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Gentian Violet

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Chemistry

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Also known as: Crystal violet, 548-62-9, Basic violet 3, Methyl violet 10b, Hexamethylpararosaniline chloride, Methylrosaniline chloride

Molecular Formula

C₂₅H₃₀ClN₃

Molecular Weight

408.0 g/mol

InChI Key

ZXJXZNDDNMQXFV-UHFFFAOYSA-M

FDA UNII

J4Z741D6O5

A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.

1 2D Structure

Gentian Violet

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[4-[bis[4-(dimethylamino)phenyl]methylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium;chloride

2.1.2 InChI

InChI=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

2.1.3 InChI Key

ZXJXZNDDNMQXFV-UHFFFAOYSA-M

2.1.4 Canonical SMILES

CN(C)C1=CC=C(C=C1)C(=C2C=CC(=[N+](C)C)C=C2)C3=CC=C(C=C3)N(C)C.[Cl-]

2.2 Other Identifiers

2.2.1 UNII

J4Z741D6O5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. C.i. 42555

2. Chloride, Hexamethylpararosaniline

3. Chloride, Methylrosaniline

4. Crystal Violet

5. Fna, Gentiaanviolet

6. Gentiaanviolet Fna

7. Hexamethylpararosaniline Chloride

8. Kristallviolett Lsung

9. Kristallviolett-lsung

10. Methyl Violet

11. Methylrosaniline Chloride

12. Vigencial

13. Violet, Crystal

14. Violet, Gentian

15. Violet, Methyl

2.3.2 Depositor-Supplied Synonyms

1. Crystal Violet

2. 548-62-9

3. Basic Violet 3

4. Methyl Violet 10b

5. Hexamethylpararosaniline Chloride

6. Methylrosaniline Chloride

7. Methylrosanilinium Chloride

8. Aniline Violet

9. Hexamethyl Violet

10. Gentiaverm

11. Pyoktanin

12. Adergon

13. Atmonil

14. Avermin

15. Axuris

16. Vianin

17. Viocid

18. Badil

19. Bismuth Violet

20. C.i. Basic Violet 3

21. Basic Violet Bn

22. Gentioletten

23. Genapax

24. Gentersal

25. Genticid

26. Oxiuran

27. Oxycolor

28. Oxyozyl

29. Vermicid

30. Calcozine Violet C

31. Meroxyl-wander

32. Brilliant Violet 5b

33. Meroxylan-wander

34. Calcozine Violet 6bn

35. Hecto Violet R

36. Crystal Violet O

37. Violet Cp

38. Paper Blue R

39. Crystal Violet Chloride

40. Violet Xxiii

41. Crystal Violet Ao

42. Crystal Violet Bp

43. Crystal Violet Fn

44. Crystal Violet Ss

45. Violet 5bo

46. Violet 6bn

47. Gentianaviolett

48. Crystal Violet 6b

49. Meroxylan

50. Crystal Violet Aon

51. Crystal Violet Bpc

52. Crystal Violet Usp

53. Meroxyl

54. Methyl Violet 5bo

55. Aizen Crystal Violet

56. Crystal Violet 5bo

57. Crystal Violet 6bo

58. Crystal Violet Hl2

59. Hexamethyl-p-rosaniline Chloride

60. Hectograph Violet Sr

61. Methyl Violet 5bno

62. Crystal Violet 10b

63. Hidaco Crystal Violet

64. Methyl Violet 10bd

65. Methyl Violet 10bk

66. Methyl Violet 10bn

67. Methyl Violet 10bo

68. Mitsui Crystal Violet

69. Methyl Violet 10bns

70. Plastoresin Violet 5bo

71. Crystal Violet Technical

72. 12416 Violet

73. Aniline Violet Pyoktanine

74. Crystal Violet Pure Dsc

75. Methylrosanilinii Chloridum

76. Crystal Violet Extra Pure

77. Ci Basic Violet 3

78. C.i. 42555

79. Crystal Violet Chloride Salt

80. Blaues Pyoktanin

81. Crystal Violet Extra Pure Apn

82. Hidaco Brilliant Crystal Violet

83. Aizen Crystal Violet Extra Pure

84. Crystal Violet Extra Pure Apnx

85. Crystal Violet Pure Dsc Brilliant

86. Hexamethyl Pararosaniline Chloride

87. Cloruro De Metilrosanilina

88. Ci 42555

89. Crystal Violet Base

90. Nci-c55969

91. Gvs

92. Gentian Violet [usp]

93. Gv-eleven

94. Methylrosanilinium Chloride [inn]

95. Basic Violet-3

96. Nsc-3090

97. Mfcd00011750

98. C.i.basic Violet 11:1

99. Methanaminium, N-(4-(bis(4-(dimethylamino)phenyl)methylene)-2,5-cyclohexadien-1-ylidene)-n-methyl-, Chloride

100. Chebi:41688

101. J4z741d6o5

102. (4-(bis(p-(dimethylamino)phenyl)methylene)-2,5-cyclohexadien-1-ylidene)dimethylammonium Chloride

103. Methanaminium,n-[4-[bis[4-(dimethylamino)phenyl]methylene]-2,5-cyclohexadien-1-ylidene]-n-methyl-, Chloride

104. N-(4-(bis(4-(dimethylamino)phenyl)methylene)cyclohexa-2,5-dien-1-ylidene)-n-methylmethanaminium Chloride

105. Crystal Violet Solution

106. Gentian Violet (usp)

107. Ncgc00091112-02

108. Methylviolett

109. Pyoverm

110. Dsstox_cid_653

111. Violet Cristallise

112. Methylrosanilini Chloridum

113. Dsstox_rid_75713

114. Dsstox_gsid_20653

115. Methylrosanilinum Chloratum

116. Caswell No. 264a

117. Methylviolett [german]

118. Metilrosanilinio Cloruro

119. Gentianaviolett [german]

120. Kristall-violett

121. (4-(4,4'-bis(dimethylamino)benzhydrylidene)cyclohexa-2,5-dien-1-ylidene)dimethylammonium Chloride

122. Blaues Pyoktanin [german]

123. Kristall-violett [german]

124. Violet Gencianova

125. Violet Gencianova [czech]

126. Violet Krystalova

127. Violet Krystalova [czech]

128. Gnf-pf-880

129. Violet Zasadita 3 [czech]

130. Hexamethyl P-rosaniline Hydrochloride

131. Violet Zasadita 3

132. Nsc3090

133. Cas-548-62-9

134. Methanaminium, N-(4-(bis(4-(dimethylamino)phenyl)methylene)-2,5-cyclohexadien-1-ylidene)-n-methyl-, Chloride (1:1)

135. N-(4-{bis[4-(dimethylamino)phenyl]methylidene}cyclohexa-2,5-dien-1-ylidene)-n-methylmethanaminium Chloride

136. Ccris 2464

137. Methylrosanilinchlorid [german]

138. Metilrosanilinio Cloruro [dcit]

139. Hsdb 4366

140. Nsc 3090

141. Einecs 208-953-6

142. Methyl Violet 6b (biological Stain)

143. Epa Pesticide Chemical Code 039502

144. Methylrosanilinii Chloridum [inn-latin]

145. Chlorure De Methylrosanilinum

146. Cloruro De Metilrosanilina [inn-spanish]

147. Unii-j4z741d6o5

148. Chlorure De Methylrosanilinum [inn-french]

149. Violeta Genciana

150. Lowacryl Violet 1

151. Violeta De Genciana

152. Genapax (tn)

153. Hexamethyl-p-rosaniline Hydrochloride

154. Violetta Di Genziana

155. Le Violet De Gentiane

156. Gentian Violet Solution

157. Pararosaniline, N,n,n',n',n'',n''-hexamethyl-, Chloride

158. Crystal Violet, Micronized

159. Crystal Violet-d6 Hydrate

160. Sentry Aq Mardel Quick Aid

161. Ec 208-953-6

162. Gentian Violet (~90%)

163. Schembl9171

164. Gentian Violet [mi]

165. C25h30n3cl

166. Chlorure De Methylrosanilinium

167. Chembl64894

168. Gentian Violet [hsdb]

169. Spectrum1500315

170. Gentian Violet [vandf]

171. Gram's Crystal Violet Solution

172. Basic Violet 3 [inci]

173. Dtxsid5020653

174. Gentian Violet [usp-rs]

175. Crystal Violet, Saj First Grade

176. Hms500b13

177. Hy-b0324a

178. Crystal Violet, A.c.s. Reagent

179. Crystal Violet, Jis Special Grade

180. Crystal Violet, Saj Special Grade

181. Gram-hucker's Stain Solution (i)

182. Hms1920b11

183. Hms2091h15

184. Hms3655d03

185. Pharmakon1600-01500315

186. 548-62-9 (comp.)

187. 3-(aminomethyl)indoleoxalate

188. Gentian Violet, 95.0-105.0%

189. Tox21_111084

190. Tox21_201762

191. Tox21_300571

192. Ccg-39763

193. Crystal Violet, 97.0-103.0%

194. Gentian Violet [orange Book]

195. Nsc757050

196. S1917

197. Gentian Violet [usp Impurity]

198. Akos000282988

199. Akos015901288

200. Crystal Violet, Dye Content >=90 %

201. Gentian Violet [usp Monograph]

202. Tox21_111084_1

203. Gentian Violet Solution, For Microscopy

204. Nsc-757050

205. Methylrosanilinium Chloride (jp17/inn)

206. Methylrosanilinium Chloride [jan]

207. Ncgc00091112-01

208. Ncgc00091112-09

209. Ncgc00094687-01

210. Ncgc00094687-02

211. Ncgc00254524-01

212. Ncgc00259311-01

213. Ac-12933

214. Ammonium, (4-(bis(p-(dimethylamino)phenyl)methylene)-2,5-cyclohexadien-1-ylidene)dimethyl-, Chloride

215. As-49338

216. Methylrosanilinium Chloride [mart.]

217. Basic Violet 3 100 Microg/ml In Methanol

218. Methylrosanilinium Chloride [who-dd]

219. Methylrosanilinium Chloride [who-ip]

220. Ft-0628821

221. Sw219351-1

222. Crystal Violet Solution, 1%, Aqueous Solution

223. C-8650

224. C-8651

225. C-8652

226. D01046

227. Gentian Violet Usp Grade (crystal Violet Usp)

228. Gentian Violet, For Microscopy (bact., Hist.)

229. H10682

230. Gentian Violet, Meets Usp Testing Specifications

231. Gentian Violet; Hexamethylpararosaniline Chloride

232. Methylrosanilinii Chloridum [who-ip Latin]

233. Methylrosanilinium Chloride [ep Monograph]

234. Q420705

235. Sr-05000001923

236. Crystal Violet, Vetranal(tm), Analytical Standard

237. Sr-05000001923-1

238. Crystal Violet, Acs Reagent, >=90.0% Anhydrous Basis

239. Pararosaniline,n,n',n',n'',n''-hexamethyl-, Chloride

240. Z2786051713

241. Crystal Violet, Certified By The Biological Stain Commission

242. Wln: L6y Dyj Auyr Dn1&1&r Dn1&1& Duk1&1 &q &g

243. Gentian Violet, United States Pharmacopeia (usp) Reference Standard

244. Methylrosanilinium Chloride, European Pharmacopoeia (ep) Reference Standard

245. 4-{bis[4-(dimethylamino)phenyl]methylene}-n,n-dimethylcyclohexa-2,5-dien-1-iminium Chloride

246. Basic Violet 3;gentian Violet;hexamethylpararosaniline Chloride;methyl Violet 10b

247. Crystal Violet, For Microscopy (bact., Bot., Hist., Vit.), Indicator (ph 0.1-2.0)

248. Crystal Violet, Indicator For The Determination Of The Redox Potential, S. No.: 785

249. Methylrosanilinium For System Suitability, European Pharmacopoeia (ep) Reference Standard

250. (4-{bis[-(dimethylamino)phenyl]methylene}-2,5-cyclohexadien-1-ylidene)dimethylammonium Chloride

251. 4-{bis[4-(dimethylamino)phenyl]methylidene}-n,n-dimethylcyclohexa-2,5-dien-1-iminium Chloride

252. Methanaminium,n-[4-[bis[4-(dimethylamino)phenyl]methylene]-2,5-cyclohexadien-1-ylidene]-n-methyl-,chloride

253. N-(-4-{bis[4-(dimethylamino)phenyl]methylene}2,5-cyclohexadien-1-ylidene)-n-methyltrimethanaminium Chloride

254. N-(4-(bis(4-(dimethylamino)phenyl)methylene)cyclohexa-2,5-dienylidene)-n-methylmethanaminium Chloride

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₃₀ClN₃
Molecular Weight	408.0 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	407.2128257 g/mol
Monoisotopic Mass	407.2128257 g/mol
Topological Polar Surface Area	9.5 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	542
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Therapeutic Uses

Anti-Infective Agents, Local; Antinematodal Agents; Rosaniline Dyes

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

Gentian violet has been used in medicine for almost 100 years: as an antiseptic for external use, as an antihelminthic agent by oral administration, and more recently, as a blood additive to prevent transmission of Chagas' disease. ...

PMID:2272286 Docampo R, Moreno SN; Drug Metab Rev 22 (2-3): 161-78 (1990)

THERAPEUTIC CATEGORY: Anti-infective (topical). Has been used as anthelmintic (Nematodes), Blood additive to prevent transmission of Chagas disease by blood transfusion

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 757

THERAPEUTIC CATEGORY (VET): Anti-infective (topical); mycostatic agent in poultry feed

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 757

For more Therapeutic Uses (Complete) data for Gentian Violet (7 total), please visit the HSDB record page.

4.2 Drug Warning

Permanent pigmentation of the skin can result from contact of gentian violet with granulation tissue, & the dye should not be applied to ulcerative lesions of the face. The staining properties are a distinct disadvantage.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 979

Oral ulceration developed in 6 neonates who were treated for oral candidiasis with gentian (crystal) violet. A 0.5 or 1% aq soln was used and applications were made twice daily.

HORSFIELD P ET AL; ORAL IRRITATION WITH GENTIAN VIOLET; BR MED J 2(AUG 28) 529 (1976)

4.3 Minimum/Potential Fatal Human Dose

4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OZ FOR 70 KG PERSON (150 LB).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-235

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)

5.2 Absorption, Distribution and Excretion

Nine male and 9 female Hubbard adult broiler breeders were used to study tissue residues of gentian violet, each bird was given (14)C-gentian violet orally. T/2 of radioactivity from (14)C-gentian violet in blood differed between sexes (1.43 hr and 1.68 hr for males and females, respectively). At 8 hr after administration only 1 bird had detectable amt of radioactivity in muscle. Detectable levels of radioactivity were found in liver at 120 hr after dosing and in kidney at 432 hr after dosing. All eggs collected during 1St 144 hr contained very low but detectable levels of radioactivity.

OLENTINE CG JR ET AL; CARBON-14 LABELED GENTIAN VIOLET RESIDUES IN TISSUES OF BROILER BREEDERS; POULT SCI 59(3) 500 (1980)

5.3 Metabolism/Metabolites

Gentian violet is shown to undergo a one-electron reduction by the cytochrome P450 monooxygenase system to produce a carbon-centered free radical as demonstrated by direct electron spin resonance techniques.

HARRELSON WG JR, MASON RP; MICROSOMAL REDUCTION OF GENTIAN VIOLET. EVIDENCE FOR CYTOCHROME P-450-CATALYZED FREE RADICAL FORMATION; MOL PHARMACOL 22(2) 239 (1982)

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