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Chemical Compound Review:

Octogen 1,3,5,7-tetranitro-1,3,5,7- tetrazocane

Synonyms: Oktogen, beta-Hmy, HW 4, CHEBI:33176, HSDB 5893, ...

Testud, F. et al., Balakrishnan, V.K. et al., Kitts, C.L. et al., Oh, S.Y. et al., Zhao, J.S. et al., et al.

Testud, Descotes, Le Meur, Hawari, Halasz, Beaudet, Paquet, Ampleman, Thiboutot, Robidoux, Hawari, Thiboutot, Ampleman, Sunahara, Pan, Zhang, Tian, Jones, Liu, Anderson, Wang, Cobb,

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Disease relevance of Tetramethylenetetranitramine

Three species of the family Enterobacteriaceae that biochemically reduced hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) were isolated from nitramine explosive-contaminated soil [1].
Chronic toxicity of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) in soil determined using the earthworm (Eisenia andrei) reproduction test [2].
Metabolism of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine by Clostridium bifermentans strain HAW-1 and several other H2-producing fermentative anaerobic bacteria [3].
CONCLUSION: The rarity of acute human poisonings by octogen is due to the infrequent use of this explosive and, more importantly, its very low oral bioavailability [4].

High impact information on Tetramethylenetetranitramine

NDAB is also produced during the alkaline hydrolysis of either RDX or octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) and during the photolysis of RDX [5].
Enzyme catalyzed biotransformation of the energetic chemical octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) is not known [6].
Biodegradation of the nitramine explosives hexahydro-1,3,5-trinitro-1,3,5-triazine and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine in cold marine sediment under anaerobic and oligotrophic conditions [7].
Elevated octogen concentrations were measured in his plasma, which confirmed occupational exposure to the explosive [4].
CASE REPORT: A 28-year-old man with no history of epilepsy was admitted to the Emergency Department for seizures that had developed during the night after a full working day when he manually sieved large amounts of dry octogen [4].

Biological context of Tetramethylenetetranitramine

Biotransformation routes of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine by municipal anaerobic sludge [8].
In the present study, we examined the kinetics, products, and mechanisms of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) degradation with elemental iron [9].

Associations of Tetramethylenetetranitramine with other chemical compounds

RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine) and HMX (octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine) are cyclic nitramines ((CH2NNO2)n; n = 3 or 4, respectively) widely used as energetic chemicals [10].
Hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX, I) and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) hydrolyze at pH > 10 to form end products including NO2-, HCHO, HCOOH, NH3, and N2O, but little information is available on intermediates, apart from the tentatively identified pentahydro-3,5-dinitro-1,3,5-triazacyclohex-1-ene (II) [11].

Analytical, diagnostic and therapeutic context of Tetramethylenetetranitramine

Liquid chromatography/electrospray ionization tandem mass spectrometry analysis of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) [12].

References

Isolation of three hexahydro-1,3,5-trinitro-1,3,5-triazine-degrading species of the family Enterobacteriaceae from nitramine explosive-contaminated soil. Kitts, C.L., Cunningham, D.P., Unkefer, P.J. Appl. Environ. Microbiol. (1994) [Pubmed]
Chronic toxicity of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) in soil determined using the earthworm (Eisenia andrei) reproduction test. Robidoux, P.Y., Hawari, J., Thiboutot, S., Ampleman, G., Sunahara, G.I. Environ. Pollut. (2001) [Pubmed]
Metabolism of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine by Clostridium bifermentans strain HAW-1 and several other H2-producing fermentative anaerobic bacteria. Zhao, J.S., Paquet, L., Halasz, A., Manno, D., Hawari, J. FEMS Microbiol. Lett. (2004) [Pubmed]
Acute occupational poisoning by octogen: first case report. Testud, F., Descotes, J., Le Meur, B. Clinical toxicology (Philadelphia, Pa.) (2006) [Pubmed]
Metabolism of the aliphatic nitramine 4-nitro-2,4-diazabutanal by Methylobacterium sp. strain JS178. Fournier, D., Trott, S., Hawari, J., Spain, J. Appl. Environ. Microbiol. (2005) [Pubmed]
Mechanism of xanthine oxidase catalyzed biotransformation of HMX under anaerobic conditions. Bhushan, B., Paquet, L., Halasz, A., Spain, J.C., Hawari, J. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
Biodegradation of the nitramine explosives hexahydro-1,3,5-trinitro-1,3,5-triazine and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine in cold marine sediment under anaerobic and oligotrophic conditions. Zhao, J.S., Greer, C.W., Thiboutot, S., Ampleman, G., Hawari, J. Can. J. Microbiol. (2004) [Pubmed]
Biotransformation routes of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine by municipal anaerobic sludge. Hawari, J., Halasz, A., Beaudet, S., Paquet, L., Ampleman, G., Thiboutot, S. Environ. Sci. Technol. (2001) [Pubmed]
Reductive transformation of hexahydro-1,3,5-trinitro-1,3,5-triazine, octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine, and methylenedinitramine with elemental iron. Oh, S.Y., Cha, D.K., Kim, B.J., Chiu, P.C. Environ. Toxicol. Chem. (2005) [Pubmed]
Reduction of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine by zerovalent iron: product distribution. Monteil-Rivera, F., Paquet, L., Halasz, A., Montgomery, M.T., Hawari, J. Environ. Sci. Technol. (2005) [Pubmed]
Alkaline hydrolysis of the cyclic nitramine explosives RDX, HMX, and CL-20: new insights into degradation pathways obtained by the observation of novel intermediates. Balakrishnan, V.K., Halasz, A., Hawari, J. Environ. Sci. Technol. (2003) [Pubmed]
Liquid chromatography/electrospray ionization tandem mass spectrometry analysis of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX). Pan, X., Zhang, B., Tian, K., Jones, L.E., Liu, J., Anderson, T.A., Wang, J.S., Cobb, G.P. Rapid Commun. Mass Spectrom. (2006) [Pubmed]

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