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Chemistry

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Also known as: 175591-09-0, Tapentadol hcl, Nucynta, Palexia, Tapentadol (hydrochloride), Nucynta er
Molecular Formula
C14H24ClNO
Molecular Weight
257.80  g/mol
InChI Key
ZELFLGGRLLOERW-YECZQDJWSA-N
FDA UNII
71204KII53

Tapentadol
An opioid analgesic, MU OPIOID RECEPTOR agonist, and noradrenaline reuptake inhibitor that is used in the treatment of moderate to severe pain, and of pain associated with DIABETIC NEUROPATHIES.
1 2D Structure

Tapentadol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol;hydrochloride
2.1.2 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
2.1.3 InChI Key
ZELFLGGRLLOERW-YECZQDJWSA-N
2.1.4 Canonical SMILES
CCC(C1=CC(=CC=C1)O)C(C)CN(C)C.Cl
2.1.5 Isomeric SMILES
CC[C@@H](C1=CC(=CC=C1)O)[C@@H](C)CN(C)C.Cl
2.2 Other Identifiers
2.2.1 UNII
71204KII53
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-((1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl)phenol

2. Nucynta

3. Tapentadol

2.3.2 Depositor-Supplied Synonyms

1. 175591-09-0

2. Tapentadol Hcl

3. Nucynta

4. Palexia

5. Tapentadol (hydrochloride)

6. Nucynta Er

7. Bn-200 Hydrochloride

8. Cg5503 Hydrochloride

9. Cg-5503 Hydrochloride

10. 3-((2r,3r)-1-(dimethylamino)-2-methylpentan-3-yl)phenol Hydrochloride

11. 71204kii53

12. 175591-09-0 (hcl)

13. Tapentadol Hydrochloride (jan)

14. Tapentadol Hydrochloride [jan]

15. 3-[(1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol Hydrochloride

16. Palexia Retard

17. 3-((1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl)phenol Hydrochloride

18. Unii-71204kii53

19. Palexia Sr

20. Phenol, 3-[(1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl]-, Hydrochloride (1:1)

21. Phenol, 3-((1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl)-, Hydrochloride (1:1)

22. Nucynta (tn)

23. Schembl238138

24. Jns-024 Er

25. Chembl1201777

26. Dtxsid00938677

27. Amy25232

28. Hy-70042a

29. Mfcd00944992

30. Tapentadol Hydrochloride [mi]

31. Akos016842888

32. Cs-0879

33. Tapentadol Hydrochloride [mart.]

34. Tapentadol Hydrochloride [vandf]

35. Tapentadol Hydrochloride [who-dd]

36. Ac-32018

37. Tapentadol Hydrochloride [orange Book]

38. D10199

39. Tapentadol Hydrochloride [ep Monograph]

40. 591t238

41. Tapentadol Hydrochloride (1.0 Mg/ml In Methanol)

42. R-331333

43. Q27265914

44. 3-((1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl) Phenol Hydrochloride

45. 3-((1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl)-phenol Hydrochloride

46. 3-[(2r,3r)-1-(dimethylamino)-2-methylpentan-3-yl]phenol;hydrochloride

47. 3-[1-(dimethylamino)-2-methylpentan-3-yl]phenol--hydrogen Chloride (1/1)

48. (-)-(1r,2r)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol Hydrochloride

49. (-)-(1r,2r)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)-phenol Hydrochloride

50. 3-[(1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol Monohydrochloride

51. Phenol, 3-((1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl)-, Hydrochloride

52. Phenol, 3-(3-(dimethylamino)-1-ethyl-2-methylpropyl)-, Hydrochloride, (r-(r*,r*))-

53. Tapentadol Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 257.80 g/mol
Molecular Formula C14H24ClNO
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass257.1546421 g/mol
Monoisotopic Mass257.1546421 g/mol
Topological Polar Surface Area23.5 Ų
Heavy Atom Count17
Formal Charge0
Complexity193
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameNucynta
PubMed HealthTapentadol (By mouth)
Drug ClassesAnalgesic
Drug LabelNUCYNTA ER (tapentadol) is a mu-opioid receptor agonist, supplied in extended-release film-coated tablets for oral administration, containing 58.24, 116.48, 174.72, 232.96, and 291.20 mg of tapentadol hydrochloride in each tablet strength, correspo...
Active IngredientTapentadol hydrochloride
Dosage FormTablet; Solution
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 75mg base; eq 20mg base/ml
Market StatusPrescription
CompanyJanssen Pharms

2 of 4  
Drug NameNucynta er
Drug LabelNUCYNTA ER (tapentadol) is a mu-opioid receptor agonist, supplied in extended-release film-coated tablets for oral administration, containing 58.24, 116.48, 174.72, 232.96, and 291.20 mg of tapentadol hydrochloride in each tablet strength, correspo...
Active IngredientTapentadol hydrochloride
Dosage FormTablet, extended release
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 250mg base; eq 150mg base; eq 200mg base
Market StatusPrescription
CompanyJanssen Pharms

3 of 4  
Drug NameNucynta
PubMed HealthTapentadol (By mouth)
Drug ClassesAnalgesic
Drug LabelNUCYNTA ER (tapentadol) is a mu-opioid receptor agonist, supplied in extended-release film-coated tablets for oral administration, containing 58.24, 116.48, 174.72, 232.96, and 291.20 mg of tapentadol hydrochloride in each tablet strength, correspo...
Active IngredientTapentadol hydrochloride
Dosage FormTablet; Solution
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 75mg base; eq 20mg base/ml
Market StatusPrescription
CompanyJanssen Pharms

4 of 4  
Drug NameNucynta er
Drug LabelNUCYNTA ER (tapentadol) is a mu-opioid receptor agonist, supplied in extended-release film-coated tablets for oral administration, containing 58.24, 116.48, 174.72, 232.96, and 291.20 mg of tapentadol hydrochloride in each tablet strength, correspo...
Active IngredientTapentadol hydrochloride
Dosage FormTablet, extended release
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 250mg base; eq 150mg base; eq 200mg base
Market StatusPrescription
CompanyJanssen Pharms

4.2 Drug Indication

Treatment of acute pain


Treatment of acute pain


Treatment of acute pain


Treatment of chronic pain


Treatment of chronic pain


Treatment of acute pain


Treatment of chronic pain


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Adrenergic Uptake Inhibitors

Drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants (ANTIDEPRESSIVE AGENTS, TRICYCLIC) and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin. (See all compounds classified as Adrenergic Uptake Inhibitors.)


Analgesics, Opioid

Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Opioid Agonists [MoA]; Opioid Agonist [EPC]

API Reference Price

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09-Feb-2021
10-Oct-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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Taste Masking

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