The Wassenaar Arrangement is an international framework that was established with the objective of “promoting transparency and greater responsibility in transfers of conventional arms and dual-use goods and technologies.”
Within its Munitions List 7 (ML7), the Wassenaar Arrangement features chemical agents, biological agents, riot control agents, radioactive materials, related equipment, components, and materials.
In particular, with regards to chemical agents, ML7 comprises all of the CWC Schedule 1 chemicals, the central incapacitating agent 3-quinuclidinyl benzilate (BZ), which is a CWC Schedule 2 chemical, as well as a list of defoliants and a list of riot control agents, neither of which is in the CWC schedules.
The table below lists all of the entries of the Wassenaar Arrangement’s Munitions List 7 (ML7), annotated with chemical structures and with a reference to the corresponding entry in the CWC Schedules and the AG Chemical Weapons Precursors list. For entries that identify individual chemicals, the Chemical Abstract Service (CAS) registry number is given as well.
New. This table is presented in a new format, with live links to PubChem cards, 3D structures (through iCn3D), and NIST Chemistry WebBook cards.
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Wassenaar Arrangement’s Munitions List 7 (ML7) Chemicals
Curated and Structurally Annotated by Costanzi Research – www.costanziresearch.com (Last Update: August 01, 2020) |
Disclaimer. The information in this table is provided for research and general information purposes only. The authors do not guarantee the accuracy of the information and do not take any responsibility for any consequence, including, but not limited to, financial or legal consequences, that may occur due to inaccuracies or omissions. |
| Color Code: |
Individual Chemicals Mixtures of Chemicals Proteins Families of Chemicals Examples: Individual Compounds Belonging to a Family of Chemicals Exceptions: Compounds Belonging to a Family of Chemicals but Excluded from the CWC Schedules |
Notes. 1. For entry ML7 b.4.b (Agent Orange), there is a discrepancy between the name, which indicates the free acid form, and the CAS number, which indicates the butyl ester form. 2. For entries lacking a CAS registry number, a sequential registry number assinged by Costanzi Research (CR number) is provided instead. 3. For proteins, the UNIPROT ID is provided instead. 4. Overlaps among CWC schedules, Australia Group chemicals, and Wassenaar ML7 chemicals are provided. 5. 2D structures curated by Costanzi Research are provided as SDF and MRV files (MRV files require ChemAxon’s MarvinSketch to open). 6. 3D strucures from PubChem are shown with NCBI’s iCn3D. 7. NIST Chemistry WebBook cards provide chemical and physical data compiled by the National Institute of Standards and Technology, including, inter alia, analytical spectra. |
| Category | Wassenaar Entry Number1 | Wassenaar Entry Name | CAS Registry Number2 | PubChem ID3 | Structure (click to enlarge) |
SMILES | InChI | Overlaps4 | Links5-7 |
|---|---|---|---|---|---|---|---|---|---|
| Nerve agents | WA ML7 b.1.a | O-Alkyl (<=C10, incl. cycloalkyl) alkyl (Me, Et, n-Pr or i-Pr)-phosphonofluoridates | CR0001 | — |  |
— | — | CWC 1A1 | — |
| Nerve agents | WA ML7 b.1.a Example 1 | Sarin: O-Isopropyl methylphosphonofluoridate | 107-44-8 | 7871 |
 |
CC(C)O[P](C)(F)=O | InChI=1S/C4H10FO2P/c1-4(2)7-8(3,5)6/h4H,1-3H3 InChIKey=DYAHQFWOVKZOOW-UHFFFAOYSA-N |
CWC 1A1 Example 1 |
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| Nerve agents | WA ML7 b.1.a Example 2 | Soman: O-Pinacolyl methylphosphonofluoridate | 96-64-0 | 7305 |
 |
CC(O[P](C)(F)=O)C(C)(C)C | InChI=1S/C7H16FO2P/c1-6(7(2,3)4)10-11(5,8)9/h6H,1-5H3 InChIKey=GRXKLBBBQUKJJZ-UHFFFAOYSA-N |
CWC 1A1 Example 2 |
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| Nerve agents | WA ML7 b.1.b | O-Alkyl (<=C10, incl. cycloalkyl) N,N-dialkyl (Me, Et, n-Pr or i-Pr) phosphoramidocyanidates | CR0002 | — |  |
— | — | CWC 1A2 | — |
| Nerve agents | WA ML7 b.1.b Example 1 | Tabun:O-Ethyl N,N-dimethyl phosphoramidocyanidate | 77-81-6 | 6500 |
 |
CCO[P](=O)(C#N)N(C)C | InChI=1S/C5H11N2O2P/c1-4-9-10(8,5-6)7(2)3/h4H2,1-3H3 InChIKey=PJVJTCIRVMBVIA-UHFFFAOYSA-N |
CWC 1A2 Example 1 |
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| Nerve agents | WA ML7 b.1.c | O-Alkyl (H or <=C10, incl. cycloalkyl) S-2-dialkyl (Me, Et, n-Pr or i-Pr)-aminoethyl alkyl (Me, Et, n-Pr or i-Pr) phosphonothiolates and corresponding alkylated or protonated salts | CR0003 | — |  |
— | — | CWC 1A3 | — |
| Nerve agents | WA ML7 b.1.c Example 1 | VX: O-Ethyl S-2-diisopropylaminoethyl methyl phosphonothiolate | 50782-69-9 | 39793 |
 |
CCO[P](C)(=O)SCCN(C(C)C)C(C)C | InChI=1S/C11H26NO2PS/c1-7-14-15(6,13)16-9-8-12(10(2)3)11(4)5/h10-11H,7-9H2,1-6H3 InChIKey=JJIUCEJQJXNMHV-UHFFFAOYSA-N |
CWC 1A3 Example 1 |
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| Vesicants (Sulfur mustards) | WA ML7 b.2.a.1 | 2-Chloroethylchloromethylsulfide | 2625-76-5 | 14557887 |
 |
C(CCl)SCCl | InChI=1S/C3H6Cl2S/c4-1-2-6-3-5/h1-3H2 InChIKey=HHQVSDLFPSFPST-UHFFFAOYSA-N |
CWC 1A4-1 |
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| Vesicants (Sulfur mustards) | WA ML7 b.2.a2 | Mustard gas: Bis(2-chloroethyl)sulfide | 505-60-2 | 10461 |
 |
ClCCSCCCl | InChI=1S/C4H8Cl2S/c5-1-3-7-4-2-6/h1-4H2 InChIKey=QKSKPIVNLNLAAV-UHFFFAOYSA-N |
CWC 1A4-2 |
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| Vesicants (Sulfur mustards) | WA ML7 b.2.a.3 | Bis(2-chloroethylthio)methane | 63869-13-6 | 522107 |
 |
ClCCSCSCCCl | InChI=1S/C5H10Cl2S2/c6-1-3-8-5-9-4-2-7/h1-5H2 InChIKey=RKTJTTAEKCRXNL-UHFFFAOYSA-N |
CWC 1A4-3 |
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| Vesicants (Sulfur mustards) | WA ML7 b.2.a.4 | Sesquimustard: 1,2-Bis(2-chloroethylthio)ethane | 3563-36-8 | 19092 |
 |
ClCCSCCSCCCl | InChI=1S/C6H12Cl2S2/c7-1-3-9-5-6-10-4-2-8/h1-6H2 InChIKey=AMGNHZVUZWILSB-UHFFFAOYSA-N |
CWC 1A4-4 |
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| Vesicants (Sulfur mustards) | WA ML7 b.2.a.5 | 1,3-Bis(2-chloroethylthio)-n-propane | 63905-10-2 | 522108 |
 |
C(CSCCCl)CSCCCl | InChI=1S/C7H14Cl2S2/c8-2-6-10-4-1-5-11-7-3-9/h1-7H2 InChIKey=YHRGRBPJIRKFND-UHFFFAOYSA-N |
CWC 1A4-5 |
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| Vesicants (Sulfur mustards) | WA ML7 b.2.a.6 | 1,4-Bis(2-chloroethylthio)-n-butane | 142868-93-7 | 518918 |
 |
ClCCSCCCCSCCCl | InChI=1S/C8H16Cl2S2/c9-3-7-11-5-1-2-6-12-8-4-10/h1-8H2 InChIKey=AYSIRJGVBLMLAS-UHFFFAOYSA-N |
CWC 1A4-6 |
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| Vesicants (Sulfur mustards) | WA ML7 b.2.a.7 | 1,5-Bis(2-chloroethylthio)-n-pentane | 142868-94-8 | 22608774 |
 |
ClCCSCCCCCSCCCl | InChI=1S/C9H18Cl2S2/c10-4-8-12-6-2-1-3-7-13-9-5-11/h1-9H2 InChIKey=CUJOZMZOOCTTAZ-UHFFFAOYSA-N |
CWC 1A4-7 |
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| Vesicants (Sulfur mustards) | WA ML7 b.2.a.8 | Bis(2-chloroethylthiomethyl)ether | 63918-90-1 | 22608780 |
 |
C(CCl)SCOCSCCCl | InChI=1S/C6H12Cl2OS2/c7-1-3-10-5-9-6-11-4-2-8/h1-6H2 InChIKey=IJGBNRTYNRKNHS-UHFFFAOYSA-N |
CWC 1A4-8 |
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| Vesicants (Sulfur mustards) | WA ML7 b.2.a.9 | O-Mustard: Bis(2-chloroethylthioethyl)ether | 63918-89-8 | 45452 |
 |
ClCCSCCOCCSCCCl | InChI=1S/C8H16Cl2OS2/c9-1-5-12-7-3-11-4-8-13-6-2-10/h1-8H2 InChIKey=FWVCSXWHVOOTFJ-UHFFFAOYSA-N |
CWC 1A4-9 |
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| Vesicants (Lewisites) | WA ML7 b.2.b.1 | Lewisite 1: 2-Chlorovinyldichloroarsine | 541-25-3 | 5372798 |
 |
Cl/C=C/[As](Cl)Cl | InChI=1S/C2H2AsCl3/c4-2-1-3(5)6/h1-2H/b2-1+ InChIKey=GIKLTQKNOXNBNY-OWOJBTEDSA-N |
CWC 1A5-1 |
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| Vesicants (Lewisites) | WA ML7 b.2.b.2 | Lewisite 2: Bis(2-chlorovinyl)chloroarsine | 40334-69-8 | 5368106 |
 |
Cl/C=C/[As](Cl)/C=C/Cl | InChI=1S/C4H4AsCl3/c6-3-1-5(8)2-4-7/h1-4H/b3-1+,4-2+ InChIKey=YRFJGLQNTWLXKO-ZPUQHVIOSA-N |
CWC 1A5-2 |
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| Vesicants (Lewisites) | WA ML7 b.2.b.3 | Lewisite 3: Tris(2-chlorovinyl)arsine | 40334-70-1 | 5352143 |
 |
Cl/C=C/[As](/C=C/Cl)/C=C/Cl | InChI=1S/C6H6AsCl3/c8-4-1-7(2-5-9)3-6-10/h1-6H/b4-1+,5-2+,6-3+ InChIKey=AOAVIJUEFJPSAI-GZDDRBCLSA-N |
CWC 1A5-3 |
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| Vesicant (Nitrogen mustards) | WA ML7 b.2.c.1 | HN1: Bis(2-chloroethyl)ethylamine | 538-07-8 | 10848 |
 |
CCN(CCCl)CCCl | InChI=1S/C6H13Cl2N/c1-2-9(5-3-7)6-4-8/h2-6H2,1H3 InChIKey=UQZPGHOJMQTOHB-UHFFFAOYSA-N |
CWC 1A6-1 |
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| Vesicant (Nitrogen mustards) | WA ML7 b.2.c.2 | HN2: Bis(2-chloroethyl)methylamine | 51-75-2 | 4033 |
 |
CN(CCCl)CCCl | InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3 InChIKey=HAWPXGHAZFHHAD-UHFFFAOYSA-N |
CWC 1A6-2 |
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| Vesicant (Nitrogen mustards) | WA ML7 b.2.c.3 | HN3: Tris(2-chloroethyl)amine | 555-77-1 | 5561 |
 |
[H+].[Cl-].ClCCN(CCCl)CCCl | InChI=1S/C6H12Cl3N/c7-1-4-10(5-2-8)6-3-9/h1-6H2 InChIKey=FDAYLTPAFBGXAB-UHFFFAOYSA-N |
CWC 1A6-3 |
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| Central incapacitants | WA ML7 b.3.a | BZ: 3-Quinuclidinyl benzilate (*) | 6581-06-2 | 23056 |
 |
OC(C(=O)OC1CN2CCC1CC2)(c3ccccc3)c4ccccc4 | InChI=1S/C21H23NO3/c23-20(25-19-15-22-13-11-16(19)12-14-22)21(24,17-7-3-1-4-8-17)18-9-5-2-6-10-18/h1-10,16,19,24H,11-15H2 InChIKey=HGMITUYOCPPQLE-UHFFFAOYSA-N |
CWC 2A3 |
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| Defoliants | WA ML7 b.4.a | Butyl 2-chloro-4-fluorophenoxyacetate (LNF) | 1692-85-9 | 54941708 |
 |
CCCCOC(=O)COC1=C(Cl)C=C(F)C=C1 | InChI=1S/C12H14ClFO3/c1-2-3-6-16-12(15)8-17-11-5-4-9(14)7-10(11)13/h4-5,7H,2-3,6,8H2,1H3 InChIKey=IDEJTUXAJQPPPL-UHFFFAOYSA-N |
— |
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| Defoliants | WA ML7 b.4.b Free Acid Form | 2,4,5-trichlorophenoxyacetic acid mixed with 2,4-dichlorophenoxyacetic acid (Agent Orange) Note: this is the entry name given in ML7 |
8015-35-8 Note: this CAS Registry Number is not given in ML7 but can be inferred from the name given in ML7 |
24683 |
 |
OC(=O)COc1ccc(Cl)cc1Cl.OC(=O)COc1cc(Cl)c(Cl)cc1Cl | InChI=1S/C8H5Cl3O3.C8H6Cl2O3/c9-4-1-6(11)7(2-5(4)10)14-3-8(12)13;9-5-1-2-7(6(10)3-5)13-4-8(11)12/h1-2H,3H2,(H,12,13);1-3H,4H2,(H,11,12) InChIKey=WWPVVPNDJBRXMS-UHFFFAOYSA-N |
— |
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| Defoliants | WA ML7 b.4.b Butyl Ester Form | 2,4,5-trichlorophenoxyacetic acid butyl ester mixed with 2,4-dichlorophenoxyacetic acid butyl ester (Agent Orange) Note: this name is not given in ML7 but can inferred from the CAS Registry Number given in ML7 (39277-47-9) |
39277-47-9 Note: this is the entry CAS Registry Number given in ML7 |
38264 |
 |
CCCCOC(=O)COc1ccc(Cl)cc1Cl.CCCCOC(=O)COc2cc(Cl)c(Cl)cc2Cl | InChI=1S/C12H13Cl3O3.C12H14Cl2O3/c1-2-3-4-17-12(16)7-18-11-6-9(14)8(13)5-10(11)15;1-2-3-6-16-12(15)8-17-11-5-4-9(13)7-10(11)14/h5-6H,2-4,7H2,1H3;4-5,7H,2-3,6,8H2,1H3 InChIKey=OLAOGBRYSBMLAO-UHFFFAOYSA-N |
NA |
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| Defoliants | WA ML7 b.4.b Component 1 | 2,4,5-trichlorophenoxyacetic acid | 93-76-5 | 1480 |
 |
OC(=O)COc1cc(Cl)c(Cl)cc1Cl | InChI=1S/C8H5Cl3O3/c9-4-1-6(11)7(2-5(4)10)14-3-8(12)13/h1-2H,3H2,(H,12,13) InChIKey=SMYMJHWAQXWPDB-UHFFFAOYSA-N |
— |
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| Defoliants | WA ML7 b.4.b Component 2 | 2,4-dichlorophenoxyacetic acid | 94-75-7 | 1486 |
 |
OC(=O)COc1ccc(Cl)cc1Cl | InChI=1S/C8H6Cl2O3/c9-5-1-2-7(6(10)3-5)13-4-8(11)12/h1-3H,4H2,(H,11,12) InChIKey=OVSKIKFHRZPJSS-UHFFFAOYSA-N |
— |
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| Precursor | WA ML7 c.1 | Alkyl (Me, Et, n-Pr or i-Pr) phosphonyldifluorides | CR0004 | — |  |
— | — | CWC 1B9 AG 4, 23 |
— |
| Precursor | WA ML7 c.1 Example 1 | DF: Methylphosphonyldifluoride | 676-99-3 | 69610 |
 |
C[P](F)(F)=O | InChI=1S/CH3F2OP/c1-5(2,3)4/h1H3 InChIKey=PQIOSYKVBBWRRI-UHFFFAOYSA-N |
CWC 1B9 Example 1 AG 4 |
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| Precursor | WA ML7 c.2 | O-Alkyl (H or <=C10, incl. cycloalkyl) O-2-dalkyl (Me, Et, n-Pr or i-Pr)-aminoethyl alkyl (Me, Et, n-Pr or i-Pr) phosphonites and corresponding alkylated or protonated salts | CR0005 | — |  |
— | — | CWC 1B10 AG 29 |
— |
| Precursor | WA ML7 c.2 Example 1 | QL: O-Ethyl O-2-diisopropylaminoethyl methylphosphonite | 57856-11-8 | 170325 |
 |
CCOP(C)OCCN(C(C)C)C(C)C | InChI=1S/C11H26NO2P/c1-7-13-15(6)14-9-8-12(10(2)3)11(4)5/h10-11H,7-9H2,1-6H3 InChIKey=OIQVKKOBTVZIFE-UHFFFAOYSA-N |
CWC 1B10 Example 1 AG 29 |
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| Precursor | WA ML7 c.3 | Chlorosarin: O-Isopropyl methylphosphonochloridate | 1445-76-7 | 102124 |
 |
CC(C)O[P](C)(Cl)=O | InChI=1S/C4H10ClO2P/c1-4(2)7-8(3,5)6/h4H,1-3H3 InChIKey=RHAHLPAWJVKXAZ-UHFFFAOYSA-N |
CWC 1B11 |
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| Precursor | WA ML7 c.4 | Chlorosoman: O-Pinacolyl methylphosphonochloridate | 7040-57-5 | 145983 |
 |
CC(O[P](C)(Cl)=O)C(C)(C)C | InChI=1S/C7H16ClO2P/c1-6(7(2,3)4)10-11(5,8)9/h6H,1-5H3 InChIKey=XVNBZVNXJMOQEX-UHFFFAOYSA-N |
CWC 1B12 |
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| Riot control agents | WA ML7 d.1 | α-Bromobenzeneacetonitrile, (Bromobenzyl cyanide) (CA) | 5798-79-8 | 22044 |
 |
BrC(C#N)c1ccccc1 | InChI=1S/C8H6BrN/c9-8(6-10)7-4-2-1-3-5-7/h1-5,8H InChIKey=XUHFBOUSHUEAQZ-UHFFFAOYSA-N |
— |
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| Riot control agents | WA ML7 d.2 | [(2-chlorophenyl) methylene] propanedinitrile, (o-Chlorobenzylidenemalononitrile) (CS) | 2698-41-1 | 17604 |
 |
Clc1ccccc1C=C(C#N)C#N | InChI=1S/C10H5ClN2/c11-10-4-2-1-3-9(10)5-8(6-12)7-13/h1-5H InChIKey=JJNZXLAFIPKXIG-UHFFFAOYSA-N |
— |
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| Riot control agents | WA ML7 d.3 | 2-Chloro-1-phenylethanone, Phenylacyl chloride (ω-chloroacetophenone) (CN) | 532-27-4 | 10757 |
 |
ClCC(=O)c1ccccc1 | InChI=1S/C8H7ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H,6H2 InChIKey=IMACFCSSMIZSPP-UHFFFAOYSA-N |
— |
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| Riot control agents | WA ML7 d.4 | Dibenz-(b,f)-1,4-oxazephine, (CR) | 257-07-8 | — |
 |
O1c2ccccc2C=Nc3ccccc13 | InChI=1S/C13H9NO/c1-3-7-12-10(5-1)9-14-11-6-2-4-8-13(11)15-12/h1-9H InChIKey=NPUACKRELIJTFM-UHFFFAOYSA-N |
— |
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| Riot control agents | WA ML7 d.5 | 10-Chloro-5,10-dihydrophenarsazine, (Phenarsazine chloride), (Adamsite), (DM) | 578-94-9 | 11362 |
 |
Cl[As]1c2ccccc2Nc3ccccc13 | InChI=1S/C12H9AsClN/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8,15H InChIKey=PBNSPNYJYOYWTA-UHFFFAOYSA-N |
— |
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| Riot control agents | WA ML7 d.6 | N-Nonanoylmorpholine, (MPA) | 5299-64-9 | 79182 |
 |
CCCCCCCCC(=O)N1CCOCC1 | InChI=1S/C13H25NO2/c1-2-3-4-5-6-7-8-13(15)14-9-11-16-12-10-14/h2-12H2,1H3 InChIKey=NBRDJXSTGSUITP-UHFFFAOYSA-N |
— |
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