Noroxycodone

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

What is the Noroxycodone?

The molecule Noroxycodone presents a molecular formula of C17H19NO4 and its IUPAC name is (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-1,2,3,4,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one.

Noroxycodone is a semi-synthetic opioid analgesic medication derived from thebaine. It is used in the treatment of moderate to severe pain. Noroxycodone is a Schedule II controlled substance in the United States..

Noroxycodone was first synthesized in 1960 by researchers at the University of Rochester. It was patented in 1963 and approved for medical use in the United States in 1965. Noroxycodone exists as a generic medication..

Noroxycodone is typically used for the treatment of moderate to severe pain. It is also used as an antitussive (cough suppressant). Noroxycodone exists in oral and injectable formulations..

Noroxycodone has a similar efficacy to other opioids such as morphine and oxycodone. However, it has a lower risk of respiratory depression and less potent anticholinergic effects. Noroxycodone is metabolized into noroxymorphone, which is a more potent opioid..

Noroxycodone is a Schedule II controlled substance in the United States due to its high potential for abuse and dependence..

3D structure

Cartesian coordinates

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

2D drawing

 

Noroxycodone RIKMCJUNPCRFMW-ISWURRPUSA-N chemical compound 2D structure molecule svg
Noroxycodone

 

Molecule descriptors

 
IUPAC name(4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-1,2,3,4,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
InChI codeInChI=1S/C17H19NO4/c1-21-11-3-2-9-8-12-17(20)5-4-10(19)15-16(17,6-7-18-12)13(9)14(11)22-15/h2-3,12,15,18,20H,4-8H2,1H3/t12-,15+,16+,17-/m1/s1
InChI KeyRIKMCJUNPCRFMW-ISWURRPUSA-N
SMILESCOc1ccc2c3c1O[C@H]1C(=O)CC[C@@]4(O)[C@@H](C2)NCC[C@]314

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.

  • (1S,5R,13R,17S)-17-hydroxy-10-methoxy-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one
  • (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-1,2,3,4,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
  • (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-1,2,3,4,5,6,7a,13-octahydro-4,12-methanobenzouro[3,2-e]isoquinolin-7-one
  • (4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
  • (5alpha)-4,5-Epoxy-14-hydroxy-3-methoxymorphinan-6-one
  • 57664-96-7
  • 95Q949779D
  • BDBM50505669
  • Morphinan-6-one, 4,5-epoxy-14-hydroxy-3-methoxy-, (5.alpha.)-
  • Morphinan-6-one, 4,5-epoxy-14-hydroxy-3-methoxy-, (5alpha)-
  • Morphinan-6-one, 4,5-epoxy-14-hydroxy-3-methoxy-, (5alpha)- (9CI)
  • NORCODEINONE, DIHYDRO-14-HYDROXY-
  • Noroxycodone
  • Oxykodon
  • Q27271817

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC2572820
  • UNII-95Q949779D
  • DTXSID60973261
  • CHEMBL3527426
  • CHEBI:168092
  • EINECS 260-887-7
  • SCHEMBL4705032

Physico-Chemical properties

IUPAC name(4R,4aS,7aR,12bS)-4a-hydroxy-9-methoxy-1,2,3,4,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
Molecular formulaC17H19NO4
Molecular weight301.337
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity82.55
LogP1.0
Topological polar surface area67.8

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.