Knowledge (XXG)

Chlormethine

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1091:(sulfur mustard, Bis(2-chloroethyl) sulfide) on bone marrow and white blood cells had been known since the First World War. In 1935 several lines of chemical and biological research yielded results that would be explored after the start of the Second World War. The vesicant action of a family of chemicals related to the sulfur mustards, but with nitrogen substituting for sulfur was discovered—the "nitrogen mustards" were born. The particular nitrogen mustard chlormethine (mechlorethamine) was first synthesized. And the action of sulfur mustard on tumors in laboratory animals was investigated for the first time. 51: 405: 252: 969:. Historically, some uses of mechlorethamine have included lymphoid malignancies such as Hodgkin's disease, lymphosarcoma, chronic myelocytic leukemia, polycythemia vera, and bronchogenic carcinoma Mechlorethamine is often administered intravenously, but when compounded into a topical formulation it can also be used to treat skin diseases. There have been studies demonstrating that topical administration of mechlorethamine has efficacy in mycosis fungoides-type cutaneous T cell lymphoma. 1098:). The OSRD let contracts to study them to two universities—Yale University and the University of Chicago. Inspired perhaps by the preliminary research in 1935, independently both groups thought to test whether a medically useful differential toxicity between animals and animal tumors existed. The Yale pharmacologists Louis Goodman and Alfred Gilman were the first to conduct a clinical trial, on 27 August 1942, using the agent 42: 988:
exposure are generally delayed, the DNA damage it causes occurs very quickly. More serious exposures cause symptoms to develop sooner. Eye symptoms develop first, in the first 1–2 hours (severe exposure) or 3–12 hours (mild to moderate exposure) followed by airway (2-6/12–24 hours) and skin symptoms (6–48 hours). Hot, humid weather shortens the latent (symptom-free) period.
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The adverse effects of mechlorethamine depend on the formulation. When used in chemical warfare, it can cause immunosuppression and damage to mucous membranes of the eyes, skin, and respiratory tract. Mucous membranes and damp or damaged skin are more affected by exposure to HN-2. Though symptoms of
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Lessin SR, Duvic M, Guitart J, Pandya AG, Strober BE, Olsen EA, Hull CM, Knobler EH, Rook AH, Kim EJ, Naylor MF, Adelson DM, Kimball AB, Wood GS, Sundram U, Wu H, Kim YH. Topical chemotherapy in cutaneous T-cell lymphoma: positive results of a randomized, controlled, multicenter trial testing the
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The next year the Chicago group, led by Leon O. Jacobson, conducted trials with HN2 (chlormethine) which was the only agent in this group to see eventual clinical use. Wartime secrecy prevented any of this ground-breaking work on chemotherapy from being published, but papers were released once
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Jacobson L.O., Spurr C.L., Barron E., Smith T., Lushbaugh C., Dick G.F. (1946). "Nitrogen Mustard Therapy: Studies on the Effect of Methyl-Bis (Beta-Chloroethyl) Amine Hydrochloride on Neoplastic Diseases and Allied Disorders of the Hemopoietic System".
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Inhalation of chlormethine damages the upper and lower airways sequentially, with more severe exposures causing faster damage that afflicts lower parts of the respiratory tract. Early symptoms include
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Though ingestion is uncommon, if mechlorethamine is swallowed it causes severe chemical burns to the gastrointestinal tract and concomitant nausea, vomiting, diarrhea, abdominal pain, and hemorrhage.
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After the US entry into the Second World War the nitrogen mustards were candidate chemical warfare agents and research on them was initiated by the Office of Scientific Research and Development (
682: 2582: 1079:(inability to taste), inflammation, chronic infections, fibrosis, and cancer. Skin that has been damaged by HN2 can change pigmentation or become scarred, and may eventually develop cancer. 2339: 1045:(blistering) at first, but absorption through the skin causes systemic toxicity. In cases where more than 25% of the skin is affected, fatal exposure is likely to have occurred. 548: 833: 1408:
Lindahl LM, Fenger-Gron M, Iversen L. Topical nitrogen mustard therapy in patients with mycosis fungoides or parapsoriasis. J Eur Acad Dermatol Venereol. 2013 Feb;27(2):163-8.
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Bunn Jr, P. A.; Hoffman, S. J.; Norris, D; Golitz, L. E.; Aeling, J. L. (1994). "Systemic therapy of cutaneous T-cell lymphomas (mycosis fungoides and the Sézary syndrome)".
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Mechlorethamine is a highly toxic medication, especially for women who are pregnant, breastfeeding, or of childbearing age. At high enough levels, exposure can be fatal.
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chemotherapeutic drugs. It works by binding to DNA, crosslinking two strands and preventing cell duplication. It binds to the N7 nitrogen on the DNA base
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Alfred Gilman, Frederick S. Philips (1946). "The Biological Actions and Therapeutic Applications of the B-Chloroethyl Amines and Sulfides".
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damage. Chronic eye infections may result from exposure, but blindness is temporary. Long-term effects on the respiratory system include
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Galper SL, Smith BD, Wilson LD. Diagnosis and management of mycosis fungoides. Oncology (Williston Park). 2010 May;24(6):491-501.
1229:"Protection from cytotoxic effects induced by the nitrogen mustard mechlorethamine on human bronchial epithelial cells in vitro" 5713: 4919: 4713: 3965: 2188: 1114:
Chlormethine is combustible and becomes explosive under extreme conditions. It can react with metals to form gaseous hydrogen.
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V. Prelog, V. Štěpán (1935). "Nouvele synthèse des pipérazines N-monoalcoylées (VIIième communication sur les bis--amines)".
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McErlane, KM; Wood, RJ; Matsui, F; Lovering, EG (July 1978). "Impurities in Drugs II: Meperidine and Its Formulations".
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efficacy and safety of a novel mechlorethamine, 0.02%, gel in mycosis fungoides. JAMA Dermatol. 2013 Jan;149(1):25-32.
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Fenn, John E.; et al. (2011). "First Use of Intravenous Chemotherapy Cancer Treatment: Rectifying the Record".
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Berenblum I. (1935). "Experimental inhibition of tumor induction by mustard gas and other compounds".
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Symptoms of toxic exposure to HN-2 vary based on the route of exposure. Eye exposure causes
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Long-term effects of acute or chronic chlormethine exposure are caused by damage to the
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Einhorn, J. (1985). "Nitrogen mustard: the origin of chemotherapy for cancer".
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Actelion Pharmaceuticals Ltd. (2013) Valchlor Package Insert. Retrieved from
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Recordati Rare Diseases Inc. (2013). Mustargen Package Insert. Retrieved from
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Ward, Kyle (1935). "The Chlorinated Ethylamines — A New Type of Vesicant".
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Gilman, Alfred (1963). "The initial clinical trial of nitrogen mustard".
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http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/202317lbl.pdf
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Except where otherwise noted, data are given for materials in their
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Rappeneau S, Baeza-Squiban A, Jeulin C, Marano F (March 2000).
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https://www.nlm.nih.gov/medlineplus/druginfo/meds/a682223.html
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Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
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2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
676: 591: 1026:(nosebleed), toneless voice, sneezing, barking cough, and 689: 1087:
The effect of vesicant (blister) agents in the form of
828: 1268:"Chapter 3: Principles of Oncologic Pharmacotherapy". 1102:(tris(2-chloroethyl)amine) on a patient known as J.D. 5948: 1131: 1129: 1127: 5920: 5857: 5794: 5736: 5371: 5322: 5102: 5095: 5031: 4985: 4918: 4875: 4712: 4697: 4577: 4547: 4472: 4457: 4428: 4324: 4244: 4187: 4170: 4159: 4095: 4048: 4029: 3902: 3766: 3715: 3676: 3540: 3317: 3264: 3055: 2856: 2631: 2545: 2447: 2394: 2378: 2305: 2215: 2206: 2176: 2157: 2124: 2090: 2043: 2034: 1919: 1059:counts drop, increasing the risk of infection, and 1007:(swelling from fluid accumulation) in the eyelids, 972:Another use of chlormethine is in the synthesis of 1618:Collection of Czechoslovak Chemical Communications 1389:Medline (2012). Mechlorethamine. Retrieved from 324: 1271:Cancer Management: A Multidisciplinary Approach 124: 428:InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3 5714: 3997: 1880: 1164: 1162: 1011:(extreme sensitivity to light), severe pain, 8: 1853:: CS1 maint: multiple names: authors list ( 915:, its use is strongly restricted within the 1785:Journal of the American College of Surgeons 1003:(pinpoint pupils). More severe cases cause 708:In general: ℞ (Prescription only) 5721: 5707: 5699: 5099: 4709: 4469: 4184: 4167: 4045: 4004: 3990: 3982: 2212: 2040: 1887: 1873: 1865: 1321:Centers for Disease Control and Prevention 403: 250: 208: 33: 1244: 360: 1473:https://www.drugs.com/pro/mustargen.html 926:Mechlorethamine belongs to the group of 5955: 1361:10.7326/0003-4819-121-8-199410150-00007 1123: 449: 424: 399: 302: 228: 2768:Methylphosphonyl dichloride (dichloro) 2762:Methylphosphonyl difluoride (difluoro) 1846: 1141:Therapeutic Goods Administration (TGA) 961:. This chemical is a form of nitrogen 241: 3010:Tetramethylenedisulfotetramine (TETS) 1645:Journal of Pathology and Bacteriology 1180:from the original on 5 September 2021 1147:from the original on 5 September 2021 899:among others. It is the prototype of 431:Key: HAWPXGHAZFHHAD-UHFFFAOYSA-N 188: 168: 7: 1309: 1307: 1305: 1303: 1301: 1299: 1297: 1295: 1293: 568: 558: 4273:ribonucleotide reductase inhibitors 3099:Dimethyl(trifluoromethylthio)arsine 1539:Krumbhaar EB, Krumbhaar HD (1919). 315: 285: 4439:Ribonucleotide reductase inhibitor 4395:Ribonucleotide reductase inhibitor 2715:Dimethylamidophosphoric dichloride 1439:Journal of Pharmaceutical Sciences 25: 4198:Dihydrofolate reductase inhibitor 2730:Ethylphosphonoselenoic dichloride 2720:Dimethylamidophosphoric dicyanide 1797:10.1016/j.jamcollsurg.2010.10.018 941:It has been derivatized into the 5958: 2558:Dicyclohexyl phosphorofluoridate 2001:2,3,7,8-Tetrachlorodibenzodioxin 1833:10.1001/jama.1946.02870400011003 1106:wartime secrecy ended, in 1946. 818: 491: 485: 479: 49: 40: 3966:List of chemical warfare agents 2189:Dibutylchloromethyltin chloride 1571:from the original on 2020-02-10 1329:from the original on 2019-06-28 814:(at 25 °C , 100 kPa). 86:Bis(2-chloroethyl)(methyl)amine 4335:Thymidylate synthase inhibitor 4225:Thymidylate synthase inhibitor 473: 1: 5912:Propylbenzilylcholine mustard 4255:Adenosine deaminase inhibitor 4096:Block microtubule disassembly 1034:may develop and prove fatal. 3042:Trimethylolpropane phosphite 2588:Neopentylene fluorophosphate 1762:10.1016/0002-9610(63)90232-0 1727:10.1126/science.103.2675.409 1684:10.1016/0360-3016(85)90254-8 1672:Int J Radiat Oncol Biol Phys 1557:10.1016/0002-9610(63)90232-0 1067:counts may also drop due to 1037:Skin exposure mainly causes 999:(spasms of the eyelid), and 919:where it is classified as a 2824:3,3,5-Trimethylcyclohexanol 2684:N,N-Diisopropylaminoethanol 2553:Diisopropyl fluorophosphate 1349:Annals of Internal Medicine 957:where it has the code-name 917:Chemical Weapons Convention 6017: 5991:Nitrogen mustard vesicants 5872:Acetylethylcholine mustard 3663:Hexamethylene diisocyanate 3131:Phenylcarbylamine chloride 2457:Dimethylcarbamoyl fluoride 895:sold under the brand name 26: 5659: 5545:Omacetaxine mepesuccinate 5435:Ciltacabtagene autoleucel 5425:Brexucabtagene autoleucel 3961: 3921:Fluoroethyl fluoroacetate 3126:Perchloromethyl mercaptan 2537:4-686-293-01 (Agent 1-10) 1174:European Medicines Agency 980:Side effects and toxicity 953:. It can also be used in 808: 715: 634: 541: 460: 440: 415: 108: 80: 62: 57: 48: 39: 5839:Phenylenediamine mustard 5592:Talimogene laherparepvec 4459:Topoisomerase inhibitors 4378:DNA polymerase inhibitor 3638:Chloroacetophenone oxime 3623:Bromomethyl ethyl ketone 3231:Trifluoroacetyl chloride 3141:Tetrachlorodinitroethane 2788:Phosphorus pentachloride 2613:Methanesulfonyl fluoride 763:Dimethylaminopropylamine 27:Not to be confused with 5877:Benzilylcholine mustard 5410:Axicabtagene ciloleucel 4014:chemotherapeutic agents 3917:(variants and mixtures) 3186:Trichloronitrosomethane 3181:Trifluoronitrosomethane 2756:Methyldichlorophosphine 1657:10.1002/path.1700400312 1246:10.1093/toxsci/54.1.212 911:. As the chemical is a 790:Tris(2-aminoethyl)amine 5577:Sitimagene ceradenovec 5490:Idecabtagene vicleucel 5055:Methyl aminolevulinate 3716:Cornea-clouding agents 3211:Phosphorus trichloride 2793:Phosphorus trichloride 2527:Miotine (AR-28/T-1843) 1981:Phosphorus trifluoride 1451:10.1002/jps.2600670723 1274:. 2010. Archived from 1075:(inability to smell), 947:estramustine phosphate 800:HN3 (nitrogen mustard) 795:HN1 (nitrogen mustard) 780:-Diisopropylethylamine 5996:Chloroethyl compounds 5907:Hemicholinium mustard 5887:Decamethonium mustard 5867:Acetylcholine mustard 5796:Antineoplastic agents 5066:Porphyrin derivatives 4762:Melphalan flufenamide 4409:Hypomethylating agent 4018:antineoplastic agents 3110:Disulfur decafluoride 2911:Chlorophenylsilatrane 2819:2,4,5-Trichlorophenol 1176:. 17 September 2018. 743:-Nitrosodimethylamine 5902:Ethylcholine mustard 5395:Asparagine depleters 5324:Receptor antagonists 5238:+abiraterone acetate 3910:Methyl fluoroacetate 3738:Methyl cyanoacrylate 3658:Allyl isothiocyanate 3246:Uranium hexafluoride 3201:Dinitrogen tetroxide 3146:Chlorine trifluoride 2194:Selenium oxychloride 2064:Phenyldichloroarsine 2058:Methyldichloroarsine 1996:Nickel tetracarbonyl 1630:10.1135/cccc19350093 921:Schedule 1 substance 645:Biological half-life 5445:Denileukin diftitox 5345:Retinoid X receptor 5045:Aminolevulinic acid 4867:Triethylenemelamine 4699:Crosslinking of DNA 4430:Deoxyribonucleotide 4369:+gimeracil/oteracil 3603:Bromobenzyl cyanide 3371:Dimethylheptylpyran 3299:Diphenylcyanoarsine 3294:Diphenylchlorarsine 3226:Methyl vinyl ketone 3151:Perchloryl fluoride 3015:Bicyclic phosphates 2834:Trimethyl phosphite 2783:Phosphoryl chloride 2052:Ethyldichloroarsine 2026:Chloral cyanohydrin 2016:Acetone cyanohydrin 1986:Methyl cyanoformate 1719:1946Sci...103..409G 1603:10.1021/ja01308a041 685:(Prescription only) 506: g·mol 36: 5844:Quinacrine mustard 5686:Never to phase III 4503:Etirinotecan pegol 3971:CB military symbol 3829:Enterotoxin type B 3784:Cyclopiazonic acid 3743:N-Methylmorpholine 3643:Ethyl bromoacetate 3121:Ethyl bromoacetate 3088:Perfluoroisobutene 2829:Triethyl phosphite 2100:Levinstein mustard 1991:Iron pentacarbonyl 1526:2021-03-28 at the 1515:2018-09-20 at the 1497:2021-03-28 at the 1478:2018-09-20 at the 1396:2016-07-05 at the 1013:corneal ulceration 885:post-Soviet states 841:Infobox references 768:Diethylenetriamine 716:Related compounds 524:Fishy, ammoniacal 34: 5946: 5945: 5730:Nitrogen mustards 5696: 5695: 5655: 5654: 5612:Tigilanol tiglate 5104:Enzyme inhibitors 5027: 5026: 5023: 5022: 4723:Nitrogen mustards 4693: 4692: 4453: 4452: 4155: 4154: 3979: 3978: 3789:Histrionicotoxins 3767:Biological toxins 3648:Ethyl iodoacetate 3216:Methyl isocyanate 3176:Selenoyl fluoride 3166:Mercuric chloride 3136:Tetranitromethane 2990:Sulfuryl fluoride 2975:HN3 hydrochloride 2970:HN2 hydrochloride 2965:HN1 hydrochloride 2852: 2851: 2809:Phenacyl chloride 2804:Pinacolyl alcohol 2750:Isopropyl alcohol 2745:4-Hydroxycoumarin 2679:1,8-Dibromooctane 2202: 2201: 2126:Nitrogen mustards 1939:Cyanogen chloride 1827:(2675): 263–271. 1713:(2675): 409–436. 1015:, and blindness. 931:alkylating agents 901:alkylating agents 863:), also known as 849:Chemical compound 847: 846: 785:Triisopropylamine 704: 692: 680: 595: 514:Colorless liquid 384:CompTox Dashboard 150:Interactive image 75:-methylethanamine 71:-(2-chloroethyl)- 16:(Redirected from 6008: 5963: 5962: 5961: 5954: 5933:Phenoxybenzamine 5819:Cyclophosphamide 5723: 5716: 5709: 5700: 5617:Tisagenlecleucel 5389:Arsenic trioxide 5100: 5033:Photosensitizers 4824:Alkyl sulfonates 4738:Cyclophosphamide 4710: 4649:Anthracenediones 4470: 4444:Hydroxycarbamide 4185: 4168: 4046: 4006: 3999: 3992: 3983: 3953:White phosphorus 3930:post-combustion 3926:Depleted uranium 3753:Osmium tetroxide 3633:Phenacyl bromide 3196:Nitrogen dioxide 3171:Selenium dioxide 3161:Cadmium chloride 2618:Dimefox (TL-792) 2213: 2041: 1966:Hydrogen sulfide 1945:Hydrogen cyanide 1934:Cyanogen bromide 1900:chemical warfare 1889: 1882: 1875: 1866: 1859: 1858: 1852: 1844: 1815: 1809: 1808: 1780: 1774: 1773: 1745: 1739: 1738: 1702: 1696: 1695: 1678:(7): 1375–1378. 1667: 1661: 1660: 1640: 1634: 1633: 1613: 1607: 1606: 1591:J. Am. Chem. Soc 1586: 1580: 1579: 1577: 1576: 1536: 1530: 1507: 1501: 1488: 1482: 1469: 1463: 1462: 1434: 1428: 1424: 1418: 1415: 1409: 1406: 1400: 1387: 1381: 1380: 1344: 1338: 1337: 1335: 1334: 1311: 1288: 1287: 1285: 1283: 1265: 1259: 1258: 1248: 1224: 1218: 1217: 1215: 1213: 1196: 1190: 1189: 1187: 1185: 1166: 1157: 1156: 1154: 1152: 1143:. 30 June 2021. 1133: 1057:White blood cell 955:chemical warfare 949:, used to treat 928:nitrogen mustard 893:nitrogen mustard 891:(эмбихин), is a 831: 825: 822: 821: 758:Diisopropylamine 702: 699: 691: 688: 678: 675: 636:Pharmacokinetics 621:Intrapericardial 593: 590: 572: 562: 505: 493: 487: 481: 475: 468:Chemical formula 408: 407: 392: 390: 364: 328: 317: 306: 289: 262: 254: 243: 232: 212: 192: 172: 152: 128: 53: 44: 37: 21: 6016: 6015: 6011: 6010: 6009: 6007: 6006: 6005: 5986:Organochlorides 5971: 5970: 5969: 5959: 5957: 5949: 5947: 5942: 5916: 5882:Choline mustard 5853: 5804:Aniline mustard 5790: 5732: 5727: 5697: 5692: 5691: 5676:Clinical trials 5651: 5372:Other/ungrouped 5367: 5318: 5091: 5071:Porfimer sodium 5019: 4981: 4914: 4871: 4701: 4689: 4573: 4543: 4461: 4449: 4424: 4320: 4240: 4176: 4174:antimetabolites 4172: 4171:DNA precursors/ 4163: 4161:DNA replication 4151: 4091: 4061:Vinca alkaloids 4037: 4025: 4010: 3980: 3975: 3957: 3898: 3809:Botulinum toxin 3762: 3711: 3672: 3588:Benzyl chloride 3543: 3536: 3320: 3313: 3304:Cacodyl cyanide 3266:Vomiting agents 3260: 3058: 3051: 2960:Dimethylmercury 2882:Botulinum toxin 2848: 2627: 2541: 2443: 2396:Novichok agents 2390: 2374: 2301: 2198: 2172: 2153: 2120: 2092:Sulfur mustards 2086: 2030: 1976:Carbon monoxide 1956:Cacodyl cyanide 1915: 1914: 1898:Agents used in 1893: 1863: 1862: 1845: 1817: 1816: 1812: 1782: 1781: 1777: 1747: 1746: 1742: 1704: 1703: 1699: 1669: 1668: 1664: 1642: 1641: 1637: 1615: 1614: 1610: 1588: 1587: 1583: 1574: 1572: 1538: 1537: 1533: 1528:Wayback Machine 1517:Wayback Machine 1508: 1504: 1499:Wayback Machine 1489: 1485: 1480:Wayback Machine 1470: 1466: 1436: 1435: 1431: 1425: 1421: 1416: 1412: 1407: 1403: 1398:Wayback Machine 1388: 1384: 1346: 1345: 1341: 1332: 1330: 1313: 1312: 1291: 1281: 1279: 1267: 1266: 1262: 1226: 1225: 1221: 1211: 1209: 1208:. 3 August 2022 1198: 1197: 1193: 1183: 1181: 1168: 1167: 1160: 1150: 1148: 1135: 1134: 1125: 1120: 1112: 1085: 982: 965:and a powerful 951:prostate cancer 939: 865:mechlorethamine 850: 843: 838: 837: 836:  ?) 827: 823: 819: 815: 804: 723: 711: 659: 647: 630: 612: 609: 601: 584: 581: 551: 503: 490: 484: 478: 470: 456: 453: 448: 447: 436: 433: 432: 429: 423: 422: 411: 393: 386: 367: 347: 331: 318: 304:Mechlorethamine 292: 272: 235: 215: 195: 175: 155: 142: 131: 118: 104: 103: 89:mechlorethamine 76: 32: 23: 22: 15: 12: 11: 5: 6014: 6012: 6004: 6003: 5998: 5993: 5988: 5983: 5973: 5972: 5968: 5967: 5944: 5943: 5941: 5940: 5935: 5930: 5924: 5922: 5918: 5917: 5915: 5914: 5909: 5904: 5899: 5894: 5889: 5884: 5879: 5874: 5869: 5863: 5861: 5855: 5854: 5852: 5851: 5846: 5841: 5836: 5831: 5826: 5821: 5816: 5811: 5806: 5800: 5798: 5792: 5791: 5789: 5788: 5783: 5778: 5773: 5768: 5763: 5758: 5753: 5748: 5742: 5740: 5734: 5733: 5728: 5726: 5725: 5718: 5711: 5703: 5694: 5693: 5690: 5689: 5688: 5687: 5684: 5673: 5667: 5661: 5660: 5657: 5656: 5653: 5652: 5650: 5649: 5644: 5639: 5634: 5629: 5624: 5619: 5614: 5609: 5604: 5599: 5594: 5589: 5584: 5579: 5574: 5569: 5563: 5552: 5547: 5542: 5537: 5532: 5527: 5522: 5517: 5512: 5507: 5502: 5497: 5492: 5487: 5482: 5477: 5472: 5467: 5462: 5457: 5452: 5447: 5442: 5437: 5432: 5427: 5422: 5417: 5412: 5407: 5391: 5386: 5381: 5375: 5373: 5369: 5368: 5366: 5365: 5353: 5341: 5328: 5326: 5320: 5319: 5317: 5316: 5310: 5305: 5300: 5295: 5283: 5277: 5272: 5267: 5262: 5251: 5245: 5240: 5232: 5225:PARP inhibitor 5221: 5209: 5197: 5185: 5184: 5183: 5178: 5173: 5168: 5156: 5150: 5145: 5140: 5135: 5121: 5108: 5106: 5097: 5093: 5092: 5090: 5089: 5083: 5078: 5073: 5062: 5057: 5052: 5047: 5041: 5039: 5029: 5028: 5025: 5024: 5021: 5020: 5018: 5017: 5011: 5006: 5001: 4991: 4989: 4983: 4982: 4980: 4979: 4973: 4968: 4957: 4952: 4947: 4942: 4930: 4924: 4922: 4916: 4915: 4913: 4912: 4907: 4902: 4897: 4892: 4887: 4881: 4879: 4877:Platinum-based 4873: 4872: 4870: 4869: 4864: 4859: 4854: 4842: 4841: 4835: 4819: 4818: 4813: 4808: 4803: 4793: 4788: 4776: 4775: 4770: 4765: 4755: 4750: 4744: 4735: 4730: 4718: 4716: 4707: 4695: 4694: 4691: 4690: 4688: 4687: 4682: 4677: 4672: 4667: 4661: 4656: 4645: 4639: 4634: 4629: 4624: 4619: 4614: 4604: 4599: 4592:Anthracyclines 4587: 4585: 4575: 4574: 4572: 4571: 4565: 4553: 4551: 4545: 4544: 4542: 4541: 4535: 4530: 4525: 4520: 4515: 4510: 4505: 4500: 4495: 4490: 4478: 4476: 4467: 4455: 4454: 4451: 4450: 4448: 4447: 4434: 4432: 4426: 4425: 4423: 4422: 4416: 4404: 4403: 4390: 4389: 4373: 4372: 4362: 4357: 4352: 4347: 4342: 4330: 4328: 4322: 4321: 4319: 4318: 4312: 4310:Mercaptopurine 4301: 4296: 4291: 4285: 4280: 4264: 4263: 4250: 4248: 4242: 4241: 4239: 4238: 4232: 4221: 4215: 4210: 4205: 4193: 4191: 4182: 4165: 4157: 4156: 4153: 4152: 4150: 4149: 4137: 4131: 4126: 4121: 4116: 4111: 4099: 4097: 4093: 4092: 4090: 4089: 4083: 4078: 4073: 4068: 4056: 4054: 4043: 4027: 4026: 4012:Intracellular 4011: 4009: 4008: 4001: 3994: 3986: 3977: 3976: 3974: 3973: 3968: 3962: 3959: 3958: 3956: 3955: 3950: 3945: 3936: 3935: 3934: 3932:uranium oxides 3923: 3918: 3912: 3906: 3904: 3900: 3899: 3897: 3896: 3891: 3886: 3881: 3876: 3871: 3866: 3861: 3856: 3851: 3846: 3841: 3836: 3831: 3826: 3821: 3816: 3811: 3806: 3801: 3796: 3791: 3786: 3781: 3776: 3770: 3768: 3764: 3763: 3761: 3760: 3755: 3750: 3745: 3740: 3735: 3730: 3725: 3719: 3717: 3713: 3712: 3710: 3709: 3704: 3699: 3694: 3689: 3683: 3681: 3674: 3673: 3671: 3670: 3668:Crotonaldehyde 3665: 3660: 3655: 3650: 3645: 3640: 3635: 3630: 3625: 3620: 3615: 3610: 3605: 3600: 3595: 3593:Benzyl bromide 3590: 3585: 3580: 3575: 3570: 3565: 3560: 3554: 3548: 3546: 3538: 3537: 3535: 3534: 3532:Chlorpromazine 3529: 3524: 3519: 3514: 3509: 3504: 3499: 3494: 3489: 3484: 3479: 3474: 3469: 3464: 3459: 3454: 3449: 3444: 3439: 3434: 3429: 3424: 3419: 3414: 3409: 3404: 3399: 3394: 3389: 3384: 3379: 3374: 3368: 3363: 3358: 3353: 3348: 3342: 3337: 3332: 3325: 3323: 3319:Incapacitating 3315: 3314: 3312: 3311: 3306: 3301: 3296: 3291: 3282: 3277: 3270: 3268: 3262: 3261: 3259: 3258: 3253: 3248: 3243: 3238: 3233: 3228: 3223: 3218: 3213: 3208: 3206:Sulfur dioxide 3203: 3198: 3193: 3188: 3183: 3178: 3173: 3168: 3163: 3158: 3153: 3148: 3143: 3138: 3133: 3128: 3123: 3118: 3113: 3107: 3101: 3096: 3090: 3085: 3080: 3074: 3069: 3063: 3061: 3059:choking agents 3053: 3052: 3050: 3049: 3044: 3039: 3034: 3033: 3032: 3027: 3022: 3012: 3007: 3002: 2997: 2992: 2987: 2982: 2977: 2972: 2967: 2962: 2957: 2955:Tetraethyllead 2952: 2946: 2941: 2935: 2930: 2925: 2919: 2913: 2908: 2902: 2896: 2891: 2885: 2879: 2874: 2868: 2862: 2860: 2854: 2853: 2850: 2849: 2847: 2846: 2841: 2836: 2831: 2826: 2821: 2816: 2811: 2806: 2801: 2796: 2790: 2785: 2780: 2775: 2770: 2765: 2759: 2753: 2747: 2742: 2737: 2732: 2727: 2722: 2717: 2712: 2707: 2702: 2697: 2692: 2687: 2681: 2676: 2671: 2666: 2661: 2659:A.P.C. complex 2656: 2651: 2646: 2641: 2635: 2633: 2629: 2628: 2626: 2625: 2620: 2615: 2610: 2605: 2600: 2595: 2590: 2585: 2580: 2575: 2570: 2565: 2560: 2555: 2549: 2547: 2543: 2542: 2540: 2539: 2534: 2529: 2524: 2519: 2514: 2509: 2504: 2499: 2494: 2489: 2484: 2479: 2474: 2469: 2464: 2459: 2453: 2451: 2445: 2444: 2442: 2441: 2436: 2431: 2426: 2421: 2416: 2411: 2406: 2400: 2398: 2392: 2391: 2389: 2388: 2382: 2380: 2376: 2375: 2373: 2372: 2370:V-sub x (GD-7) 2367: 2362: 2357: 2352: 2347: 2342: 2337: 2332: 2327: 2322: 2317: 2311: 2309: 2303: 2302: 2300: 2299: 2294: 2289: 2284: 2279: 2274: 2268: 2263: 2257: 2251: 2245: 2239: 2233: 2228: 2221: 2219: 2210: 2204: 2203: 2200: 2199: 2197: 2196: 2191: 2186: 2180: 2178: 2174: 2173: 2171: 2170: 2167:Phosgene oxime 2163: 2161: 2155: 2154: 2152: 2151: 2146: 2141: 2136: 2130: 2128: 2122: 2121: 2119: 2118: 2113: 2108: 2103: 2096: 2094: 2088: 2087: 2085: 2079: 2073: 2067: 2061: 2055: 2049: 2047: 2038: 2036:Blister agents 2032: 2031: 2029: 2028: 2023: 2018: 2013: 2008: 2006:Glycolonitrile 2003: 1998: 1993: 1988: 1983: 1978: 1973: 1968: 1963: 1958: 1953: 1948: 1942: 1936: 1931: 1925: 1923: 1917: 1916: 1913: 1912: 1907: 1905:incapacitation 1902: 1895: 1894: 1892: 1891: 1884: 1877: 1869: 1861: 1860: 1810: 1791:(3): 413–417. 1775: 1756:(5): 574–578. 1740: 1697: 1662: 1651:(3): 549–558. 1635: 1608: 1597:(5): 914–916. 1581: 1551:(5): 497–508. 1531: 1502: 1483: 1464: 1445:(7): 958–961. 1429: 1419: 1410: 1401: 1382: 1355:(8): 592–602. 1339: 1289: 1278:on 15 May 2009 1260: 1219: 1191: 1158: 1122: 1121: 1119: 1116: 1111: 1108: 1084: 1081: 1061:red blood cell 1041:(redness) and 1022:(runny nose), 981: 978: 976:(meperidine). 938: 935: 848: 845: 844: 839: 817: 816: 812:standard state 809: 806: 805: 803: 802: 797: 792: 787: 782: 770: 765: 760: 755: 750: 745: 737: 735:Trimethylamine 732: 726: 724: 722:Related amines 721: 718: 717: 713: 712: 710: 709: 706: 697: 686: 672: 670: 664: 663: 660: 655: 652: 651: 648: 643: 640: 639: 632: 631: 629: 628: 625: 622: 619: 615: 613: 610:administration 606: 603: 602: 600: 599: 597: 587: 585: 578: 575: 574: 552: 547: 544: 543: 539: 538: 535: 526: 525: 522: 516: 515: 512: 508: 507: 501: 495: 494: 488: 482: 476: 471: 466: 463: 462: 458: 457: 455: 454: 451: 443: 442: 441: 438: 437: 435: 434: 430: 427: 426: 418: 417: 416: 413: 412: 410: 409: 396: 394: 382: 379: 378: 375: 369: 368: 366: 365: 357: 355: 349: 348: 346: 345: 341: 339: 333: 332: 330: 329: 321: 319: 311: 308: 307: 300: 294: 293: 291: 290: 282: 280: 274: 273: 271: 270: 266: 264: 256: 255: 245: 237: 236: 234: 233: 225: 223: 217: 216: 214: 213: 205: 203: 197: 196: 194: 193: 185: 183: 177: 176: 174: 173: 165: 163: 157: 156: 154: 153: 145: 143: 136: 133: 132: 130: 129: 121: 119: 114: 111: 110: 106: 105: 102: 101: 96: 93: 90: 87: 83: 82: 78: 77: 66: 60: 59: 55: 54: 46: 45: 24: 14: 13: 10: 9: 6: 4: 3: 2: 6013: 6002: 5999: 5997: 5994: 5992: 5989: 5987: 5984: 5982: 5979: 5978: 5976: 5966: 5956: 5952: 5939: 5936: 5934: 5931: 5929: 5926: 5925: 5923: 5919: 5913: 5910: 5908: 5905: 5903: 5900: 5898: 5895: 5893: 5890: 5888: 5885: 5883: 5880: 5878: 5875: 5873: 5870: 5868: 5865: 5864: 5862: 5860: 5856: 5850: 5847: 5845: 5842: 5840: 5837: 5835: 5832: 5830: 5827: 5825: 5822: 5820: 5817: 5815: 5812: 5810: 5807: 5805: 5802: 5801: 5799: 5797: 5793: 5787: 5784: 5782: 5779: 5777: 5774: 5772: 5769: 5767: 5764: 5762: 5759: 5757: 5754: 5752: 5749: 5747: 5744: 5743: 5741: 5739: 5735: 5731: 5724: 5719: 5717: 5712: 5710: 5705: 5704: 5701: 5685: 5683: 5680: 5679: 5677: 5674: 5671: 5668: 5666: 5663: 5662: 5658: 5648: 5645: 5643: 5640: 5638: 5635: 5633: 5630: 5628: 5625: 5623: 5620: 5618: 5615: 5613: 5610: 5608: 5605: 5603: 5600: 5598: 5595: 5593: 5590: 5588: 5585: 5583: 5580: 5578: 5575: 5573: 5570: 5567: 5564: 5562: 5558: 5557: 5553: 5551: 5548: 5546: 5543: 5541: 5538: 5536: 5533: 5531: 5528: 5526: 5523: 5521: 5520:Lurbinectedin 5518: 5516: 5513: 5511: 5508: 5506: 5503: 5501: 5498: 5496: 5493: 5491: 5488: 5486: 5483: 5481: 5478: 5476: 5473: 5471: 5468: 5466: 5463: 5461: 5458: 5456: 5453: 5451: 5448: 5446: 5443: 5441: 5438: 5436: 5433: 5431: 5428: 5426: 5423: 5421: 5418: 5416: 5413: 5411: 5408: 5405: 5401: 5397: 5396: 5392: 5390: 5387: 5385: 5382: 5380: 5377: 5376: 5374: 5370: 5363: 5359: 5358: 5354: 5351: 5347: 5346: 5342: 5339: 5335: 5334: 5330: 5329: 5327: 5325: 5321: 5314: 5311: 5309: 5306: 5304: 5301: 5299: 5296: 5294: 5290: 5288: 5284: 5281: 5278: 5276: 5273: 5271: 5268: 5266: 5263: 5261: 5257: 5256: 5252: 5249: 5246: 5244: 5241: 5239: 5236: 5233: 5231: 5227: 5226: 5222: 5219: 5215: 5214: 5210: 5207: 5203: 5202: 5198: 5195: 5191: 5190: 5186: 5182: 5179: 5177: 5174: 5172: 5169: 5167: 5164: 5163: 5162: 5161: 5157: 5154: 5151: 5149: 5146: 5144: 5141: 5139: 5136: 5134: 5130: 5129: 5126: 5122: 5119: 5115: 5114: 5110: 5109: 5107: 5105: 5101: 5098: 5094: 5087: 5084: 5082: 5079: 5077: 5074: 5072: 5068: 5067: 5063: 5061: 5058: 5056: 5053: 5051: 5048: 5046: 5043: 5042: 5040: 5038: 5034: 5030: 5015: 5012: 5010: 5007: 5005: 5002: 5000: 4996: 4993: 4992: 4990: 4988: 4987:Intercalation 4984: 4977: 4974: 4972: 4969: 4967: 4963: 4962: 4958: 4956: 4953: 4951: 4948: 4946: 4943: 4940: 4936: 4935: 4931: 4929: 4926: 4925: 4923: 4921: 4917: 4911: 4908: 4906: 4903: 4901: 4898: 4896: 4895:Dicycloplatin 4893: 4891: 4888: 4886: 4883: 4882: 4880: 4878: 4874: 4868: 4865: 4863: 4860: 4858: 4855: 4853: 4850: 4848: 4844: 4843: 4839: 4836: 4834: 4830: 4827: 4825: 4821: 4820: 4817: 4814: 4812: 4809: 4807: 4804: 4801: 4797: 4794: 4792: 4789: 4787: 4784: 4782: 4778: 4777: 4774: 4771: 4769: 4768:Prednimustine 4766: 4763: 4759: 4756: 4754: 4751: 4748: 4745: 4743: 4739: 4736: 4734: 4731: 4729: 4726: 4724: 4720: 4719: 4717: 4715: 4711: 4708: 4705: 4700: 4696: 4686: 4683: 4681: 4678: 4676: 4673: 4671: 4668: 4665: 4662: 4660: 4657: 4655: 4651: 4650: 4646: 4643: 4640: 4638: 4635: 4633: 4630: 4628: 4625: 4623: 4620: 4618: 4615: 4612: 4608: 4605: 4603: 4600: 4598: 4594: 4593: 4589: 4588: 4586: 4584: 4583:Intercalation 4580: 4576: 4569: 4566: 4564: 4560: 4559: 4555: 4554: 4552: 4550: 4546: 4539: 4536: 4534: 4531: 4529: 4526: 4524: 4521: 4519: 4516: 4514: 4511: 4509: 4506: 4504: 4501: 4499: 4496: 4494: 4491: 4489: 4485: 4484: 4480: 4479: 4477: 4475: 4471: 4468: 4465: 4460: 4456: 4445: 4441: 4440: 4436: 4435: 4433: 4431: 4427: 4420: 4417: 4415: 4411: 4410: 4406: 4405: 4401: 4397: 4396: 4392: 4391: 4387: 4386:+daunorubicin 4384: 4380: 4379: 4375: 4374: 4370: 4366: 4363: 4361: 4358: 4356: 4353: 4351: 4350:Doxifluridine 4348: 4346: 4343: 4341: 4337: 4336: 4332: 4331: 4329: 4327: 4323: 4316: 4313: 4311: 4307: 4306: 4302: 4300: 4299:Rabacfosadine 4297: 4295: 4292: 4289: 4286: 4284: 4281: 4279: 4275: 4274: 4270: 4266: 4265: 4261: 4257: 4256: 4252: 4251: 4249: 4247: 4243: 4236: 4233: 4231: 4227: 4226: 4222: 4219: 4216: 4214: 4211: 4209: 4206: 4204: 4200: 4199: 4195: 4194: 4192: 4190: 4186: 4183: 4180: 4175: 4169: 4166: 4162: 4158: 4147: 4143: 4142: 4138: 4135: 4132: 4130: 4127: 4125: 4122: 4120: 4117: 4115: 4112: 4110: 4106: 4105: 4101: 4100: 4098: 4094: 4087: 4084: 4082: 4079: 4077: 4074: 4072: 4069: 4067: 4063: 4062: 4058: 4057: 4055: 4052: 4047: 4044: 4041: 4036: 4032: 4028: 4023: 4019: 4015: 4007: 4002: 4000: 3995: 3993: 3988: 3987: 3984: 3972: 3969: 3967: 3964: 3963: 3960: 3954: 3951: 3949: 3946: 3944: 3943:its compounds 3940: 3937: 3933: 3929: 3928: 3927: 3924: 3922: 3919: 3916: 3913: 3911: 3908: 3907: 3905: 3901: 3895: 3892: 3890: 3887: 3885: 3882: 3880: 3879:Tetanospasmin 3877: 3875: 3874:T-2 mycotoxin 3872: 3870: 3867: 3865: 3862: 3860: 3857: 3855: 3852: 3850: 3847: 3845: 3842: 3840: 3837: 3835: 3832: 3830: 3827: 3825: 3822: 3820: 3817: 3815: 3812: 3810: 3807: 3805: 3804:Batrachotoxin 3802: 3800: 3797: 3795: 3792: 3790: 3787: 3785: 3782: 3780: 3777: 3775: 3772: 3771: 3769: 3765: 3759: 3756: 3754: 3751: 3749: 3748:Allyl alcohol 3746: 3744: 3741: 3739: 3736: 3734: 3731: 3729: 3726: 3724: 3721: 3720: 3718: 3714: 3708: 3705: 3703: 3700: 3698: 3695: 3693: 3690: 3688: 3685: 3684: 3682: 3679: 3675: 3669: 3666: 3664: 3661: 3659: 3656: 3654: 3651: 3649: 3646: 3644: 3641: 3639: 3636: 3634: 3631: 3629: 3626: 3624: 3621: 3619: 3616: 3614: 3613:Chloroacetone 3611: 3609: 3606: 3604: 3601: 3599: 3598:Benzyl iodide 3596: 3594: 3591: 3589: 3586: 3584: 3581: 3579: 3576: 3574: 3571: 3569: 3566: 3564: 3561: 3558: 3555: 3553: 3552:Xylyl bromide 3550: 3549: 3547: 3545: 3539: 3533: 3530: 3528: 3525: 3523: 3520: 3518: 3515: 3513: 3510: 3508: 3505: 3503: 3500: 3498: 3495: 3493: 3490: 3488: 3485: 3483: 3480: 3478: 3475: 3473: 3470: 3468: 3465: 3463: 3460: 3458: 3455: 3453: 3450: 3448: 3445: 3443: 3440: 3438: 3435: 3433: 3430: 3428: 3425: 3423: 3420: 3418: 3415: 3413: 3410: 3408: 3405: 3403: 3400: 3398: 3395: 3393: 3390: 3388: 3385: 3383: 3380: 3378: 3375: 3372: 3369: 3367: 3364: 3362: 3359: 3357: 3354: 3352: 3349: 3346: 3343: 3341: 3340:Butyrophenone 3338: 3336: 3333: 3330: 3327: 3326: 3324: 3322: 3316: 3310: 3309:o-Dianisidine 3307: 3305: 3302: 3300: 3297: 3295: 3292: 3290: 3286: 3283: 3281: 3278: 3275: 3272: 3271: 3269: 3267: 3263: 3257: 3254: 3252: 3249: 3247: 3244: 3242: 3239: 3237: 3234: 3232: 3229: 3227: 3224: 3222: 3219: 3217: 3214: 3212: 3209: 3207: 3204: 3202: 3199: 3197: 3194: 3192: 3189: 3187: 3184: 3182: 3179: 3177: 3174: 3172: 3169: 3167: 3164: 3162: 3159: 3157: 3156:Cadmium oxide 3154: 3152: 3149: 3147: 3144: 3142: 3139: 3137: 3134: 3132: 3129: 3127: 3124: 3122: 3119: 3117: 3114: 3111: 3108: 3105: 3102: 3100: 3097: 3094: 3091: 3089: 3086: 3084: 3081: 3078: 3075: 3073: 3070: 3068: 3065: 3064: 3062: 3060: 3054: 3048: 3045: 3043: 3040: 3038: 3035: 3031: 3028: 3026: 3023: 3021: 3018: 3017: 3016: 3013: 3011: 3008: 3006: 3005:Batrachotoxin 3003: 3001: 2998: 2996: 2993: 2991: 2988: 2986: 2983: 2981: 2978: 2976: 2973: 2971: 2968: 2966: 2963: 2961: 2958: 2956: 2953: 2950: 2947: 2945: 2942: 2939: 2936: 2934: 2931: 2929: 2926: 2923: 2920: 2917: 2914: 2912: 2909: 2906: 2903: 2900: 2897: 2895: 2892: 2889: 2888:Tetanospasmin 2886: 2883: 2880: 2878: 2875: 2872: 2869: 2867: 2864: 2863: 2861: 2859: 2855: 2845: 2842: 2840: 2837: 2835: 2832: 2830: 2827: 2825: 2822: 2820: 2817: 2815: 2812: 2810: 2807: 2805: 2802: 2800: 2797: 2794: 2791: 2789: 2786: 2784: 2781: 2779: 2776: 2774: 2771: 2769: 2766: 2763: 2760: 2757: 2754: 2751: 2748: 2746: 2743: 2741: 2738: 2736: 2733: 2731: 2728: 2726: 2723: 2721: 2718: 2716: 2713: 2711: 2708: 2706: 2703: 2701: 2698: 2696: 2693: 2691: 2688: 2685: 2682: 2680: 2677: 2675: 2672: 2670: 2667: 2665: 2662: 2660: 2657: 2655: 2652: 2650: 2647: 2645: 2642: 2640: 2637: 2636: 2634: 2630: 2624: 2621: 2619: 2616: 2614: 2611: 2609: 2606: 2604: 2601: 2599: 2596: 2594: 2591: 2589: 2586: 2584: 2581: 2579: 2576: 2574: 2571: 2569: 2566: 2564: 2561: 2559: 2556: 2554: 2551: 2550: 2548: 2544: 2538: 2535: 2533: 2530: 2528: 2525: 2523: 2520: 2518: 2515: 2513: 2510: 2508: 2505: 2503: 2500: 2498: 2495: 2493: 2490: 2488: 2485: 2483: 2480: 2478: 2475: 2473: 2470: 2468: 2465: 2463: 2460: 2458: 2455: 2454: 2452: 2450: 2446: 2440: 2437: 2435: 2432: 2430: 2427: 2425: 2422: 2420: 2417: 2415: 2412: 2410: 2407: 2405: 2402: 2401: 2399: 2397: 2393: 2387: 2384: 2383: 2381: 2377: 2371: 2368: 2366: 2363: 2361: 2358: 2356: 2353: 2351: 2348: 2346: 2343: 2341: 2338: 2336: 2333: 2331: 2328: 2326: 2323: 2321: 2318: 2316: 2313: 2312: 2310: 2308: 2304: 2298: 2295: 2293: 2290: 2288: 2285: 2283: 2280: 2278: 2275: 2272: 2269: 2267: 2264: 2261: 2258: 2255: 2252: 2249: 2246: 2243: 2240: 2237: 2234: 2232: 2229: 2226: 2223: 2222: 2220: 2218: 2214: 2211: 2209: 2205: 2195: 2192: 2190: 2187: 2185: 2182: 2181: 2179: 2175: 2168: 2165: 2164: 2162: 2160: 2159:Nettle agents 2156: 2150: 2147: 2145: 2142: 2140: 2137: 2135: 2132: 2131: 2129: 2127: 2123: 2117: 2114: 2112: 2109: 2107: 2104: 2101: 2098: 2097: 2095: 2093: 2089: 2083: 2080: 2077: 2074: 2071: 2068: 2065: 2062: 2059: 2056: 2053: 2050: 2048: 2046: 2042: 2039: 2037: 2033: 2027: 2024: 2022: 2019: 2017: 2014: 2012: 2009: 2007: 2004: 2002: 1999: 1997: 1994: 1992: 1989: 1987: 1984: 1982: 1979: 1977: 1974: 1972: 1969: 1967: 1964: 1962: 1961:Cacodyl oxide 1959: 1957: 1954: 1952: 1949: 1946: 1943: 1940: 1937: 1935: 1932: 1930: 1927: 1926: 1924: 1922: 1918: 1911: 1908: 1906: 1903: 1901: 1897: 1896: 1890: 1885: 1883: 1878: 1876: 1871: 1870: 1867: 1856: 1850: 1842: 1838: 1834: 1830: 1826: 1822: 1814: 1811: 1806: 1802: 1798: 1794: 1790: 1786: 1779: 1776: 1771: 1767: 1763: 1759: 1755: 1751: 1744: 1741: 1736: 1732: 1728: 1724: 1720: 1716: 1712: 1708: 1701: 1698: 1693: 1689: 1685: 1681: 1677: 1673: 1666: 1663: 1658: 1654: 1650: 1646: 1639: 1636: 1631: 1627: 1623: 1619: 1612: 1609: 1604: 1600: 1596: 1592: 1585: 1582: 1570: 1566: 1562: 1558: 1554: 1550: 1546: 1542: 1535: 1532: 1529: 1525: 1522: 1518: 1514: 1511: 1506: 1503: 1500: 1496: 1493: 1487: 1484: 1481: 1477: 1474: 1468: 1465: 1460: 1456: 1452: 1448: 1444: 1440: 1433: 1430: 1423: 1420: 1414: 1411: 1405: 1402: 1399: 1395: 1392: 1386: 1383: 1378: 1374: 1370: 1366: 1362: 1358: 1354: 1350: 1343: 1340: 1328: 1324: 1322: 1316: 1310: 1308: 1306: 1304: 1302: 1300: 1298: 1296: 1294: 1290: 1277: 1273: 1272: 1264: 1261: 1256: 1252: 1247: 1242: 1239:(1): 212–21. 1238: 1234: 1230: 1223: 1220: 1207: 1206: 1205:Health Canada 1201: 1195: 1192: 1179: 1175: 1171: 1170:"Ledaga EPAR" 1165: 1163: 1159: 1146: 1142: 1138: 1132: 1130: 1128: 1124: 1117: 1115: 1109: 1107: 1103: 1101: 1097: 1092: 1090: 1082: 1080: 1078: 1074: 1070: 1066: 1062: 1058: 1054: 1053:immune system 1049: 1046: 1044: 1040: 1035: 1033: 1029: 1025: 1021: 1016: 1014: 1010: 1006: 1002: 998: 997:blepharospasm 994: 989: 985: 979: 977: 975: 970: 968: 964: 960: 956: 952: 948: 944: 936: 934: 932: 929: 924: 922: 918: 914: 913:blister agent 910: 906: 903:, a group of 902: 898: 894: 890: 886: 882: 878: 874: 870: 866: 862: 858: 854: 842: 835: 830: 813: 807: 801: 798: 796: 793: 791: 788: 786: 783: 781: 779: 775: 771: 769: 766: 764: 761: 759: 756: 754: 753:Triethylamine 751: 749: 746: 744: 742: 738: 736: 733: 731: 730:Dimethylamine 728: 727: 725: 720: 719: 714: 707: 705: Rx-only 698: 696: 687: 684: 674: 673: 671: 669: 666: 665: 662:50% (Kidney) 661: 658: 654: 653: 650:<1 minute 649: 646: 642: 641: 637: 633: 626: 623: 620: 618:Intracavitary 617: 616: 614: 611: 605: 604: 598: 589: 588: 586: 583: 577: 576: 571: 566: 561: 556: 553: 550: 546: 545: 542:Pharmacology 540: 536: 534: 533: 528: 527: 523: 521: 518: 517: 513: 510: 509: 502: 500: 497: 496: 472: 469: 465: 464: 459: 450: 446: 439: 425: 421: 414: 406: 402: 401:DTXSID2020975 398: 397: 395: 385: 381: 380: 376: 374: 371: 370: 363: 359: 358: 356: 354: 351: 350: 343: 342: 340: 338: 335: 334: 327: 323: 322: 320: 314: 310: 309: 305: 301: 299: 296: 295: 288: 284: 283: 281: 279: 276: 275: 268: 267: 265: 263: 258: 257: 253: 249: 246: 244: 242:ECHA InfoCard 239: 238: 231: 227: 226: 224: 222: 219: 218: 211: 207: 206: 204: 202: 199: 198: 191: 187: 186: 184: 182: 179: 178: 171: 167: 166: 164: 162: 159: 158: 151: 147: 146: 144: 140: 135: 134: 127: 123: 122: 120: 117: 113: 112: 107: 100: 97: 94: 91: 88: 85: 84: 79: 74: 70: 65: 61: 56: 52: 47: 43: 38: 35:Chlormethine 30: 29:Chloromethane 19: 6001:Orphan drugs 5849:Spiromustine 5824:Mannomustine 5814:Chlorambucil 5809:Bendamustine 5597:Tazemetostat 5561:Alitretinoin 5554: 5480:Estramustine 5460:Elsamitrucin 5450:Eflornithine 5404:Pegaspargase 5400:Asparaginase 5393: 5362:Testolactone 5355: 5343: 5331: 5285: 5270:Panobinostat 5253: 5223: 5211: 5199: 5187: 5158: 5123: 5111: 5064: 5060:Padeliporfin 4999:Dactinomycin 4995:Streptomyces 4976:Temozolomide 4971:Mitozolomide 4959: 4950:Mitobronitol 4939:Procarbazine 4932: 4920:Nonclassical 4845: 4822: 4816:Streptozocin 4781:Nitrosoureas 4779: 4753:Chlorambucil 4747:Trofosfamide 4733:Chlormethine 4732: 4728:Bendamustine 4721: 4659:Mitoxantrone 4654:Losoxantrone 4647: 4607:Daunorubicin 4590: 4556: 4493:Camptothecin 4481: 4437: 4407: 4393: 4376: 4360:Fluorouracil 4340:Capecitabine 4333: 4303: 4267: 4253: 4223: 4218:Pralatrexate 4208:Methotrexate 4196: 4139: 4102: 4059: 3884:Tetrodotoxin 3834:Grayanotoxin 3618:Bromoacetone 3608:Thiophosgene 3563:Mace (spray) 3557:Pepper spray 3542:Lachrymatory 3527:Fluphenazine 3522:Procarbazine 3432:Sleeping gas 3280:Chloropicrin 3191:Nitric oxide 3093:Chloropicrin 3037:Cloflubicyne 3000:Oxotremorine 2949:Antillatoxin 2928:Tetrodotoxin 2877:Bungarotoxin 2773:Nitromethane 2735:Formaldoxime 2674:Cyclohexanol 2639:Acetonitrile 2386:GV (EA-5365) 2208:Nerve agents 2138: 2011:Lactonitrile 1921:Blood agents 1910:riot control 1849:cite journal 1824: 1820: 1813: 1788: 1784: 1778: 1753: 1749: 1743: 1710: 1706: 1700: 1675: 1671: 1665: 1648: 1644: 1638: 1621: 1617: 1611: 1594: 1590: 1584: 1573:. Retrieved 1548: 1544: 1534: 1505: 1486: 1467: 1442: 1438: 1432: 1422: 1413: 1404: 1385: 1352: 1348: 1342: 1331:. Retrieved 1318: 1280:. Retrieved 1276:the original 1270: 1263: 1236: 1233:Toxicol. Sci 1232: 1222: 1210:. Retrieved 1203: 1194: 1182:. Retrieved 1173: 1149:. Retrieved 1140: 1113: 1104: 1093: 1086: 1050: 1047: 1036: 1017: 990: 986: 983: 971: 958: 940: 925: 896: 888: 880: 876: 864: 853:Chlormethine 852: 851: 777: 773: 748:Diethylamine 740: 668:Legal status 531: 452:CN(CCCl)CCCl 337:RTECS number 109:Identifiers 98: 81:Other names 72: 68: 5859:Neurotoxins 5672:from market 5642:Vorasidenib 5622:Trabectedin 5607:Tiazofurine 5602:Tebentafusp 5587:Tagraxofusp 5550:Plitidepsin 5525:Mitoguazone 5470:Epacadostat 5440:Demecolcine 5384:Aflibercept 5357:Sex steroid 5230:Fuzuloparib 5171:Carfilzomib 5143:Palbociclib 5133:Abemaciclib 5086:Verteporfin 5050:Efaproxiral 4966:Dacarbazine 4928:Altretamine 4910:Satraplatin 4905:Oxaliplatin 4885:Carboplatin 4862:Triaziquone 4833:Mannosulfan 4811:Ranimustine 4791:Fotemustine 4632:Pirarubicin 4617:Doxorubicin 4611:+cytarabine 4597:Aclarubicin 4558:Podophyllum 4483:Camptotheca 4414:Azacitidine 4400:Gemcitabine 4355:Floxuridine 4288:Fludarabine 4283:Clofarabine 4269:Halogenated 4260:Pentostatin 4235:Raltitrexed 4203:Aminopterin 4146:Ixabepilone 4141:Epothilones 4109:Cabazitaxel 4086:Vinorelbine 4071:Vincristine 4066:Vinblastine 4051:microtubule 3894:Veratridine 3869:Shiga toxin 3824:Domoic acid 3687:Thioacetone 3653:Iodoacetone 3517:Pentazocine 3512:Sevoflurane 3477:CAR-302,668 3472:CAR-302,282 3467:CAR-302,196 3462:CAR-301,060 3457:CAR-226,086 3437:Carfentanil 3335:Apomorphine 3256:Green Cross 3047:Domoic acid 2858:Neurotoxins 2778:OPA mixture 2669:Chlorosoman 2664:Chlorosarin 2598:Phospholine 2297:Crotylsarin 2282:Fluorotabun 2254:Chlorosoman 2236:Chlorosarin 1184:5 September 1151:5 September 1089:mustard gas 1069:bone marrow 1009:photophobia 993:lacrimation 963:mustard gas 624:Intravenous 511:Appearance 461:Properties 248:100.000.110 170:CHEBI:28925 5975:Categories 5928:Dibenamine 5637:Verdinexor 5632:Venetoclax 5540:Oblimersen 5535:Navitoclax 5515:Lucanthone 5510:Lonidamine 5505:Lifileucel 5500:Ivosidenib 5495:Imetelstat 5465:Enasidenib 5455:Elesclomol 5420:Bexarotene 5415:Belzutifan 5350:Bexarotene 5338:Atrasentan 5313:Umbralisib 5308:Idelalisib 5298:Copanlisib 5280:Vorinostat 5275:Romidepsin 5265:Entinostat 5260:Belinostat 5218:Masoprocol 5206:Tiazofurin 5194:Anagrelide 5166:Bortezomib 5153:Seliciclib 5148:Ribociclib 5128:inhibitors 5118:Tipifarnib 5081:Temoporfin 5076:Talaporfin 5014:Plicamycin 5009:Mitomycins 4955:Pipobroman 4934:Hydrazines 4900:Nedaplatin 4852:Carboquone 4847:Aziridines 4838:Treosulfan 4786:Carmustine 4773:Uramustine 4742:Ifosfamide 4714:Alkylating 4675:Bisantrene 4664:Pixantrone 4637:Valrubicin 4627:Idarubicin 4622:Epirubicin 4568:Teniposide 4523:Lurtotecan 4518:Irinotecan 4419:Decitabine 4383:Cytarabine 4326:Pyrimidine 4315:Tioguanine 4305:Thiopurine 4294:Nelarabine 4278:Cladribine 4230:Pemetrexed 4213:Pemetrexed 4189:Folic acid 4129:Paclitaxel 4081:Vinflunine 3844:Maitotoxin 3839:Guanitoxin 3819:Ciguatoxin 3814:Brevetoxin 3799:Anatoxin-a 3794:Aflatoxins 3707:Putrescine 3702:Cadaverine 3678:Malodorant 3502:Isoflurane 3487:Desflurane 3482:Benperidol 3427:Psilocybin 3422:PAVA spray 3104:Diphosgene 3057:Pulmonary/ 2985:Picrotoxin 2944:Strychnine 2938:Brevetoxin 2922:Maitotoxin 2905:Guanitoxin 2899:Ciguatoxin 2866:Anatoxin-a 2799:Pinacolone 2632:Precursors 2593:Selenophos 2449:Carbamates 2365:Chinese VX 2271:Cyclosarin 2260:Ethylsarin 2231:Sarin (GB) 2082:Lewisite 3 2076:Lewisite 2 2045:Arsenicals 1624:: 93–102. 1575:2018-10-14 1333:2016-04-20 1118:References 1043:vesication 1020:rhinorrhea 905:anticancer 883:, and (in 499:Molar mass 362:50D9XSG0VR 201:ChemSpider 137:3D model ( 116:CAS Number 64:IUPAC name 5834:Mustamine 5829:Melphalan 5738:Vesicants 5682:Phase III 5670:Withdrawn 5647:Vosaroxin 5627:Veliparib 5582:Sotorasib 5572:Selinexor 5566:Tretinoin 5556:Retinoids 5485:Glasdegib 5430:Celecoxib 5379:Adagrasib 5303:Duvelisib 5293:Alpelisib 5248:Rucaparib 5235:Niraparib 5176:Oprozomib 5138:Alvocidib 5004:Bleomycin 4961:Triazenes 4945:Etoglucid 4890:Cisplatin 4806:Nimustine 4800:Semustine 4796:Lomustine 4758:Melphalan 4685:Menogaril 4680:Crisnatol 4670:Amsacrine 4642:Zorubicin 4602:Amrubicin 4563:Etoposide 4538:Topotecan 4533:Silatecan 4528:Rubitecan 4513:Gimatecan 4498:Cositecan 4488:Belotecan 4164:inhibitor 4134:Tesetaxel 4124:Ortataxel 4119:Larotaxel 4114:Docetaxel 4076:Vindesine 3939:Plutonium 3889:Volkensin 3864:Saxitoxin 3854:Palytoxin 3779:Aconitine 3507:Halothane 3497:Bufotenin 3492:Enflurane 3412:Kolokol-1 3392:Pethidine 3366:Etoxadrol 3351:Etorphine 3347:(CS-4640) 3331:(CS-4030) 3289:glycerine 3236:Salcomine 2995:Tremorine 2933:Aconitine 2916:Palytoxin 2894:Ryanodine 2871:Saxitoxin 2608:Ro 3-0422 2379:GV agents 2242:Thiosarin 1971:Phosphine 1750:Am J Surg 1545:J Med Res 1510:Mustargen 1282:8 October 1110:Chemistry 1032:Pneumonia 1024:epistaxis 974:pethidine 945:analogue 897:Mustargen 657:Excretion 608:Routes of 580:Pregnancy 373:UN number 344:IA1750000 269:200-120-5 261:EC Number 190:ChEMBL427 67:2-Chloro- 5965:Medicine 5530:Mitotane 5475:Eribulin 5243:Olaparib 5181:Ixazomib 4857:Thiotepa 4829:Busulfan 4508:Exatecan 4345:Carmofur 4053:assembly 4016: / 3948:Polonium 3849:Modeccin 3758:Acrolein 3723:Lewisite 3628:Acrolein 3452:CS-27349 3402:Ibogaine 3285:Litharge 3274:Adamsite 3251:Diborane 3241:Fluomine 3221:Ethenone 3116:Acrolein 3083:Fluorine 3077:Phosgene 3067:Chlorine 2467:EA-3887A 2439:C01-A042 2434:C01-A039 2429:C01-A035 2307:V-agents 2217:G-agents 2102:(EA-229) 2070:Lewisite 1929:Cyanogen 1841:20997209 1805:21247779 1770:13947966 1735:17751251 1569:Archived 1565:13947966 1524:Archived 1521:Valchlor 1513:Archived 1495:Archived 1476:Archived 1394:Archived 1377:22909007 1327:Archived 1255:10746948 1212:25 March 1178:Archived 1145:Archived 1137:"Ledaga" 1065:platelet 1039:erythema 967:vesicant 943:estrogen 889:embikhin 596: B3 582:category 549:ATC code 221:DrugBank 4464:S phase 4365:Tegafur 4179:S phase 4104:Taxanes 4040:M phase 3697:Skatole 3692:Allicin 3407:EA-3834 3397:EA-3580 3387:EA-3443 3382:EA-3167 3377:EA-2148 3361:CS-4297 3356:EA-2092 3345:EA-4941 3072:Bromine 2710:EA-1224 2690:EA-1250 2603:R-16661 2578:EA-2613 2573:EA-2098 2568:EA-2054 2563:EA-2012 2532:3152 CT 2522:TL-1317 2517:TL-1299 2512:TL-1238 2482:EA-4056 2477:EA-3990 2472:EA-3966 2462:EA-3887 2360:EA-1763 2320:EA-3148 2315:EA-2192 2292:EA-4352 2287:EA-1356 2021:Stibine 1715:Bibcode 1707:Science 1692:3891698 1369:8085692 1083:History 1077:ageusia 1073:anosmia 1028:dyspnea 909:guanine 877:mustine 834:what is 832: ( 693:: 627:Topical 567: ( 565:L01AA05 563:) 557: ( 555:D08AX04 313:PubChem 230:DB00888 126:51-75-2 92:mustine 18:Mustine 5981:Amines 5951:Portal 5786:TL-995 5781:TL-695 5776:TL-513 5771:TL-512 5766:TL-481 5761:TL-301 5665:WHO-EM 5289:(Pi3K) 4246:Purine 4049:Block 3915:Napalm 3680:agents 3544:agents 3447:JB-336 3442:JB-318 3417:LSD-25 3373:(DMHP) 3321:agents 2980:A-8564 2940:(PbTX) 2890:(TeNT) 2507:TL-599 2497:T-1194 2492:T-1152 2487:T-1123 2256:(ClGD) 2238:(ClGB) 2149:TL-301 1951:Arsine 1839:  1803:  1768:  1733:  1690:  1563:  1459:660515 1457:  1375:  1367:  1253:  1001:miosis 829:verify 826:  695:℞-only 681: 504:156.05 445:SMILES 181:ChEMBL 99:Ledaga 58:Names 5938:SY-28 5921:Other 5897:DSP-4 5201:IMPDI 5096:Other 3903:Other 3859:Ricin 3774:Abrin 3733:KB-16 3020:IPTBO 2951:(ATX) 2924:(MTX) 2918:(PTX) 2907:(GTX) 2901:(CTX) 2884:(BTX) 2740:Nital 2546:Other 2424:A-262 2419:A-242 2414:A-234 2409:A-232 2404:A-208 2248:Soman 2244:(SGB) 2225:Tabun 2184:KB-16 2177:Other 1373:S2CID 1323:(CDC) 1319:U.S. 1005:edema 537:0.91 420:InChI 377:2810 287:D0767 161:ChEBI 139:JSmol 5892:DMEA 5287:PIKI 5255:HDAC 4704:CCNS 3941:and 3559:(OC) 3276:(DM) 3106:(DP) 3095:(PS) 3079:(CG) 3030:TBPS 3025:TBPO 2873:(TZ) 2795:(TH) 2764:(DF) 2758:(SW) 2752:(TB) 2725:DMHP 2705:DEHP 2695:DIHP 2686:(KB) 2623:MSPI 2273:(GF) 2262:(GE) 2250:(GD) 2227:(GA) 2169:(CX) 2116:CEES 2084:(L3) 2078:(L2) 2066:(PD) 2060:(MD) 2054:(ED) 1947:(AC) 1941:(CK) 1855:link 1837:PMID 1821:JAMA 1801:PMID 1766:PMID 1731:PMID 1688:PMID 1561:PMID 1519:and 1455:PMID 1365:PMID 1284:2023 1251:PMID 1214:2024 1186:2021 1153:2021 1096:OSRD 1063:and 937:Uses 869:USAN 530:log 520:Odor 353:UNII 326:4033 298:MeSH 278:KEGG 210:3893 95:HN-2 5756:HN3 5751:HN2 5746:HN1 5333:ERA 5189:PhI 5160:PrI 5125:CDK 5037:PDT 4035:MIs 4031:SPs 4022:L01 3583:CNS 3112:(Z) 2654:AlP 2649:ATO 2144:HN3 2139:HN2 2134:HN1 2072:(L) 1829:doi 1825:132 1793:doi 1789:212 1758:doi 1754:105 1723:doi 1711:103 1680:doi 1653:doi 1626:doi 1599:doi 1553:doi 1447:doi 1357:doi 1353:121 1241:doi 1100:HN3 959:HN2 881:HN2 875:), 873:USP 861:BAN 857:INN 570:WHO 560:WHO 389:EPA 316:CID 5977:: 5678:: 5213:LI 5113:FI 4579:II 4549:II 4371:)) 3728:CX 3578:CR 3573:CS 3568:CN 3329:BZ 2844:TG 2839:TC 2814:QL 2700:ZS 2644:AT 2355:VX 2350:VS 2345:VR 2340:VP 2335:VM 2330:VG 2325:VE 2277:GP 2266:GH 1851:}} 1847:{{ 1835:. 1823:. 1799:. 1787:. 1764:. 1752:. 1729:. 1721:. 1709:. 1686:. 1676:11 1674:. 1649:40 1647:. 1620:. 1595:57 1593:. 1567:. 1559:. 1549:40 1547:. 1543:. 1453:. 1443:67 1441:. 1371:. 1363:. 1351:. 1325:. 1317:. 1292:^ 1249:. 1237:54 1235:. 1231:. 1202:. 1172:. 1161:^ 1139:. 1126:^ 1055:. 933:. 923:. 887:) 879:, 871:, 859:, 701:EU 690:CA 683:S4 677:AU 638:: 592:AU 573:) 486:Cl 483:11 5953:: 5722:e 5715:t 5708:v 5568:) 5559:( 5406:) 5402:/ 5398:( 5364:) 5360:( 5352:) 5348:( 5340:) 5336:( 5315:) 5291:( 5282:) 5258:( 5250:) 5228:( 5220:) 5216:( 5208:) 5204:( 5196:) 5192:( 5155:) 5131:( 5120:) 5116:( 5088:) 5069:( 5035:/ 5016:) 4997:( 4978:) 4964:( 4941:) 4937:( 4849:: 4840:) 4831:( 4826:: 4802:) 4798:( 4783:: 4764:) 4760:( 4749:) 4740:( 4725:: 4706:) 4702:( 4666:) 4652:( 4644:) 4613:) 4609:( 4595:( 4581:+ 4570:) 4561:( 4540:) 4486:( 4474:I 4466:) 4462:( 4446:) 4442:( 4421:) 4412:( 4402:) 4398:( 4388:) 4381:( 4367:( 4338:( 4317:) 4308:( 4290:) 4276:( 4271:/ 4262:) 4258:( 4237:) 4228:( 4220:) 4201:( 4181:) 4177:( 4148:) 4144:( 4136:) 4107:( 4088:) 4064:( 4042:) 4038:( 4033:/ 4024:) 4020:( 4005:e 3998:t 3991:v 3287:- 2111:Q 2106:T 1888:e 1881:t 1874:v 1857:) 1843:. 1831:: 1807:. 1795:: 1772:. 1760:: 1737:. 1725:: 1717:: 1694:. 1682:: 1659:. 1655:: 1632:. 1628:: 1622:7 1605:. 1601:: 1578:. 1555:: 1461:. 1449:: 1379:. 1359:: 1336:. 1286:. 1257:. 1243:: 1216:. 1188:. 1155:. 867:( 855:( 824:N 778:N 776:, 774:N 741:N 703:: 679:: 594:: 532:P 492:N 489:2 480:H 477:5 474:C 391:) 387:( 141:) 73:N 69:N 31:. 20:)

Index

Mustine
Chloromethane
Skeletal formula of chlormethine
Space-filling model of the chlormethine molecule
IUPAC name
CAS Number
51-75-2
JSmol
Interactive image
ChEBI
CHEBI:28925
ChEMBL
ChEMBL427
ChemSpider
3893
DrugBank
DB00888
ECHA InfoCard
100.000.110
Edit this at Wikidata
EC Number
KEGG
D0767
MeSH
Mechlorethamine
PubChem
4033
RTECS number
UNII
50D9XSG0VR

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