Dimetacrine

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

What is the Dimetacrine?

The molecule Dimetacrine presents a molecular formula of C17H14O4S and its IUPAC name is 3-(9,9-dimethylacridin-10-yl)-N,N-dimethylpropan-1-amine.

Dimetacrine (INN, also known as dimethylacrylaminopropionate, DMAP) is a pharmaceutical drug of the acridine class. It is a central nervous system stimulant and has been used in the treatment of ADHD and narcolepsy. Dimetacrine has also been investigated as a potential treatment for Alzheimer's disease and dementia..

The mechanism of action of dimetacrine is not fully understood, but it is thought to work by increasing levels of norepinephrine and dopamine in the brain. Dimetacrine is structurally similar to other acridine drugs such as lisdexamfetamine and amphetamines..

Dimetacrine is not approved for use in the United States, but exists in other countries such as Canada and the United Kingdom..

There is limited information on the safety and efficacy of dimetacrine in humans. Some studies have suggested that dimetacrine may be associated with an increased risk of seizures. Dimetacrine should be used with caution in patients with a history of seizure disorders..

Dimetacrine is a prescription medication and should only be used under the supervision of a healthcare provider..

3D structure

Cartesian coordinates

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

2D drawing

 

Dimetacrine RZJQGNCSTQAWON-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Dimetacrine

 

Molecule descriptors

 
IUPAC name3-(9,9-dimethylacridin-10-yl)-N,N-dimethylpropan-1-amine
InChI codeInChI=1S/C17H14O4S/c1-22(19,20)14-9-7-12(8-10-14)15-11-21-17(18)16(15)13-5-3-2-4-6-13/h2-10H,11H2,1H3
InChI KeyRZJQGNCSTQAWON-UHFFFAOYSA-N
SMILESCS(=O)(=O)c1ccc(C2=C(c3ccccc3)C(=O)OC2)cc1

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.

  • 10(9H)-Acridinepropanamine, N,N,9,9-tetramethyl-
  • 10(9H)-Acridinepropanamine,N,9,9-tetramethyl-
  • 10-(3-(Dimethylamino)propyl)-9,9-dimethylacridan
  • 10-[3-(Dimethylamino)propyl]-9,9-dimethylacridan
  • 3-(9,9-Dimethyl-10(9H)-acridinyl)-N,N-dimethyl-1-propanamine
  • 3-(9,9-Dimethyl-10(9H)-acridinyl)-N,N-dimethyl-1-propanamine #
  • 3-(9,9-dimethylacridin-10(9H)-yl)-N,N-dimethylpropan-1-amine
  • 3-(9,9-dimethylacridin-10-yl)-N,N-dimethyl-propan-1-amine
  • 3-(9,9-dimethylacridin-10-yl)-N,N-dimethylpropan-1-amine
  • 4757-55-5
  • 9,9-Dimethyl-10-(3-(dimethylamino)propyl)acridan
  • 9,9-Dimethyl-10-(3-dimethylaminopropyl)-9,10-dihydroacridin
  • ACRIDAN, 9,9-DIMETHYL-10-(3-(DIMETHYLAMINO)PROPYL)-
  • Acridan, 10-(3-(dimethylamino)propyl)-9,9-dimethyl-
  • BRN 1349663
  • CCG-36282
  • CS-0017455
  • D02565
  • DB08996
  • DSSTox_CID_2941
  • DSSTox_GSID_22941
  • DSSTox_RID_76798
  • Dimetacrin
  • Dimetacrina
  • Dimetacrine
  • Dimetacrine (INN)
  • Dimetacrino
  • Dimetacrinum
  • Dimethacin
  • Dimethacine
  • Dimethacrin
  • Dimethacrine
  • HY-B2075
  • N,9,9-Tetramethyl-10(9H)-acridinepropanamine
  • N,N,9,9-Tetramethyl-10(9H)-acridinepropanamine
  • NCGC00014044
  • NCGC00014044-01
  • NCGC00014044-02
  • NCGC00097153-01
  • NCI100297
  • NCI60_000010
  • NCIStruc1_000731
  • NCIStruc2_000432
  • NSC 100297
  • NSC-100297
  • NSC100297
  • O341NY501N
  • Oprea1_290546
  • Q5277302
  • WLN: T C666 BN IHJ B3N1&1 I1 I1

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1482035
  • CAS-4757-55-5
  • UNII-O341NY501N
  • DTXSID4022941
  • CHEMBL1328913
  • CHEBI:135233
  • Tox21_110043
  • SCHEMBL50120

Physico-Chemical properties

IUPAC name3-(9,9-dimethylacridin-10-yl)-N,N-dimethylpropan-1-amine
Molecular formulaC17H14O4S
Molecular weight314.356
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity83.69
LogP3.6
Topological polar surface area68.8

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.