View source for MMDA (psychedelic)

{| border="1" cellpadding="2" cellspacing="0" align="right" style="margin-left:1em"
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! colspan="2" bgcolor="#cccccc" | MMDA
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| [[IUPAC nomenclature|Chemical name]]
| 3-methoxy-4,5-Methylenedioxyamphetamine <br>or<br>1-(7-methoxy-1,3-benzodioxol-5-yl)propan-2-amine
|-----
| [[Chemical formula]]
| [[carbon|C]]<sub>11</sub>[[hydrogen|H]]<sub>15</sub>[[nitrogen|N]][[oxygen|O]]<sub>3</sub>
|-----
| [[Molecular mass]] || 209.2417 g/mol
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| [[Melting point]] ||  133-134 °C ([[hydrochloride]])
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| [[CAS registry number|CAS numbers]] || 13674-05-0
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| [[Simplified molecular input line entry specification|SMILES]]
| CC(N)Cc1cc2OCOc2c(c1)OC
|}
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==Overview==
'''MMDA''', or '''3-[[methoxy]]-4,5-[[methylene]]di[[oxygen|oxy]][[amphetamine]]''', is a [[stimulant]], a [[psychedelic]] drug, an [[entheogen]], and an [[empathogen-entactogen|entactogen]]. It is a substituted Amphetamine and an [[analog (chemistry)|analogue]] of [[MDA]], [[Lophophine]] and [[MDMA]] (Ecstasy). It bears resemblance to the [[psychopharmacology|psychopharmacologically]] active essential oils [[elemicin]] and [[myristicin]] found in nutmeg. MMDA is most typically taken orally (as pressed tablets) or intranasaly (as a powder).

MMDA was written up by [[Alexander Shulgin]] in his book, "[[PiHKAL]]." Shulgin lists the dosage range of MMDA as 100-250 [[milligram|mg]]. The first symptoms appear within 30-60 minutes following [[Wiktionary:oral|oral administration]]. MMDA causes accentuation of feelings such as [[anxiety]], [[Euphoria (emotion)|euphoria]], loneliness, and loving warmth. MMDA also produces eyes-closed visuals, a state of [[drowsiness]] and [[muscle relaxant|muscular relaxation]], and time distortion. [[Adverse drug reaction|Side effects]] include moderate [[mydriasis]], [[dizziness]], sensations of [[hot flashes|heat or cold]], and [[trembling]]. The imagery is generally realistic, and often related to everyday [[perception]] of people, landscapes, or objects. The effects of MMDA usually reach a peak after the first hour following the initial symptoms, and begin to wane during the second hour, and usually completely disappear by the end of the fifth hour.

== Analogs ==
===MMDA-2===
''Dosage'': 25-50 mgs

''Duration'': 8-12 hours

''Effects'': slow, [[3,4-methylenedioxyamphetamine|MDA]]-like effects, [[muscle]] stiffness, inability to defecate

===Methyl-MMDA-2===
''Dosage'': unknown

''Duration'': unknown

''Effects'': Few to none

===MMDA-3a===
''Dosage'': 20-80 mgs

''Duration'': 10-16 hours

''Effects'': mild open-eye visuals, visual enhancement of music, slowing of time, slight [[diarrhea]] and body load

===MMDA-3b===
''Dosage'': unknown

''Duration'': unknown

''Effects'': Few to none

===2T-MMDA-3a===
''Dosage'': unknown

''Duration'': unknown

''Effects'': Few to none

===4T-MMDA-2===
''Dosage'': 25 mg

''Duration'': unknown

''Effects'': Slight [[tremor]]s

==Psychotherapuetic actions==
In his 1973 book, "The Healing Journey," Claudio Naranjo explored the [[psychotherapeutic]] potential of MMDA. Like MDA, he found that MMDA facilitates communication and suggested it has potential applications in [[psychotherapy]]. Worldwide as of 2005, MMDA has not been approved for any human applications.

==Pharmacology==
The mechanism that produces the psychedelic activity of MMDA has not been definitively established. There are, as of the present time, no reported studies on the human [[pharmacokinetics]] or [[metabolism]] of MMDA. Based on its structural relationship with other similar drugs for which the pharmacology is known, it is likely that MMDA has multiple mechanisms of action, and probably acts both as a 5HT<sub>2A</sub> [[agonist]] in a similar manner to hallucinogenic amphetamines such as [[2,5-dimethoxy-4-methylamphetamine|DOM]], and also as a serotonin releaser by reversing the direction of the [[serotonin transporter|serotonin reuptake transporter]] in a similar manner to [[MDMA]].

==Legality==
MMDA is classified as a [[Controlled Substances Act#Schedule I drugs|Schedule 1]] substance in the United States, and is similarly controlled in other parts of the world. Internationally, MMDA is a Schedule I drug under the [[Convention on Psychotropic Substances]][http://www.incb.org/pdf/e/list/green.pdf].

==See also==
*[[MDA]]
*[[MDMA]]
*[[PiHKAL]]

==External links==
*[http://www.erowid.org/library/books_online/pihkal/pihkal132.shtml PIHKAL entry for MMDA]
*[http://www.erowid.org/archive/rhodium/chemistry/mmda.shulgin.html MMDA: A New Psychotomimetic Agent]
*[http://www.erowid.org/archive/rhodium/chemistry/mmda.pharmacology.shulgin.html Animal Pharmacology and Human Psychopharmacology of MMDA]
*[http://www.erowid.org/references/refs_view.php?A=ShowDoc1&ID=3598 A Pharmacological Comparison of MMDA and LSD In The Dog]




{{Entactogens}}
{{Hallucinogenic phenethylamines}}
{{PiHKAL}}

[[Category:Amphetamines|Methoxy-4,5-methylendioxyamphetamine, 3-]]
[[Category:Alkaloids|Methoxy-4,5-methylendioxyamphetamine, 3-]]
[[Category:Class A drugs|Methoxy-4,5-methylendioxyamphetamine, 3-]]
[[Category:Entactogens and Empathogens|Methoxy-4,5-methylendioxyamphetamine, 3-]]
[[Category:Psychedelic phenethylamines|Methoxy-4,5-methylendioxyamphetamine, 3-]]
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