化学性质
无色晶体或白色结晶性粉末。熔点114℃,沸点319℃(98.8kPa),211-212℃(1.33kPa),相对密度1.0747(20/4℃),折光率1.5697。溶于苯、乙醇、水、氯仿,略溶于醚。无臭,有微苦味。
用途
该品为解热镇痛药,这类非甾体抗炎药具有较强的解热镇痛、抗炎及抗风湿作用。但由于不良反应严重,临床应用已日趋减少,其中的一些老品种已逐渐趋向淘汰。安替比林、氨基比林、安乃近等片剂都是卫生部1982年9月公布的淘汰药品。安替比林是一种分析试剂,用于硝酸、亚硝酸及碘的分析,测定形成络合阳离子的元素(如铋、锡、锑和汞等),以及重量分析测定钛。
生产方法
由1-苯基-3-甲基吡唑酮-5经甲基化、水解而得。具体步骤如下:在干燥的甲基化罐中,加入吡唑酮,再加入硫酸二甲酯,升温至160℃反应6小时,然后加热水煮沸2小时。将此甲基化反应物放入盛有氢氧化钠溶液的水解罐中,在100-110℃搅拌下水解3小时。静置分层后,取安替比林油层放在结晶罐内,加蒸馏水稀释,搅拌,降温至10℃以下,析出晶体,甩滤、水洗、甩干得安替比林粗品。粗品用蒸馏水重结晶、活性炭脱色即得成品。
另一种方法是,使用等摩尔的N,N-苯基甲基肼和乙酰乙酸乙酯在130-160℃油浴上加热回流制得。从浓稠的油状液体中用沸水萃取安替比林,再蒸发除去水分而得到晶体。
类别
有毒物品
毒性分级
中毒
急性毒性
口服-大鼠 LD50: 1705 毫克/公斤;口服-小鼠 LD50: 1310 毫克/公斤
可燃性危险特性
可燃,燃烧时会产生有毒氮氧化物烟雾
储运特性
库房需保持通风、低温干燥
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
2-苄基-1,2-二氢-3-甲基-1-苯基吡唑-5-酮 | 2-benzyl-1,2-dihydro-3-methyl-1-phenylpyrazol-5-one | 55774-20-4 | C17H16N2O | 264.327 |
4-安替比林甲醛 | 4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one | 950-81-2 | C12H12N2O2 | 216.239 |
5-甲基-2-苯基-1,2-二氢吡唑-3-酮 | 1-phenyl-3-methyl-2-pyrazolin-5-one | 19735-89-8 | C10H10N2O | 174.202 |
氨基比林 | aminopyrine | 58-15-1 | C13H17N3O | 231.297 |
—— | 1-phenyl-2,3-dimethyl-4-(NN-dimethylaminomethyl)-pyrazol-5-one | 81115-76-6 | C14H19N3O | 245.324 |
—— | 1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(2-methyl-2-aza-propanediyl)-bis-pyrazol-3-one | —— | C25H29N5O2 | 431.538 |
1,5-二甲基-3-氧代-2-苯基-2,3-二氢-1H-吡唑-4-羧酸 | antipyric acid | 83-10-3 | C12H12N2O3 | 232.239 |
—— | 2,3-Dimethyl-4-(1-hydroxybenzyl)-1-phenyl-3-pyrazolin-5-one | 54463-56-8 | C18H18N2O2 | 294.353 |
中文名称 | 英文名称 | CAS号 | 化学式 | 分子量 |
---|---|---|---|---|
1,2-二氢-5-乙基-1-甲基-2-苯基-3H-吡唑-3-酮 | 1,2-dihydro-5-ethyl-1-methyl-2-phenyl-3H-pyrazol-3-one | 109249-29-8 | C12H14N2O | 202.256 |
5-(羟基甲基)-1-甲基-2-苯基-1H-吡唑-3(2H)-酮 | 3-Hydroxymethylantipyrine | 18125-49-0 | C11H12N2O2 | 204.228 |
—— | 4-(2,3-dimethyl-5-oxo-2,5-dihydro-pyrazol-1-yl)-benzenesulfonic acid | —— | C11H12N2O4S | 268.293 |
1,4,5-三甲基-2-苯基吡唑-3-酮 | 1,4,5-trimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one | 5677-84-9 | C12H14N2O | 202.256 |
—— | 4-fluoroantipyrine | 56924-65-3 | C11H11FN2O | 206.22 |
—— | 18F-labelled 4-fluoroantipyrine | 80333-82-0 | C11H11FN2O | 205.221 |
4-羟基安替比林 | 4-hydroxyantipyrine | 1672-63-5 | C11H12N2O2 | 204.228 |
4-氯-2-环己-2,4-二烯-1-基-1,5-二甲基吡唑-3-酮 | 4-chloro-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one | 43068-92-4 | C11H11ClN2O | 222.674 |
4-氨基安替比林 | 4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one | 83-07-8 | C11H13N3O | 203.244 |
4-溴胺酸吡啶 | 4-bromoantipyrine | 5426-65-3 | C11H11BrN2O | 267.125 |
碘安替比林 | iodoantipyrine | 129-81-7 | C11H11IN2O | 314.126 |
—— | 4-iodoantipyrine | 17687-50-2 | C11H11IN2O | 312.221 |
4-碘-1,5-二甲基-2-苯基吡唑-3-酮 | 4-<131I>Jod-2,3-dimethyl-1-phenyl-pyrazolon-(5) | 3791-63-7 | C11H11IN2O | 318.221 |
—— | 4,4'-Dihydroxy-antipyrine | 72732-51-5 | C11H12N2O3 | 220.228 |
—— | 1-phenyl-2,3-dimethyl-4-hydroxymethyl-pyrazoline-5-on | 10013-09-9 | C12H14N2O2 | 218.255 |
4-安替比林甲醛 | 4-formyl-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one | 950-81-2 | C12H12N2O2 | 216.239 |
2-(2-甲氧基苯基)-1,5-二甲基-1H-吡唑-3-(2H)-酮 | 2-(2-methoxyphenyl)-1,5-dimethyl-1H-pyrazol-3(2H)-one | 104510-22-7 | C12H14N2O2 | 218.255 |
—— | 4-cyano-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one | 5702-70-5 | C12H11N3O | 213.239 |
2,3-二甲基-4-亚硝基-1-苯基-3-吡唑啉-5-酮 | 1,5-dimethyl-4-nitroso-2-phenyl-1,2-dihydro-pyrazol-3-one | 885-11-0 | C11H11N3O2 | 217.227 |
—— | 4-Brom-3-brommethyl-2-methyl-1-phenyl-3-pyrazolin-5-on | 5767-66-8 | C11H10Br2N2O | 346.021 |
3-羟甲基-4-溴安替比林 | 3-hydroxymethyl-4-bromoantipyrine | 81122-69-2 | C11H11BrN2O2 | 283.125 |
—— | 1,5-dimethyl-2-phenyl-4-thiocyanato-1,2-dihydro-3H-pyrazol-3-one | 91397-05-6 | C12H11N3OS | 245.305 |
—— | 4-(2-amino-ethyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one | —— | C13H17N3O | 231.297 |
氨基比林 | aminopyrine | 58-15-1 | C13H17N3O | 231.297 |
—— | 4-tert-butyl-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one | —— | C15H20N2O | 244.337 |
—— | 1-phenyl-2,3-dimethyl-4-(NN-dimethylaminomethyl)-pyrazol-5-one | 81115-76-6 | C14H19N3O | 245.324 |
—— | 1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-disulfanediyl-bis-pyrazol-3-one | 102314-29-4 | C22H22N4O2S2 | 438.574 |
—— | (2E)-3-(2,5-dihydro-2,3-dimethyl-5-oxo-1-phenyl-1H-pyrazol-4-yl)acrylonitrile | —— | C14H13N3O | 239.277 |
二安替比林甲烷 | diantipyrinylmethane | 1251-85-0 | C23H24N4O2 | 388.469 |
—— | 1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(2-methyl-2-aza-propanediyl)-bis-pyrazol-3-one | —— | C25H29N5O2 | 431.538 |
—— | 3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-propionic acid | 109688-82-6 | C14H16N2O3 | 260.293 |
—— | Bis(1,2-dihydro-1,5-dimethyl-3-oxo-2-phenyl-3H-pyrazol-4-yl)sulfid | 95136-36-0 | C22H22N4O2S | 406.508 |
1,5-二甲基-3-氧代-2-苯基-2,3-二氢-1H-吡唑-4-羧酸 | antipyric acid | 83-10-3 | C12H12N2O3 | 232.239 |
—— | 3t-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-acrylic acid | —— | C14H14N2O3 | 258.277 |
—— | 1,2-dihydro-2,3-dimethyl-1-phenyl-4-styrylpyrazol-5-one | —— | C19H18N2O | 290.365 |
—— | (2E)-3-(2,5-dihydro-2,3-dimethyl-5-oxo-1-phenyl-1H-pyrazol-4-yl)-N,N-dimethylacrylamide | —— | C16H19N3O2 | 285.346 |
—— | 1,2-dihydro-2,3-dimethyl-1,4-diphenylpyrazol-5-one | 821798-41-8 | C17H16N2O | 264.327 |
4-乙酰安替比林 | 4-acetyl-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one | 40570-67-0 | C13H14N2O2 | 230.266 |
—— | N,N'-bis(antipyryl-4-methylene)-piperazine | 29331-48-4 | C28H34N6O2 | 486.617 |
—— | (2E)-methyl 3-(2,5-dihydro-2,3-dimethyl-5-oxo-1-phenyl-1H-pyrazol-4-yl)acrylate | —— | C15H16N2O3 | 272.304 |
4-(苯亚甲基氨基)-1,5-二甲基-2-苯基吡唑-3-酮 | 4-(benzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one | 83-17-0 | C18H17N3O | 291.352 |
1,5-二甲基-4-硝基-2-苯基-1,2-二氢吡唑-3-酮 | 4-nitroantipyrine | 30672-29-8 | C11H11N3O3 | 233.227 |
—— | 4-(4-hydroxy-benzyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one | —— | C18H18N2O2 | 294.353 |
—— | 4-piperidinomethylantipyrine | 93725-17-8 | C17H23N3O | 285.389 |
—— | (2E)-ethyl 3-(2,5-dihydro-2,3-dimethyl-5-oxo-1-phenyl-1H-pyrazol-4-yl)acrylate | —— | C16H18N2O3 | 286.331 |
—— | 4-(N-morpholinylmethyl) antipyrine | 101268-93-3 | C16H21N3O2 | 287.362 |
黄曲霉毒素H1 | Thiopyrin | 5702-69-2 | C11H12N2S | 204.296 |
—— | 4-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one | —— | C18H26N4O2 | 330.43 |
—— | 4-(4-chlorobenzylideneamino)-1,2-dihydro-1,5-dimethyl-2-phenylpyrazol-3-one | 61098-04-2 | C18H16ClN3O | 325.798 |
—— | 1,5-dimethyl-2-phenyl-4-(p-tolyl)-1H-pyrazol-3(2H)-one | —— | C18H18N2O | 278.354 |
—— | (2E)-tert-butyl 3-(2,5-dihydro-2,3-dimethyl-5-oxo-1-phenyl-1H-pyrazol-4-yl)acrylate | —— | C18H22N2O3 | 314.384 |
4-[(对羟基亚苄基)氨基]安替比林 | 4-((4-hydroxybenzylidene)amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one | 65144-69-6 | C18H17N3O2 | 307.352 |
—— | (2E)-butyl 3-(2,5-dihydro-2,3-dimethyl-5-oxo-1-phenyl-1H-pyrazol-4-yl)acrylate | —— | C18H22N2O3 | 314.384 |
—— | 4-(4-dimethylamino-benzyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one | —— | C20H23N3O | 321.422 |
—— | 1-phenyl-3-methyl-4-hydroxy-pyrazoline-5-on | 96337-49-4 | C10H10N2O2 | 190.202 |
—— | 4,4',4''-Tris(1,5-dimethyl-3-oxo-2-phenyl-1,2-dihydro-3H-pyrazolyl)methane | 2316-06-5 | C34H34N6O3 | 574.682 |
—— | 4-(3,5-dimethylphenyl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one | —— | C19H20N2O | 292.381 |
—— | 4-(2-hydroxybenzylideneamino)-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one | 30957-66-5 | C18H17N3O2 | 307.352 |
4-(2-氯乙酰基)-1,5-二甲基-2-苯基-1,2-二氢吡唑-3-酮 | 4-(chloroacetyl)antipyrine | 6630-73-5 | C13H13ClN2O2 | 264.711 |
—— | 1,5-dimethyl-2-phenyl-4-(4-(trifluoromethyl)phenyl)-1H-pyrazol-3(2H)-one | —— | C18H15F3N2O | 332.325 |
—— | 4-(3,4-dichlorobenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one | —— | C18H15Cl2N3O | 360.243 |
—— | Cambridge id 6945597 | —— | C24H22N2O | 354.4 |
—— | 4-(4-ethoxyphenyl)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one | —— | C19H20N2O2 | 308.38 |
—— | 1,5-dimethyl-4-nitro-2-(4-nitro-phenyl)-1,2-dihydro-pyrazol-3-one | 30672-31-2 | C11H10N4O5 | 278.224 |
—— | 3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzaldehyde | —— | C18H16N2O2 | 292.337 |
—— | (2E)-ethyl 3-(2,5-dihydro-2,3-dimethyl-5-oxo-1-phenyl-1H-pyrazol-4-yl)-2-methylacrylate | —— | C17H20N2O3 | 300.357 |
—— | 4-(4-nitrobenzylideneamino)antipyrine | —— | C18H16N4O3 | 336.35 |
—— | 4-(2,6-dichlorobenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one | —— | C18H15Cl2N3O | 360.243 |
—— | 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-sulfonic acid | 5677-80-5 | C11H12N2O4S | 268.293 |
—— | 1,2-dihydro-2,3-dimethyl-1-phenyl-4-((E)-2-(phenylsulfonyl)vinyl)pyrazol-5-one | —— | C19H18N2O3S | 354.43 |
—— | 4-[(2,4-dichloro-benzylidene)-amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one | —— | C18H15Cl2N3O | 360.243 |
—— | methyl 4-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl)benzoate | —— | C20H19N3O3 | 349.389 |
—— | 4-(4-(benzyloxy)benzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one | —— | C25H23N3O2 | 397.477 |
—— | 1,5-dimethyl-2-phenyl-4-(2,2,2-trichloro-1-hydroxy-ethyl)-1,2-dihydro-pyrazol-3-one | 66379-85-9 | C13H13Cl3N2O2 | 335.617 |
—— | 4-acetyl-1,2-dihydro-1-methyl-2-phenyl-3H-pyrazol-3-one | 15182-98-6 | C12H12N2O2 | 216.239 |
—— | 1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-phenylmethanediyl-bis-pyrazol-3-one | 1861-84-3 | C29H28N4O2 | 464.567 |
—— | 4-(3-nitrobenzylideneamino)-1,2-dihydro-1,5-dimethyl-2-phenylpyrazol-3-one | 72425-89-9 | C18H16N4O3 | 336.35 |
—— | diantipyrylmethylmethane | 1606-56-0 | C24H26N4O2 | 402.496 |
—— | 1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(4-methyl-phenylmethanediyl)-bis-pyrazol-3-one | 14135-13-8 | C30H30N4O2 | 478.594 |
—— | bis[1-(2,3-dimethyl-1-phenyl-3-pyrazolin-5-one)]-4-hydroxyphenylmethane | 80337-07-1 | C29H28N4O3 | 480.566 |
—— | ethyl 4-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)-4H-pyridine-1-carboxylate | 74529-77-4 | C19H21N3O3 | 339.394 |
—— | 1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(4-chloro-phenylmethanediyl)-bis-pyrazol-3-one | 1606-54-8 | C29H27ClN4O2 | 499.012 |
—— | 1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(2-methyl-phenylmethanediyl)-bis-pyrazol-3-one | 15073-48-0 | C30H30N4O2 | 478.594 |
—— | 4-(3-ethoxy-4-hydroxybenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one | 198488-80-1 | C20H21N3O3 | 351.405 |
—— | 1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(4-bromo-phenylmethanediyl)-bis-pyrazol-3-one | 2316-05-4 | C29H27BrN4O2 | 543.463 |
4-苯甲酰基-1,5-二甲基-2-苯基吡唑-3-酮 | 4-benzoyl-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one | 30182-86-6 | C18H16N2O2 | 292.337 |
—— | (1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-glyoxylic acid | 6538-52-9 | C13H12N2O4 | 260.249 |
—— | 4-(2-bromo-propionyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one | 100887-17-0 | C14H15BrN2O2 | 323.189 |
—— | 1,5-dimethyl-3-oxo-N,2-diphenyl-2,3-dihydro-1H-pyrazole-4-carboxamide | 5702-66-9 | C18H17N3O2 | 307.352 |
—— | bis[1-(2,3-dimethyl-1-phenyl-3-pyrazolin-5-one)]-4-phenylphenylmethane | —— | C35H32N4O2 | 540.665 |
—— | 1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(4-methoxy-phenylmethanediyl)-bis-pyrazol-3-one | 1808-49-7 | C30H30N4O3 | 494.593 |
—— | diantipyryldimethyl-p-aminophenyl methane | 2088-76-8 | C31H33N5O2 | 507.635 |
—— | 1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-[1]naphthylmethanediyl-bis-pyrazol-3-one | 92887-61-1 | C33H30N4O2 | 514.627 |
—— | 1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(2-hydroxy-phenylmethanediyl)-bis-pyrazol-3-one | 1606-55-9 | C29H28N4O3 | 480.566 |
—— | 1,5,1',5'-tetramethyl-2,2'-diphenyl-1,2,1',2'-tetrahydro-4,4'-(3-methoxy-benzylidene)-bis-pyrazol-3-one | 56479-69-7 | C30H30N4O3 | 494.593 |
—— | 4-(4-chlorobenzoyl)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one | 15183-00-3 | C18H15ClN2O2 | 326.782 |
—— | bis[1-(2,3-dimethyl-1-phenyl-3-pyrazolin-5-one)]-4-nitrophenylmethane | 55774-19-1 | C29H27N5O4 | 509.564 |
—— | 1,5-dimethyl-2-phenyl-4-(pyridin-2-yl)-1H-pyrazol-3(2H)-one | 18250-49-2 | C16H15N3O | 265.315 |
—— | 4-(2-bromo-butyryl)-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one | 80550-03-4 | C15H17BrN2O2 | 337.216 |