Nalorphine

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

What is the Nalorphine?

The molecule Nalorphine presents a molecular formula of C19H21NO3 and its IUPAC name is (4R,4aR,7S,7aR,12bS)-3-prop-2-enyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol.

Nalorphine is a molecule that was first synthesized in 1932. It is an opioid analgesic that is structurally related to morphine. Nalorphine is a potent agonist of the μ-opioid receptor and has similar effects to morphine, including analgesia, sedation, and respiratory depression. However, it also has some unique effects, such as reversal of morphine-induced respiratory depression and potentiation of the effects of other opioids. Nalorphine has been used medically for the treatment of pain and as an antidote for opioid overdose..

3D structure

Cartesian coordinates

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

2D drawing

 

Nalorphine UIQMVEYFGZJHCZ-SSTWWWIQSA-N chemical compound 2D structure molecule svg
Nalorphine

 

Molecule descriptors

 
IUPAC name(4R,4aR,7S,7aR,12bS)-3-prop-2-enyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
InChI codeInChI=1S/C19H21NO3/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20/h2-6,12-13,15,18,21-22H,1,7-10H2/t12-,13+,15-,18-,19-/m0/s1
InChI KeyUIQMVEYFGZJHCZ-SSTWWWIQSA-N
SMILESC=CCN1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5

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,14S,17R)-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraene-10,14-diol
  • (4R,4aR,7S,7aR,12bS)-3-allyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
  • (5alpha,6alpha)-17-prop-2-en-1-yl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol
  • 62-67-9
  • 7,8-Didehydro-4,5-epoxy-17-(2-propenyl)morphinan-3,6-diol
  • Acetorfin
  • Allorphine
  • Anarcon
  • Anthorphine
  • Antorfin
  • Antorphin
  • Antorphine
  • BDBM50367061
  • D08247
  • DB11490
  • DEA No. 9400
  • GTPL1629
  • HSDB 3278
  • MORPHINAN-3,6-DIOL, 7,8-DIDEHYDRO-4,5-EPOXY-17-(2-PROPENYL)-(5.ALPHA.,6.ALPHA.)-
  • Morphinan-3,6-alpha-diol, 17-allyl-7,8-didehydro-4,5-alpha-epoxy-
  • Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-(2-propenyl)-, (5alpha,6alpha)-
  • N-Allyl-7,8-dehydro-4,5-epoxy-3,6-dihydroxymorphinan
  • N-Allyl-N-desmethylmorphine
  • N-Allylnormorphine
  • N-allyl-normorphine
  • NANM
  • NCGC00168255-01
  • Nalorfina
  • Nalorphin
  • Nalorphine
  • Nalorphine (INN)
  • Nalorphine serb
  • Nalorphinium
  • Nalorphinum
  • Nallin
  • Norfin
  • Normorphine, N-allyl-
  • PDSP2_001572
  • Q2622916
  • U59WB2WRY2

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3875420
  • UNII-U59WB2WRY2
  • DTXSID3023348
  • CHEMBL415284
  • CHEBI:7458
  • EINECS 200-546-1
  • SCHEMBL38920

Physico-Chemical properties

IUPAC name(4R,4aR,7S,7aR,12bS)-3-prop-2-enyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
Molecular formulaC19H21NO3
Molecular weight311.375
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity91.41
LogP1.7
Topological polar surface area52.9

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.