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Methylated Amphetamines- MDA and MDMA

Methylated Amphetamines- MDA and MDMA. Methylenedioxymethamphetamine (MDMA, Ecstasy, XTC)- MDA is a metabolite of MDMA and may be responsible for much of the MDMA effect. Synthesized in 1912 Structurally related to amphetamines Sympathomimetic W eak in altering perceptual functions

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Methylated Amphetamines- MDA and MDMA

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  1. Methylated Amphetamines-MDA and MDMA • Methylenedioxymethamphetamine (MDMA, Ecstasy, XTC)-MDA is a metabolite of MDMA and may be responsible for much of the MDMA effect. • Synthesized in 1912 • Structurally related to amphetamines • Sympathomimetic • Weak in altering perceptual functions • But strong effects on emotions - empathogen • Used in combo with psychotherapy Of interest: http://www.biopsychiatry.com/interview/index.html

  2. Ecstasy (MDMA): Physiological Effects • Sympathomimetic • Bruxism & Trismus—teeth grinding & jaw clenching (pacifiers) • Dehydration/Overhydration • Hyperthermia • Tachycardia

  3. Ecstasy (MDMA): Psychological Effects • Increased alertness, arousal, insomnia--stimulant effects • Euphoria, increased emotional warmth • Increased empathy and insight? • Hallucinogenic effects are largely absent

  4. History • Patented by Merck in 1914 • Advocated by some as adjunct to psychotherapy (1970s-80s) • A “Designer Drug”…Picked up the name “ecstasy” & became significant street drug (1980s) • Schedule I drug (1986- The Analogue drug Act) • Prototype “club drug” (1990s)

  5. MDMA: Prototype Club Drug

  6. Pharmacodynamics Monoamine neurotransmission • increase synaptic DA and 5-HT • blocks 5-HT transporter • enters neuron and causes release of 5-HT

  7. Ecstasy and brain Damage?:Preclinical research • Serotonin depletion, damage to serotonergic neurons reported in several species including rats and primates (see Morton, 2005 for a review) • Effects were present in primate brain 7 years after MDMA exposure Hatzidimitrious et al., 1999)

  8. MDMA & MDA neurotoxicity 5-HT immunoreactive fibers in rat parietal cortex MDMA MDA Normal 9.9

  9. Are doses used in preclinical research too high? • neurotoxic doses in non-humans (5-20 mg/kg twice or more/day for several days) are generally higher than would be typical of human use. • However, people often take several tablets at a time or throughout a night’s binge and a tablet may contain up to 300 mg: 4-5 mg/kg in an average person.

  10. X Toxicity • Malignant hyperthermia and dehydration • Idiopathic toxic response (not common but nasty) • Renal failure • Rhabdomyolysis – disintegration of muscle tissue • seizures, arrhythmias, heart failure, stroke, • Most MDMA-related fatalities have been attributed to symptoms of heat stroke and hyperthermia

  11. Residual (long-term) adverse effects? • Topp et al. (1999) Australia study • Physical side effects • Loss of energy (65%), Muscular aches (60%) • Hot/cold flashes (48%), Numbness (47%) • Profuse sweating (43%), Tremors (42%) • Psychological side effects • Depression (56%), rritability (63%), • Sleep difficulty (56%), Confusion (47%) • Anxiety (45%), Paranoia (40%) • Memory deficits? • ( note issue of sample problems/poly-drug use etc..)

  12. What is PMA? • Paramethoxy-amphetamine • "Death" "Mitsubishi Double Stack" "Killer" "Red Mitsubishi" • Substitute for MDMA • Cheaper to make • Slower, longer effects • More hallucinogenic • Incidence of toxic side effects much higher than MDMA (narrow safety margin)

  13. Myristin and Elemicin • Found in nutmeg and mace • Structurally similar to mescaline • Significant nausea and vomiting • The sickness usually limits use

  14. GlutamatergicPsychedelics AKA-Dissociative Anesthetics: -Phencyclidine (PCP, Angel dust, Lovely) -Ketamine (Special K)

  15. Phencyclidine • PCP • Glutamate (NMDA) receptor antagonist • Blocks the function of glutamate • Used as an analgesic and anesthetic • Can be administered by any route • Oddly enough, animals self-administer (euphoria)

  16. PCP- physiological effects • numbness, loss of motor coordination, slurred speech, blurred vision, Nystagmus • Higher doses lead to: • hyper excitability or stupor • coma • seizures • death • A perfect example of a Schedule I drug • High rate of psychotic episodes some long-term

  17. Subjective Effects of PCP/Ketamine • Sensations of light coming through the body and/or colorful visions • Complete loss of time sense • Bizarre distortions of body shape or size • Altered perception of body consistency • Sensations of floating or hovering in space • Feelings of leaving one’s body • Visions of spiritual or supernatural beings • Emotions ranging from euphoria to hositlity • true psychosis • Hallucinations, paranoia, agitation, dissociation Dalgarno & Shewan (1996)

  18. Ketamine • Special K • Very similar to PCP, not as powerful • Liquid, but can be powdered for snorting or smoking • Another perfect example of a Schedule I drug

  19. Dextromethorphan • Active ingredient in most OTC cough medicine • NMDA receptor blockade at high doses • Mostly teenage males abuse it • Like PCP and K at 20-30 X OTC dose • Coricidin –Bad news

  20. CholinergicHallucinogens

  21. Anticholinergic hallucinogens • Atropine-Deadly nightshade, Datura, Jimson weed, and Mandrake, Atropa belladonna • Scopolamine-from Datura, Jimson weed, Mandrake and Henbane

  22. CholinergicHallucinogens Acetylcholine receptor (muscarinic) antagonists Dissociatives that induces delirium , hallucinations, and amnesia Classic anti-cholinergic symptoms Hot as hell Dry as a bone Mad as a hatter Blind as a bat Red as a beet Used in the treatment of motion sickness & to dilate pupils during eye-exams.

  23. Datura

  24. Jimson weed

  25. Anticholinergic effects • Dry mouth, blurred vision, loss of motor control • Dream-like trance state • Little or no memory of experience

  26. Muscarine/Muscimol • Found in mushrooms (Amanita Muscaria) • Muscimol is a GABAA agonist • Trance-like, dreamy state with dreamlike illusions • Like Ambien • Muscarine is an Acetylcholine agonist (muscarinic receptors) • Not psychotropic • Peripheral effects: sweating, limb twitching, seizure activity

  27. Salvia Divinorum • Plant used by the Mazatec people of Southern Mexico: Diviner’s sage—leaves chewed or smoked • Active substance = salvinorum A (affects Kappa receptors)--most potent natural hallucinogen (100 microgram ED50)

  28. Salvia Divinorum Brief (30-60 min) intense trip: visual hallucinations, dissociative state, some bad trips, recent highly publicized suicide Marketed legally in US (in most states) as herbal dietary supplement—currently under DEA review

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