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.*
|
Wassenaar Arrangement’s Munitions List 7 (ML7) Chemicals
Curated and Structurally Annotated by Costanzi Research – www.costanziresearch.com (Last Update: May 18, 2020) |
Disclaimer. The information in this spreadsheet 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 MRV files (requires ChemAxon’s MarvinSketch to open). 6. 3D strucures from PubChem are shown with NCBI’s iCn3D. 7. MolView cards provide a good compendium of the available data, 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 | Wassenaar ML7 b.1.a | O-Alkyl (<=C10, incl. cycloalkyl) alkyl (Me, Et, n-Pr or i-Pr)-phosphonofluoridates | CR0001 | — |  |
— | — | CWC 1A1 | — |
| Nerve agents | Wassenaar 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 | CWC 1A1 Example 1 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Nerve agents | Wassenaar 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 | CWC 1A1 Example 2 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Nerve agents | Wassenaar 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 | Wassenaar 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 | CWC 1A2 Example 1 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Nerve agents | Wassenaar 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 | Wassenaar 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 | CWC 1A3 Example 1 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Sulfur mustards | Wassenaar 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 | CWC 1A4-1 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Sulfur mustards | Wassenaar 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 | CWC 1A4-2 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Sulfur mustards | Wassenaar 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 | CWC 1A4-3 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Sulfur mustards | Wassenaar 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 | CWC 1A4-4 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Sulfur mustards | Wassenaar 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 | CWC 1A4-5 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Sulfur mustards | Wassenaar 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 | CWC 1A4-6 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Sulfur mustards | Wassenaar 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 | CWC 1A4-7 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Sulfur mustards | Wassenaar 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 | CWC 1A4-8 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Sulfur mustards | Wassenaar 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 | CWC 1A4-9 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Lewisites | Wassenaar 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+ | CWC 1A5-1 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Lewisites | Wassenaar 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+ | CWC 1A5-2 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Lewisites | Wassenaar 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+ | CWC 1A5-3 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Nitrogen mustards | Wassenaar 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 | CWC 1A6-1 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Nitrogen mustards | Wassenaar 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 | CWC 1A6-2 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Nitrogen mustards | Wassenaar 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 | CWC 1A6-3 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Central incapacitants | Wassenaar 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 | CWC 2A3 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Defoliants | Wassenaar 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 | — |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Defoliants | Wassenaar 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 |
 |
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 | — |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Defoliants | Wassenaar 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 |
 |
OC(=O)COc1ccc(Cl)cc1Cl.OC(=O)COc1cc(Cl)c(Cl)cc1Cl | 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 | NA |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Defoliants | Wassenaar ML7 b.4.b Component 1 Free Acid Form | 2,4,5-trichlorophenoxyacetic acid Note: name given in ML7 |
93-76-5 Note: CAS Registry Number given in ML7 |
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) | — |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Defoliants | Wassenaar ML7 b.4.b Component 2 Free Acid Form | 2,4-dichlorophenoxyacetic acid Note: name given in ML7 |
94-75-7 Note: CAS Registry Number given in ML7 |
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) | — |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Defoliants | Wassenaar ML7 b.4.b Component 1 Butyl Ester Form | 2,4,5-trichlorophenoxyacetic acid butyl ester Note: this entry is not given in ML7 but can be inferred from the CAS Registry Number given for the mixture (39277-47-9) |
93-79-8 Note: this entry is not given in ML7 but can be inferred from the CAS Registry Number given for the mixture (39277-47-9) |
7161 |
 |
CCCCOC(=O)COc1cc(Cl)c(Cl)cc1Cl | InChI=1S/C12H13Cl3O3/c1-2-3-4-17-12(16)7-18-11-6-9(14)8(13)5-10(11)15/h5-6H,2-4,7H2,1H3 | — |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Defoliants | Wassenaar ML7 b.4.b Component 2 Butyl Ester Form | 2,4-dichlorophenoxyacetic acid butyl ester Note: this entry is not given in ML7 but can be inferred from the CAS Registry Number given for the mixture (39277-47-9) |
94-80-4 Note: this entry is not given in ML7 but can be inferred from the CAS Registry Number given for the mixture (39277-47-9) |
7206 |
 |
CCCCOC(=O)COc1ccc(Cl)cc1Cl | InChI=1S/C12H14Cl2O3/c1-2-3-6-16-12(15)8-17-11-5-4-9(13)7-10(11)14/h4-5,7H,2-3,6,8H2,1H3 | — |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Precursor | Wassenaar ML7 c.1 | Alkyl (Me, Et, n-Pr or i-Pr) phosphonyldifluorides | CR0004 | — |  |
— | — | CWC 1B9 AG 4, 23 |
— |
| Precursor | Wassenaar 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 | CWC 1B9 Example 1 AG 4 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Precursor | Wassenaar 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 | Wassenaar 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 | CWC 1B10 Example 1 AG 29 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Precursor | Wassenaar 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 | CWC 1B11 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Precursor | Wassenaar 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 | CWC 1B12 |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Riot control agents | Wassenaar 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 | — |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Riot control agents | Wassenaar 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 | — |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Riot control agents | Wassenaar 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 | — |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Riot control agents | Wassenaar 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 | — |
Download 2D Structure (MRV) Show MolView Card |
| Riot control agents | Wassenaar 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 | — |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |
| Riot control agents | Wassenaar 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 | — |
Download 2D Structure (MRV) Show 3D Structure Show MolView Card |