{{위키데이터 속성 추적}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 632164040
| drug_name = MDMA
| INN = Midomafetamine<ref name=INN>{{뉴스 인용|title=FDA Substance Registration System|url=https://fdasis.nlm.nih.gov/srs/unii/KE1SEN21RM|access-date=31 August 2017|publisher=United States National Library of Medicine|archive-date=2017-08-31|archive-url=https://web.archive.org/web/20170831220013/https://fdasis.nlm.nih.gov/srs/unii/KE1SEN21RM|url-status=}}</ref>
| chirality = [[Racemic mixture]]
| image = MDMA (simple).svg
| width = 250px
| alt = MDMA structure
| image2 = MDMA molecule from xtal ball.png
| alt2 = Ball-and-stick model of an MDMA molecule
| width2 = 250px

<!--Identifiers-->
| IUPAC_name = (''RS'')-1-(1,3-benzodioxol-5-yl)-''N''-methylpropan-2-amine<!--From PubChem-->
| pronounce = methylenedioxy{{shy}}methamphetamine:<br/>{{IPAc-en|ˌ|m|ɛ|θ|ɪ|l|iː|n|d|aɪ|ˈ|ɒ|k|s|i}}<br />{{IPAc-en|ˌ|m|ɛ|θ|æ|m|ˈ|f|ɛ|t|əm|iː|n}}
| ATC_prefix = none
| Drugs.com = {{Drugs.com|parent|MDMA}}
| CAS_number_Ref = {{cascite|correct|TOXNET}}
| CAS_number = 42542-10-9
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1556
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = KE1SEN21RM
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01454
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 1391
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 43048
| PubChem = 1615
| IUPHAR_ligand = 4574
| KEGG = D11172
| KEGG_Ref = {{keggcite|correct|kegg}}
| synonyms = {{abbr|3,4-MDMA|3,4-Methylenedioxymethamphetamine}}; Ecstasy (E, X, XTC); Molly; Mandy<ref name="nature.com">{{저널 인용| vauthors = Luciano RL, Perazella MA | title = Nephrotoxic effects of designer drugs: synthetic is not better! | journal = Nature Reviews. Nephrology | volume = 10 | issue = 6 | pages = 314–24 | date = June 2014 | pmid = 24662435 | doi = 10.1038/nrneph.2014.44 }}</ref><ref name="DrugFacts">{{웹 인용|title=DrugFacts: MDMA (Ecstasy or Molly)|url=http://www.drugabuse.gov/publications/drugfacts/mdma-ecstasy-or-molly|publisher=National Institute on Drug Abuse|access-date=2 December 2014|url-status=live|archive-url=https://web.archive.org/web/20141203115531/http://www.drugabuse.gov/publications/drugfacts/mdma-ecstasy-or-molly|archive-date=3 December 2014|df=dmy-all}}</ref>
| PDB_ligand = B41

<!--Chemical data-->
| C=11 | H=15 | N=1 | O=2
| SMILES = CC(NC)CC1=CC=C(OCO2)C2=C1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SHXWCVYOXRDMCX-UHFFFAOYSA-N
| density =
| melting_point =
| melting_notes =
| boiling_point = 105
| boiling_notes = at 0.4&nbsp;mmHg (experimental)<!--Pubchem-->

<!--Clinical/legal data-->
| legal_AU = S9
| legal_BR = F<!-- F2 -->
| legal_CA = Schedule I
| legal_DE = Anlage I
| legal_NZ = Class B
| legal_UK = Class A
| legal_US = Schedule I
| legal_UN = Psychotropic Schedule I
| legal_status =
| pregnancy_category = 
| pregnancy_US =
| licence_US =
| class = [[empathogen–entactogen]]<br /> [[stimulant]]

<!--Pharmacological data-->
| dependency_liability = [[Physical dependence|Physical]]: not typical<ref name=palmer>{{서적 인용|last1=Palmer|first1=Robert B.| name-list-format = vanc |title=Medical toxicology of drug abuse : synthesized chemicals and psychoactive plants|date=2012|publisher=John Wiley & Sons|location=Hoboken, N.J. |isbn=978-0-471-72760-6|page=139|url=https://books.google.com/books?id=OWFiVaDZnkQC&pg=PA139}}</ref><br />[[Psychological dependence|Psychological]]: moderate
| addiction_liability= Low–moderate<ref name="NHM-MDMA">{{서적 인용|vauthors=Malenka RC, Nestler EJ, Hyman SE |veditors=Sydor A, Brown RY | title = Molecular Neuropharmacology: A Foundation for Clinical Neuroscience | year = 2009 | publisher = McGraw-Hill Medical | location = New York | isbn = 978-0-07-148127-4 | pages = 375 | edition = 2nd | chapter = Chapter 15: Reinforcement and Addictive Disorders}}</ref><ref name=Betzler2017>{{저널 인용| vauthors = Betzler F, Viohl L, Romanczuk-Seiferth N | title = Decision-making in chronic ecstasy users: a systematic review | journal = The European Journal of Neuroscience | volume = 45 | issue = 1 | pages = 34–44 | date = January 2017 | pmid = 27859780 | doi = 10.1111/ejn.13480 | quote = ...the addictive potential of MDMA itself is relatively small. }}</ref><ref name="Substance abuse">{{저널 인용| vauthors = Jerome L, Schuster S, Yazar-Klosinski BB | title = Can MDMA play a role in the treatment of substance abuse? | journal = Current Drug Abuse Reviews | volume = 6 | issue = 1 | pages = 54–62 | date = March 2013 | pmid = 23627786 | doi = 10.2174/18744737112059990005 | quote = Animal and human studies demonstrate moderate abuse liability for MDMA, and this effect may be of most concern to those treating substance abuse disorders. }}</ref>
| elimination_half-life = (''R'')-MDMA: 5.8&nbsp;±&nbsp;2.2&nbsp;hours (variable)<ref name="Toxnet MDMA">{{웹 인용|title=3,4-Methylenedioxymethamphetamine|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search2/r?dbs+hsdb:@term+@rn+@rel+42542-10-9|website=Hazardous Substances Data Bank|publisher=National Library of Medicine|access-date=22 August 2014|date=28 August 2008|quote=}}</ref><br />(''S'')-MDMA: 3.6&nbsp;±&nbsp;0.9&nbsp;hours (variable)<ref name="Toxnet MDMA" />
| metabolism = [[Liver]], [[Cytochrome P450 oxidase|CYP450]] extensively involved, including [[CYP2D6]]
| metabolites = [[3,4-methylenedioxyamphetamine|MDA]], [[4-Hydroxy-3-methoxymethamphetamine|HMMA]], [[4-Hydroxy-3-methoxyamphetamine|HMA]], [[Alpha-Methyldopamine|DHA]], [[MDP2P]], [[Methylenedioxyhydroxyamphetamine|MDOH]]<ref name="pmid22392347">{{저널 인용| vauthors = Carvalho M, Carmo H, Costa VM, Capela JP, Pontes H, Remião F, Carvalho F, Bastos M | title = Toxicity of amphetamines: an update | journal = Archives of Toxicology | volume = 86 | issue = 8 | pages = 1167–231 | date = August 2012 | pmid = 22392347 | doi = 10.1007/s00204-012-0815-5 }}</ref>
| excretion = [[Kidney]]
| routes_of_administration = Common: [[oral route|by mouth]]<ref name=EU2015 /><br /> Uncommon: [[insufflation (medicine)|snorting]],<ref name=EU2015 /> [[inhalation]] ([[vaporization]]),<ref name=EU2015 /> [[injection (medicine)|injection]],<ref name=EU2015>{{웹 인용|title=Methylenedioxymethamphetamine (MDMA or 'Ecstasy')|url=http://www.emcdda.europa.eu/publications/drug-profiles/mdma|website=EMCDDA|publisher=European Monitoring Centre for Drugs and Drug Addiction|access-date=17 October 2014|ref=EMCDDA}}</ref><ref>{{웹 인용|title = Methylenedioxymethamphetamine (MDMA, ecstasy)|url = http://www.nhtsa.dot.gov/people/injury/research/job185drugs/methylenedioxymethamphetamine.htm|work = Drugs and Human Performance Fact Sheets.|publisher = [[National Highway Traffic Safety Administration]]|url-status = dead|archive-url = https://www.webcitation.org/683mpsNYA?url=http://www.nhtsa.gov/people/injury/research/job185drugs/methylenedioxymethamphetamine.htm|archive-date = 31 May 2012|df = dmy-all}}</ref> [[rectal (medicine)|rectal]]
| onset = 30–45&nbsp;minutes (by mouth)<ref name=Freye2009/>
| duration_of_action = 4–6&nbsp;hours<ref name=Betzler2017/><ref name=Freye2009/>
| bioavailability =
| protein_bound =
}}
'''3,4-메틸렌디옥시메탐페타민'''({{llang|en|3,4-methylenedioxymethamphetamine}}) 줄여서 '''MDMA''' 또는 일명 '''엑스터시'''({{llang|en|Ecstasy}})은 [[신경정신약물|향정신성 물질]]의 일종이다. 기본적으로 [[각성제]]이나 뇌 속에 [[세로토닌]]·[[도파민]]· [[노르에피네프린]]의 분비를 촉진시켜 [[환각]]도 일으킬 수 있다. 복용 후 30분에서 1시간 사이 서서히 작용하며 6시간 ~ 10시간 지속적이다. 상당히 강한 중독성과 부작용으로 대부분의 국가에서 사용이 금지되어 있으나 일부 국가에서는 의료적 사용에 대한 실험적 시도가 있다.

엑스터시를 복용한 상태에서는 갈증을 느끼지 못하기 때문에 심각한 [[탈수]] 증세를 일으킬 수 있다. 특히, [[술|알콜]]과 동시에 투약할 경우 [[약물 상호작용]]에 의한 갈증과 체온상승 등 [[부작용]]으로 사망할 수 있다. 반대로 [[저나트륨증]]에 의한 ‘[[수분 중독]]’ 현상도 있는 것으로 알려져 있다.

== 합성 ==
MDMA는 Safrole의 유도체이다. Safrole은 일반적으로 썩은 생강에서 자연적으로 생성된다.
MDMA는 Safrole의 Wacker Oxydation으로 MDP2P(3,4-Methylenedioxy Phenyl-2-Propanone)라는 유도체를 만들어서 알루미늄 아말감이나 NaBH3CN같은 것으로 수소를 첨가해서 합성 할 수 있다.
Wacker Oxidation이란, Pb같은 금속 Chloride의 화합물의 존재하에, 에틸렌을 아세트알데하이드로 바꾸는 방법이다.
Safrole이나 iso-Safrole을 메탄올과 Lead(II) Chloride로 Wacker Oxidation을 일으켜서 MDP2P로 만듬 다음,
MDP2P를 메틸아민이나 NaBH3CN으로 환원하고 HN과 메틸기를 붙혀서 합성한다.

== 같이 보기 ==
{{위키공용분류}}
* [[메스암페타민]](일명: 필로폰)

== 각주 ==
{{각주}}

{{전거 통제}}

[[분류:알칼로이드]]
[[분류:TAAR1 작용제]]
[[분류:의식용 환각제]]
[[분류:세로토닌 수용체 작용제]]
[[분류:5-HT1A 작용제]]
[[분류:5-HT2A 작용제]]
[[분류:5-HT2B 작용제]]
[[분류:5-HT2C 작용제]]
[[분류:벤조다이옥솔]]
[[분류:VMAT 억제제]]