmacol., 52, 494 (2008)
• Herrera, Y., et al.: J. Pharmacol. Exper. Ther., 327, 491 (2008)
• Dresen, S., et al.: Anal. Bioanal. Chem., 396, 2425 (2008)