PMA

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PMA
PMA.png
Identifiers
CAS Number
PubChem CID
E number{{#property:P628}}
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Chemical and physical data
FormulaC10H15NO
Molar mass165.232 g/mol

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8 pills of PMA recovered by the DEA
PMA 3D structure

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [2]


Overview

PMA (paramethoxyamphetamine, p-methoxyamphetamine or 4-methoxyamphetamine) is a synthetic phenethylamine drug, psychostimulant and hallucinogen. It is commonly sold as "Ecstasy" and both dealers and users are likely to be unaware that a particular batch of pills contains PMA rather than MDMA.[1][2] Notable batches of pills containing PMA have included Mitsubishi Turbo or Red/Blue Mitsubishi and Yellow Euro pills.[3] 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.[4] Once thought to be a human invention [3], recent research suggests PMA occurs as a trace alkaloid in plants including certain Acacia species. [5]. 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 [4].

PMA has been associated with numerous adverse reactions including death.[6][7] 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.[8][9][10][11][12] 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.[13] 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.[14] 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.[15]

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,[16] effectively causing serotonin syndrome [5]. 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).[17][18][19] 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.[20]

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.[21] 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. [6][7]. Due to the variations in street "Ecstasy" pills, the only way to reduce the risk of ingestion of PMA is to test any "Ecstasy" pill that is bought with a pill testing kit before it is consumed, and to monitor reported results from police or government drug testing laboratories and avoid any pills that are reported to contain PMA.

Four analogues of PMA have been reported to be sold on the black market: PMMA, PMEA[22] , 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. [23] 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

  1. http://www.erowid.org/experiences/exp.php?ID=22245
  2. http://www.erowid.org/experiences/exp.php?ID=6292
  3. 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.
  4. Waumans D, Bruneel N, Tytgat J. Anise oil as para-methoxyamphetamine (PMA) precursor. Forensic Science International. 2003 Apr 23;133(1-2):159-70.
  5. Clement, Beverly A., Goff, Christina M. and Forbes, T. David A. "Toxic amines and alkaloids from Acacia berlandieri". Phytochemistry 46(2), pp. 249-254 [1]
  6. Martin TL. Three cases of fatal paramethoxyamphetamine overdose. Journal of Analytical Toxicology. 2001 Oct;25(7):649-51.
  7. Becker J, Neis P, Röhrich J, Zörntlein S. A fatal paramethoxymethamphetamine intoxication. Legal Medicine (Tokyo). 2003 Mar;5 Suppl 1:S138-41.
  8. http://www.erowid.org/experiences/exp.php?ID=32091
  9. http://www.erowid.org/experiences/exp.php?ID=10681
  10. http://www.erowid.org/experiences/exp.php?ID=7993
  11. http://www.erowid.org/experiences/exp.php?ID=4180
  12. http://www.erowid.org/experiences/exp.php?ID=7897
  13. 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.
  14. 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.
  15. 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.
  16. 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.
  17. 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.
  18. 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.
  19. 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
  20. Refstad S. Paramethoxyamphetamine (PMA) poisoning; a 'party drug' with lethal effects. Acta Anaesthesiologica Scandinavia. 2003 Nov;47(10):1298-9.
  21. Galloway JH, Forrest AR. Caveat Emptor: Death involving the use of 4-methoxyamphetamine. Journal of Clinical Forensic Medicine. 2002 Sep;9(3):160.
  22. 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)
  23. Alexander & Ann Shulgin, PIHKAL #97

External links


de:4-Methoxyamphetamin gl:PMA lt:PMA fi:Parametoksiamfetamiini



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