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Chlormethine

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1080:(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. 40: 394: 241: 958:. 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. 31: 1087:). 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 5949: 809: 977:
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
1019:(in smokers and asthmatics). Later symptoms include pain in the nose/sinuses and inflammation of the airway. In severe cases, there may be epithelial necrosis throughout the respiratory tract, causing pseudomembrane formation, which can obstruct the airway. 1807:
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 (
1068:(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. 671: 1034:(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. 5900: 1397:
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.
1218:"Protection from cytotoxic effects induced by the nitrogen mustard mechlorethamine on human bronchial epithelial cells in vitro" 1103:
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)".
1530:"The blood and bone marrow in yellow cross gas (mustard gas) poisoning: changes produced in the bone marrow of fatal cases" 5979: 5275: 3087: 909: 1426:
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
1084: 508: 266: 1425: 1335: 1015:(nosebleed), toneless voice, sneezing, barking cough, and 3405: 2958: 1076:
The effect of vesicant (blister) agents in the form of
1257:"Chapter 3: Principles of Oncologic Pharmacotherapy". 1091:(tris(2-chloroethyl)amine) on a patient known as J.D. 5937: 1604: 1120: 1118: 1116: 1048:counts drop, increasing the risk of infection, and 996:(swelling from fluid accumulation) in the eyelids, 961:Another use of chlormethine is in the synthesis of 1607:Collection of Czechoslovak Chemical Communications 1527: 1113: 5961: 1378:Medline (2012). Mechlorethamine. Retrieved from 313: 1260:Cancer Management: A Multidisciplinary Approach 113: 1736: 417:InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3 5703: 3986: 1869: 1771: 1153: 1151: 1000:(extreme sensitivity to light), severe pain, 1842:: CS1 maint: multiple names: authors list ( 1631: 968: 904:, its use is strongly restricted within the 1774:Journal of the American College of Surgeons 1658: 1209: 992:(pinpoint pupils). More severe cases cause 697:In general: ℞ (Prescription only) 5710: 5696: 3993: 3979: 1876: 1862: 1577: 1310:Centers for Disease Control and Prevention 1148: 392: 239: 197: 1233: 349: 1462:https://www.drugs.com/pro/mustargen.html 915:Mechlorethamine belongs to the group of 1350:10.7326/0003-4819-121-8-199410150-00007 388: 291: 217: 5962: 2757:Methylphosphonyl dichloride (dichloro) 2751:Methylphosphonyl difluoride (difluoro) 1130:Therapeutic Goods Administration (TGA) 950:. This chemical is a form of nitrogen 689: 230: 5717: 5691: 3974: 2999:Tetramethylenedisulfotetramine (TETS) 1857: 1634:Journal of Pathology and Bacteriology 1169:from the original on 5 September 2021 1136:from the original on 5 September 2021 888:among others. It is the prototype of 420:Key: HAWPXGHAZFHHAD-UHFFFAOYSA-N 177: 157: 1298: 1296: 1294: 1292: 1290: 1288: 1286: 1284: 1282: 557: 547: 4262:ribonucleotide reductase inhibitors 3088:Dimethyl(trifluoromethylthio)arsine 1528:Krumbhaar EB, Krumbhaar HD (1919). 304: 274: 13: 4428:Ribonucleotide reductase inhibitor 4384:Ribonucleotide reductase inhibitor 2704:Dimethylamidophosphoric dichloride 1428:Journal of Pharmaceutical Sciences 14: 6001: 4187:Dihydrofolate reductase inhibitor 2719:Ethylphosphonoselenoic dichloride 2709:Dimethylamidophosphoric dicyanide 1786:10.1016/j.jamcollsurg.2010.10.018 1279: 930:It has been derivatized into the 665: 580: 5947: 2547:Dicyclohexyl phosphorofluoridate 1990:2,3,7,8-Tetrachlorodibenzodioxin 1822:10.1001/jama.1946.02870400011003 1095:wartime secrecy ended, in 1946. 807: 480: 474: 468: 38: 29: 3955:List of chemical warfare agents 2178:Dibutylchloromethyltin chloride 1800: 1765: 1730: 1687: 1652: 1625: 1598: 1571: 1560:from the original on 2020-02-10 1521: 1492: 1473: 1454: 1419: 1409: 1400: 1318:from the original on 2019-06-28 803:(at 25 °C , 100 kPa). 75:Bis(2-chloroethyl)(methyl)amine 4324:Thymidylate synthase inhibitor 4214:Thymidylate synthase inhibitor 1391: 1372: 1329: 1250: 1181: 678: 462: 1: 5901:Propylbenzilylcholine mustard 4244:Adenosine deaminase inhibitor 4085:Block microtubule disassembly 1106: 1023:may develop and prove fatal. 3031:Trimethylolpropane phosphite 2577:Neopentylene fluorophosphate 1751:10.1016/0002-9610(63)90232-0 1716:10.1126/science.103.2675.409 1673:10.1016/0360-3016(85)90254-8 1661:Int J Radiat Oncol Biol Phys 1546:10.1016/0002-9610(63)90232-0 1098: 1056:counts may also drop due to 1026:Skin exposure mainly causes 988:(spasms of the eyelid), and 908:where it is classified as a 7: 2813:3,3,5-Trimethylcyclohexanol 2673:N,N-Diisopropylaminoethanol 2542:Diisopropyl fluorophosphate 1338:Annals of Internal Medicine 946:where it has the code-name 906:Chemical Weapons Convention 10: 6006: 5980:Nitrogen mustard vesicants 5861:Acetylethylcholine mustard 3652:Hexamethylene diisocyanate 3120:Phenylcarbylamine chloride 2446:Dimethylcarbamoyl fluoride 1071: 884:sold under the brand name 15: 5909: 5846: 5783: 5725: 5648: 5534:Omacetaxine mepesuccinate 5424:Ciltacabtagene autoleucel 5414:Brexucabtagene autoleucel 5360: 5311: 5091: 5084: 5020: 4974: 4907: 4864: 4701: 4686: 4566: 4536: 4461: 4446: 4417: 4313: 4233: 4176: 4159: 4148: 4084: 4037: 4018: 3950: 3910:Fluoroethyl fluoroacetate 3891: 3755: 3704: 3665: 3529: 3306: 3253: 3115:Perchloromethyl mercaptan 3044: 2845: 2620: 2534: 2526:4-686-293-01 (Agent 1-10) 2436: 2383: 2367: 2294: 2204: 2195: 2165: 2146: 2113: 2079: 2032: 2023: 1908: 1163:European Medicines Agency 969:Side effects and toxicity 942:. It can also be used in 797: 704: 623: 530: 449: 429: 404: 97: 69: 51: 46: 37: 28: 5828:Phenylenediamine mustard 5581:Talimogene laherparepvec 4448:Topoisomerase inhibitors 4367:DNA polymerase inhibitor 3627:Chloroacetophenone oxime 3612:Bromomethyl ethyl ketone 3220:Trifluoroacetyl chloride 3130:Tetrachlorodinitroethane 2777:Phosphorus pentachloride 2602:Methanesulfonyl fluoride 752:Dimethylaminopropylamine 16:Not to be confused with 5866:Benzilylcholine mustard 5399:Axicabtagene ciloleucel 4003:chemotherapeutic agents 3906:(variants and mixtures) 3175:Trichloronitrosomethane 3170:Trifluoronitrosomethane 2745:Methyldichlorophosphine 1646:10.1002/path.1700400312 1235:10.1093/toxsci/54.1.212 925: 900:. As the chemical is a 779:Tris(2-aminoethyl)amine 5566:Sitimagene ceradenovec 5479:Idecabtagene vicleucel 5044:Methyl aminolevulinate 3705:Cornea-clouding agents 3200:Phosphorus trichloride 2782:Phosphorus trichloride 2516:Miotine (AR-28/T-1843) 1970:Phosphorus trifluoride 1440:10.1002/jps.2600670723 1263:. 2010. Archived from 1064:(inability to smell), 936:estramustine phosphate 789:HN3 (nitrogen mustard) 784:HN1 (nitrogen mustard) 769:-Diisopropylethylamine 5985:Chloroethyl compounds 5896:Hemicholinium mustard 5876:Decamethonium mustard 5856:Acetylcholine mustard 5785:Antineoplastic agents 5055:Porphyrin derivatives 4751:Melphalan flufenamide 4398:Hypomethylating agent 4007:antineoplastic agents 3099:Disulfur decafluoride 2900:Chlorophenylsilatrane 2808:2,4,5-Trichlorophenol 1165:. 17 September 2018. 732:-Nitrosodimethylamine 5891:Ethylcholine mustard 5384:Asparagine depleters 5313:Receptor antagonists 5227:+abiraterone acetate 3899:Methyl fluoroacetate 3727:Methyl cyanoacrylate 3647:Allyl isothiocyanate 3235:Uranium hexafluoride 3190:Dinitrogen tetroxide 3135:Chlorine trifluoride 2183:Selenium oxychloride 2053:Phenyldichloroarsine 2047:Methyldichloroarsine 1985:Nickel tetracarbonyl 1619:10.1135/cccc19350093 910:Schedule 1 substance 634:Biological half-life 5434:Denileukin diftitox 5334:Retinoid X receptor 5034:Aminolevulinic acid 4856:Triethylenemelamine 4688:Crosslinking of DNA 4419:Deoxyribonucleotide 4358:+gimeracil/oteracil 3592:Bromobenzyl cyanide 3360:Dimethylheptylpyran 3288:Diphenylcyanoarsine 3283:Diphenylchlorarsine 3215:Methyl vinyl ketone 3140:Perchloryl fluoride 3004:Bicyclic phosphates 2823:Trimethyl phosphite 2772:Phosphoryl chloride 2041:Ethyldichloroarsine 2015:Chloral cyanohydrin 2005:Acetone cyanohydrin 1975:Methyl cyanoformate 1708:1946Sci...103..409G 1592:10.1021/ja01308a041 674:(Prescription only) 495: g·mol 25: 5833:Quinacrine mustard 5675:Never to phase III 4492:Etirinotecan pegol 3960:CB military symbol 3818:Enterotoxin type B 3773:Cyclopiazonic acid 3732:N-Methylmorpholine 3632:Ethyl bromoacetate 3110:Ethyl bromoacetate 3077:Perfluoroisobutene 2818:Triethyl phosphite 2089:Levinstein mustard 1980:Iron pentacarbonyl 1515:2021-03-28 at the 1504:2018-09-20 at the 1486:2021-03-28 at the 1467:2018-09-20 at the 1385:2016-07-05 at the 1002:corneal ulceration 874:post-Soviet states 830:Infobox references 757:Diethylenetriamine 705:Related compounds 513:Fishy, ammoniacal 23: 5935: 5934: 5719:Nitrogen mustards 5685: 5684: 5644: 5643: 5601:Tigilanol tiglate 5093:Enzyme inhibitors 5016: 5015: 5012: 5011: 4712:Nitrogen mustards 4682: 4681: 4442: 4441: 4144: 4143: 3968: 3967: 3778:Histrionicotoxins 3756:Biological toxins 3637:Ethyl iodoacetate 3205:Methyl isocyanate 3165:Selenoyl fluoride 3155:Mercuric chloride 3125:Tetranitromethane 2979:Sulfuryl fluoride 2964:HN3 hydrochloride 2959:HN2 hydrochloride 2954:HN1 hydrochloride 2841: 2840: 2798:Phenacyl chloride 2793:Pinacolyl alcohol 2739:Isopropyl alcohol 2734:4-Hydroxycoumarin 2668:1,8-Dibromooctane 2191: 2190: 2115:Nitrogen mustards 1928:Cyanogen chloride 1816:(2675): 263–271. 1702:(2675): 409–436. 1004:, and blindness. 920:alkylating agents 890:alkylating agents 852:), also known as 838:Chemical compound 836: 835: 774:Triisopropylamine 693: 681: 669: 584: 503:Colorless liquid 373:CompTox Dashboard 139:Interactive image 64:-methylethanamine 60:-(2-chloroethyl)- 5997: 5952: 5951: 5950: 5943: 5922:Phenoxybenzamine 5808:Cyclophosphamide 5712: 5705: 5698: 5689: 5688: 5606:Tisagenlecleucel 5378:Arsenic trioxide 5089: 5088: 5022:Photosensitizers 4813:Alkyl sulfonates 4727:Cyclophosphamide 4699: 4698: 4638:Anthracenediones 4459: 4458: 4433:Hydroxycarbamide 4174: 4173: 4157: 4156: 4035: 4034: 3995: 3988: 3981: 3972: 3971: 3942:White phosphorus 3919:post-combustion 3915:Depleted uranium 3742:Osmium tetroxide 3622:Phenacyl bromide 3185:Nitrogen dioxide 3160:Selenium dioxide 3150:Cadmium chloride 2607:Dimefox (TL-792) 2202: 2201: 2030: 2029: 1955:Hydrogen sulfide 1934:Hydrogen cyanide 1923:Cyanogen bromide 1889:chemical warfare 1878: 1871: 1864: 1855: 1854: 1848: 1847: 1841: 1833: 1804: 1798: 1797: 1769: 1763: 1762: 1734: 1728: 1727: 1691: 1685: 1684: 1667:(7): 1375–1378. 1656: 1650: 1649: 1629: 1623: 1622: 1602: 1596: 1595: 1580:J. Am. Chem. Soc 1575: 1569: 1568: 1566: 1565: 1525: 1519: 1496: 1490: 1477: 1471: 1458: 1452: 1451: 1423: 1417: 1413: 1407: 1404: 1398: 1395: 1389: 1376: 1370: 1369: 1333: 1327: 1326: 1324: 1323: 1300: 1277: 1276: 1274: 1272: 1254: 1248: 1247: 1237: 1213: 1207: 1206: 1204: 1202: 1185: 1179: 1178: 1176: 1174: 1155: 1146: 1145: 1143: 1141: 1132:. 30 June 2021. 1122: 1046:White blood cell 944:chemical warfare 938:, used to treat 917:nitrogen mustard 882:nitrogen mustard 880:(эмбихин), is a 820: 814: 811: 810: 747:Diisopropylamine 691: 688: 680: 677: 667: 664: 625:Pharmacokinetics 610:Intrapericardial 582: 579: 561: 551: 494: 482: 476: 470: 464: 457:Chemical formula 397: 396: 381: 379: 353: 317: 306: 295: 278: 251: 243: 232: 221: 201: 181: 161: 141: 117: 42: 33: 26: 22: 6005: 6004: 6000: 5999: 5998: 5996: 5995: 5994: 5975:Organochlorides 5960: 5959: 5958: 5948: 5946: 5938: 5936: 5931: 5905: 5871:Choline mustard 5842: 5793:Aniline mustard 5779: 5721: 5716: 5686: 5681: 5680: 5665:Clinical trials 5640: 5361:Other/ungrouped 5356: 5307: 5080: 5060:Porfimer sodium 5008: 4970: 4903: 4860: 4690: 4678: 4562: 4532: 4450: 4438: 4413: 4309: 4229: 4165: 4163:antimetabolites 4161: 4160:DNA precursors/ 4152: 4150:DNA replication 4140: 4080: 4050:Vinca alkaloids 4026: 4014: 3999: 3969: 3964: 3946: 3887: 3798:Botulinum toxin 3751: 3700: 3661: 3577:Benzyl chloride 3532: 3525: 3309: 3302: 3293:Cacodyl cyanide 3255:Vomiting agents 3249: 3047: 3040: 2949:Dimethylmercury 2871:Botulinum toxin 2837: 2616: 2530: 2432: 2385:Novichok agents 2379: 2363: 2290: 2187: 2161: 2142: 2109: 2081:Sulfur mustards 2075: 2019: 1965:Carbon monoxide 1945:Cacodyl cyanide 1904: 1903: 1887:Agents used in 1882: 1852: 1851: 1835: 1834: 1805: 1801: 1770: 1766: 1735: 1731: 1692: 1688: 1657: 1653: 1630: 1626: 1603: 1599: 1576: 1572: 1563: 1561: 1526: 1522: 1517:Wayback Machine 1506:Wayback Machine 1497: 1493: 1488:Wayback Machine 1478: 1474: 1469:Wayback Machine 1459: 1455: 1424: 1420: 1414: 1410: 1405: 1401: 1396: 1392: 1387:Wayback Machine 1377: 1373: 1334: 1330: 1321: 1319: 1302: 1301: 1280: 1270: 1268: 1256: 1255: 1251: 1214: 1210: 1200: 1198: 1197:. 3 August 2022 1187: 1186: 1182: 1172: 1170: 1157: 1156: 1149: 1139: 1137: 1124: 1123: 1114: 1109: 1101: 1074: 971: 954:and a powerful 940:prostate cancer 928: 854:mechlorethamine 839: 832: 827: 826: 825:  ?) 816: 812: 808: 804: 793: 712: 700: 648: 636: 619: 601: 598: 590: 573: 570: 540: 492: 479: 473: 467: 459: 445: 442: 437: 436: 425: 422: 421: 418: 412: 411: 400: 382: 375: 356: 336: 320: 307: 293:Mechlorethamine 281: 261: 224: 204: 184: 164: 144: 131: 120: 107: 93: 92: 78:mechlorethamine 65: 21: 12: 11: 5: 6003: 5993: 5992: 5987: 5982: 5977: 5972: 5957: 5956: 5933: 5932: 5930: 5929: 5924: 5919: 5913: 5911: 5907: 5906: 5904: 5903: 5898: 5893: 5888: 5883: 5878: 5873: 5868: 5863: 5858: 5852: 5850: 5844: 5843: 5841: 5840: 5835: 5830: 5825: 5820: 5815: 5810: 5805: 5800: 5795: 5789: 5787: 5781: 5780: 5778: 5777: 5772: 5767: 5762: 5757: 5752: 5747: 5742: 5737: 5731: 5729: 5723: 5722: 5715: 5714: 5707: 5700: 5692: 5683: 5682: 5679: 5678: 5677: 5676: 5673: 5662: 5656: 5650: 5649: 5646: 5645: 5642: 5641: 5639: 5638: 5633: 5628: 5623: 5618: 5613: 5608: 5603: 5598: 5593: 5588: 5583: 5578: 5573: 5568: 5563: 5558: 5552: 5541: 5536: 5531: 5526: 5521: 5516: 5511: 5506: 5501: 5496: 5491: 5486: 5481: 5476: 5471: 5466: 5461: 5456: 5451: 5446: 5441: 5436: 5431: 5426: 5421: 5416: 5411: 5406: 5401: 5396: 5380: 5375: 5370: 5364: 5362: 5358: 5357: 5355: 5354: 5342: 5330: 5317: 5315: 5309: 5308: 5306: 5305: 5299: 5294: 5289: 5284: 5272: 5266: 5261: 5256: 5251: 5240: 5234: 5229: 5221: 5214:PARP inhibitor 5210: 5198: 5186: 5174: 5173: 5172: 5167: 5162: 5157: 5145: 5139: 5134: 5129: 5124: 5110: 5097: 5095: 5086: 5082: 5081: 5079: 5078: 5072: 5067: 5062: 5051: 5046: 5041: 5036: 5030: 5028: 5018: 5017: 5014: 5013: 5010: 5009: 5007: 5006: 5000: 4995: 4990: 4980: 4978: 4972: 4971: 4969: 4968: 4962: 4957: 4946: 4941: 4936: 4931: 4919: 4913: 4911: 4905: 4904: 4902: 4901: 4896: 4891: 4886: 4881: 4876: 4870: 4868: 4866:Platinum-based 4862: 4861: 4859: 4858: 4853: 4848: 4843: 4831: 4830: 4824: 4808: 4807: 4802: 4797: 4792: 4782: 4777: 4765: 4764: 4759: 4754: 4744: 4739: 4733: 4724: 4719: 4707: 4705: 4696: 4684: 4683: 4680: 4679: 4677: 4676: 4671: 4666: 4661: 4656: 4650: 4645: 4634: 4628: 4623: 4618: 4613: 4608: 4603: 4593: 4588: 4581:Anthracyclines 4576: 4574: 4564: 4563: 4561: 4560: 4554: 4542: 4540: 4534: 4533: 4531: 4530: 4524: 4519: 4514: 4509: 4504: 4499: 4494: 4489: 4484: 4479: 4467: 4465: 4456: 4444: 4443: 4440: 4439: 4437: 4436: 4423: 4421: 4415: 4414: 4412: 4411: 4405: 4393: 4392: 4379: 4378: 4362: 4361: 4351: 4346: 4341: 4336: 4331: 4319: 4317: 4311: 4310: 4308: 4307: 4301: 4299:Mercaptopurine 4290: 4285: 4280: 4274: 4269: 4253: 4252: 4239: 4237: 4231: 4230: 4228: 4227: 4221: 4210: 4204: 4199: 4194: 4182: 4180: 4171: 4154: 4146: 4145: 4142: 4141: 4139: 4138: 4126: 4120: 4115: 4110: 4105: 4100: 4088: 4086: 4082: 4081: 4079: 4078: 4072: 4067: 4062: 4057: 4045: 4043: 4032: 4016: 4015: 4001:Intracellular 3998: 3997: 3990: 3983: 3975: 3966: 3965: 3963: 3962: 3957: 3951: 3948: 3947: 3945: 3944: 3939: 3934: 3925: 3924: 3923: 3921:uranium oxides 3912: 3907: 3901: 3895: 3893: 3889: 3888: 3886: 3885: 3880: 3875: 3870: 3865: 3860: 3855: 3850: 3845: 3840: 3835: 3830: 3825: 3820: 3815: 3810: 3805: 3800: 3795: 3790: 3785: 3780: 3775: 3770: 3765: 3759: 3757: 3753: 3752: 3750: 3749: 3744: 3739: 3734: 3729: 3724: 3719: 3714: 3708: 3706: 3702: 3701: 3699: 3698: 3693: 3688: 3683: 3678: 3672: 3670: 3663: 3662: 3660: 3659: 3657:Crotonaldehyde 3654: 3649: 3644: 3639: 3634: 3629: 3624: 3619: 3614: 3609: 3604: 3599: 3594: 3589: 3584: 3582:Benzyl bromide 3579: 3574: 3569: 3564: 3559: 3554: 3549: 3543: 3537: 3535: 3527: 3526: 3524: 3523: 3521:Chlorpromazine 3518: 3513: 3508: 3503: 3498: 3493: 3488: 3483: 3478: 3473: 3468: 3463: 3458: 3453: 3448: 3443: 3438: 3433: 3428: 3423: 3418: 3413: 3408: 3403: 3398: 3393: 3388: 3383: 3378: 3373: 3368: 3363: 3357: 3352: 3347: 3342: 3337: 3331: 3326: 3321: 3314: 3312: 3308:Incapacitating 3304: 3303: 3301: 3300: 3295: 3290: 3285: 3280: 3271: 3266: 3259: 3257: 3251: 3250: 3248: 3247: 3242: 3237: 3232: 3227: 3222: 3217: 3212: 3207: 3202: 3197: 3195:Sulfur dioxide 3192: 3187: 3182: 3177: 3172: 3167: 3162: 3157: 3152: 3147: 3142: 3137: 3132: 3127: 3122: 3117: 3112: 3107: 3102: 3096: 3090: 3085: 3079: 3074: 3069: 3063: 3058: 3052: 3050: 3048:choking agents 3042: 3041: 3039: 3038: 3033: 3028: 3023: 3022: 3021: 3016: 3011: 3001: 2996: 2991: 2986: 2981: 2976: 2971: 2966: 2961: 2956: 2951: 2946: 2944:Tetraethyllead 2941: 2935: 2930: 2924: 2919: 2914: 2908: 2902: 2897: 2891: 2885: 2880: 2874: 2868: 2863: 2857: 2851: 2849: 2843: 2842: 2839: 2838: 2836: 2835: 2830: 2825: 2820: 2815: 2810: 2805: 2800: 2795: 2790: 2785: 2779: 2774: 2769: 2764: 2759: 2754: 2748: 2742: 2736: 2731: 2726: 2721: 2716: 2711: 2706: 2701: 2696: 2691: 2686: 2681: 2676: 2670: 2665: 2660: 2655: 2650: 2648:A.P.C. complex 2645: 2640: 2635: 2630: 2624: 2622: 2618: 2617: 2615: 2614: 2609: 2604: 2599: 2594: 2589: 2584: 2579: 2574: 2569: 2564: 2559: 2554: 2549: 2544: 2538: 2536: 2532: 2531: 2529: 2528: 2523: 2518: 2513: 2508: 2503: 2498: 2493: 2488: 2483: 2478: 2473: 2468: 2463: 2458: 2453: 2448: 2442: 2440: 2434: 2433: 2431: 2430: 2425: 2420: 2415: 2410: 2405: 2400: 2395: 2389: 2387: 2381: 2380: 2378: 2377: 2371: 2369: 2365: 2364: 2362: 2361: 2359:V-sub x (GD-7) 2356: 2351: 2346: 2341: 2336: 2331: 2326: 2321: 2316: 2311: 2306: 2300: 2298: 2292: 2291: 2289: 2288: 2283: 2278: 2273: 2268: 2263: 2257: 2252: 2246: 2240: 2234: 2228: 2222: 2217: 2210: 2208: 2199: 2193: 2192: 2189: 2188: 2186: 2185: 2180: 2175: 2169: 2167: 2163: 2162: 2160: 2159: 2156:Phosgene oxime 2152: 2150: 2144: 2143: 2141: 2140: 2135: 2130: 2125: 2119: 2117: 2111: 2110: 2108: 2107: 2102: 2097: 2092: 2085: 2083: 2077: 2076: 2074: 2068: 2062: 2056: 2050: 2044: 2038: 2036: 2027: 2025:Blister agents 2021: 2020: 2018: 2017: 2012: 2007: 2002: 1997: 1995:Glycolonitrile 1992: 1987: 1982: 1977: 1972: 1967: 1962: 1957: 1952: 1947: 1942: 1937: 1931: 1925: 1920: 1914: 1912: 1906: 1905: 1902: 1901: 1896: 1894:incapacitation 1891: 1884: 1881: 1880: 1873: 1866: 1858: 1850: 1849: 1799: 1780:(3): 413–417. 1764: 1745:(5): 574–578. 1729: 1686: 1651: 1640:(3): 549–558. 1624: 1597: 1586:(5): 914–916. 1570: 1540:(5): 497–508. 1520: 1491: 1472: 1453: 1434:(7): 958–961. 1418: 1408: 1399: 1390: 1371: 1344:(8): 592–602. 1328: 1278: 1267:on 15 May 2009 1249: 1208: 1180: 1147: 1111: 1110: 1108: 1105: 1100: 1097: 1073: 1070: 1050:red blood cell 1030:(redness) and 1011:(runny nose), 970: 967: 965:(meperidine). 927: 924: 837: 834: 833: 828: 806: 805: 801:standard state 798: 795: 794: 792: 791: 786: 781: 776: 771: 759: 754: 749: 744: 739: 734: 726: 724:Trimethylamine 721: 715: 713: 711:Related amines 710: 707: 706: 702: 701: 699: 698: 695: 686: 675: 661: 659: 653: 652: 649: 644: 641: 640: 637: 632: 629: 628: 621: 620: 618: 617: 614: 611: 608: 604: 602: 599:administration 595: 592: 591: 589: 588: 586: 576: 574: 567: 564: 563: 541: 536: 533: 532: 528: 527: 524: 515: 514: 511: 505: 504: 501: 497: 496: 490: 484: 483: 477: 471: 465: 460: 455: 452: 451: 447: 446: 444: 443: 440: 432: 431: 430: 427: 426: 424: 423: 419: 416: 415: 407: 406: 405: 402: 401: 399: 398: 385: 383: 371: 368: 367: 364: 358: 357: 355: 354: 346: 344: 338: 337: 335: 334: 330: 328: 322: 321: 319: 318: 310: 308: 300: 297: 296: 289: 283: 282: 280: 279: 271: 269: 263: 262: 260: 259: 255: 253: 245: 244: 234: 226: 225: 223: 222: 214: 212: 206: 205: 203: 202: 194: 192: 186: 185: 183: 182: 174: 172: 166: 165: 163: 162: 154: 152: 146: 145: 143: 142: 134: 132: 125: 122: 121: 119: 118: 110: 108: 103: 100: 99: 95: 94: 91: 90: 85: 82: 79: 76: 72: 71: 67: 66: 55: 49: 48: 44: 43: 35: 34: 9: 6: 4: 3: 2: 6002: 5991: 5988: 5986: 5983: 5981: 5978: 5976: 5973: 5971: 5968: 5967: 5965: 5955: 5945: 5944: 5941: 5928: 5925: 5923: 5920: 5918: 5915: 5914: 5912: 5908: 5902: 5899: 5897: 5894: 5892: 5889: 5887: 5884: 5882: 5879: 5877: 5874: 5872: 5869: 5867: 5864: 5862: 5859: 5857: 5854: 5853: 5851: 5849: 5845: 5839: 5836: 5834: 5831: 5829: 5826: 5824: 5821: 5819: 5816: 5814: 5811: 5809: 5806: 5804: 5801: 5799: 5796: 5794: 5791: 5790: 5788: 5786: 5782: 5776: 5773: 5771: 5768: 5766: 5763: 5761: 5758: 5756: 5753: 5751: 5748: 5746: 5743: 5741: 5738: 5736: 5733: 5732: 5730: 5728: 5724: 5720: 5713: 5708: 5706: 5701: 5699: 5694: 5693: 5690: 5674: 5672: 5669: 5668: 5666: 5663: 5660: 5657: 5655: 5652: 5651: 5647: 5637: 5634: 5632: 5629: 5627: 5624: 5622: 5619: 5617: 5614: 5612: 5609: 5607: 5604: 5602: 5599: 5597: 5594: 5592: 5589: 5587: 5584: 5582: 5579: 5577: 5574: 5572: 5569: 5567: 5564: 5562: 5559: 5556: 5553: 5551: 5547: 5546: 5542: 5540: 5537: 5535: 5532: 5530: 5527: 5525: 5522: 5520: 5517: 5515: 5512: 5510: 5509:Lurbinectedin 5507: 5505: 5502: 5500: 5497: 5495: 5492: 5490: 5487: 5485: 5482: 5480: 5477: 5475: 5472: 5470: 5467: 5465: 5462: 5460: 5457: 5455: 5452: 5450: 5447: 5445: 5442: 5440: 5437: 5435: 5432: 5430: 5427: 5425: 5422: 5420: 5417: 5415: 5412: 5410: 5407: 5405: 5402: 5400: 5397: 5394: 5390: 5386: 5385: 5381: 5379: 5376: 5374: 5371: 5369: 5366: 5365: 5363: 5359: 5352: 5348: 5347: 5343: 5340: 5336: 5335: 5331: 5328: 5324: 5323: 5319: 5318: 5316: 5314: 5310: 5303: 5300: 5298: 5295: 5293: 5290: 5288: 5285: 5283: 5279: 5277: 5273: 5270: 5267: 5265: 5262: 5260: 5257: 5255: 5252: 5250: 5246: 5245: 5241: 5238: 5235: 5233: 5230: 5228: 5225: 5222: 5220: 5216: 5215: 5211: 5208: 5204: 5203: 5199: 5196: 5192: 5191: 5187: 5184: 5180: 5179: 5175: 5171: 5168: 5166: 5163: 5161: 5158: 5156: 5153: 5152: 5151: 5150: 5146: 5143: 5140: 5138: 5135: 5133: 5130: 5128: 5125: 5123: 5119: 5118: 5115: 5111: 5108: 5104: 5103: 5099: 5098: 5096: 5094: 5090: 5087: 5083: 5076: 5073: 5071: 5068: 5066: 5063: 5061: 5057: 5056: 5052: 5050: 5047: 5045: 5042: 5040: 5037: 5035: 5032: 5031: 5029: 5027: 5023: 5019: 5004: 5001: 4999: 4996: 4994: 4991: 4989: 4985: 4982: 4981: 4979: 4977: 4976:Intercalation 4973: 4966: 4963: 4961: 4958: 4956: 4952: 4951: 4947: 4945: 4942: 4940: 4937: 4935: 4932: 4929: 4925: 4924: 4920: 4918: 4915: 4914: 4912: 4910: 4906: 4900: 4897: 4895: 4892: 4890: 4887: 4885: 4884:Dicycloplatin 4882: 4880: 4877: 4875: 4872: 4871: 4869: 4867: 4863: 4857: 4854: 4852: 4849: 4847: 4844: 4842: 4839: 4837: 4833: 4832: 4828: 4825: 4823: 4819: 4816: 4814: 4810: 4809: 4806: 4803: 4801: 4798: 4796: 4793: 4790: 4786: 4783: 4781: 4778: 4776: 4773: 4771: 4767: 4766: 4763: 4760: 4758: 4757:Prednimustine 4755: 4752: 4748: 4745: 4743: 4740: 4737: 4734: 4732: 4728: 4725: 4723: 4720: 4718: 4715: 4713: 4709: 4708: 4706: 4704: 4700: 4697: 4694: 4689: 4685: 4675: 4672: 4670: 4667: 4665: 4662: 4660: 4657: 4654: 4651: 4649: 4646: 4644: 4640: 4639: 4635: 4632: 4629: 4627: 4624: 4622: 4619: 4617: 4614: 4612: 4609: 4607: 4604: 4601: 4597: 4594: 4592: 4589: 4587: 4583: 4582: 4578: 4577: 4575: 4573: 4572:Intercalation 4569: 4565: 4558: 4555: 4553: 4549: 4548: 4544: 4543: 4541: 4539: 4535: 4528: 4525: 4523: 4520: 4518: 4515: 4513: 4510: 4508: 4505: 4503: 4500: 4498: 4495: 4493: 4490: 4488: 4485: 4483: 4480: 4478: 4474: 4473: 4469: 4468: 4466: 4464: 4460: 4457: 4454: 4449: 4445: 4434: 4430: 4429: 4425: 4424: 4422: 4420: 4416: 4409: 4406: 4404: 4400: 4399: 4395: 4394: 4390: 4386: 4385: 4381: 4380: 4376: 4375:+daunorubicin 4373: 4369: 4368: 4364: 4363: 4359: 4355: 4352: 4350: 4347: 4345: 4342: 4340: 4339:Doxifluridine 4337: 4335: 4332: 4330: 4326: 4325: 4321: 4320: 4318: 4316: 4312: 4305: 4302: 4300: 4296: 4295: 4291: 4289: 4288:Rabacfosadine 4286: 4284: 4281: 4278: 4275: 4273: 4270: 4268: 4264: 4263: 4259: 4255: 4254: 4250: 4246: 4245: 4241: 4240: 4238: 4236: 4232: 4225: 4222: 4220: 4216: 4215: 4211: 4208: 4205: 4203: 4200: 4198: 4195: 4193: 4189: 4188: 4184: 4183: 4181: 4179: 4175: 4172: 4169: 4164: 4158: 4155: 4151: 4147: 4136: 4132: 4131: 4127: 4124: 4121: 4119: 4116: 4114: 4111: 4109: 4106: 4104: 4101: 4099: 4095: 4094: 4090: 4089: 4087: 4083: 4076: 4073: 4071: 4068: 4066: 4063: 4061: 4058: 4056: 4052: 4051: 4047: 4046: 4044: 4041: 4036: 4033: 4030: 4025: 4021: 4017: 4012: 4008: 4004: 3996: 3991: 3989: 3984: 3982: 3977: 3976: 3973: 3961: 3958: 3956: 3953: 3952: 3949: 3943: 3940: 3938: 3935: 3933: 3932:its compounds 3929: 3926: 3922: 3918: 3917: 3916: 3913: 3911: 3908: 3905: 3902: 3900: 3897: 3896: 3894: 3890: 3884: 3881: 3879: 3876: 3874: 3871: 3869: 3868:Tetanospasmin 3866: 3864: 3863:T-2 mycotoxin 3861: 3859: 3856: 3854: 3851: 3849: 3846: 3844: 3841: 3839: 3836: 3834: 3831: 3829: 3826: 3824: 3821: 3819: 3816: 3814: 3811: 3809: 3806: 3804: 3801: 3799: 3796: 3794: 3793:Batrachotoxin 3791: 3789: 3786: 3784: 3781: 3779: 3776: 3774: 3771: 3769: 3766: 3764: 3761: 3760: 3758: 3754: 3748: 3745: 3743: 3740: 3738: 3737:Allyl alcohol 3735: 3733: 3730: 3728: 3725: 3723: 3720: 3718: 3715: 3713: 3710: 3709: 3707: 3703: 3697: 3694: 3692: 3689: 3687: 3684: 3682: 3679: 3677: 3674: 3673: 3671: 3668: 3664: 3658: 3655: 3653: 3650: 3648: 3645: 3643: 3640: 3638: 3635: 3633: 3630: 3628: 3625: 3623: 3620: 3618: 3615: 3613: 3610: 3608: 3605: 3603: 3602:Chloroacetone 3600: 3598: 3595: 3593: 3590: 3588: 3587:Benzyl iodide 3585: 3583: 3580: 3578: 3575: 3573: 3570: 3568: 3565: 3563: 3560: 3558: 3555: 3553: 3550: 3547: 3544: 3542: 3541:Xylyl bromide 3539: 3538: 3536: 3534: 3528: 3522: 3519: 3517: 3514: 3512: 3509: 3507: 3504: 3502: 3499: 3497: 3494: 3492: 3489: 3487: 3484: 3482: 3479: 3477: 3474: 3472: 3469: 3467: 3464: 3462: 3459: 3457: 3454: 3452: 3449: 3447: 3444: 3442: 3439: 3437: 3434: 3432: 3429: 3427: 3424: 3422: 3419: 3417: 3414: 3412: 3409: 3407: 3404: 3402: 3399: 3397: 3394: 3392: 3389: 3387: 3384: 3382: 3379: 3377: 3374: 3372: 3369: 3367: 3364: 3361: 3358: 3356: 3353: 3351: 3348: 3346: 3343: 3341: 3338: 3335: 3332: 3330: 3329:Butyrophenone 3327: 3325: 3322: 3319: 3316: 3315: 3313: 3311: 3305: 3299: 3298:o-Dianisidine 3296: 3294: 3291: 3289: 3286: 3284: 3281: 3279: 3275: 3272: 3270: 3267: 3264: 3261: 3260: 3258: 3256: 3252: 3246: 3243: 3241: 3238: 3236: 3233: 3231: 3228: 3226: 3223: 3221: 3218: 3216: 3213: 3211: 3208: 3206: 3203: 3201: 3198: 3196: 3193: 3191: 3188: 3186: 3183: 3181: 3178: 3176: 3173: 3171: 3168: 3166: 3163: 3161: 3158: 3156: 3153: 3151: 3148: 3146: 3145:Cadmium oxide 3143: 3141: 3138: 3136: 3133: 3131: 3128: 3126: 3123: 3121: 3118: 3116: 3113: 3111: 3108: 3106: 3103: 3100: 3097: 3094: 3091: 3089: 3086: 3083: 3080: 3078: 3075: 3073: 3070: 3067: 3064: 3062: 3059: 3057: 3054: 3053: 3051: 3049: 3043: 3037: 3034: 3032: 3029: 3027: 3024: 3020: 3017: 3015: 3012: 3010: 3007: 3006: 3005: 3002: 3000: 2997: 2995: 2994:Batrachotoxin 2992: 2990: 2987: 2985: 2982: 2980: 2977: 2975: 2972: 2970: 2967: 2965: 2962: 2960: 2957: 2955: 2952: 2950: 2947: 2945: 2942: 2939: 2936: 2934: 2931: 2928: 2925: 2923: 2920: 2918: 2915: 2912: 2909: 2906: 2903: 2901: 2898: 2895: 2892: 2889: 2886: 2884: 2881: 2878: 2877:Tetanospasmin 2875: 2872: 2869: 2867: 2864: 2861: 2858: 2856: 2853: 2852: 2850: 2848: 2844: 2834: 2831: 2829: 2826: 2824: 2821: 2819: 2816: 2814: 2811: 2809: 2806: 2804: 2801: 2799: 2796: 2794: 2791: 2789: 2786: 2783: 2780: 2778: 2775: 2773: 2770: 2768: 2765: 2763: 2760: 2758: 2755: 2752: 2749: 2746: 2743: 2740: 2737: 2735: 2732: 2730: 2727: 2725: 2722: 2720: 2717: 2715: 2712: 2710: 2707: 2705: 2702: 2700: 2697: 2695: 2692: 2690: 2687: 2685: 2682: 2680: 2677: 2674: 2671: 2669: 2666: 2664: 2661: 2659: 2656: 2654: 2651: 2649: 2646: 2644: 2641: 2639: 2636: 2634: 2631: 2629: 2626: 2625: 2623: 2619: 2613: 2610: 2608: 2605: 2603: 2600: 2598: 2595: 2593: 2590: 2588: 2585: 2583: 2580: 2578: 2575: 2573: 2570: 2568: 2565: 2563: 2560: 2558: 2555: 2553: 2550: 2548: 2545: 2543: 2540: 2539: 2537: 2533: 2527: 2524: 2522: 2519: 2517: 2514: 2512: 2509: 2507: 2504: 2502: 2499: 2497: 2494: 2492: 2489: 2487: 2484: 2482: 2479: 2477: 2474: 2472: 2469: 2467: 2464: 2462: 2459: 2457: 2454: 2452: 2449: 2447: 2444: 2443: 2441: 2439: 2435: 2429: 2426: 2424: 2421: 2419: 2416: 2414: 2411: 2409: 2406: 2404: 2401: 2399: 2396: 2394: 2391: 2390: 2388: 2386: 2382: 2376: 2373: 2372: 2370: 2366: 2360: 2357: 2355: 2352: 2350: 2347: 2345: 2342: 2340: 2337: 2335: 2332: 2330: 2327: 2325: 2322: 2320: 2317: 2315: 2312: 2310: 2307: 2305: 2302: 2301: 2299: 2297: 2293: 2287: 2284: 2282: 2279: 2277: 2274: 2272: 2269: 2267: 2264: 2261: 2258: 2256: 2253: 2250: 2247: 2244: 2241: 2238: 2235: 2232: 2229: 2226: 2223: 2221: 2218: 2215: 2212: 2211: 2209: 2207: 2203: 2200: 2198: 2194: 2184: 2181: 2179: 2176: 2174: 2171: 2170: 2168: 2164: 2157: 2154: 2153: 2151: 2149: 2148:Nettle agents 2145: 2139: 2136: 2134: 2131: 2129: 2126: 2124: 2121: 2120: 2118: 2116: 2112: 2106: 2103: 2101: 2098: 2096: 2093: 2090: 2087: 2086: 2084: 2082: 2078: 2072: 2069: 2066: 2063: 2060: 2057: 2054: 2051: 2048: 2045: 2042: 2039: 2037: 2035: 2031: 2028: 2026: 2022: 2016: 2013: 2011: 2008: 2006: 2003: 2001: 1998: 1996: 1993: 1991: 1988: 1986: 1983: 1981: 1978: 1976: 1973: 1971: 1968: 1966: 1963: 1961: 1958: 1956: 1953: 1951: 1950:Cacodyl oxide 1948: 1946: 1943: 1941: 1938: 1935: 1932: 1929: 1926: 1924: 1921: 1919: 1916: 1915: 1913: 1911: 1907: 1900: 1897: 1895: 1892: 1890: 1886: 1885: 1879: 1874: 1872: 1867: 1865: 1860: 1859: 1856: 1845: 1839: 1831: 1827: 1823: 1819: 1815: 1811: 1803: 1795: 1791: 1787: 1783: 1779: 1775: 1768: 1760: 1756: 1752: 1748: 1744: 1740: 1733: 1725: 1721: 1717: 1713: 1709: 1705: 1701: 1697: 1690: 1682: 1678: 1674: 1670: 1666: 1662: 1655: 1647: 1643: 1639: 1635: 1628: 1620: 1616: 1612: 1608: 1601: 1593: 1589: 1585: 1581: 1574: 1559: 1555: 1551: 1547: 1543: 1539: 1535: 1531: 1524: 1518: 1514: 1511: 1507: 1503: 1500: 1495: 1489: 1485: 1482: 1476: 1470: 1466: 1463: 1457: 1449: 1445: 1441: 1437: 1433: 1429: 1422: 1412: 1403: 1394: 1388: 1384: 1381: 1375: 1367: 1363: 1359: 1355: 1351: 1347: 1343: 1339: 1332: 1317: 1313: 1311: 1305: 1299: 1297: 1295: 1293: 1291: 1289: 1287: 1285: 1283: 1266: 1262: 1261: 1253: 1245: 1241: 1236: 1231: 1228:(1): 212–21. 1227: 1223: 1219: 1212: 1196: 1195: 1194:Health Canada 1190: 1184: 1168: 1164: 1160: 1159:"Ledaga EPAR" 1154: 1152: 1135: 1131: 1127: 1121: 1119: 1117: 1112: 1104: 1096: 1092: 1090: 1086: 1081: 1079: 1069: 1067: 1063: 1059: 1055: 1051: 1047: 1043: 1042:immune system 1038: 1035: 1033: 1029: 1024: 1022: 1018: 1014: 1010: 1005: 1003: 999: 995: 991: 987: 986:blepharospasm 983: 978: 974: 966: 964: 959: 957: 953: 949: 945: 941: 937: 933: 923: 921: 918: 913: 911: 907: 903: 902:blister agent 899: 895: 892:, a group of 891: 887: 883: 879: 875: 871: 867: 863: 859: 855: 851: 847: 843: 831: 824: 819: 802: 796: 790: 787: 785: 782: 780: 777: 775: 772: 770: 768: 764: 760: 758: 755: 753: 750: 748: 745: 743: 742:Triethylamine 740: 738: 735: 733: 731: 727: 725: 722: 720: 719:Dimethylamine 717: 716: 714: 709: 708: 703: 696: 694: Rx-only 687: 685: 676: 673: 663: 662: 660: 658: 655: 654: 651:50% (Kidney) 650: 647: 643: 642: 639:<1 minute 638: 635: 631: 630: 626: 622: 615: 612: 609: 607:Intracavitary 606: 605: 603: 600: 594: 593: 587: 578: 577: 575: 572: 566: 565: 560: 555: 550: 545: 542: 539: 535: 534: 531:Pharmacology 529: 525: 523: 522: 517: 516: 512: 510: 507: 506: 502: 499: 498: 491: 489: 486: 485: 461: 458: 454: 453: 448: 439: 438: 435: 428: 414: 413: 410: 403: 395: 391: 390:DTXSID2020975 387: 386: 384: 374: 370: 369: 365: 363: 360: 359: 352: 348: 347: 345: 343: 340: 339: 332: 331: 329: 327: 324: 323: 316: 312: 311: 309: 303: 299: 298: 294: 290: 288: 285: 284: 277: 273: 272: 270: 268: 265: 264: 257: 256: 254: 252: 247: 246: 242: 238: 235: 233: 231:ECHA InfoCard 228: 227: 220: 216: 215: 213: 211: 208: 207: 200: 196: 195: 193: 191: 188: 187: 180: 176: 175: 173: 171: 168: 167: 160: 156: 155: 153: 151: 148: 147: 140: 136: 135: 133: 129: 124: 123: 116: 112: 111: 109: 106: 102: 101: 96: 89: 86: 83: 80: 77: 74: 73: 68: 63: 59: 54: 50: 45: 41: 36: 32: 27: 24:Chlormethine 19: 18:Chloromethane 5990:Orphan drugs 5838:Spiromustine 5813:Mannomustine 5803:Chlorambucil 5798:Bendamustine 5586:Tazemetostat 5550:Alitretinoin 5543: 5469:Estramustine 5449:Elsamitrucin 5439:Eflornithine 5393:Pegaspargase 5389:Asparaginase 5382: 5351:Testolactone 5344: 5332: 5320: 5274: 5259:Panobinostat 5242: 5212: 5200: 5188: 5176: 5147: 5112: 5100: 5053: 5049:Padeliporfin 4988:Dactinomycin 4984:Streptomyces 4965:Temozolomide 4960:Mitozolomide 4948: 4939:Mitobronitol 4928:Procarbazine 4921: 4909:Nonclassical 4834: 4811: 4805:Streptozocin 4770:Nitrosoureas 4768: 4742:Chlorambucil 4736:Trofosfamide 4722:Chlormethine 4721: 4717:Bendamustine 4710: 4648:Mitoxantrone 4643:Losoxantrone 4636: 4596:Daunorubicin 4579: 4545: 4482:Camptothecin 4470: 4426: 4396: 4382: 4365: 4349:Fluorouracil 4329:Capecitabine 4322: 4292: 4256: 4242: 4212: 4207:Pralatrexate 4197:Methotrexate 4185: 4128: 4091: 4048: 3873:Tetrodotoxin 3823:Grayanotoxin 3607:Bromoacetone 3597:Thiophosgene 3552:Mace (spray) 3546:Pepper spray 3531:Lachrymatory 3516:Fluphenazine 3511:Procarbazine 3421:Sleeping gas 3269:Chloropicrin 3180:Nitric oxide 3082:Chloropicrin 3026:Cloflubicyne 2989:Oxotremorine 2938:Antillatoxin 2917:Tetrodotoxin 2866:Bungarotoxin 2762:Nitromethane 2724:Formaldoxime 2663:Cyclohexanol 2628:Acetonitrile 2375:GV (EA-5365) 2197:Nerve agents 2127: 2000:Lactonitrile 1910:Blood agents 1899:riot control 1838:cite journal 1813: 1809: 1802: 1777: 1773: 1767: 1742: 1738: 1732: 1699: 1695: 1689: 1664: 1660: 1654: 1637: 1633: 1627: 1610: 1606: 1600: 1583: 1579: 1573: 1562:. Retrieved 1537: 1533: 1523: 1494: 1475: 1456: 1431: 1427: 1421: 1411: 1402: 1393: 1374: 1341: 1337: 1331: 1320:. Retrieved 1307: 1269:. Retrieved 1265:the original 1259: 1252: 1225: 1222:Toxicol. Sci 1221: 1211: 1199:. Retrieved 1192: 1183: 1171:. Retrieved 1162: 1138:. Retrieved 1129: 1102: 1093: 1082: 1075: 1039: 1036: 1025: 1006: 979: 975: 972: 960: 947: 929: 914: 885: 877: 869: 865: 853: 842:Chlormethine 841: 840: 766: 762: 737:Diethylamine 729: 657:Legal status 520: 441:CN(CCCl)CCCl 326:RTECS number 98:Identifiers 87: 70:Other names 61: 57: 5848:Neurotoxins 5661:from market 5631:Vorasidenib 5611:Trabectedin 5596:Tiazofurine 5591:Tebentafusp 5576:Tagraxofusp 5539:Plitidepsin 5514:Mitoguazone 5459:Epacadostat 5429:Demecolcine 5373:Aflibercept 5346:Sex steroid 5219:Fuzuloparib 5160:Carfilzomib 5132:Palbociclib 5122:Abemaciclib 5075:Verteporfin 5039:Efaproxiral 4955:Dacarbazine 4917:Altretamine 4899:Satraplatin 4894:Oxaliplatin 4874:Carboplatin 4851:Triaziquone 4822:Mannosulfan 4800:Ranimustine 4780:Fotemustine 4621:Pirarubicin 4606:Doxorubicin 4600:+cytarabine 4586:Aclarubicin 4547:Podophyllum 4472:Camptotheca 4403:Azacitidine 4389:Gemcitabine 4344:Floxuridine 4277:Fludarabine 4272:Clofarabine 4258:Halogenated 4249:Pentostatin 4224:Raltitrexed 4192:Aminopterin 4135:Ixabepilone 4130:Epothilones 4098:Cabazitaxel 4075:Vinorelbine 4060:Vincristine 4055:Vinblastine 4040:microtubule 3883:Veratridine 3858:Shiga toxin 3813:Domoic acid 3676:Thioacetone 3642:Iodoacetone 3506:Pentazocine 3501:Sevoflurane 3466:CAR-302,668 3461:CAR-302,282 3456:CAR-302,196 3451:CAR-301,060 3446:CAR-226,086 3426:Carfentanil 3324:Apomorphine 3245:Green Cross 3036:Domoic acid 2847:Neurotoxins 2767:OPA mixture 2658:Chlorosoman 2653:Chlorosarin 2587:Phospholine 2286:Crotylsarin 2271:Fluorotabun 2243:Chlorosoman 2225:Chlorosarin 1173:5 September 1140:5 September 1078:mustard gas 1058:bone marrow 998:photophobia 982:lacrimation 952:mustard gas 613:Intravenous 500:Appearance 450:Properties 237:100.000.110 159:CHEBI:28925 5964:Categories 5917:Dibenamine 5626:Verdinexor 5621:Venetoclax 5529:Oblimersen 5524:Navitoclax 5504:Lucanthone 5499:Lonidamine 5494:Lifileucel 5489:Ivosidenib 5484:Imetelstat 5454:Enasidenib 5444:Elesclomol 5409:Bexarotene 5404:Belzutifan 5339:Bexarotene 5327:Atrasentan 5302:Umbralisib 5297:Idelalisib 5287:Copanlisib 5269:Vorinostat 5264:Romidepsin 5254:Entinostat 5249:Belinostat 5207:Masoprocol 5195:Tiazofurin 5183:Anagrelide 5155:Bortezomib 5142:Seliciclib 5137:Ribociclib 5117:inhibitors 5107:Tipifarnib 5070:Temoporfin 5065:Talaporfin 5003:Plicamycin 4998:Mitomycins 4944:Pipobroman 4923:Hydrazines 4889:Nedaplatin 4841:Carboquone 4836:Aziridines 4827:Treosulfan 4775:Carmustine 4762:Uramustine 4731:Ifosfamide 4703:Alkylating 4664:Bisantrene 4653:Pixantrone 4626:Valrubicin 4616:Idarubicin 4611:Epirubicin 4557:Teniposide 4512:Lurtotecan 4507:Irinotecan 4408:Decitabine 4372:Cytarabine 4315:Pyrimidine 4304:Tioguanine 4294:Thiopurine 4283:Nelarabine 4267:Cladribine 4219:Pemetrexed 4202:Pemetrexed 4178:Folic acid 4118:Paclitaxel 4070:Vinflunine 3833:Maitotoxin 3828:Guanitoxin 3808:Ciguatoxin 3803:Brevetoxin 3788:Anatoxin-a 3783:Aflatoxins 3696:Putrescine 3691:Cadaverine 3667:Malodorant 3491:Isoflurane 3476:Desflurane 3471:Benperidol 3416:Psilocybin 3411:PAVA spray 3093:Diphosgene 3046:Pulmonary/ 2974:Picrotoxin 2933:Strychnine 2927:Brevetoxin 2911:Maitotoxin 2894:Guanitoxin 2888:Ciguatoxin 2855:Anatoxin-a 2788:Pinacolone 2621:Precursors 2582:Selenophos 2438:Carbamates 2354:Chinese VX 2260:Cyclosarin 2249:Ethylsarin 2220:Sarin (GB) 2071:Lewisite 3 2065:Lewisite 2 2034:Arsenicals 1613:: 93–102. 1564:2018-10-14 1322:2016-04-20 1107:References 1032:vesication 1009:rhinorrhea 894:anticancer 872:, and (in 488:Molar mass 351:50D9XSG0VR 190:ChemSpider 126:3D model ( 105:CAS Number 53:IUPAC name 5823:Mustamine 5818:Melphalan 5727:Vesicants 5671:Phase III 5659:Withdrawn 5636:Vosaroxin 5616:Veliparib 5571:Sotorasib 5561:Selinexor 5555:Tretinoin 5545:Retinoids 5474:Glasdegib 5419:Celecoxib 5368:Adagrasib 5292:Duvelisib 5282:Alpelisib 5237:Rucaparib 5224:Niraparib 5165:Oprozomib 5127:Alvocidib 4993:Bleomycin 4950:Triazenes 4934:Etoglucid 4879:Cisplatin 4795:Nimustine 4789:Semustine 4785:Lomustine 4747:Melphalan 4674:Menogaril 4669:Crisnatol 4659:Amsacrine 4631:Zorubicin 4591:Amrubicin 4552:Etoposide 4527:Topotecan 4522:Silatecan 4517:Rubitecan 4502:Gimatecan 4487:Cositecan 4477:Belotecan 4153:inhibitor 4123:Tesetaxel 4113:Ortataxel 4108:Larotaxel 4103:Docetaxel 4065:Vindesine 3928:Plutonium 3878:Volkensin 3853:Saxitoxin 3843:Palytoxin 3768:Aconitine 3496:Halothane 3486:Bufotenin 3481:Enflurane 3401:Kolokol-1 3381:Pethidine 3355:Etoxadrol 3340:Etorphine 3336:(CS-4640) 3320:(CS-4030) 3278:glycerine 3225:Salcomine 2984:Tremorine 2922:Aconitine 2905:Palytoxin 2883:Ryanodine 2860:Saxitoxin 2597:Ro 3-0422 2368:GV agents 2231:Thiosarin 1960:Phosphine 1739:Am J Surg 1534:J Med Res 1499:Mustargen 1271:8 October 1099:Chemistry 1021:Pneumonia 1013:epistaxis 963:pethidine 934:analogue 886:Mustargen 646:Excretion 597:Routes of 569:Pregnancy 362:UN number 333:IA1750000 258:200-120-5 250:EC Number 179:ChEMBL427 56:2-Chloro- 5954:Medicine 5519:Mitotane 5464:Eribulin 5232:Olaparib 5170:Ixazomib 4846:Thiotepa 4818:Busulfan 4497:Exatecan 4334:Carmofur 4042:assembly 4005: / 3937:Polonium 3838:Modeccin 3747:Acrolein 3712:Lewisite 3617:Acrolein 3441:CS-27349 3391:Ibogaine 3274:Litharge 3263:Adamsite 3240:Diborane 3230:Fluomine 3210:Ethenone 3105:Acrolein 3072:Fluorine 3066:Phosgene 3056:Chlorine 2456:EA-3887A 2428:C01-A042 2423:C01-A039 2418:C01-A035 2296:V-agents 2206:G-agents 2091:(EA-229) 2059:Lewisite 1918:Cyanogen 1830:20997209 1794:21247779 1759:13947966 1724:17751251 1558:Archived 1554:13947966 1513:Archived 1510:Valchlor 1502:Archived 1484:Archived 1465:Archived 1383:Archived 1366:22909007 1316:Archived 1244:10746948 1201:25 March 1167:Archived 1134:Archived 1126:"Ledaga" 1054:platelet 1028:erythema 956:vesicant 932:estrogen 878:embikhin 585: B3 571:category 538:ATC code 210:DrugBank 4453:S phase 4354:Tegafur 4168:S phase 4093:Taxanes 4029:M phase 3686:Skatole 3681:Allicin 3396:EA-3834 3386:EA-3580 3376:EA-3443 3371:EA-3167 3366:EA-2148 3350:CS-4297 3345:EA-2092 3334:EA-4941 3061:Bromine 2699:EA-1224 2679:EA-1250 2592:R-16661 2567:EA-2613 2562:EA-2098 2557:EA-2054 2552:EA-2012 2521:3152 CT 2511:TL-1317 2506:TL-1299 2501:TL-1238 2471:EA-4056 2466:EA-3990 2461:EA-3966 2451:EA-3887 2349:EA-1763 2309:EA-3148 2304:EA-2192 2281:EA-4352 2276:EA-1356 2010:Stibine 1704:Bibcode 1696:Science 1681:3891698 1358:8085692 1072:History 1066:ageusia 1062:anosmia 1017:dyspnea 898:guanine 866:mustine 823:what is 821: ( 682:: 616:Topical 556: ( 554:L01AA05 552:) 546: ( 544:D08AX04 302:PubChem 219:DB00888 115:51-75-2 81:mustine 5970:Amines 5940:Portal 5775:TL-995 5770:TL-695 5765:TL-513 5760:TL-512 5755:TL-481 5750:TL-301 5654:WHO-EM 5278:(Pi3K) 4235:Purine 4038:Block 3904:Napalm 3669:agents 3533:agents 3436:JB-336 3431:JB-318 3406:LSD-25 3362:(DMHP) 3310:agents 2969:A-8564 2929:(PbTX) 2879:(TeNT) 2496:TL-599 2486:T-1194 2481:T-1152 2476:T-1123 2245:(ClGD) 2227:(ClGB) 2138:TL-301 1940:Arsine 1828:  1792:  1757:  1722:  1679:  1552:  1448:660515 1446:  1364:  1356:  1242:  990:miosis 818:verify 815:  684:℞-only 670: 493:156.05 434:SMILES 170:ChEMBL 88:Ledaga 47:Names 5927:SY-28 5910:Other 5886:DSP-4 5190:IMPDI 5085:Other 3892:Other 3848:Ricin 3763:Abrin 3722:KB-16 3009:IPTBO 2940:(ATX) 2913:(MTX) 2907:(PTX) 2896:(GTX) 2890:(CTX) 2873:(BTX) 2729:Nital 2535:Other 2413:A-262 2408:A-242 2403:A-234 2398:A-232 2393:A-208 2237:Soman 2233:(SGB) 2214:Tabun 2173:KB-16 2166:Other 1362:S2CID 1312:(CDC) 1308:U.S. 994:edema 526:0.91 409:InChI 366:2810 276:D0767 150:ChEBI 128:JSmol 5881:DMEA 5276:PIKI 5244:HDAC 4693:CCNS 3930:and 3548:(OC) 3265:(DM) 3095:(DP) 3084:(PS) 3068:(CG) 3019:TBPS 3014:TBPO 2862:(TZ) 2784:(TH) 2753:(DF) 2747:(SW) 2741:(TB) 2714:DMHP 2694:DEHP 2684:DIHP 2675:(KB) 2612:MSPI 2262:(GF) 2251:(GE) 2239:(GD) 2216:(GA) 2158:(CX) 2105:CEES 2073:(L3) 2067:(L2) 2055:(PD) 2049:(MD) 2043:(ED) 1936:(AC) 1930:(CK) 1844:link 1826:PMID 1810:JAMA 1790:PMID 1755:PMID 1720:PMID 1677:PMID 1550:PMID 1508:and 1444:PMID 1354:PMID 1273:2023 1240:PMID 1203:2024 1175:2021 1142:2021 1085:OSRD 1052:and 926:Uses 858:USAN 519:log 509:Odor 342:UNII 315:4033 287:MeSH 267:KEGG 199:3893 84:HN-2 5745:HN3 5740:HN2 5735:HN1 5322:ERA 5178:PhI 5149:PrI 5114:CDK 5026:PDT 4024:MIs 4020:SPs 4011:L01 3572:CNS 3101:(Z) 2643:AlP 2638:ATO 2133:HN3 2128:HN2 2123:HN1 2061:(L) 1818:doi 1814:132 1782:doi 1778:212 1747:doi 1743:105 1712:doi 1700:103 1669:doi 1642:doi 1615:doi 1588:doi 1542:doi 1436:doi 1346:doi 1342:121 1230:doi 1089:HN3 948:HN2 870:HN2 864:), 862:USP 850:BAN 846:INN 559:WHO 549:WHO 378:EPA 305:CID 5966:: 5667:: 5202:LI 5102:FI 4568:II 4538:II 4360:)) 3717:CX 3567:CR 3562:CS 3557:CN 3318:BZ 2833:TG 2828:TC 2803:QL 2689:ZS 2633:AT 2344:VX 2339:VS 2334:VR 2329:VP 2324:VM 2319:VG 2314:VE 2266:GP 2255:GH 1840:}} 1836:{{ 1824:. 1812:. 1788:. 1776:. 1753:. 1741:. 1718:. 1710:. 1698:. 1675:. 1665:11 1663:. 1638:40 1636:. 1609:. 1584:57 1582:. 1556:. 1548:. 1538:40 1536:. 1532:. 1442:. 1432:67 1430:. 1360:. 1352:. 1340:. 1314:. 1306:. 1281:^ 1238:. 1226:54 1224:. 1220:. 1191:. 1161:. 1150:^ 1128:. 1115:^ 1044:. 922:. 912:. 876:) 868:, 860:, 848:, 690:EU 679:CA 672:S4 666:AU 627:: 581:AU 562:) 475:Cl 472:11 5942:: 5711:e 5704:t 5697:v 5557:) 5548:( 5395:) 5391:/ 5387:( 5353:) 5349:( 5341:) 5337:( 5329:) 5325:( 5304:) 5280:( 5271:) 5247:( 5239:) 5217:( 5209:) 5205:( 5197:) 5193:( 5185:) 5181:( 5144:) 5120:( 5109:) 5105:( 5077:) 5058:( 5024:/ 5005:) 4986:( 4967:) 4953:( 4930:) 4926:( 4838:: 4829:) 4820:( 4815:: 4791:) 4787:( 4772:: 4753:) 4749:( 4738:) 4729:( 4714:: 4695:) 4691:( 4655:) 4641:( 4633:) 4602:) 4598:( 4584:( 4570:+ 4559:) 4550:( 4529:) 4475:( 4463:I 4455:) 4451:( 4435:) 4431:( 4410:) 4401:( 4391:) 4387:( 4377:) 4370:( 4356:( 4327:( 4306:) 4297:( 4279:) 4265:( 4260:/ 4251:) 4247:( 4226:) 4217:( 4209:) 4190:( 4170:) 4166:( 4137:) 4133:( 4125:) 4096:( 4077:) 4053:( 4031:) 4027:( 4022:/ 4013:) 4009:( 3994:e 3987:t 3980:v 3276:- 2100:Q 2095:T 1877:e 1870:t 1863:v 1846:) 1832:. 1820:: 1796:. 1784:: 1761:. 1749:: 1726:. 1714:: 1706:: 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Index

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
UN number

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