MDMA

MDMA
INN: Midomafetamina^[1]
Data klinikal
Nama lain	3,4-MDMA; Ekstasi (E, X, XTC); Molly; Mandy; Pingers/Pingas
AHFS/Drugs.com	MDMA
Liabiliti; penggantungan	Fizikal: tidak lazim; Psikologi: sederhana
Liabiliti; ketagihan	Rendah–sederhana
Kaedah; pemberian	Lazim: mulut; Tidak lazim: hidu, sedutan (pengewapan), suntukan, rektum
Kelas ubat	Empatogen–entaktogen; Stimulan
Kod ATC	Tiada;
Status perundangan
Status perundangan	AU: S8 (PTSD); ; S9 (kegunaan lain) ; BR: Kelas F (Bahan terlarang) ; KA: Jadual I ; DE: Anlage I (Penggunaan saintifik diizinkan sahaja) ; NZ: Kelas B ; UK: Kelas A ; AS: Jadual I ; UN: Psychotropic Schedule I ;
Data farmakokinetik
Bioketersediaan	Mulut: Tidak diketahui
Metabolisme	Hati, CYP450 banyak terlibat, termasuk CYP2D6
Metabolit	MDA, HMMA, HMA, DHA, MDP2P, MDOH
Mula masa tindak	30 – 45 minit (mulut)
Penyingkiran separuh hayat	(R)-MDMA: 5.8 ± 2.2 jam (pelbagai); (S)-MDMA: 3.6 ± 0.9 jam (pelbagai)
Tempoh tindak	4 – 6 jam
Perkumuhan	Buah pinggang
Pengecam
	Nama IUPAC (RS)-1-(1,3-Benzodioksol-5-il)-N-metilpropan-2-amina;
Nombor CAS	42542-10-9 [TOXNET];
PubChem CID	1615;
IUPHAR/BPS	4574;
DrugBank	DB01454 ;
ChemSpider	1556 ;
UNII	KE1SEN21RM;
KEGG	D11172 ;
ChEBI	CHEBI:1391 ;
ChEMBL	ChEMBL43048 ;
Ligan PDB	B41 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID90860791 ;
Data kimia dan fizikal
Formula	C11H15NO2
Jisim molar	193.25 g·mol−1
Model 3D (JSmol)	Gambar interaktif;
Kekiralan	Campuran rasemik
Ketumpatan	1.1 g/cm3
Takat didih	105 °C (221 °F) at 0.4 mmHg (uji kaji)
	SMILES CC(NC)CC1=CC=C(OCO2)C2=C1;
	InChI InChI=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 ; Key:SHXWCVYOXRDMCX-UHFFFAOYSA-N ;
	(verify)

MDMA (3,4-metilenadioksimetamfetamina), atau lebih dikenali sebagai ekstasi merupakan dadah sintetik yang tergolong dalam keluarga fenetilamina. Dadah ini berkesan dalam meransang otak untuk merembes serotonin, sejenis rembesan yang menyebabkan rasa keterbukaan, meningkatkan tenaga, eforia, dan rasa sihat. Deria sentuh menjadi semakin sensitif menyebabkan sentuhan fizikal menjadi lebih seronok, tetapi MDMA bukanlah agen afrodisia (drug yang meransang nafsu seks dan keupayaan melakukan hubungan seks). MDMA digunakan kepada pesakit Gangguan Tekanan Selepas Trauma (Post Traumatic Stress Disorder) kerana kemampuannya untuk membantu pemeriksaan sendiri. Penggunaan dadah ini dibenarkan oleh FDA (Food and Drug Administration) Amerika Syarikat.

Walaupun MDMA tiada had dos, pendehidratan akut adalah antara risiko yang dihadapi oleh pengguna MDMA. Ini adalah kerana pengguna MDMA menjadi sangat aktif sehingga terlupa untuk meminum air memandangkan MDMA berupaya untuk menutup rasa haus dan kepenatan pengguna tersebut. Bahaya lain datang daripada bahan kimia lain (contohnya PMA atau metafetamina) yang selalu dicampur ke dalam ekstasi. Kesan jangka panjang MDMA masih belum diketahui.

Sejarah

MDMA dipatenkan pada 25 Disember 1914 oleh sebuah syarikat farmaseutikal Jerman, Merck selepas dua tahun disintesis. Pada masa itu, Merck mensintesis MDMA secara sistematik dan menpatenkan pelbagai jenis bahan kimia yang boleh digunakan untuk kesihatan manusia. Namun MDMA tidak terkenal dan dilupakan.

Pada 1960an, Dr. Alexander Shulgin mencadangkan MDMA untuk digunakan dalam sesi terapi. Beliau menamakan dadah ini sebagai window (tingkap). Dadah ini digunakan secara terapeutik oleh pakar psikoterapi kerana kesan empatogenik MDMA. Namun pada tahun 1980an, penggunaan MDMA untuk tujuan itu diharamkan.

Sehingga pertengahan tahun 1980an, MDMA masih boleh digunakan secara sah di Amerika Syarikat. Pada tempoh waktu yang sama MDMA mula digunakan untuk tujuan rekreasi di sesetengah Yuppie bar ( Young Urban Professional ) di Dallas, dan kemudiannya di kelab kelab homoseksual. Selepas itu, MDMA mula tersebar ke kelab malam rave, dan seterusnya ke masyarakat umum. Pada tahun 1990an, MDMA semakin terkenal di kalangan golongan muda di universiti dan sekolah tinggi. Penyebaran MDMA adalah sangat pantas sehingga muncul dalam satu dokumentari pada 2004 yang bertajuk No other drug has ever spread so fast.

Rujukan

^ "FDA Substance Registration System". United States National Library of Medicine. Diarkibkan daripada yang asal pada 31 August 2017. Dicapai pada 31 August 2017.
^ Luciano RL, Perazella MA (June 2014). "Nephrotoxic effects of designer drugs: synthetic is not better!". Nature Reviews. Nephrology. 10 (6): 314–24. doi:10.1038/nrneph.2014.44. PMID 24662435. S2CID 9817771.
^ "DrugFacts: MDMA (Ecstasy or Molly)". National Institute on Drug Abuse. Diarkibkan daripada yang asal pada 3 Disember 2014. Dicapai pada 2 Disember 2014.
^ "Pingers, pingas, pingaz: how drug slang affects the way we use and understand drugs". The Conversation. 2020-01-08. Diarkibkan daripada yang asal pada 2021.
^ Palmer RB (2012). Medical toxicology of drug abuse : synthesized chemicals and psychoactive plants. Hoboken, N.J.: John Wiley & Sons. m/s. 139. ISBN 978-0-471-72760-6.
^ Malenka RC, Nestler EJ, Hyman SE (2009). "Chapter 15: Reinforcement and Addictive Disorders". Dalam Sydor A, Brown RY (penyunting). Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (ed. 2nd). New York: McGraw-Hill Medical. m/s. 375. ISBN 978-0-07-148127-4.
^ ^a ^b Betzler F, Viohl L, Romanczuk-Seiferth N (January 2017). "Decision-making in chronic ecstasy users: a systematic review". The European Journal of Neuroscience. 45 (1): 34–44. doi:10.1111/ejn.13480. PMID 27859780. S2CID 31694072. ...the addictive potential of MDMA itself is relatively small.
^ Jerome L, Schuster S, Yazar-Klosinski BB (March 2013). "Can MDMA play a role in the treatment of substance abuse?" (PDF). Current Drug Abuse Reviews. 6 (1): 54–62. doi:10.2174/18744737112059990005. PMID 23627786. S2CID 9327169. Diarkibkan daripada yang asal (PDF) pada 2020-08-03. Animal and human studies demonstrate moderate abuse liability for MDMA, and this effect may be of most concern to those treating substance abuse disorders.
^ ^a ^b ^c ^d "Methylenedioxymethamphetamine (MDMA or 'Ecstasy')". EMCDDA. European Monitoring Centre for Drugs and Drug Addiction. Dicapai pada 17 October 2014.
^ "Methylenedioxymethamphetamine (MDMA, ecstasy)". Drugs and Human Performance Fact Sheets. National Highway Traffic Safety Administration. Diarkibkan daripada yang asal pada 3 Mei 2012.
^ ^a ^b ^c Freye E (28 July 2009). "Pharmacological Effects of MDMA in Man". Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs. Springer Netherlands. m/s. 151–160. doi:10.1007/978-90-481-2448-0_24. ISBN 978-90-481-2448-0.
^ Carvalho M, Carmo H, Costa VM, Capela JP, Pontes H, Remião F, Carvalho F, Bastos M (August 2012). "Toxicity of amphetamines: an update". Archives of Toxicology. 86 (8): 1167–231. doi:10.1007/s00204-012-0815-5. PMID 22392347. S2CID 2873101.
^ ^a ^b "3,4-Methylenedioxymethamphetamine". Hazardous Substances Data Bank. National Library of Medicine. 28 August 2008. Dicapai pada 22 August 2014.

Bacaan lanjut

Adam, David. Truth about ecstasy's unlikely trip from lab to dance floor: Pharmaceutical company unravels drug's chequered past, Guardian Unlimited, 2006-08-18.

Baggott, Matthew, and John Mendelson. “MDMA Neurotoxicity”. Ecstasy: The Complete Guide. Ed. Julie Holland. Spring 2001 from www.erowid.com.

de la Torre, Rafael et al. (2000), Non-linear pharmacokinetics of MDMA (`ecstasy') in humans. Br J Clin Pharmacol, 2000; 49(2):104-9

de la Torre, Rafael & Farré, Magí (2004). Neurotoxicity of MDMA (ecstasy): the limitations of scaling from animals to humans. Trends in Pharmacological Sciences 25, 505-508.

Eisner, Bruce. "Ecstasy: The MDMA Story-2nd ed." Berkeley, CA: Ronin Publishing, 1994.

Erowid, Earth. “Do Antioxidants Protect Against MDMA Hangover, Tolerance, and Neurotoxicity?” Erowid Extracts. December 2001; 2:6-11.

Jennings, Peter. Ecstasy Rising, ABC television documentary. 2004-01-04.

Jones, Douglas C. et al. (2004). Thioether Metabolites of 3,4-Methylenedioxyamphetamine and 3,4-Methylenedioxymethamphetamine Inhibit Human Serotonin Transporter (hSERT) Function and Simultaneously Stimulate Dopamine Uptake into hSERT-Expressing SK-N-MC Cells. J Pharmacol Exp Ther 311, 298-306.

Kalant H. (2001) The pharmacology and toxicology of "ecstasy" (MDMA) and related drugs. CMAJ. October 2;165(7):917-28. Review. PMID 11599334 Full Text

Miller, R.T. et al. (1997). 2,5-Bis-(glutathione-S-yl)-alpha-methyldopamine, a putative metabolite of (+/-)-3,4-methylenedioxyamphetamine, decreases brain serotonin concentrations. Eur J Pharmaco. 323(2-3), 173-80. Abstract retrieved April 17, 2005, from PubMed.

Monks, T.J. et al. (2004). The role of metabolism in 3,4-(+)-methylenedioxyamphetamine and 3,4-(+)-methylenedioxymethamphetamine (ecstasy) toxicity. Ther Drug Monit 26(2), 132-136.

Morgan, Michael John (2000). Ecstasy (MDMA): a review of its possible persistent psychological effects. Psychopharmacology 152, 230-248.

Shankaran, Mahalakshmi, Bryan K. Yamamoto, and Gary A. Gudelsky. “Ascorbic Acid Prevents 3,4,-Methylenedioxymethamphetamine (MDMA)- Induced Hydroxyl Radical Formation and the Behavioral and Neurochemical Consequences of the Depletion of Brain 5-HT”. Synapse. 2001; 40:55-64.

Strote, Jared et al. (2002). Increasing MDMA use among college students: results of a national survey. Journal of Adolescent Health 30, 64-72.

Sumnall, Harry R. & Cole, Jon C. (2005). Self-reported depressive symptomatology in community samples of polysubstance misusers who report Ecstasy use: a meta-analysis. Journal of Psychopharmacology 19(1), 84-92.

Vollmer, Grit. "Crossing the Barrier." Scientific American Mind. June/July 2006, 34-39.

Yeh, S. Y. “Effects of Salicylate on 3,4-Methylenedioxymethamphetamine (MDMA)-Induced Neurotoxicity in Rats”. Pharmacology Biochemistry and Behavior. 1997; Vol. 58, No. 3: 701-708.

Gerra G, Zaimovic A, Ampollini R, Giusti F, Delsignore R, Raggi MA, Laviola G, Macchia T, Brambilla F. "Experimentally induced aggressive behavior in subjects with 3,4-methylenedioxy-methamphetamine ("Ecstasy") use history: psychobiological correlates." J Subst Abuse. 2001;13(4):471-91

Reid LW, Elifson KW, Sterk CE. "Hug drug or thug drug? Ecstasy use and aggressive behavior". Violence Vict. 2007;22(1):104-19.

Ksir, Charles, Carl L. Hart, and Oakley Ray. "Drugs, Society and Human Behavior-12th ed." NY,NY: McGraw Hills, 2006.

Pautan luar

Jennings, Peter. "Primetime Special: Peter Jennings - Ecstasy Rising." ABC News, April 1, 2004.
Conant, Eve. "Ecstasy: A Possible New Role for a Banned Club Drug." Newsweek, May 2, 2005.
This is your brain on Ecstasy Diarkibkan 2010-07-19 di Wayback Machine - A slideshow that illustrates the neuropharmacokinetics of Ecstasy (how the drug affects the brain.) Some of the information on this page is at present (July 2005) outdated.
Multidisciplinary Association for Psychedelic Studies - A non-profit organization currently conducting FDA-approved studies with MDMA.
EcstasyData.org A database of photos and lab-test results of over 1500 pills of "Ecstasy."
American Council for Drug Education factsheet on Ecstasy Diarkibkan 2006-02-18 di Wayback Machine
Ecstasy.org

[INN-1] "FDA Substance Registration System". United States National Library of Medicine. Diarkibkan daripada yang asal pada 31 August 2017. Dicapai pada 31 August 2017.

[nature.com-2] Luciano RL, Perazella MA (June 2014). "Nephrotoxic effects of designer drugs: synthetic is not better!". Nature Reviews. Nephrology. 10 (6): 314–24. doi:10.1038/nrneph.2014.44. PMID 24662435. S2CID 9817771.

[DrugFacts-3] "DrugFacts: MDMA (Ecstasy or Molly)". National Institute on Drug Abuse. Diarkibkan daripada yang asal pada 3 Disember 2014. Dicapai pada 2 Disember 2014.

[4] "Pingers, pingas, pingaz: how drug slang affects the way we use and understand drugs". The Conversation. 2020-01-08. Diarkibkan daripada yang asal pada 2021.

[palmer-5] Palmer RB (2012). Medical toxicology of drug abuse : synthesized chemicals and psychoactive plants. Hoboken, N.J.: John Wiley & Sons. m/s. 139. ISBN 978-0-471-72760-6.

[NHM-MDMA-6] Malenka RC, Nestler EJ, Hyman SE (2009). "Chapter 15: Reinforcement and Addictive Disorders". Dalam Sydor A, Brown RY (penyunting). Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (ed. 2nd). New York: McGraw-Hill Medical. m/s. 375. ISBN 978-0-07-148127-4.

[Betzler2017-7] Betzler F, Viohl L, Romanczuk-Seiferth N (January 2017). "Decision-making in chronic ecstasy users: a systematic review". The European Journal of Neuroscience. 45 (1): 34–44. doi:10.1111/ejn.13480. PMID 27859780. S2CID 31694072. ...the addictive potential of MDMA itself is relatively small.

[Substance_abuse-8] Jerome L, Schuster S, Yazar-Klosinski BB (March 2013). "Can MDMA play a role in the treatment of substance abuse?" (PDF). Current Drug Abuse Reviews. 6 (1): 54–62. doi:10.2174/18744737112059990005. PMID 23627786. S2CID 9327169. Diarkibkan daripada yang asal (PDF) pada 2020-08-03. Animal and human studies demonstrate moderate abuse liability for MDMA, and this effect may be of most concern to those treating substance abuse disorders.

[EU2015-9] "Methylenedioxymethamphetamine (MDMA or 'Ecstasy')". EMCDDA. European Monitoring Centre for Drugs and Drug Addiction. Dicapai pada 17 October 2014.

[10] "Methylenedioxymethamphetamine (MDMA, ecstasy)". Drugs and Human Performance Fact Sheets. National Highway Traffic Safety Administration. Diarkibkan daripada yang asal pada 3 Mei 2012.

[Freye2009-11] Freye E (28 July 2009). "Pharmacological Effects of MDMA in Man". Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs. Springer Netherlands. m/s. 151–160. doi:10.1007/978-90-481-2448-0_24. ISBN 978-90-481-2448-0.

[pmid22392347-12] Carvalho M, Carmo H, Costa VM, Capela JP, Pontes H, Remião F, Carvalho F, Bastos M (August 2012). "Toxicity of amphetamines: an update". Archives of Toxicology. 86 (8): 1167–231. doi:10.1007/s00204-012-0815-5. PMID 22392347. S2CID 2873101.

[Toxnet_MDMA_after-effects-13] "3,4-Methylenedioxymethamphetamine". Hazardous Substances Data Bank. National Library of Medicine. 28 August 2008. Dicapai pada 22 August 2014.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

l b s Fenetilamina
Fenetilamina	Psikedelik: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Alileskalina DESOXY Eskalina Isoproslalina Jimskalina Makromerina MEPEA Meskalina Metaeskalina Metalileskalina Proskalina Psi-2C-T-4 TCB-2 Stimulan: Feniletanolamina Hordenina Fenetilamina Fenprometamina α-Metilfenetilamina (amfetamina) β-Metilfenetilamina m-Metilfenetilamina N-Metilfenetilamina o-Metilfenetilamina p-Metilfenetilamina Metilfenidat Entaktogen: Lofofina MDPEA MDMPEA Lain-lain: BOH DMPEA
Amfetamina	Psikedelik: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenil DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulan: 2-FA 2-FMA 3-FA 3-FMA Akridoreks Alfetamina Amfekloral Amfepentoreks Amfetamina (Dekstroamfetamina, Levoamfetamina) Amfetaminil Benfluoreks Benzfetamina Katina Kobenzoreks Dimetilamfetamina Efedrina Etilamfetamina Fenkamfamin Fenkamina Fenetilina Fenfluramina (Deksfenfluramina, Levofenfluramina) Fenproporeks Flusetoreks Fludoreks Formetoreks Furfenoreks Gepefrina 4-Hidroksiamfetamina Iofetamina Isopropilamfetamina Lefetamina Lisdeksamfetamina Mefenoreks Metaraminol Metamfetamina (Dekstrometamfetamina, Levometamfetamina) Metoksifenamina MMA Morforeks Norfenfluramina L-Norpseudoefedrina N,alpha-Dietilfeniletilamina Oksifentoreks Oksilofrina Ortetamina PBA PCA PFA PFMA PIA PMA PMEA PMMA Fenilpropanolamina Foledrina Prenilamina Propilamfetamina Pseudoefedrina Sibutramina Tifloreks Tranilsipromina Xilopropamina Zilofuramina Entaktogen: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Kloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamina) MDEA MDHMA MDMA (midomafetamina) MDOH Metamnetamina MMDMA Naftilaminopropana TAP Lain-lain: 3,4-DCA Amiflamina DiFMDA Selegilina (also D-Deprenil)
Fentermina	Stimulan: Klorfentermina Koforeks Kortermina Etoloreks Mefentermina Pentoreks Fentermina Entaktogen: MDPH MDMPH Lain-lain: Seriklamina
Katinon	Stimulan: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramon Benzedron Brefedron Bufedron Bupropion Kathinon Dimetilkatinon Etkatinon Eutilon Hidroksibupropion Metkatinon Metedron NEB N-Etilheksedron N-Etilpentedron Pentedron Pentilone Radafaksina Entaktogen: 3,4-DMMC 3-MMC Butilone Etilone Metilone Metilenedioksikatinon Mefedron
Fenilisobutilamina	Entaktogen: 4-CAB 4-MAB Ariadne BDB Butilon EBDB Eutilon MBDB Stimulan: Fenilisobutylamina
Fenilalkilpirolidina	Stimulan: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintana Pirovaleron
Katekolamina (dan sebatian terkait)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenokrom Siladopa D-DOPA (Dekstrodopa) Dimetofrina Dopamina Epinefrina Epinina Etilefrina Etilnorepinefrina Fenklonina Ibopamina Isoprenalina Isoetarina L-DOPA (Levodopa) L-DOPS (Droksidopa) L-Fenilalanina L-Tirosina m-Tiramina Metanefrina Metaraminol Metaterol Metirosina Metildopa N,N-Dimetildopamina Nordefrin (Levonordefrin) Norepinefrina Norfenefrina (m-Oktopamina) Normetanefrina Orsiprenalina p-Oktopamina p-Tiramina Fenilefrina Sinefrina
Lain-lain	AL-LAD Amidefrina Arbutamina Kafedrina Denopamina Desvenlafaksina Difenidina Dizosilpina Dobutamina Dopeksamina Efenidina Etafedrina ETH-LAD Famprofazon Fluorolintana Heksapradol IP-LAD Asid lisergik amida Asid lisergik 2-butil amida Asid lisergik 2,4-dimetilazetidida Asid lisergik dietilamida Metoksamina Metoksfenidina MT-45 PARGY-LAD Fenibut PRO-LAD Pronetalol Salbutamol (Levosalbutamol) Solriamfetol Teodrenalina Thiamfenikol UWA-101 Venlafaksina

Kawalan kewibawaan
Perpustakaan negara	Jerman Israel Amerika Syarikat Republik Czech
Lain-lain	Aplikasi Berfaset Terminologi Subjek