3-(1-dimethylamino-2-methyl-pentan-3-yl)phenol

  • CAT Number: M038850
  • CAS Number: 175591-23-8
  • Molecular Formula: C14H23NO
  • Molecular Weight: 221.344
  • Purity: ≥95%
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Tapentadol is a centrally acting opioid analgesic of the benzenoid class with a dual mode of action as an agonist of the μ-opioid receptor and as a norepinephrine reuptake inhibitor (NRI). Tapentadol general potency is somewhere between that of tramadol and morphine, with an analgesic efficacy comparable to that of oxycodone despite a lower incidence of side effects. It is generally regarded as a weak-moderate strength opioid.

Catalog Number M038850
CAS Number 175591-23-8
Molecular Formula

C14H23NO

Purity 95%
Storage Store at -20°C
IUPAC Name 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol
InChI InChI=1S/C14H23NO/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/t11-,14+/m0/s1
InChIKey KWTWDQCKEHXFFR-SMDDNHRTSA-N
SMILES CCC(C1=CC(=CC=C1)O)C(C)CN(C)C
Reference

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PubMed PMID: 25609974; PubMed Central PMCID: PMC4298300. </br>5: Sánchez Del Águila MJ, Schenk M, Kern KU, Drost T, Steigerwald I. Practical considerations for the use of tapentadol prolonged release for the management of severe chronic pain. Clin Ther. 2015 Jan 1;37(1):94-113. doi: 10.1016/j.clinthera.2014.07.005. Epub 2014 Aug 6. Review. PubMed PMID: 25108647. </br>6: Tzschentke TM, Christoph T, Kögel BY. The mu-opioid receptor agonist/noradrenaline reuptake inhibition (MOR-NRI) concept in analgesia: the case of tapentadol. CNS Drugs. 2014 Apr;28(4):319-29. doi: 10.1007/s40263-014-0151-9. Review. PubMed PMID: 24578192. </br>7: Desai B, Freeman E, Huang E, Hung A, Knapp E, Breunig IM, McPherson ML, Shaya FT. Clinical value of tapentadol extended-release in painful diabetic peripheral neuropathy. Expert Rev Clin Pharmacol. 2014 Mar;7(2):203-9. doi: 10.1586/17512433.2014.889562. Review. PubMed PMID: 24524594. </br>8: Singh DR, Nag K, Shetti AN, Krishnaveni N. Tapentadol hydrochloride: A novel analgesic. Saudi J Anaesth. 2013 Jul;7(3):322-6. doi: 10.4103/1658-354X.115319. Review. PubMed PMID: 24015138; PubMed Central PMCID: PMC3757808. </br>9: Afilalo M, Morlion B. Efficacy of tapentadol ER for managing moderate to severe chronic pain. Pain Physician. 2013 Jan;16(1):27-40. Review. PubMed PMID: 23340531. </br>10: Taylor R, Pergolizzi JV, Raffa RB. Tapentadol extended release for chronic pain patients. Adv Ther. 2013 Jan;30(1):14-27. doi: 10.1007/s12325-013-0002-y. Epub 2013 Jan 15. Review. PubMed PMID: 23328938. </br>11: Raffa RB, Buschmann H, Christoph T, Eichenbaum G, Englberger W, Flores CM, Hertrampf T, Kögel B, Schiene K, Straßburger W, Terlinden R, Tzschentke TM. Mechanistic and functional differentiation of tapentadol and tramadol. Expert Opin Pharmacother. 2012 Jul;13(10):1437-49. doi: 10.1517/14656566.2012.696097. Epub 2012 Jun 15. Review. PubMed PMID: 22698264. </br>12: Mendis V. Role of tapentadol in pain management. Br J Hosp Med (Lond). 2012 Mar;73(3):143-7. Review. PubMed PMID: 22411644. </br>13: Hoy SM. Tapentadol extended release: in adults with chronic pain. Drugs. 2012 Feb 12;72(3):375-93. doi: 10.2165/11208600-000000000-00000. Review. PubMed PMID: 22316353. </br>14: Pierce DM, Shipstone E. Pharmacology update: tapentadol for neuropathic pain. Am J Hosp Palliat Care. 2012 Dec;29(8):663-6. doi: 10.1177/1049909111434634. Epub 2012 Feb 5. Review. PubMed PMID: 22310021. </br>15: Hartrick CT, Rodríguez Hernandez JR. Tapentadol for pain: a treatment evaluation. Expert Opin Pharmacother. 2012 Feb;13(2):283-6. doi: 10.1517/14656566.2012.648616. Epub 2011 Dec 23. Review. PubMed PMID: 22192161. </br>16: Riemsma R, Forbes C, Harker J, Worthy G, Misso K, Schäfer M, Kleijnen J, Stürzebecher S. Systematic review of tapentadol in chronic severe pain. Curr Med Res Opin. 2011 Oct;27(10):1907-30. doi: 10.1185/03007995.2011.611494. Epub 2011 Sep 12. Review. Erratum in: Curr Med Res Opin. 2012 Jan;28(1):148. PubMed PMID: 21905968. </br>17: Pergolizzi J, Alegre C, Blake D, Alén JC, Caporali R, Casser HR, Correa-Illanes G, Fernandes P, Galilea E, Jany R, Jones A, Mejjad O, Morovic-Vergles J, Oteo-Álvaro Á, Radrigán Araya FJ, Simões ME, Uomo G. Current considerations for the treatment of severe chronic pain: the potential for tapentadol. Pain Pract. 2012 Apr;12(4):290-306. doi: 10.1111/j.1533-2500.2011.00487.x. Epub 2011 Jul 29. Review. Erratum in: Pain Pract. 2013 Sep;13(7):597. Álvaro, Ángel Oteo [corrected to Oteo-Álvaro, Ángel]. PubMed PMID: 21797962. </br>18: Hartrick CT, Rozek RJ. Tapentadol in pain management: a μ-opioid receptor agonist and noradrenaline reuptake inhibitor. CNS Drugs. 2011 May;25(5):359-70. doi: 10.2165/11589080-000000000-00000. Review. PubMed PMID: 21476608. </br>19: Tzschentke TM, Christoph T, Schröder W, Englberger W, De Vry J, Jahnel U, Kögel BY. [Tapentadol: with two mechanisms of action in one molecule effective against nociceptive and neuropathic pain. 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