3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol hydrochloride

• ChemBase ID: 178074
• Molecular Formular: C14H24ClNO
• Molecular Mass: 257.79946
• Monoisotopic Mass: 257.15464207
• SMILES: c1(cccc(c1)[C@@H]([C@H](CN(C)C)C)CC)O.Cl
• Canonical SMILES: CC[C@@H](c1cccc(c1)O)[C@H](CN(C)C)C.Cl
• InChI: InChI=1S/C14H23NO.ClH/c1-5-14(11(2)10-15(3)4)12-7-6-8-13(16)9-12;/h6-9,11,14,16H,5,10H2,1-4H3;1H/t11-,14+;/m0./s1
• InChIKey: ZELFLGGRLLOERW-YECZQDJWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol hydrochloride
• IUPAC Traditional name: tapentadol hydrochloride
• Synonyms: 3-[(1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl]phenol Hydrochloride; Tapentadol Hydrochloride

Database IDs

• CAS Number: 175591-09-0
• PubChem SID: 164233984
• PubChem CID: 9838021

CALCULATED PROPERTIES

• Acid pKa: 10.277116
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.0030566354
• LogD (pH = 7.4): 1.0680987
• Log P: 2.9585335
• Molar Refractivity: 69.5588 cm^3
• Polarizability: 27.14646 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Yellow to Light Brown Solid
• Melting Point: 178-184°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T007200

A novel, centrally acting oral analgesic with a dual mode of action that has demonstrated efficacy in preclinical and clinical models of pain relief.

REFERENCES

• Boxenbaum, H., et al.: J. Pharm. Sci., 2, 47 (1999)
• Boase, S., et al.: Br. J. Clin. Pharmacol., 54, 493 (1999)
• Armstrong, S., et al.: Psychosomatics, 44, 515 (1999)
• Bjornsson, T., et al.: Drug Metab. Dispos., 31, 815 ( 2003),