HN3 (nitrogen mustard)

Names
Preferred IUPAC name

2-Chloro-N,N-bis(2-chloroethyl)ethanamine

Other names

Trichlormethine
Tris(2-chloroethyl)amine
EA-1053
TL-145

Identifiers

CAS Number

* 555-77-1 Y

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL443613 N

ChemSpider |

* 5360 N

MeSH | 2,2',2+-trichlorotriethylamine

PubChem CID

* 5561

UNII |

* 66WBM7N0NM Y

InChI

* InChI=1S/C6H12Cl3N/c7-1-4-10(5-2-8)6-3-9/h1-6H2 N

Key: FDAYLTPAFBGXAB-UHFFFAOYSA-N N

SMILES

* ClCCN(CCCl)CCCl

Properties

Chemical formula

| C6H12Cl3N
Molar mass | 204.52 g·mol−1
Appearance  | Colourless liquid
Odor | Fishy, ammoniacal
Density | 1.24 g mL−1
Melting point |  −4 to −3.7 °C (24.8 to 25.3 °F; 269.1 to 269.4 K)
Boiling point |  143 °C (289 °F; 416 K)
log P | 1.306
Related compounds

Related amines

* Dimethylamine
* Trimethylamine
* N-Nitrosodimethylamine
* Diethylamine
* Triethylamine
* Diisopropylamine
* Dimethylaminopropylamine
* Diethylenetriamine
* N,N-Diisopropylethylamine
* Triisopropylamine
* Tris(2-aminoethyl)amine
* Mechlorethamine
* HN1 (nitrogen mustard)

Related compounds

* Unsymmetrical dimethylhydrazine
* Biguanide
* Dithiobiuret
* Agmatine

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

2-Chloro-N,N-bis(2-chloroethyl)ethanamine, also known as trichlormethine, tris(2-chloroethyl)amine is the organic compound with the formula N(CH2CH2Cl)3. Often abbreviated HN3 or HN-3, it is a powerful blister agent and a nitrogen mustard used for chemical warfare. HN3 was the last of the nitrogen mustard agents developed. It was designed as a military agent and is the only one of the nitrogen mustards that is still used for military purposes. It is the principal representative of the nitrogen mustards because its vesicant properties are almost equal to those of HD and thus the analogy between the two types of mustard is the strongest.[1] As a vesicant the use and production is strongly restricted within the Chemical Weapons Convention where it is classified as a Schedule 1 substance.

## Contents

* 1 Mode of action
* 2 Applications
* 3 Exposure
* 4 See also
* 5 References

## Mode of action

Nitrogen mustards react via an initial cyclization to the corresponding quaternary aziridine salt. The rate of this reaction is pH dependent because the protonated amine cannot cyclize.

## Applications

HN-3 has found some applications in chemotherapy, e.g., for Hodgkin's disease, and in some compound semiconductor research[2] but it is mainly of interest for its military uses and is the only one of these agents that remains anywhere as a military agent.[citation needed] These agents are more immediately toxic than the sulfur mustards.

## Exposure

HN-3 can be absorbed into the body by inhalation, ingestion, eye contact, and skin contact (though inhalation is the most common). The chemical is extremely toxic and may damage the eyes, skin, and respiratory tract and suppress the immune system. HN-3 penetrates and binds quickly to cells of the body, but its health effects develop slowly. The full extent of cellular injury may not be known for days.[1]

## See also

* Nitrogen mustard

## References

1. ↑ 1.0 1.1 NITROGEN MUSTARD HN-3. Emergency Response Safety and Health Database. National Institute for Occupational Safety and Health. August 22, 2008. Accessed April 10, 2009.
2. ↑ Benard, C. (1997). Chemical Vapor Deposition. Pennington, NJ, USA: The Electrochemical Society, INC. pp. 78. ISBN 1-56677-178-1.

* v
* t
* e

* Agents used in chemical warfare
* incapacitation
* riot control

Blood|

* Cyanogen
* Cyanogen bromide
* Cyanogen chloride (CK)
* Hydrogen cyanide (AC)
* Arsine
* Vinyl arsine

Blister|

* Arsenicals
* Ethyldichloroarsine (ED)
* Methyldichloroarsine (MD)
* Phenyldichloroarsine (PD)
* Lewisite (L)
* Mustard gas (HD H HT HL HQ)
* Nitrogen mustard
* HN1
* HN2
* HN3
* TL-301
* Nitrosocarbamates
* KB-16

Nerve|

| G-agents|

* Tabun (GA)
* Sarin (GB)
* Chlorosarin (GC)
* Soman (GD)
* Ethylsarin (GE)
* Cyclosarin (GF)
* GH
* GJ
* GK
* GL
* GM
* GN
* GO
* GP
* GQ
* GR
* GS
* GT
* GU
* Fluorotabun
* GV
* GV1
* GV2
* GV3
* GV4
* GV5
* GV6
* EA-1356
* EA-3534
* EA-4352
* EA-5414
* EA-5488
* Thiosarin
* Thiosoman
* Thiocyclosarin
* Crotylsarin

|

V-agents|

* EA-2192
* EA-3148
* EA-3317
* VD
* VE
* VF
* VG
* VH
* VJ
* VK
* VL
* VM
* VN
* VO
* VP
* VQ
* VR
* VS
* VT
* VU
* VV
* VW
* VY
* VZ
* VX
* V1
* V2
* V3
* V4
* V5
* V6
* IVX
* IIVx
* Chinese VX
* V-sub x (GD-7)

Novichok agents|

* A-230
* A-232
* A-234
* A-242
* A-262
* C01-A035
* C01-A039
* C01-A042

Carbamates|

* EA-3887
* EA-3887A
* EA-3948
* EA-3966
* EA-3990
* EA-4026
* EA-4038
* EA-4048
* EA-4056
* EA-4057
* EA-4181
* T-1123
* Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)

Other|

* EA-2012
* EA-2054
* EA-2098
* EA-2613
* 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
* Neopentylene fluorophosphate

Precursors|

* Chlorosarin
* Chlorosoman
* Cyclohexanol
* 1,8-Dibromooctane
* N,N-Diisopropylaminoethanol
* Dimethylamidophosphoric dichloride
* Dimethylamidophosphoric dicyanide
* Isopropyl alcohol
* Methyldichlorophosphine
* Methylphosphonic acid dichloride
* Methylphosphonyl difluoride
* Pinacolone
* Pinacolyl alcohol
* QL
* 3,3,5-Trimethylcyclohexanol

Neurotoxins|

* Saxitoxin (TZ)
* Botulinum toxin (BTX)
* Tetanospasmin (TeNT)
* Chlorophenylsilatrane
* Tetrodotoxin

Nettle|

* Phosgene oxime (CX)

Pulmonary/Choking agent|

* Chlorine
* Phosgene (CG)
* Perfluoroisobutene
* Chloropicrin (PS)
* Diphosgene (DP)
* Disulfur decafluoride
* Acrolein
* Ethyl bromoacetate
* Perchloromethyl mercaptan

Vomiting agent|

* Adamsite
* Chloropicrin
* Diphenylchlorarsine
* Diphenylcyanoarsine
* Diphenylaminecyanoarsine

Incapacitating|

* Agent 15 (BZ)
* Dimethylheptylpyran (DMHP)
* EA-3167
* EA-3443
* EA-3580
* EA-3834
* Kolokol-1
* LSD-25
* PAVA spray
* Sleeping gas

Riot control|

* Xylyl bromide
* Pepper spray (OC)
* Mace (spray)
* CN
* CS
* CR
* CNS

Other|

* Methyl fluoroacetate
* Fluoroethyl fluoroacetate
* Ricin
* Abrin
* Enterotoxin type B
* Depleted uranium
* post-combustion uranium oxides

* List of chemical warfare agents
* CB military symbol

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