MDMA

MDMA
Clinical data
Pronunciation	methylenedioxymethamphetamine:; /ˈmɛ.θɪ.liːn.daɪ.ˈɒk.si./; /ˌmɛθæmˈfɛtəmiːn/
AHFS/Drugs.com	entry
Dependence; liability	Pheesical: nae teepical; Psychological: moderate
Addiction; liability	Law–moderate
Routes o; admeenistration	Common: bi mooth; Uncommon: snortin, inhalation (vapourisation), injection, rectal
Drog cless	empathogen–entactogen; stimulant
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibitit) ; CA: Schedule I ; DE: Anlage I (Controlled) ; NZ: Class B ; UK: Cless A ; US: Schedule I ; UN: Psychotropic Schedule I ;
Pharmacokinetic data
Metabolism	Liver, CYP450 extensively involved, includin CYP2D6
Metabolites	MDA, HMMA, HMA, DHA, MDP2P, MDOH
Onset o action	30–45 minutes (bi mooth)
Biological hauf-life	(R)-MDMA: 5.8 ± 2.2 oors; (S)-MDMA: 3.6 ± 0.9 oors
Duration o action	4–6 hours
Excretion	Neer
Identifiers
	IUPAC name (RS)-1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine;
Synonyms	3,4-MDMA, ecstasy (E, X, XTC), molly, mandy
CAS Nummer	42542-10-9 [TOXNET];
PubChem CID	1615;
IUPHAR/BPS	4574;
DrugBank	DB01454 ;
ChemSpider	1556 ;
UNII	KE1SEN21RM;
KEGG	C07577 ;
ChEBI	CHEBI:1391 ;
ChEMBL	CHEMBL43048 ;
PDB ligand	B41 (PDBe, RCSB PDB);
Chemical and physical data
Formula	C11H15NO2
Molar mass	193.25 g·mol−1
3D model (Jmol)	Interactive eemage;
Chirality	Racemic mixtur
Bylin pynt	105 °C (221 °F) at 0.4 mmHg (experimental)
	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)

3,4-Methylenedioxymethamphetamine (MDMA),^{[note 1]} commonly kent as ecstasy (E), is a psychoactive drog uised primarily as a recreautional drog.

Notes

↑ The term MDMA is a contraction o 3,4-methylenedioxy-methamphetamine; it is kent as ecstasy (shortened tae "E", "X", or "XTC"), mandy, an molly an aw.^[10]^[11]

References

↑ Palmer, Robert B. (2012). Medical toxicology of drug abuse : synthesized chemicals and psychoactive plants. Hoboken, N.J.: John Wiley & Sons. p. 139. ISBN 9780471727606.
↑ Malenka RC, Nestler EJ, Hyman SE (2009). "Chapter 15: Reinforcement and Addictive Disorders". In Sydor A, Brown RY (eds.). Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (2nd ed.). New York: McGraw-Hill Medical. p. 375. ISBN 9780071481274. 3,4-Methylenedioxymethamphetamine (MDMA), commonly called ecstasy, is an amphetamine derivative. It produces a combination of psychostimulant-like and weak LSD-like effects at low doses. Unlike LSD, MDMA is reinforcing—most likely because of its interactions with dopamine systems—and accordingly is subject to compulsive abuse. ... MDMA has been proven to produce lesions of serotonin neurons in animals and humans.
↑ ^a ^b Betzler, Felix; Viohl, Leonard; Romanczuk-Seiferth, Nina; Foxe, John (Januar 2017). "Decision-making in chronic ecstasy users: a systematic review". European Journal of Neuroscience. 45 (1): 34–44. doi:10.1111/ejn.13480. PMID 27859780. ...the addictive potential of MDMA itself is relatively small.
↑ Jerome, Lisa; Schuster, Shira; Berra Yazar-Klosinski, B. (Mairch 2013). "Can MDMA Play a Role in the Treatment of Substance Abuse?". Current Drug Abuse Reviews. 6 (1): 54–62. doi:10.2174/18744737112059990005. PMID 23627786. Retrieved 18 Juin 2015. 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. Retrieved 17 October 2014.
↑ "Methylenedioxymethamphetamine (MDMA, ecstasy)". Drugs and Human Performance Fact Sheets. National Highway Traffic Safety Administration. Archived frae the original on 31 Mey 2012. Retrieved 2 Mey 2017.
↑ Carvalho M, Carmo H, Costa VM, Capela JP, Pontes H, Remião F, Carvalho F, Bastos Mde L (August 2012). "Toxicity of amphetamines: an update". Arch. Toxicol. 86 (8): 1167–1231. doi:10.1007/s00204-012-0815-5. PMID 22392347.
↑ ^a ^b Freye, Enno (28 Julie 2009). "Pharmacological Effects of MDMA in Man". Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs. Springer Netherlands. pp. 151–160. ISBN 978-90-481-2448-0. Retrieved 18 Juin 2015.
↑ ^a ^b "3,4-Methylenedioxymethamphetamine". Hazardous Substances Data Bank. National Library of Medicine. 28 August 2008. Retrieved 22 August 2014.
↑ ^a ^b Luciano, Randy L.; Perazella, Mark A. (25 Mairch 2014). "Nephrotoxic effects of designer drugs: synthetic is not better!". Nature Reviews Nephrology. 10 (6): 314–324. doi:10.1038/nrneph.2014.44. Retrieved 2 December 2014.
↑ ^a ^b "DrugFacts: MDMA (Ecstasy or Molly)". National Institute on Drug Abuse. Archived frae the original on 3 December 2014. Retrieved 2 December 2014.

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[12] The term MDMA is a contraction o 3,4-methylenedioxy-methamphetamine; it is kent as ecstasy (shortened tae "E", "X", or "XTC"), mandy, an molly an aw.^[10]^[11]

[palmer-1] Palmer, Robert B. (2012). Medical toxicology of drug abuse : synthesized chemicals and psychoactive plants. Hoboken, N.J.: John Wiley & Sons. p. 139. ISBN 9780471727606.

[NHM-MDMA-2] Malenka RC, Nestler EJ, Hyman SE (2009). "Chapter 15: Reinforcement and Addictive Disorders". In Sydor A, Brown RY (eds.). Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (2nd ed.). New York: McGraw-Hill Medical. p. 375. ISBN 9780071481274. 3,4-Methylenedioxymethamphetamine (MDMA), commonly called ecstasy, is an amphetamine derivative. It produces a combination of psychostimulant-like and weak LSD-like effects at low doses. Unlike LSD, MDMA is reinforcing—most likely because of its interactions with dopamine systems—and accordingly is subject to compulsive abuse. ... MDMA has been proven to produce lesions of serotonin neurons in animals and humans.

[Betzler2017-3] Betzler, Felix; Viohl, Leonard; Romanczuk-Seiferth, Nina; Foxe, John (Januar 2017). "Decision-making in chronic ecstasy users: a systematic review". European Journal of Neuroscience. 45 (1): 34–44. doi:10.1111/ejn.13480. PMID 27859780. ...the addictive potential of MDMA itself is relatively small.

[Substance_abuse-4] Jerome, Lisa; Schuster, Shira; Berra Yazar-Klosinski, B. (Mairch 2013). "Can MDMA Play a Role in the Treatment of Substance Abuse?". Current Drug Abuse Reviews. 6 (1): 54–62. doi:10.2174/18744737112059990005. PMID 23627786. Retrieved 18 Juin 2015. Animal and human studies demonstrate moderate abuse liability for MDMA, and this effect may be of most concern to those treating substance abuse disorders.

[EMCDDA-5] "Methylenedioxymethamphetamine (MDMA or 'Ecstasy')". EMCDDA. European Monitoring Centre for Drugs and Drug Addiction. Retrieved 17 October 2014.

[6] "Methylenedioxymethamphetamine (MDMA, ecstasy)". Drugs and Human Performance Fact Sheets. National Highway Traffic Safety Administration. Archived frae the original on 31 Mey 2012. Retrieved 2 Mey 2017.

[pmid22392347-7] Carvalho M, Carmo H, Costa VM, Capela JP, Pontes H, Remião F, Carvalho F, Bastos Mde L (August 2012). "Toxicity of amphetamines: an update". Arch. Toxicol. 86 (8): 1167–1231. doi:10.1007/s00204-012-0815-5. PMID 22392347.

[Freye2009-8] Freye, Enno (28 Julie 2009). "Pharmacological Effects of MDMA in Man". Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs. Springer Netherlands. pp. 151–160. ISBN 978-90-481-2448-0. Retrieved 18 Juin 2015.

[Toxnet_MDMA-9] "3,4-Methylenedioxymethamphetamine". Hazardous Substances Data Bank. National Library of Medicine. 28 August 2008. Retrieved 22 August 2014.

[nature.com-10] Luciano, Randy L.; Perazella, Mark A. (25 Mairch 2014). "Nephrotoxic effects of designer drugs: synthetic is not better!". Nature Reviews Nephrology. 10 (6): 314–324. doi:10.1038/nrneph.2014.44. Retrieved 2 December 2014.

[DrugFacts-11] "DrugFacts: MDMA (Ecstasy or Molly)". National Institute on Drug Abuse. Archived frae the original on 3 December 2014. Retrieved 2 December 2014.

[note 1]

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

Clinical data


Pronunciation	methylenedioxymethamphetamine: /ˈmɛ.θɪ.liːn.daɪ.ˈɒk.si./ /ˌmɛθæmˈfɛtəmiːn/
AHFS/Drugs.com	entry
Dependence liability	Pheesical: nae teepical^[1] Psychological: moderate
Addiction liability	Law–moderate^[2]^[3]^[4]
Routes o admeenistration	Common: bi mooth^[5] Uncommon: snortin,^[5] inhalation (vapourisation),^[5] injection,^[5]^[6] rectal
Drog cless	empathogen–entactogen stimulant
ATC code	none
Legal status
Legal status	AU: S9 (Prohibitit) CA: Schedule I DE: Anlage I (Controlled) NZ: Class B UK: Cless A US: Schedule I UN: Psychotropic Schedule I
Pharmacokinetic data
Metabolism	Liver, CYP450 extensively involved, includin CYP2D6
Metabolites	MDA, HMMA, HMA, DHA, MDP2P, MDOH^[7]
Onset o action	30–45 minutes (bi mooth)^[8]
Biological hauf-life	(R)-MDMA: 5.8 ± 2.2 oors^[9] (S)-MDMA: 3.6 ± 0.9 oors^[9]
Duration o action	4–6 hours^[3]^[8]
Excretion	Neer
Identifiers
IUPAC name (RS)-1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
Synonyms	3,4-MDMA, ecstasy (E, X, XTC), molly, mandy^[10]^[11]
CAS Nummer	42542-10-9^Y[TOXNET]
PubChem CID	1615
IUPHAR/BPS	4574
DrugBank	DB01454^Y
ChemSpider	1556^Y
UNII	KE1SEN21RM
KEGG	C07577^Y
ChEBI	CHEBI:1391^Y
ChEMBL	CHEMBL43048^Y
PDB ligand	B41 (PDBe, RCSB PDB)
Chemical and physical data
Formula	C₁₁H₁₅NO₂
Molar mass	193.25 g·mol⁻¹
3D model (Jmol)	Interactive eemage
Chirality	Racemic mixtur
Bylin pynt	105 °C (221 °F) at 0.4 mmHg (experimental)
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^Y Key:SHXWCVYOXRDMCX-UHFFFAOYSA-N^Y
(verify)