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. 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. The compound is also used medically for certain conditions. It sublimes in vacuum at 280 °C. It has a tetrahedral cage-like structure similar to adamantane. 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.