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CAS 151-56-4
PharmaCompass
CAS 151-56-4
Also known as: Ethyleneimine, Ethylenimine, Azacyclopropane, 151-56-4, Dimethyleneimine, Ethylene imine
Molecular Formula
C2H5N
Molecular Weight
43.069  g/mol
InChI Key
NOWKCMXCCJGMRR-UHFFFAOYSA-N
FDA UNII
54P5FEX9FH

1 2D Structure

CAS 151-56-4

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
aziridine
2.1.2 InChI
InChI=1S/C2H5N/c1-2-3-1/h3H,1-2H2
2.1.3 InChI Key
NOWKCMXCCJGMRR-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CN1
2.2 Other Identifiers
2.2.1 UNII
54P5FEX9FH
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Ethyleneimine

2. Ethylenimine

3. Azacyclopropane

4. 151-56-4

5. Dimethyleneimine

6. Ethylene Imine

7. Polyethyleneimine

8. Poly(ethylenimine)

9. Dihydroazirene

10. Everamine

11. Aziran

12. Polymin

13. 9002-98-6

14. Aziridine, Homopolymer

15. Polymine P

16. Polymin P

17. Polymin Fl

18. Montrek 6

19. Ethylenimine Resins

20. Everamine 50t

21. Dihydro-1h-azirine

22. Everamine 210t

23. Montrek Pei 6

24. Aziridine Homopolymer

25. Aethylenimin

26. Dihydroazirine

27. Ethyleenimine

28. Etilenimina

29. Azirane

30. Aziridin

31. Epamine 150t

32. Epomine 150t

33. Montrek Pei 18

34. Tydex 12

35. Epomine 1000

36. Montrek 1000

37. 1h-azirine, Dihydro-

38. Epomine P 1000

39. Dow Pei-6

40. Cf 218 (polymer)

41. Ethylenimine, Homopolymer

42. Dow Pei-600e

43. Dow Pei-18

44. P 1000 (polyamine)

45. Aziridin [german]

46. Rcra Waste Number P054

47. Pei 1

48. Pei 2

49. Pei 6

50. Polyethylenimine, M.w.600

51. Aethylenimin [german]

52. Ethyleenimine [dutch]

53. Ethylenimine, Polymers

54. Etilenimina [italian]

55. Polyaziridine

56. Polyethylenimine, M.w.1800

57. Pei 12

58. Pei 18

59. Polyethyleneimine (van)

60. Pei 100

61. Pei 400

62. Pei-600

63. Ethyleneimine, Homopolymer

64. Unii-54p5fex9fh

65. Pei 1000

66. Pei 1120

67. Polyethylenimine 7

68. Pei-7

69. Ent-50324

70. Tl 337

71. Dimethylenimine

72. Ccris 296

73. Polyethylenimine 15

74. Polyethylenimine 30

75. Polyethylenimine 45

76. Ethyleneimine Polymer

77. Ccris 8979

78. Hsdb 540

79. Pei-15

80. Pei-30

81. Pei-45

82. Polyethylenimine 275

83. Polyethylenimine 700

84. Pei-275

85. Pei-700

86. Polyethylenimine 1000

87. Polyethylenimine 1400

88. Polyethylenimine 1500

89. Polyethylenimine 1750

90. Polyethylenimine 2500

91. Pei-1000

92. Pei-1400

93. Pei-1500

94. Pei-1750

95. Pei-2500

96. Polyethylenimine 14000

97. Einecs 205-793-9

98. P 1000 (van)

99. Un1185

100. Rcra Waste No. P054

101. Nsc 124034

102. Nsc 124035

103. Nsc 124036

104. Nsc 134422

105. Nsc 196335

106. Brn 0102380

107. Polyethylenimine (10,000)

108. Polyethylenimine (20,000)

109. Polyethylenimine (35,000)

110. Polyethylenimine (40,000)

111. Ai3-50324

112. Ethoxylated Polyethylenimine, M.w. 60,000

113. Chebi:30969

114. Nowkcmxccjgmrr-uhfffaoysa-n

115. Ethylenimine Polymer

116. Ei

117. Pei 600

118. Mfcd00803910

119. P 1000

120. C2h5n

121. Ethoxylated Polyethylenepolyamine

122. Aziridine, Homopolymer, Ethoxylated

123. Vinylidenimine

124. Ethyleneimine, Inhibited

125. Ac1q1i6u

126. 54p5fex9fh

127. Wln: /t3mtj/

128. 5-20-01-00003 (beilstein Handbook Reference)

129. Un 1185 (salt/mix)

130. Ethylenimine, Polymers (8ci)

131. Ac1l1s64

132. Chembl540990

133. Phosphonomethylated (ethoxylated Polyethylenepolyamine)

134. Jsp002910

135. Aziridine, Homopolymer, Ethoxylated, Phosphonomethylated

136. Dtxsid8020599

137. Ctk7d1409

138. Ethoxylated Polyethylenimine,000

139. Ks-00002bjf

140. Polyethyleneimine, 30% In Water

141. Molport-001-781-685

142. Ltbb004476

143. Str07159

144. Anw-42996

145. Mfcd00039669

146. Nsc124034

147. Nsc124035

148. Nsc124036

149. Nsc134422

150. Nsc196335

151. Stl168030

152. Akos005366671

153. Ls-2117

154. Nsc-124034

155. Nsc-124035

156. Nsc-124036

157. Nsc-134422

158. Nsc-196335

159. Rtr-028282

160. Polyethyleneimine, Branched, M.w. 600

161. 145379-92-6

162. 68130-98-3

163. 68130-99-4

164. An-44026

165. Cc-28289

166. He019787

167. He110335

168. He318909

169. He410286

170. Polyethyleneimine, Branched, M.w. 1800

171. Polyethyleneimine, Linear, M.w. 25,000

172. Ls-118030

173. Polyethyleneimine, Branched, M.w. 1,200

174. Ft-0080175

175. Ft-0688199

176. Ft-0699349

177. Polyethyleneimine, Branched, M.w. 10,000

178. W3310

179. Ethyleneimine, Inhibited [un1185] [poison]

180. C11687

181. Ethyleneimine, Inhibited [un1185] [poison]

182. Inchi=1/c2h5n/c1-2-3-1/h3h,1-2h

183. 27146-ep2269983a1

184. 27146-ep2269984a1

185. 27146-ep2270010a1

186. 27146-ep2272972a1

187. 27146-ep2272973a1

188. 27146-ep2275408a1

189. 27146-ep2277872a1

190. 27146-ep2281818a1

191. 27146-ep2287152a2

192. 27146-ep2292593a2

193. 27146-ep2292606a1

194. 27146-ep2292611a1

195. 27146-ep2295399a2

196. 27146-ep2298312a1

197. 27146-ep2298729a1

198. 27146-ep2298763a1

199. 27146-ep2298778a1

200. 27146-ep2301627a1

201. 27146-ep2308510a1

202. 27146-ep2308562a2

203. 27146-ep2308857a1

204. 27146-ep2308861a1

205. 27146-ep2311815a1

206. 27146-ep2314575a1

207. 27146-ep2371811a2

208. 34090-ep2272537a2

209. 34090-ep2295055a2

210. 34090-ep2295416a2

211. 34090-ep2298748a2

212. 34090-ep2305642a2

213. 34090-ep2311453a1

214. 56058-ep2280008a2

215. 56058-ep2298734a2

216. 56058-ep2298744a2

217. 56058-ep2298764a1

218. 56058-ep2298765a1

219. 56058-ep2301930a1

220. 56058-ep2305033a1

221. 56058-ep2305254a1

222. 56058-ep2308871a1

223. 56058-ep2308873a1

224. 151e564

225. 190357-ep2275408a1

226. C-24451

227. I05-0617

228. Polyethyleneimine, Linear, Mw ~ 25,000 250mg

229. S05-0148

230. Aziridine (ethyleneimine), Stabilized With 1-2% Naoh

231. I14-19966

232. I14-20791

233. Polyethyleneimine, Branched, M.w. 50,000 - 100,000

234. Polyethyleneimine, M.w. 60.000, 50% W/w Aqueous Solution

235. Polyethyleneimine, Branched, M.w. 70,000, 30% W/v Aqueous Solution

236. 217821-63-1

237. 391936-72-4

238. 39289-19-5

239. 461012-73-7

240. 66456-64-2

241. 69522-69-6

242. 81210-07-3

243. 81210-08-4

244. 81210-09-5

245. 9077-52-5

246. 92047-44-4

247. 96956-22-8

248. 96956-23-9

249. 96956-24-0

250. 99932-76-0

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 43.069 g/mol
Molecular Formula C2H5N
XLogP3-0.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass43.042 g/mol
Monoisotopic Mass43.042 g/mol
Topological Polar Surface Area21.9 A^2
Heavy Atom Count3
Formal Charge0
Complexity10.3
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Pharmacology

Ethyleneimine is a monofunctional alkylating agent with potential antineoplastic activity. Reacting with DNA mainly at guanine and adenine residues, ethylenimine alkylates DNA, thereby producing DNA interstrand crosslinks and DNA breaks, and interfering with DNA replication and cell division. (NCI04)


4.2 Absorption, Distribution and Excretion

Goups of 5-6 male Dow-Wistar rats were injected intraperitoneally with 0.3-0.42 mg/kg 14-C-aziridine (ethyleneimine) and were sacrificed after 24 and 96 hours. In both cases, ca. 50% of the administered dose was excreted in the urine; small amounts were present in the feces and expired air (3-5%). A small amount of the test substance itself was detected in urine, the major part of the radioactivity was due to unknown metabolites. Radioactivity was distributed throughout the rats, with a slight accumulation in liver, intestine, caecum, spleen, and kidneys.

European Chemicals Bureau; IUCLID Dataset, Ethyleneimine (151-56-4) (2000 CD-ROM edition). Available from, as of February 14, 2006: http://esis.jrc.ec.europa.eu/


... /It/ penetrates animal skin so rapidly that its percutaneous toxicity is not decreased if it is washed off 1 min after contact.

International Labour Office. Encyclopedia of Occupational Health and Safety. Vols. I&II. Geneva, Switzerland: International Labour Office, 1983., p. 231


4.3 Metabolism/Metabolites

When (14)C-ethyleneimine (0.30-0.42 mg/kg body weight) was injected ip into rats, approx one-half of the (14)C was excreted into the urine and 2-6% in feces after 96 hr. Only a small amount of urinary (14)C was ethyleneimine; the major portion of the urinary (14)C was found in a number of unidentified products. Three to 5% of the (14)C was expired as CO2, and 1-3% was expired as ethyleneimine.

Wright GJ, Rowe VK; Toxicol Appl Pharmacol 11: 575-84 (1967)


4.4 Mechanism of Action

The ethylenimines are classic alkylating agents with biologic effects similar to the beta-chloroethylamines. /Ethylenimines/

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 2672


Ethyleneimine reacted with guanosine in aqueous medium to yield two identified products: imidazole-ring-opened 7-alkylguanosine (80%) and intact 1-alkylguanosine (14%). Incubation of ethyleneimine with guanosine or deoxyguanosine at pH 6.0 (1 hr, 37 deg C) yielded some intact 7-alkylated products. Half-life of imidazole ring opening of 7-alkylguanosine was 11, 5, and 2.8 min at pH 7.0, 7.7, and was 21 min at pH 7.7.

Hemminki K; Chem-Biol Interactions 48: 249-260 (1984)


... Examples of direct-acting mutagens include alkylating agents such as ... ethyleneimine ... Direct-acting carcinogens are typically carcinogenic at multiple sites and in all species examined ...

Klaassen, C.D. (ed). Casarett and Doull's Toxicology. The Basic Science of Poisons. 6th ed. New York, NY: McGraw-Hill, 2001., p. 257


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