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T3D0092 - Cyclotrimethylenetrinitramine

Record Information
Version 1.0
Creation Date 2009-03-06 18:58:04 UTC
Update Date 2013-04-25 08:32:48 UTC
Accession Number T3D0092
Identification
Common Name Cyclotrimethylenetrinitramine
Description Cyclotrimethylenetrinitramine is a chemical compound also called RDX, which stands for Royal Demolition Explosive. It is also known as cyclonite or hexogen. The chemical name for RDX is 1,3,5-trinitro-1,3,5-triazine and it is a very explosive white powder that creates fumes when it is burned with other substances. As such, it is used as an explosive and it is also used in combination with other ingredients in explosives. RDX is a synthetic product that does not occur naturally in the environment. (R478)
Compound Type
  • Organic Compound
  • Amine
  • Explosive
  • Nitrite
Chemical Structure
Thumb
MOL SDF SMILES InChI
Synonyms
  1. 1,3, 5-Trinitrohexahydro-1,3,5-triazine
  2. 1,3,5-Triaza-1,3,5-trinitrocyclohexane
  3. 1,3,5-Triazacyclohexane 1,3,5-trinitro-
  4. 1,3,5-Trinitro-1,3, 5-triazacyclohexane
  5. 1,3,5-Trinitro-1,3,5-triazacyclohexane
  6. 1,3,5-Trinitro-1,3,5-triazinane
  7. 1,3,5-Trinitrohexahydro-1,3,5-triazine
  8. 1,3,5-trinitrohexahydro-p-triazine
  9. 1,3,5-Trinitrohexahydro-s-triazine
  10. 1,3,5-Trinitroperhydro-1,3, 5-triazine
  11. 1,3,5-Trinitroperhydro-1,3,5-triazine
  12. Cyclonit
  13. Cyclonite
  14. Cyclonite (cyclotrimethylene trinitramine)
  15. Cyclotrimethylenenitramine
  16. Cyclotrimethylenetrinitramine
  17. Cyclotrimethylenetrinitramine (RDX)
  18. Cyklonit [czech]
  19. Esaidro-1,3,5-trinitro-1,3,5-triazina [Italian]
  20. Geksogen
  21. Heksogen [polish]
  22. Hexahydro-1,3 ,5-trinitro-1,3 5-triazine
  23. Hexahydro-1,3, 5-trinitro-1,3,5-triazine
  24. Hexahydro-1,3,5-trinitro-1,3,5-triazin [German]
  25. Hexahydro-1,3,5-trinitro-1,3,5-triazine
  26. Hexahydro-1,3,5-trinitro-s-triazine
  27. Hexogeen(dutch)
  28. Hexogen
  29. Hexogen (explosive)
  30. Hexolite
  31. Perhydro-1,3,5-trinitro-1,3,5-triazine
  32. RDX
  33. SYM-trimethylene trinitramine
  34. SYM-trimethylenetrinitramine
  35. Trimethyleentrinitramine(dutch)
  36. Trinitrocyclotrimethylene triamine
  37. Trinitrohexahydrotriazine
  38. Trinitrotrimethylenetriamine
Chemical Formula C3H6N6O6
Average Molecular Weight 222.1163
Monoisotopic Molecular Weight 222.034881954
Chemical IUPAC Name
hexogen
CAS Registry Number 121-82-4
SMILES
[O-][N+](=O)N1CN(CN(C1)[N+]([O-])=O)[N+]([O-])=O
InChI Identifier
InChI=1S/C3H6N6O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H2
InChI Key InChIKey=XTFIVUDBNACUBN-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Heterocyclic Compounds
Class Nitro Compounds
Sub Class Not Available
Direct Parent Nitro Compounds
Alternative Parents
  • Organic Oxoazanium Compounds
  • Aminals
Molecular Framework Aliphatic Heteromonocyclic Compounds
Substituents
  • organonitrogen compound
  • organic oxoazanium
  • aminal
External Descriptors
  • 1,3,5-triazinanes(ChEBI)
  • N-nitro compound(ChEBI)
DrugBank ID Not Available
PubChem Compound ID 8490 Link_out
KEGG ID Not Available
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID 24556 Link_out
BioCyc ID CPD-9356 Link_out
CTD ID C009160 Link_out
Stitch ID Cyclotrimethylenetrinitramine Link_out
PDB ID Not Available
ACToR ID 3621
Wikipedia Link Not Available
Physical Properties
Appearance White powder.
Melting Point 205.5 C
Solubility 0.0597 mg/mL at 25 °C [YALKOWSKY,SH & HE,Y (2003)]
Predicted LogP -0.4816021589999989
Toxicity Profile
Route of Exposure Oral (R478); inhalation (R478) ; dermal (R478)
Mechanism of Action RDX can get into the lungs after breathing in the fumes of burning RDX or breathing in the dust from powdered RDX. It can also enter the body after ingestion of contaminated water. It may also pass through the skin into the bloodstream or enter through cuts or breaks in the skin. It also blocks electron transport. (R029, R478)
Metabolism There are no studies available regarding RDX metabolites in humans following inhalation, oral, or dermal exposure. Some studies reported that 4-nitro-2,4-diazabutanal, and nitrite ions are produced through biotransformation of RDX by cytochrome P450. The limited toxicological data show that RDX is absorbed through the gastrointestinal system, lungs, and skin, and is distributed to the cerebrospinal fluid, plasma, urine, and feces. RDX will leaves the body in the breath and urine within a few days. (R478,R489)
Toxicity Values Not Available
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources RDX is used as an explosive and is also used in combination with other ingredients in explosives. Exposure may occur by breathing dust containing RDX, contact with the skin, or drinking contaminated water. (R478)
Minimum Risk Level Acute Oral: 0.06 mg/kg/day (Rat) (R478) Intermediate Oral: 0.03 mg/kg/day (Rat) (R478)
Health Effects RDX can cause seizures. Inhalation exposure to RDX can lead to gastrointestinal, hematological, hepatic, and renal effects. (R478)
Symptoms Symptoms of RDX exposure include epileptiform seizures, insomnia, restlessness, headache, dizziness, nausea, vomiting and irritability. Temporary postconvulsive amnesia, malaise, fatigue, and asthenia can follow the seizures. (R327)
Treatment Following oral exposure, symptomatic patients should be given adequate respiratory support during seizures. Monitor liver and renal function tests and urinalysis in patients with significant exposure. Following inhalation exposure, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Following eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. (R383)
References
General References
  • R478 — ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for cyclotrimethylenetrinitramine (RDX). U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  • R029 — Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
  • R489 — Bhushan B, Trott S, Spain JC, Halasz A, Paquet L, Hawari J: Biotransformation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by a rabbit liver cytochrome P450: insight into the mechanism of RDX biodegradation by Rhodococcus sp. strain DN22. Appl Environ Microbiol. 2003 Mar;69(3):1347-51. [12620815 Link_out]
  • R327 — Bingham, E, Cohrssen, B, and Powell, CH (2001). Patty's Toxicology Volumes 1-9. 5th ed. New York, N.Y: John Wiley & Sons.
  • R383 — Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.

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