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para-Methoxymethamphetamine

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para-Methoxymethamphetamine
Systematic (IUPAC) name
1-(4-methoxyphenyl)-N-methyl-propan-2-amine
Clinical data
Pregnancy cat.  ?
Legal status Controlled under Federal Analog Act
Identifiers
CAS number 3398-68-3 YesY
ATC code  ?
PubChem CID 90766
Chemical data
Formula C11H17NO 
Mol. mass 179.259 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

para-Methoxymethamphetamine (PMMA), is a stimulant drug related to para-methoxyamphetamine (PMA).

8 pills of PMMA recovered by the DEA

PMMA reputedly produces similar effects to PMA, but is apparently slightly more similar to MDMA in effects[1][2] and has slightly less tendency to produce severe hyperthermia, at least at low doses. At higher doses however the side effects and danger of death are just as severe as those of PMA itself.[3]

PMMA is a lesser-known psychedelic drug. It is the 4-methoxy analog of methamphetamine. PMMA was probably first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), the minimum dosage is listed as 100 mg, and the duration unknown. Shulgin reported that methyl-MA produces an increase in blood pressure and in heart rate, but causes no psychoactive effects, however user reports following the subsequent appearance of this drug on the illicit market as an analogue of "Ecstasy" (MDMA) suggest that PMMA does produce some empathogenic effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of PMMA, and given the known toxicity of the related compound PMA it is likely to have considerable potential to cause harmful side effects or overdose which can be fatal.[4]

Contents

[edit] Reported deaths

 This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (January 2012)
  • 22 January 2012 Nanton, Canada. Another overdose due to the chemical PMMA, present in MDMA tablets. [5]
  • 21 January 2012, Calgary, Alberta, Canada. Death of a 23 year old college student due to possible overdose of PMMA, present in MDMA. No confirmation that death related to same fatal batch of MDMA that claimed the life of Nanton, Alberta man. [6]
  • 12 January 2012 Vancouver, Canada. Media reports that 16 deaths may be related to this drug, although toxicology reports have not yet been completed in order to confirm this.[7] On January 15, 2012, toxicology reports confirmed that five of the 18 ecstasy related deaths since January 2011, contained the chemical PMMA.[8]
  • 11 January 2012, Calgary, Alberta, Canada. Calgary Police Service issues a press release stating that PMMA "was present in toxicology results for each of five recent Calgary-area street-drug deaths."[9] [10]
  • 31 March 2011 Dutch media reported that the Netherlands (Limburg province) had seen 4 deaths related to this drug since November 2010.[11]
  • 30 April 2011 Icelandic media reported that Iceland had seen 1 death of a young woman that may have been related to this drug.(citation needed)

[edit] See also

[edit] External links

[edit] References

  1. ^ Glennon, RA; Young, R; Dukat, M; Cheng, Y (1997). "Initial characterization of PMMA as a discriminative stimulus". Pharmacology, biochemistry, and behavior 57 (1-2): 151–8. doi:10.1016/S0091-3057(96)00306-1. PMID 9164566. 
  2. ^ Rangisetty, JB; Bondarev, ML; Chang-Fong, J; Young, R; Glennon, RA (2001). "PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA". Pharmacology, biochemistry, and behavior 69 (1-2): 261–7. doi:10.1016/S0091-3057(01)00530-5. PMID 11420094. 
  3. ^ Johansen, SS; Hansen, AC; Müller, IB; Lundemose, JB; Franzmann, MB (2003). "Three fatal cases of PMA and PMMA poisoning in Denmark". Journal of analytical toxicology 27 (4): 253–6. PMID 12820749. 
  4. ^ Becker, J; Neis, P; Röhrich, J; Zörntlein, S (2003). "A fatal paramethoxymethamphetamine intoxication". Legal medicine (Tokyo, Japan). 5 Suppl 1: S138–41. PMID 12935573. 
  5. ^ http://www.nantonnews.com/ArticleDisplay.aspx?e=3446181 Nanton News, Overdose death investigated January 24, 2012.
  6. ^ http://www.calgaryherald.com/news/alberta/Update+Seized+substances+sent+testing+after+suspected+overdose+SAIT/6037966/story.html Retrieved January 24, 2012.
  7. ^ Tainted ecstasy linked to five Calgary deaths could be from B.C., http://www.vancouversun.com/touch/story.html?id=5980841, Vancouver Sun, January 12, 2012, Retrieved January 12, 2012.
  8. ^ http://www.theprovince.com/life/Rare+chemical+found+fatal+ecstasy/5998482/story.html, The Province, January 15, 2012, Retrieved January 12, 2012.
  9. ^ "Authorities renew warning about street drugs". The City of Calgary Newsroom. http://newsroom.calgary.ca/pr/calgary/authorities-renew-warning-about-221684.aspx. Retrieved 11 January 2012. 
  10. ^ "Ecstasy laced with meth in overdose cases". http://www.cbc.ca/news/canada/calgary/story/2012/01/11/calgary-ecstasy-meth-deaths.html. Retrieved 12 January 2012. 
  11. ^ "PMMA deaths in Holland". www.nu.nl. http://translate.google.com/translate?js=n&prev=_t&hl=nl&ie=UTF-8&layout=2&eotf=1&sl=nl&tl=en&u=http%3A%2F%2Fwww.nu.nl%2Fbinnenland%2F2535695%2Fpinkpopgangers-moeten-uitkijken-met-xtc.html. Retrieved 8 June 2011. 
Drugs from PiHKAL

AEM • AL • Aleph • Aleph-2 • Aleph-4 • Aleph-6 • Aleph-7 • Ariadne • Asymbescaline • Buscaline • Beatrice • Bis-TOM • BOB • BOD • BOH • BOHD • BOM • 4-Bromo-3,5-dimethoxyamphetamine • 2-Bromo-4,5-methylenedioxyamphetamine • 2C-B • 3C-BZ • 2C-C • 2C-D • 2C-E • 3C-E • 2C-F • 2C-G • 2C-G-3 • 2C-G-4 • 2C-G-5 • 2C-G-N • 2C-H • 2C-I • 2C-N • 2C-O • 2C-O-4 • 2C-P • CPM • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • psi-2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 4-D • beta-D • DESOXY • 2,4-DMA • 2,5-DMA • 3,4-DMA • DMCPA • DME • DMMDA • DMMDA-2 • DMPEA • DOAM • DOB • DOBU • DOC • DOEF • DOET • DOI • DOM • psi-DOM • DON • DOPR • Escaline • EEE • EEM • EME • EMM • Ethyl-J (EBDB) • Ethyl-K • F-2 • F-22 • Flea • G-3 • G-4 • G-5 • G-N • Ganesha • HOT-2 • HOT-7 • HOT-17 • IDNNA • Isomescaline • Isoproscaline • Iris • J (BDB) • Lophophine • PMA • Mescaline • Madam-6 • Methallylescaline • MDA • MDAL • MDBU • MDBZ • MDCPM • MDDM • MDE • MDHOET • MDIP • MDMA • MDMC (EDMA) • MDMEO • MDMEOET • MDMP • MDOH • MDPEA • MDPH • MDPL • MDPR • Metaescaline • MEDA • MEE • MEM • MEPEA • Meta-DOB • Meta-DOT • Methyl-DMA • Methyl-DOB • Methyl-J (MBDB) • Methyl-K • Methyl-MA (PMMA) • Methyl-MMDA-2 • MMDA • MMDA-2 • MMDA-3a • MMDA-3b • MME • Metaproscaline • MPM • Ortho-DOT • Proscaline • Phenescaline • Phenethylamine • Propynyl • Symbescaline • 2,3,4,5-Tetramethoxyamphetamine • 3-TASB • 4-TASB • 5-TASB • Thiobuscaline • 3-TE • 4-TE • 3-TIM • 4-TIM • 5-TIM • 3-TM • 4-TM • TMA • TMA-2 • TMA-3 • TMA-4 • TMA-5 • TMA-6 • 3-TME • 4-TME • 5-TME • 2T-MMDA-3a • 4T-MMDA-2 • 2-TOET • 5-TOET • 2-TOM • 5-TOM • TOMSO • Thioproscaline • Trisescaline • 3-TSB • 4-TSB • 3-T-Trisescaline • 4-T-Trisescaline
Phenethylamines
Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-P • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • Allylescaline • DESOXY • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2
Stimulants: 2-OH-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA)
Entactogens: Lophophine • MDPEA • MDMPEA
Others: BOH • DMPEA
Amphetamines
Phenylisopropylamines
Psychedelics: 3C-BZ • 3C-E • 3C-P • Aleph • Beatrice • Bromo-DragonFLY • D-Deprenyl • DMA • DMCPA • DMMDA • DOB • DOC • DOEF • DOET • DOI • DOM • DON • DOPR • DOTFM • Ganesha • MMDA • MMDA-2 • Psi-DOM • TMA • TeMA
Stimulants: 4-MA • 4-MMA • 4-MTA • 5-IT • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Lefetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methoxyphenamine • MMA • Norfenfluramine • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine
Entactogens: 5-APDB • 6-APB • 6-APDB • EDA • IAP • MDA • MDEA • MDHMA (FLEA) • MDMA ("Ecstasy") • MDOH • MMDMA • NAP • TAP
Others: Amiflamine • DFMDA • D-Deprenyl • L-Deprenyl (Selegiline)
Phentermines
Stimulants: Chlorphentermine • Cloforex • Clortermine • Etolorex • Mephentermine • Pentorex (Phenpentermine) • Phentermine
Entactogens: MDPH • MDMPH
Cathinones
Stimulants: Amfepramone • Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone
Entactogens: Ethylone • Methylone
Phenylisobutylamines
Entactogens: 4-CAB • 4-MAB • Ariadne (α-Et-DOM) • BDB (J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • Eutylone (bk-EBDB) • MBDB (Methyl-J)
Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines
Stimulants: α-PBP • α-PPP • α-PVP • MDPBP • MDPPP • MDPV • MOPPP • MPBP • MPHP • MPPP • Naphyrone • PEP • Prolintane • Pyrovalerone
Catecholamines
(and relatives..)
6-FNE • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • Ciladopa • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • meta-Octopamine • meta-Tyramine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • para-Octopamine • para-Tyramine
Miscellaneous


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