Misplaced Pages

:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Crystal violet: Difference between pages - Misplaced Pages

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Difference between pages)
Page 1
Page 2
Content deleted Content addedVisualWikitext
Revision as of 12:58, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475247487 of page Crystal_violet for the Chem/Drugbox validation project (updated: 'DrugBank').  Latest revision as of 15:59, 8 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,127 edits removed Category:Anilines using HotCat 
Line 1: Line 1:
{{Short description|Triarylmethane dye used as a histological stain and in Gram's method of classifying bacteria}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{distinguish|Cresyl violet}}
{{Chembox {{Chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460108792
| verifiedrevid = 476997552
| ImageFile = Methyl Violet 10B.png
| ImageFile = Kristallviolett.svg
| ImageSize = 244
| ImageSize = 230
| ImageName = Kekulé, skeletal formula of a crystal violet minor tautomer
| ImageAlt = Kekulé, skeletal formula of a crystal violet minor tautomer
| IUPACName = Tris(4-(dimethylamino)phenyl)methylium chloride{{Citation needed|date = June 2011}}
| ImageFile1 = Methyl violet 10B 3D ball.png
| OtherNames = Aniline violet{{Citation needed|date = June 2011}}<br />
| ImageAlt1 = Ball-and-stick model of crystal violet as a chloride salt
Basic violet 3<br />
| PIN = 4-{Bismethylidene}-''N'',''N''-dimethylcyclohexa-2,5-dien-1-iminium chloride
Baszol Violet 57L{{Citation needed|date = June 2011}}<br />
| OtherNames = {{bulletedlist|Aniline violet|Basic violet 3|Baszol Violet 57L|Brilliant Violet 58|Hexamethyl-''p''-rosaniline chloride|Methylrosanilide chloride|Methyl Violet 10B|Methyl Violet 10BNS|Pyoktanin}}
Brilliant Violet 58{{Citation needed|date = June 2011}}<br />
|Section1={{Chembox Identifiers
Hexamethyl-''p''-rosaniline chloride{{Citation needed|date = June 2011}}<br />
| CASNo_Ref = {{cascite|correct|CAS}}
Methylrosanilide chloride{{Citation needed|date = June 2011}}<br />
| CASNo = 548-62-9
Methyl Violet 10B{{Citation needed|date = June 2011}}<br />
| CASNo1_Ref = {{cascite|correct|CAS}}
Methyl Violet 10BNS{{Citation needed|date = June 2011}}<br />
| CASNo1 = 1733-13-7
Pyoktanin{{Citation needed|date = June 2011}}<br />
| CASNo1_Comment = (base)
| Section1 = {{Chembox Identifiers
| CASNo = 548-62-9 | PubChem = 11057
| PubChemOther = {{PubChemCID|68050}} (base)
| CASNo_Ref = {{cascite|correct|CAS}}
| ChemSpiderID = 10588
| CASOther = <br />{{CAS|467-63-0}} (base)
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| PubChem = 11057
| PubChem_Ref = {{Pubchemcite|correct|pubchem}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = J4Z741D6O5
| PubChemOther = {{PubChemCID|68050}} (base)
| UNII1_Ref = {{fdacite|correct|FDA}}
| ChemSpiderID = 10588
| UNII1 = B4JIJ2C6AT
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII1_Comment = (base)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = J4Z741D6O5 | EINECS = 208-953-6
| EINECS = 208-953-6 | UNNumber = 3077
| ChEBI_Ref = {{ebicite|correct|EBI}}
| UNNumber = 3077
| ChEBI = 41688
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = <!-- blanked - oldvalue: DB00406 -->
| KEGG = D01046 | DrugBank = DB00406
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D01046
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = Gentian+violet | MeSHName = Gentian+violet
| ChEMBL = 64894 | ChEMBL = 64894
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = BO9000000 | RTECS = BO9000000
| Beilstein = 3580948 | Beilstein = 3580948
| SMILES = .CN(C)c1ccc(cc1)(c1ccc(cc1)N(C)C)c1ccc(cc1)N(C)C
| ATCCode_prefix = D01
| SMILES1 = .CN(C)C1=CC=C(C=C1)(C1=CC=C(C=C1)N(C)C)C1=CC=C(C=C1)N(C)C
| ATCCode_suffix = AE02
| StdInChI = 1S/C25H30N3.ClH/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;1H/q+1;/p-1
| ATC_Supplemental = {{ATC|G01|AX09}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| SMILES = .CN(C)c1ccc(cc1)(c1ccc(cc1)N(C)C)c1ccc(cc1)N(C)C
| InChI = 1/C25H30N3.ClH/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;1H/q+1;/p-1
| SMILES1 = .CN(C)C1=CC=C(C=C1)(C1=CC=C(C=C1)N(C)C)C1=CC=C(C=C1)N(C)C
| StdInChIKey = ZXJXZNDDNMQXFV-UHFFFAOYSA-M
| StdInChI = 1S/C25H30N3.ClH/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;1H/q+1;/p-1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = ZXJXZNDDNMQXFV-REWHXWOFAV
| InChI = 1/C25H30N3.ClH/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;1H/q+1;/p-1
| StdInChIKey = ZXJXZNDDNMQXFV-UHFFFAOYSA-M
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = ZXJXZNDDNMQXFV-REWHXWOFAV
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = {{Chem|C|25|N|3|H|30|Cl}} | C=25|H=30|N=3|Cl=1
| Solubility = 4 g/L at 25 °C<ref>{{Cite book |last=Green|first=Floyd J.|pages=239–240|url=https://books.google.com/books?id=D0OTFN7coVIC|title=The Sigma-Aldrich Handbook of Stains, Dyes, and Indicators |date=1990 |publisher=Sigma-Aldrich Corp.|isbn=978-0-941633-22-2|location=Milwaukee, Wisconsin|oclc=911335305}}</ref>
| MolarMass = 407.979 g mol<sup>-1</sup>
| MeltingPtC = 205
| ExactMass = 407.212825682 g mol<sup>-1</sup>
| MeltingPtC = 205
}} }}
| Section3 = {{Chembox Hazards |Section6={{Chembox Pharmacology
| ATCCode_prefix = D01
| GHSPictograms = {{GHS corrosion}} {{GHS exclamation mark}} {{GHS health hazard}} {{GHS environment}}
| ATCCode_suffix = AE02
| GHSSignalWord = '''DANGER'''
| HPhrases = {{H-phrases|302|318|351|410}} | ATC_Supplemental = {{ATC|G01|AX09}}
| PPhrases = {{P-phrases|273|280|305+351+338|501}}
| EUIndex = 612-204-00-2
| EUClass = {{Hazchem Xn}} {{Hazchem N}}
| RPhrases = {{R22}}, {{R40}}, {{R41}}, {{R50/53}}
| SPhrases = {{S2}}, {{S26}}, {{S36/37/39}}, {{S46}}, {{S60}}, {{S61}}
| LD50 = 1.2 g/kg (oral, mice)</br>
1.0 g/kg (oral, rats)<ref>{{citation | last1=Hodge | first1=H.C. | last2=Indra | first2=J. | last3=Drobeck | first3=H.P. | last4=Duprey | first4=L.P. | last5=Tainter | first5=M.L. | year=1972 | title= Acute oral toxicity of methylrosaniline chloride | volume=22 | pages=1–5 | doi=10.1016/0041-008X(72)90219-0 | journal=Toxicology and Applied Pharmacology | pmid=5034986 | issue=1 }}</ref>
}} }}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS corrosion}} {{GHS exclamation mark}} {{GHS health hazard}} {{GHS environment}}
| GHSSignalWord = '''DANGER'''
| HPhrases = {{H-phrases|302|318|351|410}}
| PPhrases = {{P-phrases|273|280|305+351+338|501}}
| LD50 = 1.2&nbsp;g/kg (oral, mice)<br>
1.0&nbsp;g/kg (oral, rats)<ref>{{Cite journal |last1=Hodge |first1=H. C. |last2=Indra |first2=J. |last3=Drobeck |first3=H. P. |last4=Duprey |first4=L. P. |last5=Tainter |first5=M. L. |year=1972 |title=Acute oral toxicity of methylrosaniline chloride |journal=] |volume=22 |issue=1 |pages=1–5 |doi=10.1016/0041-008X(72)90219-0 |pmid=5034986|bibcode=1972ToxAP..22....1H }}</ref>
}} }}
}}

'''Crystal violet''' or '''gentian violet''', also known as '''methyl violet 10B''' or '''hexamethyl pararosaniline chloride''', is a ] dye used as a ] stain and in ] of classifying bacteria. Crystal violet has ], ], and ] (]) properties and was formerly important as a ] ]. The medical use of the dye has been largely superseded by more modern drugs, although it is still listed by the ].

The name ''gentian violet'' was originally used for a mixture of methyl ] dyes (]), but is now often considered a synonym for ''crystal violet''. The name refers to its colour, being like that of the ]s of certain ] flowers; it is not made from gentians or ].

==Production==
A number of possible routes can be used to prepare crystal violet.<ref name="ci1971">{{Citation |title=Colour Index 3rd Edition Volume 4 |url=https://www.colour-index.org/help/3121_Triarylmethane.pdf |page=4391 |year=1971 |archive-url=https://web.archive.org/web/20110719160728/https://www.colour-index.org/help/3121_Triarylmethane.pdf |place=Bradford |publisher=Society of Dyers and Colourists |archive-date=2011-07-19 |url-status=dead}}</ref><ref name="gessner2002">{{Citation |last1=Gessner |first1=T. |title=Ullmann's Encyclopedia of Industrial Chemistry 6th Edition |year=2002 |contribution=Triarylmethane and Diarylmethane Dyes |place=Weinheim |publisher=Wiley-VCH |doi=10.1002/14356007.a27_179 |last2=Mayer |first2=U.|isbn=978-3-527-30385-4 }}</ref> The original procedure developed by the German chemists Kern and ] involved the reaction of ] with ] to give 4,4′-bis(dimethylamino)] (]) as an intermediate.<ref name=reinhardt2000/> This was then reacted with additional dimethylaniline in the presence of ] and ].<ref name=patents/>

The dye can also be prepared by the ] of ] and ] to give a ]:<ref name=ci1971/><ref name=gessner2002/><ref name="thetner2000">{{Citation |last=Thetner |first=D. |title=Kirk-Othmer Encyclopedia of Chemical Technology |url=https://mrw.interscience.wiley.com/emrw/9780471238966/kirk/article/tripthet.a01/current/pdf |archive-url=https://archive.today/20130105105555/http://mrw.interscience.wiley.com/emrw/9780471238966/kirk/article/tripthet.a01/current/pdf |url-status=dead |archive-date=January 5, 2013 |year=2000 |contribution=Triphenylmethane and related dyes |publisher=Wiley |doi=10.1002/0471238961 |isbn=978-0-471-48494-3 }}. Also available from {{Webarchive|url=https://web.archive.org/web/20121104145950/https://www.scribd.com/doc/30109454/Triphenylmethane-and-Related-Dyes |date=2012-11-04 }}.</ref>
:CH<sub>2</sub>O + 3&nbsp;C<sub>6</sub>H<sub>5</sub>N(CH<sub>3</sub>)<sub>2</sub> → CH(C<sub>6</sub>H<sub>4</sub>N(CH<sub>3</sub>)<sub>2</sub>)<sub>3</sub> + H<sub>2</sub>O
Second, this colourless compound is ] to the coloured ] form (hereafter with ], but a typical ] is ], MnO<sub>2</sub>):
:CH(C<sub>6</sub>H<sub>4</sub>N(CH<sub>3</sub>)<sub>2</sub>)<sub>3</sub> + HCl + {{1/2}}&nbsp;O<sub>2</sub> → Cl + H<sub>2</sub>O

==Dye colour==
{{pH indicator|indicator_name=Crystal violet|low_pH=−1.0|high_pH=2.0|low_pH_color=yellow|high_pH_color=#8800FF|high_pH_text=white}}
{{Multiple image
| align = left
| width = 150
| direction = vertical
| image1 = Sample of Crystal Violet.jpg
| alt1 = Black lumps in a glass beaker
| caption1 = Solid crystal violet
| image2 = Crystal Violet in aqueous solution.jpg
| alt2 = Purple liquid in a test tube
| caption2 = Crystal violet in aqueous solution
}}
When dissolved in water, the dye has a blue-violet colour with an ] maximum at 590&nbsp;nm and an ] of 87,000&nbsp;M<sup>−1</sup>&nbsp;cm<sup>−1</sup>.<ref name="adams1914">{{Cite journal |last1=Adams |first1=E. Q. |last2=Rosenstein |first2=L. |year=1914 |title=The color and ionization of crystal-violet |journal=J. Am. Chem. Soc. |volume=36 |issue=7 |pages=1452–1473 |doi=10.1021/ja02184a014 |hdl-access=free |hdl=2027/uc1.b3762873}}</ref> The colour of the dye depends on the acidity of the solution. At a ] of +1.0, the dye is green with absorption maxima at 420&nbsp;nm and 620&nbsp;nm, while in a strongly acidic solution (pH −1.0), the dye is yellow with an absorption maximum at 420&nbsp;nm.{{citation needed|date=December 2022}}

The different colours are a result of the different charged states of the dye molecule. In the yellow form, all three nitrogen atoms carry a positive charge, of which two are ], while the green colour corresponds to a form of the dye with two of the nitrogen atoms positively charged. At neutral pH, both extra protons are lost to the solution, leaving only one of the nitrogen atoms positive charged. The ] for the loss of the two protons are approximately 1.15 and 1.8.<ref name=adams1914/>

In ]ne solutions, ] ] attack the ] central carbon to produce the colourless ] or ] form of the dye.{{Citation needed|date = March 2015}} Some triphenylmethanol is also formed under very acidic conditions when the positive charges on the nitrogen atoms lead to an enhancement of the electrophilic character of the central carbon, which allows the ] by water molecules. This effect produces a slight fading of the yellow colour.{{citation needed|date=December 2022}}
{{clear left}}

==Applications==

===Industry===
] stained with crystal violet]]
] duplicated tests papers, inked with crystal violet. ]]
Crystal violet is used as a textile and paper dye, and is a component of ] and ]s for printing, ball-point pens, and inkjet printers. Historically, it was the most common dye used in early duplication machines, such as the ] and the ].<ref>{{Cite patent|number=US2838994A|title=Elements for use in practice of spirit duplication process|gdate=1958-06-17|invent1=Lebl|invent2=Joseph|invent3=Florence|inventor1-first=Richard C.|inventor2-first=Savit|inventor3-first=Robert T.|url=https://patents.google.com/patent/US2838994A/en}}</ref> It is sometimes used to colourize diverse products such as ], ], ], and ].{{citation needed|date=December 2022}} ], used to ] pieces in ], is composed of ], ], and gentian violet.<ref name="brink">{{Citation |last1=Brink |first1=C. |title=Engineering Fabrication & Boilermaking |page=44 |year=2008 |url=https://books.google.com/books?id=coOZXYLqqPoC&pg=PA44 |access-date=2021-07-14 |archive-url=https://web.archive.org/web/20210714054223/https://books.google.com/books?id=coOZXYLqqPoC&lpg=PA44 |archive-date=2021-07-14 |url-status=live |publisher=Pearson South Africa |isbn=978-1-77025-374-2 |last2=McNamara |first2=B.}}.</ref>

=== Science ===
When conducting ] ], crystal violet can be used as a nontoxic DNA stain as an alternative to ], intercalating dyes such as ]. Used in this manner, it may be either incorporated into the ] gel or applied after the electrophoresis process is finished. Used at a 0.001% concentration and allowed to stain a gel after electrophoresis for 30 minutes, it can detect as little as 16&nbsp;] of DNA. Through use of a ] counterstain and a more complex staining method, sensitivity can be improved further to 8&nbsp;ng of DNA.<ref>{{cite journal|last1=Yang |first1=Y. |title=Counterion-dye staining method for DNA in agarose gels using crystal violet and methyl orange |journal=Electrophoresis |volume=22 |issue=5 |pages=855–859 |year=2001 |doi=10.1002/1522-2683()22:5<855::AID-ELPS855>3.0.CO;2-Y |pmid=11332752 |last2=Jung |first2=D. W. |last3=Bai |first3=D. G. |last4=Yoo |first4=G. S. |last5=Choi |first5=J. K.|s2cid=28700868 }}</ref> When crystal violet is used as an alternative to ], it is not necessary to use ] illumination; this has made crystal violet popular as a means of avoiding UV-induced DNA destruction when performing ] ''in vitro''.{{citation needed|date=December 2022}}

In ], crystal violet can be used to stain the nuclei of adherent cells.<ref>{{Cite journal |last1=Klingenberg |first1=Marcel |last2=Becker |first2=Jürgen |last3=Eberth |first3=Sonja |last4=Kube |first4=Dieter |last5=Wilting |first5=Jörg |date=2014-04-06 |title=The NADPH Oxidase Inhibitor Imipramine-+Blue in the Treatment of Burkitt Lymphoma |journal=Molecular Cancer Therapeutics |volume=13 |issue=4 |pages=833–841 |doi=10.1158/1535-7163.mct-13-0688 |pmid=24482381 |doi-access=free}}</ref> In this application, crystal violet works as an intercalating dye and allows the quantification of DNA which is proportional to the number of cells.{{citation needed|date=December 2022}}

The dye is used as a ], particularly in ] for ].<ref>{{cite journal |last1=G |first1=Barbolini |last2=AC |first2=Pessina |date=1977 |title=Non-specificity of crystal violet staining for renin granules |journal=Acta Histochemica |publisher=Acta Histochem |volume=58 |issue=2 |pages=191–193 |doi=10.1016/S0065-1281(77)80127-X |issn=0065-1281 |pmid=70939}}</ref>

In ], crystal violet was used to develop ]s.<ref>{{Cite journal |last1=Feldman |first1=M. A. |last2=Meloan |first2=C. E. |last3=Lambert |first3=J. L. |date=1982-10-27 |title=A new method for recovering latent fingerprints from skin |url=https://pubmed.ncbi.nlm.nih.gov/7175462/ |journal=Journal of Forensic Sciences |volume=27 |issue=4 |pages=806–811 |doi=10.1520/JFS12196J |issn=0022-1198 |pmid=7175462}}</ref>

Crystal violet is also used as a ] in the preparation of ] sections.<ref>{{Cite journal |last1=Henneman |first1=Sheila A. |last2=Kohn |first2=Frank S. |date=June 1975 |title=Methylene blue staining of tissue culture monolayers |journal=Tissue Culture Association Manual |language=en |volume=1 |issue=2 |pages=103–104 |doi=10.1007/BF01352624 |issn=0361-0268 |series=Methods in Cell Science}}</ref> In laboratory, solutions containing crystal violet and ] are often used to simultaneously ] and stain cells grown in ] to preserve them and make them easily visible, since most cells are colourless. It is also sometimes used as a cheap way to put identification markings on ]; since many strains of lab mice are ], the purple colour stays on their ] for several weeks.<ref name="AssalAN">A. N. Assal: ''Review on the Identification Methods of Laboratory Mice, Rats, Rabbits, and Guinea pigs.'' In: ''].'' 15.1, 2019, p.&nbsp;19–31, ].</ref>

Crystal violet can be used as an alternative to ] (CBB) in staining of ]s separated by ], reportedly showing a 5x improved sensitivity vs CBB.<ref name="Krause2019">{{cite journal |last1=Krause |first1=Robert G.E. |last2=Goldring |first2=J.P. Dean |year=2019 |title=Crystal violet stains proteins in SDS-PAGE gels and zymograms |journal=Analytical Biochemistry |publisher=Elsevier BV |volume=566 |pages=107–115 |doi=10.1016/j.ab.2018.11.015 |issn=0003-2697 |pmid=30458124 |s2cid=53944873}}</ref>

===Medical===
Gentian violet has ], ], ], ], ], and ] properties.<ref name="docampo">{{Citation |last1=Docampo |first1=R. |title=The metabolism and mode of action of gentian violet |work=Drug Metab. Rev. |volume=22 |issue=2–3 |pages=161–178 |year=1990 |doi=10.3109/03602539009041083 |pmid=2272286 |last2=Moreno |first2=S. N.}}</ref><ref>{{Cite journal |last1=Maley |first1=Alexander M. |last2=Arbiser |first2=Jack L. |date=Dec 2013 |title=Gentian Violet: a 19th century drug re-emerges in the 21st century |journal=Experimental Dermatology |volume=22 |issue=12 |pages=775–780 |doi=10.1111/exd.12257 |pmc=4396813 |pmid=24118276}}<!--|access-date=24 July 2014--></ref> It is used medically for these properties, in particular for ], and is also known as "pyoctanin" (or "pyoctanine").<ref name="pyoctanin_Gorgas">{{Citation |last=Gorgas |first=Ferdinand J. S. |title=Pyoctanin – Methyl-Violet – Pyoctanine |url=https://chestofbooks.com/health/materia-medica-drugs/Manual-Of-Dental-Materia-Medica-And-Therapeutics/Pyoctanin-Methyl-Violet-Pyoctanine.html |work=Dental Medicine. A Manual Of Dental Materia Medica And Therapeutics, 7th edition |year=1901 |postscript=. |archive-url=https://web.archive.org/web/20110708143253/http://chestofbooks.com/health/materia-medica-drugs/Manual-Of-Dental-Materia-Medica-And-Therapeutics/Pyoctanin-Methyl-Violet-Pyoctanine.html |publisher=chestofbooks.com |access-date=2011-03-15 |archive-date=2011-07-08 |url-status=live}}</ref> It is commonly used for:
* Marking the skin for surgery preparation and ]ing;
* Treating ] and related ], such as ], yeast infections, various types of ] (], ], ]);
* Treating ]; it was used primarily before the advent of ]s, but still useful to persons who may be allergic to ].

In resource-limited settings, gentian violet is used to manage burn wounds,<ref>{{Cite journal |last1=Choudhary |first1=KN |last2=Soni |first2=PP |last3=Sao |first3=DK |last4=Murthy |first4=R |last5=Deshkar |first5=AM |last6=Nanda |first6=BR |date=April 2013 |title=Role of gentian violet paint in burn wound management: a prospective randomised control trial |journal=J Indian Med Assoc. |volume=111 |issue=4 |pages=248–50 |pmid=24475556}}</ref> inflammation of the ] stump (]) in the ] period,<ref>{{Cite journal |last1=Qamar |first1=FN |last2=Tikmani |first2=SS |last3=Mir |first3=F |last4=Zaidi |first4=AK |date=Nov 2013 |title=Community-based management and outcome of omphalitis in newborns in Karachi, Pakistan. |journal=The Journal of the Pakistan Medical Association |volume=63 |issue=11 |pages=1364–9 |pmid=24392520}}<!--|access-date=24 July 2014--></ref> oral ] in ]-infected patients<ref>{{Cite journal |last1=Jurevic |first1=RJ |last2=Traboulsi |first2=RS |last3=Mukherjee |first3=PK |last4=Salata |first4=RA |last5=Ghannoum |first5=MA |last6=Oral HIV/AIDS Research Alliance Mycology Focus |first6=group |date=May 2011 |title=Identification of gentian violet concentration that does not stain oral mucosa, possesses anti-candidal activity and is well tolerated. |journal=] |volume=30 |issue=5 |pages=629–33 |doi=10.1007/s10096-010-1131-8 |pmc=3076549 |pmid=21210170}}</ref> and ]s in children with ].<ref>{{Cite book |last1=Berman |first1=Stephen |url=https://www.aap.org/en-us/advocacy-and-policy/aap-health-initiatives/children-and-disasters/Documents/MANUAL-05-internacional-2011.pdf |title=Module 5. Management of Prevalent Infections in Children Following a Disaster |last2=Nyquist |first2=Christine |last3=Lynch |first3=Julia A. |last4=Gentile |first4=Ángela |publisher=American Association of Pediatrics |page=22 |access-date=24 July 2014 |archive-date=8 August 2014 |archive-url=https://web.archive.org/web/20140808070820/https://www.aap.org/en-us/advocacy-and-policy/aap-health-initiatives/children-and-disasters/Documents/MANUAL-05-internacional-2011.pdf |url-status=live }}</ref>

In ], gentian violet is commonly used to mark the location for placing piercings, including ]s.{{citation needed|date=December 2022}}

===Veterinary===

Because of its ] activity, it is used to treat ] in fish. However, it usually is illegal to use in fish intended for human consumption.<ref>{{Cite web |url=https://www.fao.org/fileadmin/user_upload/vetdrug/docs/15-2013-gentian-violet.pdf |title=5. Gentian violet – Food and Agriculture Organization |last1=Erdely |first1=Holly |last2=Sanders |first2=Pascal |website=Food and Agriculture Organization |access-date=2017-08-30 |quote=Residues in food and their evaluations – Conditions of use |archive-date=2017-08-30 |archive-url=https://web.archive.org/web/20170830132559/https://www.fao.org/fileadmin/user_upload/vetdrug/docs/15-2013-gentian-violet.pdf |url-status=live }}</ref>

==History==
]
===Synthesis===
Crystal violet is one of the components of ], a dye first synthesized by ] in 1861.<ref>{{Citation |last=Lauth |first=C. |title=On the new aniline dye, 'Violet de Paris' |url=https://books.google.com/books?id=QlYEAAAAYAAJ&pg=PA138 |work=Laboratory |volume=1 |pages=138–139 |year=1867}}</ref> From 1866, methyl violet was manufactured by the ]-based firm of Poirrier et Chappat and marketed under the name "Violet de Paris". It was a mixture of the tetra-, penta- and hexamethylated ]s.<ref>{{Citation |title=The British coal-tar industry : its origin, development, and decline |url=https://archive.org/stream/britishcoaltarin00gardrich#page/172/mode/2up |page=173 |year=1915 |editor-last=Gardner |editor-first=W. M. |place=Philadelphia |publisher=Lippincott}}</ref>

Crystal violet itself was first synthesized in 1883 by Alfred Kern (1850–1893) working in ] at the firm of Bindschedler and Busch.<ref name=patents>{{cite patent | inventor1-last=Caro | inventor1-first=H. | inventor2-last=Kern | inventor2-first=A. | title=Manufacture of dye-stuff | issue-date=1883 | patent-number=290856 | country-code=US }}<br>{{cite patent | inventor1-last=Kern | inventor1-first=A. | title=Manufacture of dye-stuff or coloring-matter | issue-date=1883 | patent-number=290891 | country-code=US }}<br>{{cite patent | inventor1-last=Kern | inventor1-first=A. | title=Manufacture of purple dye-stuff | issue-date=1883 | patent-number=290892 | country-code=US }}</ref> To optimize the difficult synthesis which used the highly toxic ], Kern entered into a collaboration with the German chemist ] at ].<ref name="reinhardt2000">{{Citation |last1=Reinhardt |first1=C. |title=Heinrich Caro and the creation of modern chemical industry |url=https://books.google.com/books?id=TxEQ5iQmWIoC&q=Alfred%20Kern&pg=PA208 |pages=208–209 |year=2000 |place=Dordrecht, Netherlands |publisher=Kluwer Academic |isbn=0-7923-6602-6 |last2=Travis |first2=A.S. |access-date=2020-10-30 |archive-date=2022-02-28 |archive-url=https://web.archive.org/web/20220228104550/https://books.google.com/books?id=TxEQ5iQmWIoC&q=Alfred+Kern&pg=PA208 |url-status=live }}</ref> Kern also found that by starting with ] rather than ], he could synthesize the closely related violet dye now known as C.I. 42600 or C.I. Basic violet 4.<ref>{{cite patent | inventor1-last=Kern | inventor1-first=A. | title=Manufacture of dye-stuff or coloring-matter| issue-date=1883 | patent-number=290893 | country-code=US }}; Also available from .</ref>

===Gentian violet===
The name "gentian violet" (or ''Gentianaviolett'' in German) is thought to have been introduced by the German pharmacist Georg Grübler, who in 1880 started a company in ] that specialized in the sale of staining reagents for ].<ref name="conn1922">{{Citation |last=Conn |first=H.J. |title=An investigation of American gentian violets: Report of Committee on Bacteriological Technic |url=https://jb.asm.org/cgi/reprint/7/5/529.pdf |work=J. Bacteriol. |volume=7 |issue=5 |pages=529–536 |year=1922 |doi=10.1128/JB.7.5.529-536.1922 |doi-access=free |access-date=2022-02-13 |archive-date=2022-02-28 |archive-url=https://web.archive.org/web/20220228104554/https://journals.asm.org/doi/pdf/10.1128/jb.7.5.529-536.1922 |url-status=live }}</ref><ref>{{Citation |last=Titford |first=M. |title=George Grübler and Karl Hollborn: two founders of the biological stain industry |work=J. Histotechnol. |volume=16 |issue=2 |pages=155–158 |year=1993 |doi=10.1179/his.1993.16.2.155 |pmid=11615369}}</ref> The gentian violet stain marketed by Grübler probably contained a mixture of methylated ] dyes.<ref>{{Citation |last=Titford |first=M. |title=Comparison of historic Grübler dyes with modern counterparts using thin layer chromatography |work=Biotech. Histochem. |volume=82 |issue=4–5 |pages=227–234 |year=2007 |doi=10.1080/10520290701714005 |pmid=18074269|s2cid=29539186 }}</ref> The stain proved popular and in 1884 was used by ] to stain bacteria. He credited ] for the aniline-gentian violet mixture.<ref>{{Citation |last1=Clark |first1=G. |title=The history of staining |pages=95–97 |year=1983 |edition=3rd |place=Baltimore |publisher=Williams and Wilkins |isbn=0-683-01705-5 |last2=Kasten |first2=F.H.}} (Earlier editions were authored by H.J. Conn)</ref> Grübler's gentian violet was probably very similar, if not identical, to Lauth's methyl violet, which had been used as a stain by ] in 1875.<ref>{{Citation |last=Cornil |first=V. |title=Sur la dissociation du violet de méthylaniline et sa séparation en deux couleurs sous l'influence de certains tissus normaux et pathologiques, en particulier par les tissus en dégénérescence amyloïde |url=https://gallica.bnf.fr/ark:/12148/bpt6k3037k.image.langEN.f1358.pagination |work=Comptes Rendus de l'Académie des Sciences |volume=80 |pages=1288–1291 |year=1875 |language=fr |access-date=2022-02-13 |archive-date=2022-02-15 |archive-url=https://web.archive.org/web/20220215091918/https://gallica.bnf.fr/ark:/12148/bpt6k3037k.image.langEN.f1358.pagination |url-status=live }}</ref>

Although the name gentian violet continued to be used for the histological stain, the name was not used in the dye and textile industries.<ref name="conn1925">{{Citation |last=Conn |first=H.J. |title=Biological stains: a handbook on the nature and uses of the dyes employed in the biological laboratory |url=https://archive.org/stream/biologicalstains00conn#page/68/mode/2up |pages=68–69 |year=1925 |place=Geneva, NY |publisher=Commission on Standardization of Biological Stains}}</ref> The composition of the stain was not defined and different suppliers used different mixtures. In 1922, the ] appointed a committee chaired by ] to look into the suitability of the different commercial products.<ref name=conn1922/> In his book ''Biological Stains'', Conn describes gentian violet as a "poorly defined mixture of violet ]".<ref name=conn1925/>

The German ] ] is credited with discovering the ] properties of gentian violet.<ref>{{Citation |last=Council on Pharmacy and Chemistry |title=New and Nonofficial Remedies |url=https://archive.org/stream/newnonofficialre37coun#page/210/mode/2up |pages=210–211 |year=1937 |place=Chicago |publisher=American Medical Association}}</ref> He published a monograph in 1890 on the bactericidal effects of a solution that he christened "]", which was probably a mixture of ] dyes similar to gentian violet.<ref>{{Citation |last=Stilling |first=J. |title=Anilin Farbstoffe als Antiseptica und ihre Anwendung in der Praxis |url=https://digital.ub.uni-duesseldorf.de/vester/content/titleinfo/1334819 |year=1890 |place=Strassbourg |publisher=Mittheilung |language=de |access-date=2022-02-13 |archive-date=2022-02-13 |archive-url=https://web.archive.org/web/20220213171319/https://digital.ub.uni-duesseldorf.de/vester/content/titleinfo/1334819 |url-status=live }}</ref> He set up a collaboration with ] to market "Pyoktanin caeruleum" as an antiseptic.<ref name="BerriosRL">R. L. Berrios, J. L. Arbiser: ''Novel antiangiogenic agents in dermatology.'' In: ''].'' 508.2, 2011, p.&nbsp;222–226, ].</ref>

In 1902, Drigalski and Conradi found that although crystal violet inhibited the growth of many bacteria, it has little effect on ''Bacillus coli'' ('']'') and ''Bacillus typhi'' ('']''), which are both ].<ref>{{Citation |last1=Drigalski |first1=V. |title=Ueber ein Verfahren zum Nachweis der Typhusbacillen |work=Zeitschrift für Hygiene |volume=39 |issue=1 |pages=283–300 |year=1902 |doi=10.1007/BF02140310 |last2=Conradi |first2=H.|s2cid=22908909 }}</ref> A much more detailed study of the effects of Grübler's gentian violet on different strains of bacteria was published by John Churchman in 1912.<ref>{{Citation |last=Churchman |first=J.W. |title=The selective bactericidal action of gentian violet |journal=Journal of Experimental Medicine |volume=16 |issue=2 |pages=221–247, plates 21–31 |year=1912 |doi=10.1084/jem.16.2.221 |pmc=2125249 |pmid=19867569}}</ref> He found that most ] (tainted) were sensitive to the dye, while most gram-negative bacteria (not tainted) were not, and observed that the dye tended to act as a ] rather than a ].{{citation needed|date=December 2022}}

====Precautions====
One study in mice demonstrated dose-related ]ic potential at several different organ sites.<ref>{{Citation |last1=Littlefield |first1=N.A. |title=Chronic toxicity and carcinogenicity studies of gentian violet in mice |url=https://zenodo.org/record/1258433 |work=Fundam. Appl. Toxicol. |volume=5 |issue=5 |pages=902–912 |year=1985 |doi=10.1016/0272-0590(85)90172-1 |pmid=4065463 |last2=Blackwell |first2=B.N. |last3=Hewitt |first3=C.C. |last4=Gaylor |first4=D.W. |access-date=2019-06-30 |archive-date=2022-02-28 |archive-url=https://web.archive.org/web/20220228104555/https://zenodo.org/record/1258433 |url-status=live }}</ref><ref>{{Cite web |url=https://cpdb.thomas-slone.org/chempages/GENTIAN%20VIOLET.html |title=Carcinogenic Potency Database (CPDB) |access-date=2022-02-13 |archive-date=2020-06-08 |archive-url=https://web.archive.org/web/20200608032100/https://cpdb.thomas-slone.org/chempages/GENTIAN%20VIOLET.html |url-status=live }}</ref> The ] in the US (FDA) has determined that gentian violet has not been shown by adequate scientific data to be safe for use in animal feed. Use of gentian violet in animal feed causes the feed to be ] and is a violation of the ] in the US. On June 28, 2007, the FDA issued an "import alert" on farm raised seafood from China because unapproved antimicrobials, including gentian violet, had been consistently found in the products. The FDA report states:

"Like MG (]), CV (crystal violet) is readily absorbed into fish tissue from water exposure and is reduced metabolically by fish to the leuco moiety, leucocrystal violet (LCV). Several studies by the ] reported the carcinogenic and ]ic effects of crystal violet in rodents. The leuco form induces renal, hepatic and lung tumor in mice."<ref>{{Citation |title=Questions and Answers on FDA's Import Alert on Farm-Raised Seafood From China: What evidence is there that malachite green, gentian violet and nitrofuran cause cancer? |url=https://www.fda.gov/Food/FoodSafety/Product-SpecificInformation/Seafood/ucm119105.htm#q12 |year=2009 |publisher=US Food and Drug Administration |access-date=2010-08-18 |archive-date=2010-05-28 |archive-url=https://web.archive.org/web/20100528105154/https://www.fda.gov/Food/FoodSafety/Product-SpecificInformation/Seafood/ucm119105.htm#q12 |url-status=live }}</ref><ref>{{Citation |title=How FDA Regulates Seafood |url=https://www.fda.gov/downloads/ForConsumers/ConsumerUpdates/ucm106813.pdf |year=2007 |publisher=US Food and Drug Administration |access-date=2014-10-27 |archive-date=2015-09-24 |archive-url=https://web.archive.org/web/20150924163359/https://www.fda.gov/downloads/ForConsumers/ConsumerUpdates/ucm106813.pdf |url-status=live }}</ref>

In 2019, ] found medical devices that use gentian violet to be safe for use but recommended to stop using all drug products that contain gentian violet, including on animals, causing Canadian engineering schools to revisit the usage of this dye during orientation.<ref>{{Cite web |url=https://healthycanadians.gc.ca/recall-alert-rappel-avis/hc-sc/2019/70179a-eng.php |title=Health Canada warns Canadians of potential cancer risk associated with gentian violet |date=2019-06-11 |publisher=Government of Canada |access-date=12 July 2019 |archive-date=2019-07-13 |archive-url=https://web.archive.org/web/20190713032841/https://healthycanadians.gc.ca/recall-alert-rappel-avis/hc-sc/2019/70179a-eng.php |url-status=live }}</ref><ref>{{Cite news |last=Szklarski |first=Cassandra |url=https://toronto.citynews.ca/2019/07/10/popular-campus-purpling-practice-under-review-in-wake-of-health-canada-warning/ |title=Popular campus 'purpling' practice under review in wake of Health Canada warning |date=10 July 2019 |work=] |access-date=12 July 2019 |agency=] |archive-date=11 July 2019 |archive-url=https://web.archive.org/web/20190711152600/https://toronto.citynews.ca/2019/07/10/popular-campus-purpling-practice-under-review-in-wake-of-health-canada-warning/ |url-status=live }}</ref>

==See also==
{{colbegin}}
* ]
* ]
* ]
* ]
* ]
* ]
* ]
* ]
* ]
* ]
* ]
{{colend}}

==References==
{{reflist|30em}}

==Further reading==
* {{Citation |title=WHO model prescribing information: drugs used in skin diseases |url=https://archive.org/details/whomodelprescrib0000unse/page/70 |page= |year=1997 |contribution=Methylrosanilinium chloride (gentian violet) |place=Geneva |publisher=World Health Organization |isbn=92-4-140106-0 |ref=none}}.

==External links==

{{Commons category|Crystal violet}}
{{Stains}}
{{Antifungals}}
{{Gynecological anti-infectives and antiseptics}}

{{DEFAULTSORT:Crystal Violet}}
]
]
]
]
]
]
]