Zimeldine

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

What is the Zimeldine?

The molecule Zimeldine presents a molecular formula of C16H17BrN2 and its IUPAC name is (Z)-3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-3-ylprop-2-en-1-amine.

Zimeldine is a molecule that was developed as an antidepressant in the 1970s. It was withdrawn from the market in the 1990s due to concerns about its potential to cause seizures. Despite its withdrawal, zimeldine continues to be studied as a potential treatment for a variety of conditions, including depression, anxiety, and chronic pain..

Zimeldine works by inhibiting the reuptake of norepinephrine and serotonin, two neurotransmitters that are thought to be involved in the regulation of mood. This action results in an increase in the levels of these neurotransmitters in the brain, which is thought to be the mechanism by which zimeldine produces its antidepressant effects..

Zimeldine has also been shown to bind to the kappa opioid receptor, a protein that participes in pain perception. This interaction may explain the reports of zimeldine's efficacy in treating chronic pain..

Despite its promising potential, zimeldine has not been approved for use in any country. This is due to the lack of large-scale clinical trials that would be necessary to assess the safety and efficacy of the molecule. However, zimeldine continues to be studied in smaller trials and may one day be approved for use as a treatment for depression, anxiety, and chronic pain..

3D structure

Cartesian coordinates

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

2D drawing

 

Zimeldine OYPPVKRFBIWMSX-SXGWCWSVSA-N chemical compound 2D structure molecule svg
Zimeldine

 

Molecule descriptors

 
IUPAC name(Z)-3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-3-ylprop-2-en-1-amine
InChI codeInChI=1S/C16H17BrN2/c1-19(2)11-9-16(14-4-3-10-18-12-14)13-5-7-15(17)8-6-13/h3-10,12H,11H2,1-2H3/b16-9-
InChI KeyOYPPVKRFBIWMSX-SXGWCWSVSA-N
SMILESCN(C)C/C=C(/c1ccc(Br)cc1)c1cccnc1

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.

  • (Z)-3-(1-(P-BROMOPHENYL)-3-(DIMETHYLAMINO)PROPENYL)PYRIDINE
  • (Z)-3-(4'-Bromophenyl)-3-(3''-pyridyl)dimethylallylamine
  • (Z)-3-(4-Bromophenyl)-N,N-dimethyl-3-(3-pyridinyl)-2-propen-1-amine
  • (Z)-Zimelidine
  • 2-Propen-1-amine, 3-(4-bromophenyl)-N,N-dimethyl-3-(3-pyridinyl)-
  • 2-Propen-1-amine, 3-(4-bromophenyl)-N,N-dimethyl-3-(3-pyridinyl)-, (Z)-
  • 3J928617DW
  • 56775-88-3
  • A 23140
  • A-23140
  • A23140
  • Allylamine, 3-(p-bromophenyl)-N,N-dimethyl-3-(3-pyridyl)-
  • BDBM50020706
  • BRN 0479680
  • CCG-37384
  • CS-0068635
  • DB04832
  • HSDB 7697
  • HY-118835
  • L001151
  • Lopac0_001280
  • N,N-Dimethyl-3-(3-pyridyl)-3-(4-bromophenyl)prop-2-enamine
  • N,N-Dimethyl-3-(3-pyridyl)-3-(4-bromophenyl)prop-2-enamine (Zimelidine)
  • NCGC00025286-02
  • NCGC00025286-03
  • NCGC00025286-07
  • NCGC00188940-01
  • NCI305352
  • Normud
  • Prestwick2_000092
  • Q203483
  • SBI-0051246.P002
  • SDCCGSBI-0051246.P003
  • ZIMELIDINEDIHYDROCHLORIDE
  • Zelmid
  • Zimeldina
  • Zimeldine
  • Zimeldinum
  • Zimelidine
  • Zimelidine (Z)
  • [3-(4-Bromo-phenyl)-3-pyridin-3-yl-allyl]-dimethyl-amine
  • [3-(4-Bromo-phenyl)-3-pyridin-3-yl-allyl]-dimethyl-amine (Zimelidine)
  • [3-(4-Bromo-phenyl)-3-pyridin-3-yl-allyl]-dimethyl-amine(Zimeldine)
  • cis -[3-(4-Bromo-phenyl)-3-pyridin-3-yl-allyl]-dimethyl-amine;HCl
  • cis-H 102/09
  • cis-Zimelidine
  • trans-[3-(4-Bromo-phenyl)-3-pyridin-3-yl-allyl]-dimethyl-amine;C2H4O4

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC8099545
  • UNII-3J928617DW
  • BRD-K94173644-300-01-3
  • DTXSID6048462
  • CHEMBL37744
  • CHEBI:92824
  • CHEBI:135357
  • SCHEMBL35029

Physico-Chemical properties

IUPAC name(Z)-3-(4-bromophenyl)-N,N-dimethyl-3-pyridin-3-ylprop-2-en-1-amine
Molecular formulaC16H17BrN2
Molecular weight317.224
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity83.83
LogP3.8
Topological polar surface area16.1

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.