10390. Tapentadol

Nomenclature

CAS number: 175591-23-8
3-[(1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl]phenol; CG-5503.
C14H23NO; mol wt 221.34.
C 75.97%, H 10.47%, N 6.33%, O 7.23%.

Description and references

Centrally acting analgesic; combined μ-opioid agonist and noradrenaline reuptake inhibitor. Prepn: H. Buschmann, EP 693475; eidem, US 6248737; US RE39593 (1996, 2001, 2007 all to Grünenthal). Pharmacology: T. M. Tzschentke et al., J. Pharmacol. Exp. Ther. 323, 265 (2007) DOI PubMed. Absorption, metabolism and excretion study: R. Terlinden et al, Eur. J. Drug Metab. Pharmacokinet. 32, 163 (2007) PubMed. Clinical trial in post-surgical dental pain: R. Kleinert et al., Anesth. Analg. 107, 2048 (2008) DOI PubMed; in uncontrolled osteoarthritis: C. Hartrick et al., Clin. Ther. 31, 260 (2009) DOI PubMed.

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 175591-09-0
C14H23NO.HCl; mol wt 257.80.
C 65.22%, H 9.38%, N 5.43%, O 6.21%, Cl 13.75%.

Properties

mp 168-170°. [α]D 27.5° (c = 0.97 in methanol). Log P (n-octanol/water): 2.87. pKa 9.34; 10.45. Sol in acetone, acetonitrile, isopropanol.

Therapeutic Category

Analgesic.

Keywords

Analgesic; Opioids