Cyclotrimethylenetrinitramine (T3D0092)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-03-06 18:58:04 UTC
Update Date2014-12-24 20:21:05 UTC
Accession NumberT3D0092
Identification
Common NameCyclotrimethylenetrinitramine
ClassSmall Molecule
DescriptionCyclotrimethylenetrinitramine 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. (5)
Compound Type
  • Amine
  • Explosive Agent
  • Industrial/Workplace Toxin
  • Nitrite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1,3, 5-Trinitrohexahydro-1,3,5-triazine
1,3,5-Triaza-1,3,5-trinitrocyclohexane
1,3,5-Trinitro-1,3, 5-triazacyclohexane
1,3,5-Trinitro-1,3,5-triazacyclohexane
1,3,5-Trinitro-1,3,5-triazinane
1,3,5-Trinitrohexahydro-1,3,5-triazine
1,3,5-trinitrohexahydro-p-triazine
1,3,5-Trinitrohexahydro-s-triazine
1,3,5-Trinitroperhydro-1,3, 5-triazine
1,3,5-Trinitroperhydro-1,3,5-triazine
Cyclonit
Cyclonite
Cyclonite (cyclotrimethylene trinitramine)
Cyclotrimethylenenitramine
Geksogen
Hexahydro-1,3 ,5-trinitro-1,3 5-triazine
Hexahydro-1,3, 5-trinitro-1,3,5-triazine
Hexahydro-1,3,5-trinitro-1,3,5-triazine
Hexahydro-1,3,5-trinitro-s-triazine
Hexogen
Hexolite
Perhydro-1,3,5-trinitro-1,3,5-triazine
RDX
SYM-trimethylene trinitramine
SYM-trimethylenetrinitramine
Trinitrocyclotrimethylene triamine
Trinitrohexahydrotriazine
Trinitrotrimethylenetriamine
Chemical FormulaC3H6N6O6
Average Molecular Mass222.116 g/mol
Monoisotopic Mass222.035 g/mol
CAS Registry Number121-82-4
IUPAC Name1,3,5-trinitro-1,3,5-triazinane
Traditional Namecyclotrimethylenetrinitramine
SMILES[O-][N+](=O)N1CN(CN(C1)[N+]([O-])=O)[N+]([O-])=O
InChI IdentifierInChI=1S/C3H6N6O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H2
InChI KeyInChIKey=XTFIVUDBNACUBN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,3,5-triazinanes. These are triazinanes having three nitrogen ring atoms at the 1-, 3-, and 5- positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTriazinanes
Sub Class1,3,5-triazinanes
Direct Parent1,3,5-triazinanes
Alternative Parents
Substituents
  • 1,3,5-triazinane
  • Organic nitro compound
  • Azacycle
  • Organic 1,3-dipolar compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point205.5°C
Boiling PointNot Available
Solubility0.0597 mg/mL at 25 °C [YALKOWSKY,SH & HE,Y (2003)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.34 g/LALOGPS
logP1.07ALOGPS
logP-0.48ChemAxon
logS-2.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area147.18 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.93 m³·mol⁻¹ChemAxon
Polarizability16.08 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0090000000-3bfc43492d47aef742b12021-09-24View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-16bf5c8406814589961e2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0290000000-528c091277c138ba31b52016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06wc-9310000000-ade9f5f10d78c1e4713f2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2090000000-49d83bfe928d03d90e572016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-9440000000-0c5e5b1c7f10344e7e2d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3910000000-98930ca4c173df4a75cf2016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000w-9100000000-9703866ef7f20ad53fe82014-09-20View Spectrum
Toxicity Profile
Route of ExposureOral (5); inhalation (5) ; dermal (5)
Mechanism of ToxicityRDX 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. (2, 5)
MetabolismThere 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. (5, 1)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesRDX 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. (5)
Minimum Risk LevelAcute Oral: 0.06 mg/kg/day (Rat) (5) Intermediate Oral: 0.03 mg/kg/day (Rat) (5)
Health EffectsRDX can cause seizures. Inhalation exposure to RDX can lead to gastrointestinal, hematological, hepatic, and renal effects. (5)
SymptomsSymptoms 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. (3)
TreatmentFollowing 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. (4)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID8490
ChEMBL IDNot Available
ChemSpider ID8177
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID24556
BioCyc IDCPD-9356
CTD IDC009160
Stitch IDCyclotrimethylenetrinitramine
PDB IDNot Available
ACToR ID3621
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0092.pdf
General References
  1. 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 ]
  2. Casarett LJ, Klaassen CD, and Watkins JB (2003). Casarett and Doull's essentials of toxicology. New York: McGraw-Hill/Medical Pub. Div.
  3. Bingham, E, Cohrssen, B, and Powell, CH (2001). Patty's Toxicology Volumes 1-9. 5th ed. New York, N.Y: John Wiley & Sons.
  4. Rumack BH (2009). POISINDEX(R) Information System. Englewood, CO: Micromedex, Inc. CCIS Volume 141, edition expires Aug, 2009.
  5. 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]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available