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20-September-2008 09:55:56 - PMA For other uses, see PMA disambiguation. PMA Systematic IUPAC name 1-4-methoxyphenylpropan-2-amine Identifiers CAS number 64-13-1 ATC code ? PubChem 31721 Chemical data Formula C10H15NO Mol. mass 165.232 g/mol SMILES eMolecules PubChem Pharmacokinetic data Bioavailability ? Metabolism ? Half life ? Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status Routes ? 8 pills of PMA recovered by the DEA 8 pills of PMA recovered by the DEA PMA 3D structure PMA 3D structure PMA paramethoxyamphetamine, p-methoxyamphetamine or 4-methoxyamphetamine is a synthetic phenethylamine drug, psychostimulant and hallucinogen. It is sometimes known by the street names of death or Dr Death.1 It has, however, been more commonly encountered when it has been sold as 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.23 Notable batches of pills containing PMA have included Mitsubishi Turbo or Red/Blue Mitsubishi and Yellow Euro pills.4 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.5 Once thought to be a human invention6, recent research suggests PMA occurs as a trace alkaloid in plants including certain Acacia species.7 It is classified as a Schedule I hallucinogen under the Controlled Substances Act in the United States. Internationally, PMA is a Schedule I drug under the Convention on Psychotropic Substances.8 PMA has been associated with numerous adverse reactions including death.910 Effects of PMA ingestion include many effects of the hallucinogenic amphetamines including accelerated and 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.1112131415 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.16 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.17 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.18 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.1920 Amphetamines, especially serotonergic analogues such as MDMA, are strongly contraindicated to take with MAOIs. 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.212223 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.24 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.25 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.2627 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.28 Between 1974 and the early 1990s, there appear to have been no known fatalities from PMA.29 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.30 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: PMMA, PMEA31 , 4-ETA and 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.32 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 ^ Warning of possible shift to killer drug, Sydney Morning Herald, Fairfax 7 April 2008. Retrieved on 2008-06-29. ^ Erowid Experience Vaults: PMA sold as Ecstasy - Ecstacy Nightmare - 22245 ^ Erowid Experience Vaults: Ecstasy PMA? - Chunks Ahoy - 6292 ^ 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;257:645-8. ^ Waumans D, Bruneel N, Tytgat J. Anise oil as para-methoxyamphetamine PMA precursor. Forensic Science International. 2003 Apr 23;1331-2:159-70. ^ Ask Dr. Shulgin Online September 26, 2001 ^ Clement, Beverly A., Goff, Christina M. and Forbes, T. David A. Toxic amines and alkaloids from Acacia berlandieri. Phytochemistry 462, pp. 249-254 1 ^ Annual Estimates Of Requirements Of Narcotic Drugs, Manufacture Of Synthetic Drugs, Opium Production And Cultivation Of The.... Retrieved on 2008-06-15. ^ Martin TL. Three cases of fatal paramethoxyamphetamine overdose. Journal of Analytical Toxicology. 2001 Oct;257:649-51. ^ Becker J, Neis P, Röhrich J, Zörntlein S. A fatal paramethoxymethamphetamine intoxication. Legal Medicine Tokyo. 2003 Mar;5 Suppl 1:S138-41. ^ Erowid Experience Vaults: PMA Sold as Ecstasy, Alcohol Cannabis - All is Not Lost - 32091 ^ Erowid Experience Vaults: PMA MDMA Ecstasy - I Told Them - 10681 ^ Erowid Experience Vaults: PMA - Spoiled Ecstacy - 7993 ^ Erowid Experience Vaults: Ecstasy PMA? - Shaking, Seizure, and Aftereffects - 4180 ^ Erowid Experience Vaults: Ecstasy - White Mitsubishis - Not Safe to Roll In - 7897 ^ 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;124:193-7. ^ 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;1402-3:195-206. ^ 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;275:318-22. ^ 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;246:955-77 ^ Selective inhibition of monoamine oxidase in monoa...Naunyn Schmiedebergs Arch Pharmacol. 1983 - PubMed Result ^ 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;813:485-96. ^ 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;475:350-61. ^ 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 ^ Refstad S. Paramethoxyamphetamine PMA poisoning; a 'party drug' with lethal effects. Acta Anaesthesiologica Scandinavia. 2003 Nov;4710:1298-9. ^ Galloway JH, Forrest AR. Caveat Emptor: Death involving the use of 4-methoxyamphetamine. Journal of Clinical Forensic Medicine. 2002 Sep;93:160. ^ Drug Info. Retrieved on 2008-06-15. ^ Warning: pills sold as ecstasy found to contain PMA. Retrieved on 2008-06-15. ^ DEA. The Hallucinogen PMA: Dancing With Death. Retrieved on 2008-06-29. ^ Felgate, Heather E.; Felgate, Peter D., James, Ross A., Sims, Noel, Vozzo, Dominic C. 1998. Recent Paramethoxyamphetamine Deaths. Journal of Analytical Toxicology 22 2: 169-172. Retrieved on 2008-06-29. A Canadian report from 1974 is the most recent report of death due to PMA toxicity ^ Byard, RW; Gilbert, J, James, R, Lokan, RJ 1998. Amphetamine Derivative Fatalities in South Australia-Is Ecstasy the Culprit?. The American Journal of Forensic Medicine and Pathology 19 3: 261-265. Retrieved on 2008-06-29. ^ 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; 41-4 ^ Alexander Ann Shulgin, PiHKAL #97 External links PiHKAL PMA entry The Hallucinogen PMA: Dancing With Death in PDF format from the Drug Enforcement Administration Death drug may become health crisis, news.ninemsn.com.au article, Issued 22 February 2007. v d e Amphetamines N06BA Amphetamine/Dextroamphetamine, Dextromethamphetamine, Levomethamphetamine, 4-FMP, 4-MTA, Benzphetamine, Ethylamphetamine, Propylamphetamine, MDMA, MDA, MDEA, N-methyl-β-hydroxyamphetamine, Parahydroxyamphetamine, Paramethoxyamphetamine, Paramethoxymethamphetamine, Paramethoxyethylamphetamine, Xylopropamine v d e 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 · 3C-G-3 · 3C-G-4 · 3C-G-5 · 3C-G-N · Ganesha · HOT-2 · HOT-7 · HOT-17 · IDNNA · Isomescaline · Isoproscaline · Iris · J BDB · Lophophine · Mescaline · 4-MA · 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 Retrieved from http://en..org/wiki/PMA Categories: Amphetamine alkaloids | Psychedelic phenethylamines | Amphetamines Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Česky Deutsch Français Galego Lietuvių Polski Suomi This page was last modified on 10 August 2008, at 17:49
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