Tapentadol

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Tapentadol are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Tapentadol?

The molecule Tapentadol presents a molecular formula of C14H23NO and its IUPAC name is 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol.

Tapentadol is a pain reliever that is used to treat moderate to severe pain. It is a synthetic opioid that is similar to morphine. Tapentadol is a Schedule II controlled substance in the United States..

Tapentadol was first synthesized in 1961 by Janssen Pharmaceutica. It was originally developed as an antidepressant. However, it was found to be more effective as a pain reliever. Tapentadol was approved by the United States Food and Drug Administration (FDA) in 2008..

Tapentadol exists as an oral tablet, an oral solution, and an extended-release oral tablet. The oral tablet is taken every four to six hours as needed for pain. The extended-release tablet is taken every twelve hours. Tapentadol should be taken with food..

Tapentadol works by binding to the mu-opioid receptor. This receptor belongs in the brain and spinal cord. Tapentadol reduces the amount of pain signals that are sent to the brain..

Tapentadol can cause side effects including constipation, nausea, vomiting, drowsiness, and dizziness. Tapentadol can also cause respiratory depression. This is a serious but rare side effect. Respiratory depression can be fatal..

Tapentadol can interact with other medications. Tapentadol should not be taken with alcohol or other central nervous system depressants. Tapentadol can also interact with certain antibiotics, antifungals, and HIV medications..

Tapentadol is a safe and effective pain reliever when used as directed. Tapentadol can cause serious side effects, but these are rare. Tapentadol should not be taken with alcohol or other central nervous system depressants. Tapentadol can also interact with certain medications..

3D structure

Cartesian coordinates

Geometry of Tapentadol in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Tapentadol KWTWDQCKEHXFFR-SMDDNHRTSA-N chemical compound 2D structure molecule svg
Tapentadol

 

Molecule descriptors

 
IUPAC name3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol
InChI codeInChI=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
InChI KeyKWTWDQCKEHXFFR-SMDDNHRTSA-N
SMILESCC[C@@H](c1cccc(O)c1)[C@@H](C)CN(C)C

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol
  • (R,R)-Tapentadol
  • 175591-23-8
  • 3-((1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl)phenol
  • 3-((2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl)phenol
  • 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol
  • 3-[(2R,3R)-1-dimethylamino-2-methylpentan-3-yl]phenol
  • 3-[3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol
  • A26964
  • AR-270/43507984
  • BCP9000118
  • BDBM50386381
  • BN 200
  • BN 200 (BASE)
  • BN-200
  • CG 5503
  • CG-5503
  • CG5503
  • CG5503 (BASE)
  • CG5503 IR
  • CS-M0020
  • D06007
  • DB06204
  • DEA No. 9780
  • FT-0699883
  • GTPL7477
  • H8A007M585
  • HSDB 8309
  • NSC 759619
  • NSC-759619
  • Palexia
  • Phenol, 3-((1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl)-
  • Phenol,3-[(1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl]-
  • Q414463
  • Tapentadol
  • Tapentadol (USAN/INN)
  • phenol, 3-[(1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl]-

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC20783
  • UNII-H8A007M585
  • AKOS015951190
  • DTXSID30170003
  • CHEMBL1201776
  • CHEBI:135935
  • SCHEMBL116924

Physico-Chemical properties

IUPAC name3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol
Molecular formulaC14H23NO
Molecular weight221.339
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity69.98
LogP3.1
Topological polar surface area23.5

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.