PMA
854400
222440590
2008-06-29T10:35:20Z
Wikischolar1983
5973939
/* External links */ removed external link - wrong PMA, the weblink was about Progressive Muscular Atrophy, not the drug
{{otheruses}}
{{Drugbox|
|IUPAC_name = 1-(4-methoxyphenyl)propan-2-amine
| image = PMA.png
| width= 160
| CAS_number= 64-13-1
| ATC_prefix=
| ATC_suffix=
| PubChem= 31721
| smiles = C1=CC(=CC=C1CC(C)N)OC
| DrugBank=
| C=10 | H=15 | O=1 | N=1
| molecular_weight = 165.232 g/mol
| bioavailability=
| metabolism =
| elimination_half-life=
| excretion =
| pregnancy_category =
| legal_status =
| routes_of_administration=
}}
[[Image:PMAdea.jpg|thumb|300px|right|8 pills of PMA recovered by the [[Drug Enforcement Administration|DEA]]]]
[[Image:PMA 3D.png|thumb|200px|PMA 3D structure]]
'''PMA''' ('''para[[methoxy]][[amphetamine]]''', '''p-methoxyamphetamine''' or '''4-methoxyamphetamine''') is a [[Chemical synthesis|synthetic]] [[phenethylamine]] drug, psycho[[stimulant]] and [[Psychedelics, dissociatives and deliriants|hallucinogen]]. It is sometimes known by the street names of "death" or "Dr Death".<ref>{{cite news |first= |last= |authorlink= |coauthors= |title= Warning of possible shift to killer drug|url=http://news.smh.com.au/national/warning-of-possible-shift-to-killer-drug-20080407-2482.html |work= Sydney Morning Herald|publisher= Fairfax|date= 7 April 2008|accessdate=2008-06-29 }}</ref> It has, however, been more commonly encountered when it has been sold as "[[Ecstasy (drug)|ecstasy]]", even though PMA and [[MDMA]], the principal ingredient of ecstasy, are distinctly different chemicals. Both dealers and users are likely to be unaware that a particular batch of pills contains PMA rather than [[MDMA]].<ref>[http://www.erowid.org/experiences/exp.php?ID=22245 Erowid Experience Vaults: PMA (sold as Ecstasy) - Ecstacy Nightmare - 22245<!-- Bot generated title -->]</ref><ref>[http://www.erowid.org/experiences/exp.php?ID=6292 Erowid Experience Vaults: Ecstasy (PMA?) - Chunks Ahoy - 6292<!-- Bot generated title -->]</ref> Notable batches of pills containing PMA have included Mitsubishi Turbo or Red/Blue Mitsubishi and Yellow Euro pills.<ref> Kraner JC, McCoy DJ, Evans MA, Evans LE, Sweeney BJ. Fatalities caused by the MDMA-related drug paramethoxyamphetamine (PMA). Journal of Analytical Toxicology. 2001 Oct;25(7):645-8.</ref> PMA is often synthesized from [[anethole]], the flavor compound of [[anise]] and [[fennel]], mainly because the starting material for MDMA, [[safrole]], has become less available due to law enforcement action, causing illicit drug manufacturers to use anethole as an alternative.<ref> Waumans D, Bruneel N, Tytgat J. Anise oil as para-methoxyamphetamine (PMA) precursor. Forensic Science International. 2003 Apr 23;133(1-2):159-70.</ref> Once thought to be a human invention<ref>[http://www.cognitiveliberty.org/shulgin/adsarchive/acacia.htm Ask Dr. Shulgin Online September 26, 2001]</ref>, recent research suggests PMA occurs as a trace [[alkaloid]] in plants including certain ''[[Acacia berlandieri|Acacia]]'' species.<ref>Clement, Beverly A., Goff, Christina M. and Forbes, T. David A. "Toxic amines and alkaloids from ''Acacia berlandieri''". Phytochemistry 46(2), pp. 249-254 [http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TH7-3SCB6WX-1N&_user=10&_coverDate=09%2F30%2F1997&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=b215a5ead4e2fc6cc27a4cf30ced3f5e]</ref> It is classified as a [[Schedule I (US)|Schedule I]] [[Psychedelics, dissociatives and deliriants|hallucinogen]] under the [[Controlled Substances Act]] in the [[United States]]. Internationally, PMA is a Schedule I drug under the [[Convention on Psychotropic Substances]].<ref>{{cite web|url = http://www.incb.org/pdf/e/list/green.pdf |title = Annual Estimates Of Requirements Of Narcotic Drugs, Manufacture Of Synthetic Drugs, Opium Production And Cultivation Of The... |accessdate = 2008-06-15}}</ref>
PMA has been associated with numerous adverse reactions including death.<ref> Martin TL. Three cases of fatal paramethoxyamphetamine overdose. Journal of Analytical Toxicology. 2001 Oct;25(7):649-51. </ref><ref> Becker J, Neis P, Röhrich J, Zörntlein S. A fatal paramethoxymethamphetamine intoxication. Legal Medicine (Tokyo). 2003 Mar;5 Suppl 1:S138-41.</ref> Effects of PMA ingestion include many effects of the hallucinogenic amphetamines including [[tachycardia|accelerated]] and [[arrythmia|irregular]] heartbeat, blurred vision, and a strong feeling of intoxication which is often unpleasant. While PMA can reportedly be euphoric at low doses, the [[dose-response curve]] is much steeper than that of MDMA, and at higher doses unpleasant effects such as [[nausea]] and [[vomiting]], severe [[hyperthermia]] and [[hallucinations]] quickly overpower any pleasurable effects.<ref>[http://www.erowid.org/experiences/exp.php?ID=32091 Erowid Experience Vaults: PMA (Sold as Ecstasy), Alcohol & Cannabis - All is Not Lost - 32091<!-- Bot generated title -->]</ref><ref>[http://www.erowid.org/experiences/exp.php?ID=10681 Erowid Experience Vaults: PMA & MDMA (Ecstasy) - I Told Them - 10681<!-- Bot generated title -->]</ref><ref>[http://www.erowid.org/experiences/exp.php?ID=7993 Erowid Experience Vaults: PMA - Spoiled Ecstacy - 7993<!-- Bot generated title -->]</ref><ref>[http://www.erowid.org/experiences/exp.php?ID=4180 Erowid Experience Vaults: Ecstasy (PMA?) - Shaking, Seizure, and Aftereffects - 4180<!-- Bot generated title -->]</ref><ref>[http://www.erowid.org/experiences/exp.php?ID=7897 Erowid Experience Vaults: Ecstasy - White Mitsubishis - Not Safe to Roll In - 7897<!-- Bot generated title -->]</ref> The effects of PMA also seem to be much more unpredictable and variable between individuals than those of MDMA, and sensitive individuals may die from a dose of PMA that a less susceptible person might only be mildly affected by.<ref> Smets G, Bronselaer K, De Munnynck K, De Feyter K, Van de Voorde W, Sabbe M. Amphetamine toxicity in the emergency department. European Journal of Emergency Medicine. 2005 Aug;12(4):193-7. </ref> There are approximately twice as many deaths caused by PMA as by MDMA, even though the actual proportion of PMA on the market is only a fraction of that of MDMA. While PMA alone may cause significant toxicity, the combination of PMA with MDMA has a synergistic effect which seems to be particularly hazardous.<ref> Lora-Tamayo C, Tena T, Rodriguez A, Moreno D, Sancho JR, Ensenat P, Muela F. The designer drug situation in Ibiza. Forensic Science International. 2004 Mar 10;140(2-3):195-206. </ref> Since PMA has a slow onset of effects, several deaths have occurred where individuals have taken a pill containing PMA, followed by a pill containing MDMA some time afterwards due to thinking that the first pill was not active.<ref>Dams R, De Letter EA, Mortier KA, Cordonnier JA, Lambert WE, Piette MH, Van Calenbergh S, De Leenheer AP. Fatality due to combined use of the designer drugs MDMA and PMA: a distribution study.
Journal of Analytical Toxicology. 2003 Jul-Aug;27(5):318-22. </ref>
It appears that PMA elevates body temperatures dramatically; the cause of this property is suspected to be related to its ability to inhibit [[monoamine oxidase A]] and at the same time releasing large amounts of [[serotonin]], effectively causing [[serotonin syndrome]].<ref>Daws LC, Irvine RJ, Callaghan PD, Toop NP, White JM, Bochner F. Differential behavioural and neurochemical effects of para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine in the rat. Progress in Neuropsychopharmacology and Biological Psychiatry. 2000 Aug;24(6):955-77</ref><ref>[http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Retrieve&dopt=AbstractPlus&list_uids=6646243&query_hl=13&itool=pubmed_docsum Selective inhibition of monoamine oxidase in monoa...[Naunyn Schmiedebergs Arch Pharmacol. 1983] - PubMed Result]</ref> Amphetamines, especially serotonergic analogues such as MDMA, are strongly [[contraindication|contraindicated]] to take with [[MAOI]]s. Many amphetamines and adrenergic compounds raise body temperatures; whereas some tend to produce more euphoric activity, or peripheral vasoconstriction, or tend to favor one effect over another, it appears that PMA activates the [[hypothalamus]] much more strongly than MDMA and other drugs like ephedrine, thereby causing rapid increases in body temperature (which is the major cause of death in PMA mortalities).<ref> Jaehne EJ, Salem A, Irvine RJ. Effects of 3,4-methylenedioxymethamphetamine and related amphetamines on autonomic and behavioral thermoregulation. Pharmacology Biochemistry and Behavior. 2005 Jul;81(3):485-96. </ref><ref>Callaghan PD, Irvine RJ, Daws LC. Differences in the in vivo dynamics of neurotransmitter release and serotonin uptake after acute para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine revealed by chronoamperometry. Neurochemistry International. 2005 Oct;47(5):350-61. </ref><ref> Jaehne EJ, Salem A, Irvine RJ. Pharmacological and behavioral determinants of cocaine, methamphetamine, 3,4-methylenedioxymethamphetamine, and para-methoxyamphetamine-induced hyperthermia. Psychopharmacology (Berlin). 2007 May 27 </ref> Many people taking PMA try to get rid of the heat by taking off their clothes, taking cold showers or wrapping themselves in wet towels, and even sometimes by shaving off their hair.<ref> Refstad S. Paramethoxyamphetamine (PMA) poisoning; a 'party drug' with lethal effects. Acta Anaesthesiologica Scandinavia. 2003 Nov;47(10):1298-9. </ref>
Because PMA is given out through the same venues and distribution channels that "ecstasy" tablets are, the risk of being severely injured, hospitalized or even killed from use of ecstasy increases significantly when a batch of "ecstasy" pills containing PMA starts to be sold in a particular area.<ref> Galloway JH, Forrest AR. Caveat Emptor: Death involving the use of 4-methoxyamphetamine. Journal of Clinical Forensic Medicine. 2002 Sep;9(3):160. </ref> PMA pills could be a variety of colours or logos, and there is no way of knowing just from the appearance of a pill what drugs it might contain.<ref>{{cite web|url = http://dancesafe.org/documents/druginfo/pma_faq.php |title = Drug Info |accessdate = 2008-06-15}}</ref><ref>{{cite web|url = http://ecstasy.org/testing/pma.html |title = Warning: pills sold as ecstasy found to contain PMA |accessdate = 2008-06-15}}</ref> However, it is possible to test any "ecstasy" pill that is bought with a [[pill testing]] kit before it is consumed to determine its content, and to monitor reported results from police or government drug testing laboratories and avoid any pills that are reported to contain PMA.
It is believed that PMA first came into circulation in the early 1970s, where it was retrospectively implicated in a number of deaths in the United States and Canada.<ref>{{cite web|url = http://www.erowid.org/chemicals/pma/pma_dea_intellbrief.pdf |title = The Hallucinogen PMA: Dancing With Death|accessdate = 2008-06-29 |author = DEA}}</ref> Between 1974 and the early 1990s, there appear to have been no known fatalities from PMA.<ref>{{cite journal |last= Felgate|first= Heather E.|authorlink= |coauthors= Felgate, Peter D., James, Ross A., Sims, Noel, Vozzo, Dominic C.|year= 1998|month= |title= Recent Paramethoxyamphetamine Deaths|journal= Journal of Analytical Toxicology|volume= 22|issue= 2|pages= 169-172|id= |url= http://www.erowid.org/references/refs_view.php?A=ShowDoc1&ID=174|accessdate=2008-06-29 |quote= A Canadian report from 1974 is the most recent report of death due to PMA toxicity }}</ref> Several deaths reported as MDMA-induced in [[Australia]] in the early 1990s are now considered to have been caused by PMA, the users unaware that what they were ingesting was not MDMA but in fact PMA.<ref>{{cite journal |last= Byard|first= RW|authorlink= |coauthors= Gilbert, J, James, R, Lokan, RJ|year= 1998|month= |title= Amphetamine Derivative Fatalities in South Australia-Is "Ecstasy" the Culprit?|journal= The American Journal of Forensic Medicine and Pathology|volume= 19|issue= 3|pages= 261-265|id= |url= http://www.erowid.org/references/refs_view.php?A=ShowDoc1&ID=18|accessdate=2008-06-29 |quote= }}</ref> There have been a number of PMA-induced deaths around the world since then.
Four analogues of PMA have been reported to be sold on the black market: [[paramethoxymethamphetamine|PMMA]], [[paramethoxyethylamphetamine|PMEA]]<ref> John F. Casale, Patrick A. Hays, Trinette K. Spratley, and Pamela R. Smith. The Characterization of 4-Methoxy-N-ethylamphetamine Hydrochloride. DEA Microgram Journal 2006; 4(1-4)</ref> , [[paraethoxyamphetamine|4-ETA]] and [[4-Methylthioamphetamine|4-MTA]]. These are the N-methyl, N-ethyl, 4-ethoxy and 4-methylthio analogues of PMA, respectively. PMMA and PMEA are reportedly weaker, more "ecstasy-like" and somewhat less dangerous than PMA itself, but can still produce nausea and hyperthermia similar to that produced by PMA, albeit at slightly higher doses. 4-ETA was briefly sold in Canada in the 1970s but little is known about it.<ref>Alexander & Ann Shulgin, PiHKAL #97</ref> 4-MTA however is more dangerous even than PMA and produces strong stimulant effects and intense hyperthermia, but with little euphoria, and was implicated in several deaths in the late 1990s.
== References ==
{{reflist|2}}
==External links==
*[http://www.erowid.org/library/books_online/pihkal/pihkal097.shtml PiHKAL PMA entry]
* [http://www.erowid.org/chemicals/pma/pma_dea_intellbrief.pdf The Hallucinogen PMA: Dancing With Death] (in PDF format) from the [[Drug Enforcement Administration]]
*''[http://news.ninemsn.com.au/article.aspx?id=228808 Death drug may become health crisis]'', news.ninemsn.com.au article, Issued [[22 February]] [[2007]].
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{{Amphetamines}}
{{PiHKAL}}
[[Category:Amphetamine alkaloids]]
[[Category:Psychedelic phenethylamines]]
[[Category:Amphetamines]]
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