Gentian violet cation

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

What is the Gentian violet cation?

The molecule Gentian violet cation presents a molecular formula of C25H30N3+ and its IUPAC name is [4-[bis[4-(dimethylamino)phenyl]methylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium.

Gentian violet (also known as crystal violet) is a cationic dye used as a histological stain and in Gram's method of classifying bacteria. When used as a stain, it is usually used in a solution of 0.1% in water. It is basic fuchsin dye and has a violet color..

The molecule has a molecular weight of 376.37 and a molecular formula of C22H17ClN4. The structure of the molecule is a triphenylmethane derivative. The molecule is non-polar..

Gentian violet is used to stain cells and tissues for microscopy. It is used to stain bacteria in Gram's method of classification. It can also be used to treat fungal infections of the skin and nails..

The mechanism of action of Gentian violet is not fully understood. It is thought to work by binding to DNA and inhibiting protein synthesis..

Gentian violet is considered to be a safe and effective treatment for fungal infections of the skin and nails. It is generally well tolerated, but can cause skin irritation..

3D structure

Cartesian coordinates

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

2D drawing

 

Gentian violet cation LGLFFNDHMLKUMI-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Gentian violet cation

 

Molecule descriptors

 
IUPAC name[4-[bis[4-(dimethylamino)phenyl]methylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium
InChI codeInChI=1S/C25H30N3/c1-26(2)22-13-7-19(8-14-22)25(20-9-15-23(16-10-20)27(3)4)21-11-17-24(18-12-21)28(5)6/h7-18H,1-6H3/q+1
InChI KeyLGLFFNDHMLKUMI-UHFFFAOYSA-N
SMILESCN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccc(N(C)C)cc2)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.

  • (4-(4,4'-Bis(dimethylamino)benzhydrylidene)cyclohexa-2,5-dien-1-ylidene)dimethylammonium chloride
  • 3GVJ31T6YY
  • 4-{bis[4-(dimethylamino)phenyl]methylene}-N,N-dimethylcyclohexa-2,5-dien-1-iminium
  • 7438-46-2
  • A845487
  • AB00443808-03
  • AB00443808_05
  • AB00443808_06
  • BDBM50052802
  • BSPBio_002084
  • Basic Violet-3
  • Bis(p-(dimethylamino)phenyl)(p-(dimethylammonio)phenyl)methylium
  • Crystal Violet Base
  • Crystal Violet ion(1+)
  • Crystal violet cation
  • Crystal violet ion(1)
  • Crystal-violet
  • DB00406
  • DivK1c_000031
  • GNF-PF-880
  • GV-Eleven
  • Gentian violet cation
  • Hexamethyl pararosaniline
  • IDI1_000031
  • KBio1_000031
  • KBio2_001309
  • KBio2_003877
  • KBio2_006445
  • KBio3_001304
  • KBioGR_000968
  • KBioSS_001309
  • Methanaminium, N-(4-(bis(4-(dimethylamino)phenyl)methylene)-2,5-cyclohexadien-1-ylidene)-N-methyl-
  • N-(4-(bis(4-(dimethylamino)phenyl)methylene)cyclohexa-2,5-dien-1-ylidene)-N-methylmethanaminium
  • N-(4-{bis[4-(dimethylamino)phenyl]methylidene}cyclohexa-2,5-dien-1-ylidene)-N-methylmethanaminium
  • NCGC00091112-03
  • NCGC00091112-04
  • NCGC00091112-05
  • NCGC00091112-06
  • NCGC00091112-07
  • NCGC00091112-08
  • NCI60_002648
  • NINDS_000031
  • NSC271967
  • NSC3090
  • Q63390508
  • SBI-0051393.P003
  • STL257078
  • crystal violet carbocation
  • crystal violet(1+)
  • gentian violet carbocation
  • gentian violet(1+)
  • methylrosanilinium
  • tris[4-(dimethylamino)phenyl]methylium

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC13763987
  • UNII-3GVJ31T6YY
  • AKOS005208606
  • BRD-K60025295-003-02-5
  • BRD-K60025295-003-03-3
  • DTXSID10873000
  • CHEMBL459265
  • CHEBI:77181
  • EINECS 238-398-5
  • SPBio_001136
  • SCHEMBL94116
  • Spectrum_000829
  • Spectrum2_001088
  • Spectrum3_000442
  • Spectrum4_000564
  • Spectrum5_000754

Physico-Chemical properties

IUPAC name[4-[bis[4-(dimethylamino)phenyl]methylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium
Molecular formulaC25H30N3+
Molecular weight372.526
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity122.60
LogP4.5
Topological polar surface area9.5

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.