Basic information
- CAS
15825-70-4- Standard SMILES
O=[N+]([O-])OC[C@@H](O[N+](=O)[O-])[C@@H](O[N+](=O)[O-])[C@H](O[N+](=O)[O-])[C@@H](CO[N+](=O)[O-])O[N+](=O)[O-]- InChIKey
DGMJZELBSFOPHH-KVTDHHQDSA-N- Molecular formula
- C6H8N6O18
- Average molar mass
- 452.16 g/mol
- Monoisotopic mass
- 451.98950743
Overview
Shipped as a slurry or wet mass of colorless crystals. Must be shipped wet with at least 40% water or water and denatured alcohol mixture. May explode due to shock, heat, flame, or friction if dried. The primary hazard is the blast of an instantaneous explosion and not flying projectiles and fragments.
Names & identifiers
- Preferred name
- Mannitol Hexanitrate
- IUPAC
- [(2R,3R,4R,5R)-1,2,4,5,6-pentanitrooxyhexan-3-yl] nitrate
- English name
- Mannitol hexanitrate,wetted with not less than 40% water,or mixture of alcohol and water,by mass
- Molecular formula
- C6H8N6O18
- Molecular weight
- 452.16
Names & synonyms
MANNITOL HEXANITRATEd-mannitol hexanitrate15825-70-4D-Mannitol, hexanitratemannite hexanitrateHexanitrato de manitolHexanitrate de mannitolMannityli nitrasHexanitrate of D-mannitolMannitoli hexanitrasMannitolo esanitratoMannitol hexanitrate [INN]
Show more names
MaxitateNitromannitolMannitylNitrateHexanitromannitehexanitromannitolmannitol hexanitrate nitromanniteD-Mannitol, 1,2,3,4,5,6-hexanitrate[(2R,3R,4R,5R)-1,2,4,5,6-pentanitrooxyhexan-3-yl] nitratenitric acid [(1R,2R,3R)-1-[(1R)-1,2-dinitrooxyethyl]-2,3,4-trinitrooxy-butyl] ester
NA0133Mannitylium hexanitricum130-39-2Mannitolo esanitrato [DCIT]UNII-99AU28W1G9HSDB 7834Mannitoli hexanitras [INN-Latin]99AU28W1G9
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 330 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 18
- Rotatable bonds
- 11
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 578
Experimental & physicochemical properties
Density1.8 g/cu cm at 20 °C
Color/Form
Colorless crystals
Long needles in regular clusters from alcohol
Solubility
Soluble in alcohol, acetone, ether
Very soluble in benzene
Insoluble in water
Boiling PointExplodes
DecompositionUpon decomposition it emits toxic fumes of /nitroxides/.
Melting Point107 °C
Physical Description
Shipped as a slurry or wet mass of colorless crystals. Must be shipped wet with at least 40% water or water and denatured alcohol mixture. May explode due to shock, heat, flame, or friction if dried. The primary hazard is the blast of an instantaneous explosion and not flying projectiles and fragments.
Other Experimental PropertiesUpon decomposition it emits toxic fumes of NOx.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H200: (Deleted) Unstable Explosive [Danger Explosives]
P201, P202, P281, P372, P373, P380, P401, and P501 (click each P-code to see the statement)
Danger
H201: (Deleted) Explosive; mass explosion hazard [Danger Explosives]
P210, P230, P240, P250, P280, P370+P380, P372, P373, P401, and P501 (click each P-code to see the statement)
Hazard information
DOT LabelExplosive 1.1D
Fire HazardsExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
Fire PotentialDangerous fire and explosion risk
Health HazardsExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
RCRA RequirementsD003; A solid waste containing mannitol hexanitrate may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste.
Reactivity AlertsStrong Oxidizing Agent
Reactivity Profile
Nitroalkanes, such as MANITOL HEXANITRATE, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. Nitroalkanes are milder oxidizing agents, but still react violently with reducing agents at higher temperature and pressures. Nitroalkanes react with inorganic bases to form explosive salts. The presence of metal oxides increases the thermal sensitivity of nitroalkanes. Nitroalkanes with more than one nitro group are generally explosive. Nitroalkanes are insoluble in water.
Chemistry & industry
Pharmacology
Biological Half-Life
Blood samples were drawn from the carotid artery of rats treated with radioactive glyceryl-trinitrate (C-14-GTN), isosorbide-dinitrate (C-14-ISD) or mannitol-hexanitrate (C-14-MHN). ... Results from the blood clearance investigations showed an extremely rapid initial fall in the blood concentration of the parent compound, with a half life of about 10 to 14 seconds.
Metabolism/Metabolites
The nature of the formation of nitrite ion from nitrate esters in the presence of blood and tissue suspensions from rabbits was examined. Suspensions were made by homogenizing one part fresh tissue from white-rabbits and four parts aqueous buffer. Equal volumes of the homogenate and a solution of nitrate ester were mixed. Samples for nitrite assay were removed and analyzed. Inorganic nitrite was formed rapidly when glycerol-trinitrate was incubated with the liver homogenate but not with muscle homogenate or diluted whole blood. The rate of nitrite formation from glycerol-trinitrate, l-glucosan-trinitrate, and mannitol-hexanitrate was influenced by pH. Highest volumes formed when the pH was 8.4. Heat had an inactivation effect for glycerol-trinitrate and mannitol-hexanitrate but only partial inactivation took place at low temperatures for l-glucosan-trinitrate while at temperatures between 60 and 100 degrees-C, activity increased. For mannitol-hexanitrate, the amount of nitrite liberated increased with increasing ester concentration. The authors conclude that inorganic nitrite is formed from nitrate esters of polyhydric alcohols by two systems occurring in normal rabbit tissues. The first, occurring principally in the liver, is heat labile while the second, found in liver, muscle, and blood, is activated by heat.
Absorption, Distribution and Excretion
... Blood samples were drawn from the carotid artery of rats treated with radioactive glyceryl-trinitrate (C-14-GTN), isosorbide-dinitrate (C-14-ISD) or mannitol-hexanitrate (C-14-MHN). The lifetime of the labeled organic nitrates was determined. In another experiment, female rats were intravenously administered one of the radioactive nitrates. Urine was collected hourly, and the samples were counted for radioactive material. A separate experiment was conducted with human liver homogenate, and organic nitrate-reductase activity was measured. In a fourth experiment, rats were treated orally with C-14-GTN and the lymph was collected. Results from the blood clearance investigations showed an extremely rapid initial fall in the blood concentration of the parent compound, with a half life of about 10 to 14 seconds. The disappearance of C-14-MHN was more than 99 percent complete by 90 seconds. Blood was cleared of more than 80 percent of C-14-GTN or C-14-ISD by 1 minute. In the urine samples, the sum of C-14-ISD and C-14-MHN metabolites approached 100 percent of the administered amount. However, the C-14-GTN did not approach 100 percent. The human liver contained the same enzyme capacity for denitration as the rat liver. In the fourth experiment, less than 1 percent of orally administered C-14-GTN was recovered in the lymph after 7 hours.
Related reactions
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Compound notes
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