Mazindol, (S)-
A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Mazindol, (S)- are summarized together with 3D and 2D structures and relevant physico-chemical properties.
Table of Contents
What is the Mazindol, (S)-?
The molecule Mazindol, (S)- presents a molecular formula of C16H13ClN2O and its IUPAC name is (5S)-5-(4-chlorophenyl)-2,3-dihydroimidazo[1,2-b]isoindol-5-ol.
Mazindol is a molecule that acts as a norepinephrine-dopamine reuptake inhibitor (NDRI). It was first synthesized in the 1970s and was approved for use in the United States in 1985. Mazindol has been used as a weight loss aid as it increases the levels of norepinephrine and dopamine in the brain, which leads to a decrease in appetite. It has also been used to treat ADHD and narcolepsy..
Mazindol works by inhibiting the reuptake of norepinephrine and dopamine into the presynaptic neuron. This leads to an increase in the levels of these neurotransmitters in the brain. Mazindol has a high affinity for the dopamine transporter and a moderate affinity for the norepinephrine transporter. The exact mechanism of action of mazindol is not known..
Mazindol exists as tablets and capsules. The usual dose is 2-4 mg two or three times a day. Mazindol should be taken with food..
Mazindol side effects include dry mouth, constipation, headache, dizziness, and insomnia. Mazindol can also cause an increase in blood pressure and heart rate. Mazindol should be used with caution in patients with hypertension, cardiovascular disease, or a history of drug abuse..
Mazindol is a controlled substance in the United States and lies as a Schedule IV drug. Mazindol abuse can lead to dependence and addiction..
3D structure
Cartesian coordinates
Geometry of Mazindol, (S)- in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.
2D drawing
Molecule descriptors
| IUPAC name | (5S)-5-(4-chlorophenyl)-2,3-dihydroimidazo[1,2-b]isoindol-5-ol |
| InChI code | InChI=1S/C16H13ClN2O/c17-12-7-5-11(6-8-12)16(20)14-4-2-1-3-13(14)15-18-9-10-19(15)16/h1-8,20H,9-10H2/t16-/m0/s1 |
| InChI Key | ZPXSCAKFGYXMGA-INIZCTEOSA-N |
| SMILES | O[C@@]1(c2ccc(Cl)cc2)c2ccccc2C2=NCCN21 |
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.
- (S)-mazindol
- 1337994-13-4
- 3H-Imidazo(2,1-a)isoindol-5-ol, 5-(4-chlorophenyl)-2,5-dihydro-, (5S)-
- B99NL08Q65
- Mazindol, (S)-
- Q27274542
Reference codes for other databases
There exist several different chemical codes commonly used in orded to identify molecules:- CAS number (Chemical Abstracts Service Registry Number) is a unique identifier is assigned to every chemical compound indexed in the CAS database.
- Beilstein: The Beilstein database is a comprehensive source of information on organic chemistry, including information on chemical structures, properties, and reactions. The Beilstein database assigns unique identifiers which can be used to identify compounds in scientific literature and other sources.
- ChEBI (Chemical Entities of Biological Interest): ChEBI is a database of small chemical molecules that are of interest in the field of biology.
- PubChem CID (Compound Identifier): PubChem is a database of chemical compounds that is maintained by the National Institutes of Health (NIH).
- RTECS number (Registry of Toxic Effects of Chemical Substances): The RTECS is a database of information on the toxic effects of chemicals, including information on their structures and properties.
- ChEMBL (Compound Bioactivity Data): ChEMBL is a database of bioactivity data for small molecules, including information on their properties and structures.
- CompTox Dashboard (Environmental Protection Agency): The CompTox Dashboard is a database of information on the toxicology and environmental effects of chemicals.
- ZINC896621
- UNII-B99NL08Q65
- SCHEMBL343662
Physico-Chemical properties
| IUPAC name | (5S)-5-(4-chlorophenyl)-2,3-dihydroimidazo[1,2-b]isoindol-5-ol |
| Molecular formula | C16H13ClN2O |
| Molecular weight | 284.74 |
| Melting point (ºC) | |
| Boiling point (ºC) | |
| Density (g/cm3) | |
| Molar refractivity | 86.12 |
| LogP | 2.0 |
| Topological polar surface area | 35.8 |
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.