6-Desoxy-6-methylenenaltrexone

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 6-Desoxy-6-methylenenaltrexone are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 6-Desoxy-6-methylenenaltrexone?

The molecule 6-Desoxy-6-methylenenaltrexone presents a molecular formula of C20H26N2 and its IUPAC name is (2R)-3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N,2-trimethylpropan-1-amine.

6-Desoxy-6-methylenenaltrexone (6-DMA) is a molecule that was designed as an opioid receptor antagonist. It is a derivative of naltrexone, and was first synthesized in 1992. 6-DMA has a high affinity for the μ-opioid receptor, and has been shown to block the effects of opioids in animal studies. However, the exact mechanism of action of 6-DMA is not fully understood. 6-DMA has been investigated as a potential treatment for opioid addiction, but has not been approved for clinical use..

3D structure

Cartesian coordinates

Geometry of 6-Desoxy-6-methylenenaltrexone in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

6-Desoxy-6-methylenenaltrexone ZSCDBOWYZJWBIY-MRXNPFEDSA-N chemical compound 2D structure molecule svg
6-Desoxy-6-methylenenaltrexone

 

Molecule descriptors

 
IUPAC name(2R)-3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N,2-trimethylpropan-1-amine
InChI codeInChI=1S/C20H26N2/c1-16(14-21(2)3)15-22-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)22/h4-11,16H,12-15H2,1-3H3/t16-/m1/s1
InChI KeyZSCDBOWYZJWBIY-MRXNPFEDSA-N
SMILESC[C@H](CN(C)C)CN1c2ccccc2CCc2ccccc21

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.

  • (R)-Trimipramine
  • 6-Desoxy-6-methylenenaltrexone
  • A13088

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC968275
  • SCHEMBL117756

Physico-Chemical properties

IUPAC name(2R)-3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N,2-trimethylpropan-1-amine
Molecular formulaC20H26N2
Molecular weight294.434
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity98.57
LogP4.2
Topological polar surface area6.5

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.