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Chemistry

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Also known as: 137-58-6, Lignocaine, Xylocaine, 2-(diethylamino)-n-(2,6-dimethylphenyl)acetamide, Lidoderm, Alphacaine
Molecular Formula
C14H22N2O
Molecular Weight
234.34  g/mol
InChI Key
NNJVILVZKWQKPM-UHFFFAOYSA-N
FDA UNII
98PI200987

Lidocaine
A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of PROCAINE but its duration of action is shorter than that of BUPIVACAINE or PRILOCAINE.
Lidocaine is an Amide Local Anesthetic and Antiarrhythmic. The physiologic effect of lidocaine is by means of Local Anesthesia.
1 2D Structure

Lidocaine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide
2.1.2 InChI
InChI=1S/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)
2.1.3 InChI Key
NNJVILVZKWQKPM-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCN(CC)CC(=O)NC1=C(C=CC=C1C)C
2.2 Other Identifiers
2.2.1 UNII
98PI200987
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-(diethylamino)-n-(2,6-dimethylphenyl)acetamide

2. 2-2etn-2mephacn

3. Dalcaine

4. Lidocaine Carbonate

5. Lidocaine Carbonate (2:1)

6. Lidocaine Hydrocarbonate

7. Lidocaine Hydrochloride

8. Lidocaine Monoacetate

9. Lidocaine Monohydrochloride

10. Lidocaine Monohydrochloride, Monohydrate

11. Lidocaine Sulfate (1:1)

12. Lignocaine

13. Octocaine

14. Xylesthesin

15. Xylocaine

16. Xylocitin

17. Xyloneural

2.3.2 Depositor-Supplied Synonyms

1. 137-58-6

2. Lignocaine

3. Xylocaine

4. 2-(diethylamino)-n-(2,6-dimethylphenyl)acetamide

5. Lidoderm

6. Alphacaine

7. Anestacon

8. Esracaine

9. Xylestesin

10. Duncaine

11. Cappicaine

12. Gravocain

13. Isicaina

14. L-caine

15. Leostesin

16. Maricaine

17. Xylocain

18. Xylocitin

19. Solcain

20. Isicaine

21. Rucaina

22. Xilina

23. Xycaine

24. Xylotox

25. Cito Optadren

26. Lida-mantle

27. 2-(diethylamino)-2',6'-acetoxylidide

28. Dentipatch

29. Dalcaine

30. Xyloneural (free Base)

31. Cuivasil

32. Jetocaine

33. Lidocainum

34. Remicaine

35. Xilocaina

36. 2-diethylamino-n-(2,6-dimethylphenyl)acetamide

37. Acetamide, 2-(diethylamino)-n-(2,6-dimethylphenyl)-

38. Diethylaminoaceto-2,6-xylidide

39. Ela-max

40. Ztlido

41. 2',6'-acetoxylidide, 2-(diethylamino)-

42. Alpha-diethylamino-2,6-dimethylacetanilide

43. Lidocaton

44. Alfa-dietilamino-2,6-dimetilacetanilide

45. Chebi:6456

46. Xylocaine (tn)

47. Chembl79

48. Nsc-40030

49. Lidopen

50. N-(2,6-dimethylphenyl)-n~2~,n~2~-diethylglycinamide

51. Mls000069724

52. Algrx 3268

53. Algrx-3268

54. Lignocainum

55. Xllina

56. N-(2,6-dimethylphenyl)-n(2),n(2)-diethylglycinamide

57. Lidocaine (van)

58. .alpha.-diethylaminoaceto-2,6-xylidide

59. Ncgc00015611-10

60. Xilocaina [italian]

61. Dilocaine

62. Lidocaina

63. Smr000058189

64. .alpha.-(diethylamino)-2,6-acetoxylidide

65. Lidocaine Base

66. .alpha.-diethylamino-2,6-dimethylacetanilide

67. .omega.-diethylamino-2,6-dimethylacetanilide

68. 98pi200987

69. Lidocainum [inn-latin]

70. Dsstox_cid_25166

71. Dsstox_rid_80716

72. Dsstox_gsid_45166

73. Lidocaina [inn-spanish]

74. N-(2,6-dimethylphenyl)-n2,n2-diethylglycinamide

75. 2-(diethylamino)-n-(2,6-dimethylphenyl)ethanamide

76. Embolex

77. Versatis

78. Ztilido

79. 2-(diethylamino)-n-(2,6-dimethylphenyl)-acetamide

80. Dentipatch (tn)

81. 91484-71-8

82. Cas-137-58-6

83. Lqz

84. Hsdb 3350

85. Einecs 205-302-8

86. Mfcd00026733

87. Nsc 40030

88. Alfa-dietilamino-2,6-dimetilacetanilide [italian]

89. Brn 2215784

90. Qualigens

91. Xyline

92. Lignocaine Base

93. Lidocainehclh2o

94. Lidocaine [usp:inn:ban:jan]

95. Lidocaine, Powder

96. Unii-98pi200987

97. N1-(2,6-dimethylphenyl)-n2,n2-diethylglycinamide

98. Zingo (salt/mix)

99. Cds1_000283

100. Lidocaine (alphacaine)

101. Spectrum_001118

102. Lidothesin (salt/mix)

103. Xyloneural (salt/mix)

104. Lidocaine [inn]

105. Lidocaine [jan]

106. Opera_id_385

107. Lidocaine [mi]

108. Lidocaine [hsdb]

109. Lidocaine [inci]

110. Maybridge1_002571

111. Prestwick0_000050

112. Prestwick1_000050

113. Prestwick2_000050

114. Prestwick3_000050

115. Spectrum2_001343

116. Spectrum3_001392

117. Spectrum4_000070

118. Spectrum5_001549

119. Lidocaine [vandf]

120. Lopac-l-5647

121. Lidaform Hc (salt/mix)

122. Epitope Id:116205

123. Lidocaine [mart.]

124. Lidamantle Hc (salt/mix)

125. 2', 2-(diethylamino)-

126. Lidocaine [usp-rs]

127. Lidocaine [who-dd]

128. Lidocaine [who-ip]

129. Neosporin Plus (salt/mix)

130. Lopac0_000669

131. Schembl15689

132. Bspbio_000179

133. Bspbio_001359

134. Bspbio_003004

135. Kbiogr_000079

136. Kbiogr_000599

137. Kbioss_000079

138. Kbioss_001598

139. 2-diethylamino-n-(2,6-dimethyl-phenyl)-acetamide

140. 4-12-00-02538 (beilstein Handbook Reference)

141. Mls000758263

142. Mls001074177

143. Mls001423964

144. Bidd:gt0342

145. Diethylaminoacet-2,6-xylidide

146. Divk1c_000174

147. Divk1c_001323

148. Lidocaine, Analytical Standard

149. Spbio_001525

150. Spbio_002100

151. Emla Component Lidocaine

152. Lidocaine (jp17/usp/inn)

153. Lidocaine [green Book]

154. Bpbio1_000197

155. Gtpl2623

156. Lidocaine [orange Book]

157. Dtxsid1045166

158. Lidocaine [ep Monograph]

159. Schembl17967359

160. Hms548m19

161. Kbio1_000174

162. Kbio2_000079

163. Kbio2_001598

164. Kbio2_002647

165. Kbio2_004166

166. Kbio2_005215

167. Kbio2_006734

168. Kbio3_000157

169. Kbio3_000158

170. Kbio3_002224

171. Oraqix Component Lidocaine

172. Synera Component Lidocaine

173. Zinc20237

174. Lidocaine [usp Monograph]

175. Lidocaine 1.0 Mg/ml In Methanol

176. Lidocainum [who-ip Latin]

177. Ninds_000174

178. Bio1_000379

179. Bio1_000868

180. Bio1_001357

181. Bio2_000079

182. Bio2_000559

183. Hms1791d21

184. Hms1989d21

185. Hms2051c21

186. Hms2089e15

187. Hms2235o14

188. Hms3371j04

189. Hms3393c21

190. Hms3428o07

191. Hms3651g09

192. Lidocaine Component Of Emla

193. Fortacin Component Lidocaine

194. Amy25560

195. Bcp09081

196. Hy-b0185

197. Nsc40030

198. Lidocaine Component Of Oraqix

199. Lidocaine Component Of Synera

200. Tox21_110183

201. 2-diethylamino-2',6'-acetoxylidide

202. Bdbm50017662

203. Lanabiotic Component Lidocaine

204. Nsc789222

205. S1357

206. Stk552033

207. Akos001026768

208. Lidocain Component Of Fortacine

209. Tox21_110183_1

210. Ccg-100824

211. Cs-2070

212. Db00281

213. Nc00074

214. Nsc-789222

215. Rocephin Kit Component Lidocaine

216. Sb19118

217. Sdccgsbi-0050648.p005

218. Wln: 2n2 & 1vmr B1 F1

219. .alpha.-diethylamino-2,6-acetoxylidide

220. Cas-73-78-9

221. Idi1_000174

222. Idi1_033829

223. Lidocaine Component Of Lanabiotic

224. Ncgc00015611-01

225. Ncgc00015611-02

226. Ncgc00015611-03

227. Ncgc00015611-04

228. Ncgc00015611-05

229. Ncgc00015611-06

230. Ncgc00015611-07

231. Ncgc00015611-08

232. Ncgc00015611-09

233. Ncgc00015611-11

234. Ncgc00015611-12

235. Ncgc00015611-13

236. Ncgc00015611-14

237. Ncgc00015611-15

238. Ncgc00015611-16

239. Ncgc00015611-18

240. Ncgc00015611-31

241. Ncgc00022176-05

242. Ncgc00022176-06

243. Ncgc00022176-07

244. Ncgc00022176-08

245. Ncgc00022176-09

246. Ac-10282

247. As-13718

248. Sy052029

249. 2-(diethylamino)-2'',6''-acetoxylidide

250. Lidocaine Component Of Rocephin Kit

251. Sbi-0050648.p004

252. Diethylamino-2,6-dimethylacetanilide

253. Lignocaine Base 100 Microg/ml In Methanol

254. Ab00053581

255. L0156

256. Sw196598-4

257. A18187

258. C07073

259. D00358

260. M06299

261. Ab00053581-27

262. Ab00053581-28

263. Ab00053581_29

264. Ab00053581_30

265. A833036

266. Q216935

267. (2,6-dimethylphenyl)carbamoylmethyl-diethyl-azanium

268. N1-(2,6-dimethylphenyl)-2-(diethylamino)acetamide

269. W-108233

270. 2-(diethylamino)-n-(2,6-dimethylphenyl)acetamide #

271. Brd-k52662033-001-02-6

272. Brd-k52662033-003-05-5

273. Brd-k52662033-003-14-7

274. Z55135799

275. Lidocaine, British Pharmacopoeia (bp) Reference Standard

276. Lidocaine, European Pharmacopoeia (ep) Reference Standard

277. N~1~-(2,6-dimethylphenyl)-n~2~,n~2~-diethylglycinamide

278. Lidocaine, United States Pharmacopeia (usp) Reference Standard

279. 2-(diethylamino)-n-(2,6-dimethylphenyl)acetamide Hydrate Hydrochloride

280. Lidocaine, Pharmaceutical Secondary Standard; Certified Reference Material

281. Lidocaine Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.3.3 Other Synonyms

1. Lignocaine

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 234.34 g/mol
Molecular Formula C14H22N2O
XLogP32.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass234.173213330 g/mol
Monoisotopic Mass234.173213330 g/mol
Topological Polar Surface Area32.3 Ų
Heavy Atom Count17
Formal Charge0
Complexity228
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 12  
Drug NameLidocaine
PubMed HealthLidocaine
Drug ClassesAnesthetic, Local, Antiarrhythmic, Group IB
Drug LabelLidocaine hydrochloride oral topical solution USP, 2% (viscous) contains a local anesthetic agent and is administered topically. Lidocaine hydrochloride oral topical solution USP, 2% (viscous) contains lidocaine HCl, which is chemically designated as...
Active IngredientLidocaine
Dosage FormOintment; Patch
RouteTopical
Strength5%
Market StatusPrescription
CompanyTaro; Fougera; Watson Labs; Novocol
Patent5741510; 5827529

2 of 12  
Drug NameLidoderm
PubMed HealthLidocaine
Drug ClassesAnesthetic, Local
Drug LabelDESCRIPTIONLIDODERM (lidocaine patch 5%) is comprised of an adhesive material containing 5% lidocaine, which is applied to a non-woven polyester felt backing and covered with a polyethylene terephthalate (PET) film release liner. The release liner is...
Active IngredientLidocaine
Dosage FormPatch
RouteTopical
Strength5%
Market StatusPrescription
CompanyTeikoku Pharma Usa
Patent8540665; 5630796; 5899880; 6004286; 6881200

3 of 12  
Drug NameOctocaine
PubMed HealthLidocaine
Drug ClassesAnesthetic, Local
Active Ingredientlidocaine hydrochloride; Epinephrine
Dosage FormInjectable
RouteInjection
Strength0.02mg/ml; 2%; 0.01mg/ml
Market StatusPrescription
CompanySeptodont

4 of 12  
Drug NameXylocaine
PubMed HealthLidocaine
Drug LabelXYLOCAINE - lidocaine hydrochloride injection, solutionXYLOCAINE - lidocaine hydrochloride and epinephrine bitartrate injection, solutionXYLOCAINE MPF - lidocaine hydrochloride injection, solutionXYLOCAINE - lidocaine hydrochloride and epinephrine bi...
Active IngredientLidocaine hydrochloride
Dosage FormJelly; Injectable
RouteInjection; Topical
Strength0.5%; 1%; 1.5%; 2%
Market StatusPrescription
CompanyOak Pharms; Fresenius Kabi Usa

5 of 12  
Drug NameXylocaine viscous
PubMed HealthLidocaine
Drug LabelZingo (lidocaine hydrochloride monohydrate)powder intradermal injectionsystemcontains 0.5 mg of sterile lidocaine hydrochloride monohydrate.The chemical name is 2-diethylamino-2',6'-acetoxylidide, monohydrochloride, monohydrate. Themolecul...
Active IngredientLidocaine hydrochloride
Dosage FormSolution
RouteOral
Strength2%
Market StatusPrescription
CompanyFresenius Kabi Usa

6 of 12  
Drug NameZingo
PubMed HealthLidocaine
Active IngredientLidocaine hydrochloride
Dosage FormSystem
RouteIntradermal
Strength0.5mg
Market StatusPrescription
CompanyPowder Pharms