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MedKoo Cat#: 318791 | Name: Tapentadol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tapentadol has been discontinued (DEA controlled substance). 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.

Chemical Structure

Tapentadol
Tapentadol
CAS#175591-23-8

Theoretical Analysis

MedKoo Cat#: 318791

Name: Tapentadol

CAS#: 175591-23-8

Chemical Formula: C14H23NO

Exact Mass: 221.1780

Molecular Weight: 221.34

Elemental Analysis: C, 75.97; H, 10.47; N, 6.33; O, 7.23

Price and Availability

This product was removed for the commercial reasons.
Related CAS #
175591-23-8 (free base) 175591-09-0 (HCl)
Synonym
BN 200, BN 200, BN 200, Tapentadol, Nucynta ER
IUPAC/Chemical Name
3-((2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl)phenol
InChi Key
KWTWDQCKEHXFFR-SMDDNHRTSA-N
InChi Code
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
SMILES Code
OC1=CC=CC([C@H](CC)[C@@H](C)CN(C)C)=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 221.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Wiffen PJ, Derry S, Naessens K, Bell RF. Oral tapentadol for cancer pain. Cochrane Database Syst Rev. 2015 Sep 25;9:CD011460. doi: 10.1002/14651858.CD011460.pub2. Review. PubMed PMID: 26403220. 2: Veal FC, Peterson GM. Pain in the Frail or Elderly Patient: Does Tapentadol Have a Role? Drugs Aging. 2015 Jun;32(6):419-26. doi: 10.1007/s40266-015-0268-7. Review. PubMed PMID: 26025117. 3: Santos J, Alarcão J, Fareleira F, Vaz-Carneiro A, Costa J. Tapentadol for chronic musculoskeletal pain in adults. Cochrane Database Syst Rev. 2015 May 27;5:CD009923. doi: 10.1002/14651858.CD009923.pub2. Review. PubMed PMID: 26017279. 4: Vadivelu N, Kai A, Maslin B, Kodumudi G, Legler A, Berger JM. Tapentadol extended release in the management of peripheral diabetic neuropathic pain. Ther Clin Risk Manag. 2015 Jan 14;11:95-105. doi: 10.2147/TCRM.S32193. eCollection 2015. Review. PubMed PMID: 25609974; PubMed Central PMCID: PMC4298300. 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. 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. 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. 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. 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. 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. 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. 12: Mendis V. Role of tapentadol in pain management. Br J Hosp Med (Lond). 2012 Mar;73(3):143-7. Review. PubMed PMID: 22411644. 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. 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. 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. 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. 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. 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. 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. Preclinical overview]. Schmerz. 2011 Feb;25(1):19-25. doi: 10.1007/s00482-010-1004-1. Review. German. PubMed PMID: 21258822. 20: Weichel C, Hecht B. [Tapentadol. Opioid analgesic and norepinephrine reuptake inhibitors]. Med Monatsschr Pharm. 2010 Dec;33(12):454-60. Review. German. PubMed PMID: 21189520.