MMDA (psychedelic)

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ImageFile = MMDA.gif
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IUPACName = 1-(7-methoxy-1,3-benzodioxol-5-yl)propan-2-amine
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Section1 = Chembox Identifiers
CASNo = 13674-05-0
PubChem = 26175
SMILES = CC(N)Cc1cc2OCOc2c(c1)OC
Section2 = Chembox Properties
Formula = C₁₁H₁₅NO₃
MolarMass = 209.242 g/mol
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MeltingPt = 133-134 °C (hydrochloride)
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MMDA, or 3-methoxy-4,5-methylenedioxyamphetamine, is a stimulant, a psychedelic drug, an entheogen, and an entactogen. It is a substituted amphetamine and an analogue of MDA, Lophophine and MDMA (Ecstasy). It bears resemblance to the psychopharmacologically active essential oils elemicin and myristicin found in nutmeg. MMDA is most typically taken orally (as pressed tablets) or intranasally (as a powder).

MMDA was written up by Alexander Shulgin in his book, "PiHKAL (Phenethylamines i Have Known And Loved)". Shulgin lists the dosage range of MMDA as 100-250mg. The first symptoms appear within 30-60 minutes following . MMDA causes accentuation of feelings such as anxiety, euphoria, loneliness, and loving warmth. MMDA also produces eyes-closed visuals, a state of drowsiness and muscular relaxation, and time distortion. Side effects include moderate mydriasis, dizziness, sensations of 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": 25-50mg

"Duration": 8-12 hours

"Effects": slow, MDA-like effects, muscle stiffness, inability to defecate

Methyl-MMDA-2

"Dosage": unknown

"Duration": unknown

"Effects": Few to none

MMDA-3a

"Dosage": 20-80mg

"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": 25mg

"Duration": unknown

"Effects": Slight tremors

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_2A agonist in a similar manner to hallucinogenic amphetamines such as DOM, and also as a serotonin releaser by reversing the direction of the serotonin reuptake transporter in a similar manner to MDMA.

Legality

MMDA is classified as a 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] .

ee 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]