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PMA
Systematic (IUPAC) name
1-(4-methoxyphenyl)propan-2-amine
Identifiers
CAS number 64-13-1
ATC code  ?
PubChem 31721
Chemical data
Formula C10H15NO 
Mol. mass 165.232 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

? PMA can refer to: Pacific Maritime Association Photo Marketing Association polymethyl acrylate positive mental attitude poste médical avancé, a French field hospital Power Marketing Administration pre-motor area of the motor cortex This page concerning a three-letter acronym or abbreviation is a disambiguation page — a navigational aid which... drawn in bkchem (http://www. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... PubChem is a database of chemical molecules. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... It has been suggested that Effective half-life be merged into this article or section. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status
Routes  ?
8 pills of PMA recovered by the DEA
8 pills of PMA recovered by the DEA
PMA 3D structure

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 [2], 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 [3]. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... Image File history File links PMAdea. ... Image File history File links PMAdea. ... The DEAs enforcement activities may take agents anywhere from distant countries to suburban U.S. homes. ... Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... Amphetamine or Amfetamine (Alpha-Methyl-PHenEThylAMINE), also known as beta-phenyl-isopropylamine and benzedrine, is a prescription stimulant commonly used to treat Attention-deficit hyperactivity disorder (ADHD) in adults and children. ... In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product, or several products. ... Phenethylamine, or β-Phenylethylamine, is an alkaloid and monoamine. ... Stimulants are drugs that temporarily increase alertness and wakefulness. ... The general group of pharmacological agents commonly known as hallucinogens can be divided into three broad categories: psychedelics, dissociatives, and deliriants. ... ecstasy and religious ecstasy MDMA, most commonly known today by the street name ecstasy, is a synthetic entactogen of the phenethylamine family whose primary effect is to stimulate the brain to rapidly secrete large amounts of serotonin, causing a general sense of openness, empathy, energy, euphoria, and well-being. ... For information on Mitsubishi brand computer monitors, see NEC-Mitsubishi Electronics Display of America Inc. ... Anethole Anethole (or trans-anethole) is an aromatic compound that accounts for the distinctive licorice flavor of anise, fennel, and star anise. ... This article is about the Pimpinella species, but the name anise is frequently applied to Fennel. ... Binomial name Foeniculum vulgare Mill. ... Safrole Safrole (chemical formula: C10H10O2, IUPAC name: 5-(2-propenyl)-1,3-benzodioxole), also called shikimol, is a colorless or slightly yellow oily liquid. ... Chemical structure of ephedrine, a phenethylamine alkaloid An alkaloid is, strictly speaking, a naturally occurring amine produced by a plant,[1] but amines produced by animals and fungi are also called alkaloids. ... Binomial name Acacia berlandieri Benth. ... The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... The general group of pharmacological agents commonly known as hallucinogens can be divided into three broad categories: psychedelics, dissociatives, and deliriants. ... The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... Convention on Psychotropic Substances Opened for signature February 21, 1971 in Vienna Entered into force August 16, 1976 Conditions for entry into force 40 ratifications Parties 175 The Convention on Psychotropic Substances is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, and psychedelics. ...


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] This article or section does not cite any references or sources. ... Cardiac arrhythmia is a group of conditions in which the muscle contraction of the heart is irregular or is faster or slower than normal. ... A dose-response curve is a simple X-Y graph with Y usually being the measured dose (usually in milligrams, micrograms, or grams per kilogram of body-wieght) and X being the response. ... For other uses, see Nausea (disambiguation). ... Emesis redirects here. ... This article does not cite any references or sources. ... A hallucination is a false sensory perception in the absence of an external stimulus, as distinct from an illusion, which is a misperception of an external stimulus. ...


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 [4]. 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] Monoamine oxidase A is an isozyme of monoamine oxidase. ... Serotonin (pronounced ) (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract of animals including humans. ... Serotonin syndrome is a rare, but potentially life-threatening adverse drug reaction that results from intentional self-poisoning, therapeutic drug use, or inadvertent interactions between drugs. ... In medicine, a contraindication is a condition or factor that increases the risk involved in using a particular drug, carrying out a medical procedure or engaging in a particular activity. ... Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ... The hypothalamus links the nervous system to the endocrine system via the pituitary gland (hypophysis). ...


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. [5][6]. 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. MDMA (3,4-methylenedioxymethamphetamine), most commonly known by the street names ecstasy or XTC (for more names see the full list), is a synthetic entactogen of the phenethylamine family, whose primary effect is believed to be the stimulation of secretion as well as inhibition of re-uptake of large amounts... Pill Testing is a process used to identify substances contained within a pill, usually illicit substances. ...


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. Para-methoxy-methamphetamine or PMMA is a stimulant drug related to PMA and methamphetamine. ... Para-methoxy-ethylamphetamine or PMEA is a stimulant drug related to PMA and ethylamphetamine. ... 4MT structure 4-methylthioamphetamine is a drug known as 4MT, 4-MTA, Flatliners, 1-(4-methylthiophenyl)-2-aminopropane. ...


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


  Results from FactBites:
 
PMA - Wikipedia, the free encyclopedia (266 words)
Internationally, PMA is a Schedule I drug under the Convention on Psychotropic Substances[1].
PMA is sometimes found in illicit street "Ecstacy" tablets, either alone or in combination with other drugs, and has been associated with numerous adverse reactions including death.
Two analogues of PMA are known from the street: PMMA, and 4-MTA.
Outsourcing the Pentagon - The Center for Public Integrity (869 words)
Of the $266 billion that PMA clients and their parents received in defense contracts, $167 billion—nearly two out of three dollars—were received from contracts that were awarded without "full and open" competition.
PMA's lobbyists routinely make large donations to the lawmakers they lobby, and many at the firm have revolving door connections to Congress and defense agencies that authorize and maintain the contracts of their clients.
PMA is one of the few lobbying firms that maintains a sizable Political Action Committee.
  More results at FactBites »

 
 

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