{{위키데이터 속성 추적}}
{{chembox
| Verifiedfields = changed
| Watchedfields  = changed
| verifiedrevid  = 457472844
| Name           = 
| ImageFile      = 
| ImageFileL1    = Hexamine.svg
| ImageFileR1    = Hexamine-3D-balls.png
| IUPACName      = 1,3,5,7-Tetraazatricyclo[3.3.1.1<sup>3,7</sup>]decane
| OtherNames     = Hexamine; Methenamine; <BR>Urotropine; 1,3,5,7-
tetraazaadamantane, Formin, Aminoform
| SystematicName = 
| Section1       = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3959
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = J50OIX95QV
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1201270
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00393
| Beilstein = 2018
| Gmelin =  26964
| DrugBank = DB06799
| InChI = 1/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
| InChIKey = VKYKSIONXSXAKP-UHFFFAOYAW
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H12N4/c1-7-2-9-4-8(1)5-10(3-7)6-9/h1-6H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VKYKSIONXSXAKP-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =100-97-0
| EINECS =202-905-8
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 6824
| PubChem =4101
| SMILES =C1N2CN3CN1CN(C2)C3
| MeSHName =Methenamine
  }}
| Section2       = {{Chembox Properties
| Formula =C<sub>6</sub>H<sub>12</sub>N<sub>4</sub>
| MolarMass =140.186 g/mol
| Appearance =White crystalline solid
| Odor = Fishy, ammonia like
| MeltingPtC = 280
| MeltingPt_notes = ([[Sublimation (chemistry)|sublimes]])
| BoilingPt =
| Solubility =85.3&nbsp;g/100&nbsp;mL
| SolubleOther = Soluble in [[클로로포름]], [[methanol]], [[에탄올]], [[아세톤]], [[벤젠]], [[xylene]], [[에터]]
| Solubility1 =13.4 g/100 g (20&nbsp;°C)
| Solvent1 = chloroform
| Solubility2 =7.25 g/100 g (20&nbsp;°C)
| Solvent2 = methanol
| Solubility3 =2.89 g/100 g (20&nbsp;°C)
| Solvent3 = ethanol
| Solubility4 =0.65 g/100 g (20&nbsp;°C)
| Solvent4 = acetone
| Solubility5 =0.23 g/100 g (20&nbsp;°C)
| Solvent5 = benzene
| Density =1.33&nbsp;g/cm<sup>3</sup> (at 20&nbsp;°C)
| pKa = 4.89<ref>{{저널 인용| title=The acid-base behaviour of hexamine and its ''N''-acetyl derivatives | last=Cooney | first=A. P. | author2=Crampton, M. R. | author3=Golding, P. | journal=[[Perkin Transactions|J. Chem. Soc., Perkin Trans. 2]] | year=1986 | issue=6 | pages=835–839 | doi=10.1039/P29860000835}}</ref>
  }}
| Section3       = 
| Section4       = 
| Section5       = 
| Section6       = {{Chembox Pharmacology
| ATCCode_prefix = J01
| ATCCode_suffix = XX05
}}
| Section7       = {{Chembox Hazards
| MainHazards =Highly combustible, harmful
| NFPA-H = 2
| NFPA-F = 3
| NFPA-R = 1
| GHSSignalWord = WARNING
| GHSPictograms = {{GHS02}} {{GHS07}}
| HPhrases = {{H-phrases|228|317}}
| PPhrases = {{P-phrases|210|240|241|261|272|280|302+352|321|333+313|363|370+378|501}}
| FlashPtC = 250
| AutoignitionPtC = 410
  }}
}}
'''헥사메틸렌테트라민'''({{lang|en|hexamethylenetetramine}}) 또는 '''메텐아민'''({{lang|en|methenamine}}, hexamine, urotropin)은 [[헤테로고리 화합물|헤테로고리 유기화합물]]의 하나로, 화학식은 (CH<sub>2</sub>)<sub>6</sub>N<sub>4</sub>이다. 이 흰 [[결정]] 화합물은 물과 극유기용제에 매우 잘 녹는다. [[아다만테인]]과 같은 새장과 같은 구조를 지니고 있다. 플라스틱, 약, 고무 첨가물 등 다른 화합물의 합성에 유용하다. 280&nbsp;°C의 진공에서 [[승화 (화학)|승화]]된다.

== 합성, 구조, 반응 ==
헥사메틸렌테트라민은 1859년 알렉산드르 부틀레로프에 의해 발견되었다.<ref name="Butlerow1859">{{저널 인용| url=https://books.google.com/books?id=NYs8AAAAIAAJ&pg=PA242#v=onepage&q&f=false | title=Ueber einige Derivate des Jodmethylens | author=Butlerow, A. | journal=[[:en:Liebigs Annalen|Ann. Chem. Pharm.]] | year=1859 | volume=111 | issue=2 | pages=242–252 | language=독일어 | doi=10.1002/jlac.18591110219 | trans-title=On some derivatives of methylene iodide}} In this paper, Butlerov  discovered formaldehyde, which he called "Dioxymethylen" (methylene dioxide) [page 247] because his empirical formula for it was incorrect (C<sub>4</sub>H<sub>4</sub>O<sub>4</sub>).  On pages 249–250, he describes treating formaldehyde with ammonia gas, creating hexamine.</ref><ref name="Butlerow1860">{{저널 인용| url=https://books.google.com/books?id=14lKAAAAYAAJ&pg=PA322#v=onepage&q&f=false | title=Ueber ein neues Methylenderivat | author=Butlerow, A. | journal=Ann. Chem. Pharm. | year=1860 | volume=115 | issue=3 | pages=322–327 | doi=10.1002/jlac.18601150325 | trans-title=On a new methylene derivative | language=독일어}}</ref> [[폼알데하이드]]와 [[암모니아]]를 결합시켜서 산업적으로 준비된다.<ref name="Ullmann">{{백과사전 인용| title=Amines, Aliphatic | encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry | publisher=Wiley-VCH Verlag GmbH | year=2000 | isbn=9783527306732 | doi=10.1002/14356007.a02_001 | last1=Eller | last2=Henkes | last3=Rossbacher | last4=Höke | first1=K. | first2=E. | first3=R. | first4=H.}}</ref> 반응은 기체상과 용액으로 수행할 수 있다.

[[파일:Synthesis Hexamine.svg|350px|가운데]]

== 각주 ==
{{각주}}

== 외부 링크 ==
* {{위키공용분류-줄}}

{{전거 통제}}

[[분류:질소 헤테로고리 화합물]]
[[분류:보존제]]
[[분류:항생물질]]
[[분류:연료]]
[[분류:방청제]]
[[분류:고리가 3개인 헤테로고리 화합물]]