8-Hydroxydemethylclomipramine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 8-Hydroxydemethylclomipramine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 8-Hydroxydemethylclomipramine?

The molecule 8-Hydroxydemethylclomipramine presents a molecular formula of C18H21ClN2O and its IUPAC name is 9-chloro-11-[3-(methylamino)propyl]-5,6-dihydrobenzo[b][1]benzazepin-3-ol.

8-Hydroxydemethylclomipramine is a molecule of the tricyclic antidepressant (TCA) class. It is the primary active metabolite of clomipramine, and is also sold as its own antidepressant under the brand names Anafranil and Clofranil. 8-Hydroxydemethylclomipramine has approximately one-third the potency of clomipramine as an antidepressant..

The exact mechanism of action of 8-hydroxydemethylclomipramine is unknown, but it is thought to work similarly to other TCAs by inhibiting the reuptake of norepinephrine and serotonin into the presynaptic neuron, thereby increasing neurotransmission. 8-Hydroxydemethylclomipramine has been shown to bind to and block the serotonin transporter with high affinity, and also has weak norepinephrine reuptake inhibitory activity..

8-Hydroxydemethylclomipramine has a number of adverse effects, the most common of which include dry mouth, constipation, weight gain, and drowsiness. It can also cause more serious side effects such as hypotension, arrhythmias, and seizures. As with all TCAs, 8-hydroxydemethylclomipramine should be used with caution in patients with a history of cardiovascular disease or arrhythmias..

8-Hydroxydemethylclomipramine exists in oral capsule, tablet, and solution formulations. It is typically taken once or twice daily, with or without food..

3D structure

Cartesian coordinates

Geometry of 8-Hydroxydemethylclomipramine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

8-Hydroxydemethylclomipramine MRLCQGACIDFFSH-UHFFFAOYSA-N chemical compound 2D structure molecule svg
8-Hydroxydemethylclomipramine

 

Molecule descriptors

 
IUPAC name9-chloro-11-[3-(methylamino)propyl]-5,6-dihydrobenzo[b][1]benzazepin-3-ol
InChI codeInChI=1S/C18H21ClN2O/c1-20-9-2-10-21-17-8-7-16(22)11-14(17)4-3-13-5-6-15(19)12-18(13)21/h5-8,11-12,20,22H,2-4,9-10H2,1H3
InChI KeyMRLCQGACIDFFSH-UHFFFAOYSA-N
SMILESCNCCCN1c2ccc(O)cc2CCc2ccc(Cl)cc21

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.

  • 104061-28-1
  • 17PE41HJN3
  • 5H-Dibenz(b,f)azepin-2-ol, 7-chloro-10,11-dihydro-5-(3-(methylamino)propyl)-
  • 8-Hydroxydemethylclomipramine
  • 8-Hydroxydesmethylclomipramine
  • 9-chloro-11-[3-(methylamino)propyl]-5,6-dihydrobenzo[b][1]benzazepin-3-ol
  • Q27251923

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • UNII-17PE41HJN3
  • CHEBI:169626

Physico-Chemical properties

IUPAC name9-chloro-11-[3-(methylamino)propyl]-5,6-dihydrobenzo[b][1]benzazepin-3-ol
Molecular formulaC18H21ClN2O
Molecular weight316.825
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity95.90
LogP4.3
Topological polar surface area35.5

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.