Hexamethylenetetramine

Hexamethylenetetramine
Names
	Preferred IUPAC name 1,3,5,7-Tetraazaadamantane
	Other names Hexamine; Methenamine; Urotropine; Formin; Aminoform; HMTA;
Identifiers
CAS Number	100-97-0 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	2018
ChEBI	CHEBI:6824 ;
ChEMBL	ChEMBL1201270 ;
ChemSpider	3959 ;
DrugBank	DB06799;
ECHA InfoCard	100.002.642
EC Number	202-905-8;
E number	E239 (preservatives)
Gmelin Reference	26964
KEGG	D00393 ;
MeSH	Methenamine
PubChem CID	4101;
RTECS number	MN4725000;
UNII	J50OIX95QV ;
UN number	1328
CompTox Dashboard (EPA)	DTXSID6020692 ;
	InChI InChI=1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2 Key: VKYKSIONXSXAKP-UHFFFAOYSA-N ; InChI=1/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2 Key: VKYKSIONXSXAKP-UHFFFAOYAW;
	SMILES C1N2CN3CN1CN(C2)C3;
Properties
Chemical formula	C6H12N4
Molar mass	140.186 g/mol
Appearance	White crystalline solid
Odor	Fishy, ammonia like
Density	1.33 g/cm3 (at 20 °C)
Melting point	280 °C (536 °F; 553 K) (sublimes)
Solubility in water	85.3 g/100 mL
Solubility	Soluble in chloroform, methanol, ethanol, acetone, benzene, xylene, ether
Solubility in chloroform	13.4 g/100 g (20 °C)
Solubility in methanol	7.25 g/100 g (20 °C)
Solubility in ethanol	2.89 g/100 g (20 °C)
Solubility in acetone	0.65 g/100 g (20 °C)
Solubility in benzene	0.23 g/100 g (20 °C)
Acidity (pKa)	4.89
Pharmacology
ATC code	J01XX05 (WHO)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Highly combustible, harmful
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H228, H317
Precautionary statements	P210, P240, P241, P261, P272, P280, P302+P352, P321, P333+P313, P363, P370+P378, P501
NFPA 704 (fire diamond)	2 3 1
Flash point	250 °C (482 °F; 523 K)
Autoignition; temperature	410 °C (770 °F; 683 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Hexamethylenetetramine (HMTA), also known as 1,3,5,7-tetraazaadamantane, is a heterocyclic organic compound with diverse applications.^[2]^[3] It has the chemical formula (CH₂)₆N₄ and is a white crystalline compound that is highly soluble in water and polar organic solvents. It is useful in the synthesis of other organic compounds, including plastics, pharmaceuticals, and rubber additives.^[2]^[3] The compound is also used medically for certain conditions.^[4]^[5] It sublimes in vacuum at 280 °C. It has a tetrahedral cage-like structure similar to adamantane.^[3] The four vertices are occupied by nitrogen atoms, which are linked by methylene groups. Although the molecular shape defines a cage, no void space is available at the interior.

^ Cooney AP, Crampton MR, Golding P (1986). "The acid-base behaviour of hexamine and its N-acetyl derivatives". J. Chem. Soc., Perkin Trans. 2 (6): 835–839. doi:10.1039/P29860000835.
^ ^a ^b Dreyfors JM, Jones SB, Sayed Y (November 1989). "Hexamethylenetetramine: a review". American Industrial Hygiene Association Journal. 50 (11): 579–585. doi:10.1080/15298668991375191. PMID 2688388.
^ ^a ^b ^c Blažzević, Nikola; Kolbah, D.; Belin, Branka; Šunjić, Vitomir; Kajfež, Franjo (1979). "Hexamethylenetetramine, A Versatile Reagent in Organic Synthesis". Synthesis. 1979 (3). Georg Thieme Verlag KG: 161–176. doi:10.1055/s-1979-28602. ISSN 0039-7881.
^ Cite error: The named reference LoHammerZegarra2014 was invoked but never defined (see the help page).
^ Connolly M, de Berker D (2003). "Management of primary hyperhidrosis: a summary of the different treatment modalities". Am J Clin Dermatol. 4 (10): 681–697. doi:10.2165/00128071-200304100-00003. PMID 14507230.

[1] Cooney AP, Crampton MR, Golding P (1986). "The acid-base behaviour of hexamine and its N-acetyl derivatives". J. Chem. Soc., Perkin Trans. 2 (6): 835–839. doi:10.1039/P29860000835.

[DreyforsJonesSayed1989-2] Dreyfors JM, Jones SB, Sayed Y (November 1989). "Hexamethylenetetramine: a review". American Industrial Hygiene Association Journal. 50 (11): 579–585. doi:10.1080/15298668991375191. PMID 2688388.

[BlažzevićKolbahBelin1979-3] Blažzević, Nikola; Kolbah, D.; Belin, Branka; Šunjić, Vitomir; Kajfež, Franjo (1979). "Hexamethylenetetramine, A Versatile Reagent in Organic Synthesis". Synthesis. 1979 (3). Georg Thieme Verlag KG: 161–176. doi:10.1055/s-1979-28602. ISSN 0039-7881.

[LoHammerZegarra2014-4] Cite error: The named reference LoHammerZegarra2014 was invoked but never defined (see the help page).

[ConnollydeBerker2003-5] Connolly M, de Berker D (2003). "Management of primary hyperhidrosis: a summary of the different treatment modalities". Am J Clin Dermatol. 4 (10): 681–697. doi:10.2165/00128071-200304100-00003. PMID 14507230.

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