3-Methoxy-4,5-methylenedioxyamphetamine
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| MMDA | |
|---|---|
| Chemical name | 3-methoxy-4,5-Methylenedioxyamphetamine or 1-(7-methoxy-1,3-benzodioxol-5-yl)propan-2-amine |
| Chemical formula | C11H15NO3 |
| Molecular mass | 209.2417 g/mol |
| Melting point | 133-134 °C (hydrochloride) |
| CAS numbers | 13674-05-0 |
| SMILES | CC(N)Cc1cc2OCOc2c(c1)OC |
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MMDA, 3-MeO-4,5-MDA, 3-methoxy-4,5-methylenedioxy-phenylisopropylamine, or 3-methoxy-4,5-methylendioxyamphetamine has stimulant, psychedelic, entheogenic, and entactogenic effects in man.
Contents |
[edit] Chemistry
MMDA, 1-(7-methoxy-1,3-benzodioxol-5-yl)propan-2-amine, is a biologically active phenethylamine and amphetamine derivative. Its analogues include MDA, lophophine and MDMA, and it bears resemblance to the psychopharmacologically active essential oils elemicin and myristicin found in nutmeg.
[edit] Dosage
The effective dose of MMDA is 120-150 mg. Most typically taken by mouth via pressed tablets or intranasaly via powder.
[edit] Effects
The first symptoms appear within 30-60 minutes following oral administration. Moderate mydriasis, dizziness, sensations of heat or cold, and trembling are occasionally reported as side effects. Psychologically, the most frequently reported effects are accentuation of feelings (anxiety, euphoria, loneliness, loving warmth), the visualization of images (with eyes closed), a state of drowsiness and muscular relaxation, and an overestimation of elapsed time.
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.
[edit] 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.
[edit] 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 5HT2A 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.
[edit] 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[1].
[edit] See also
[edit] External links
- PIHKAL entry for MMDA
- MMDA: A New Psychotomimetic Agent
- Animal Pharmacology and Human Psychopharmacology of MMDA
- A Pharmacological Comparison of MMDA and LSD In The Dog
{01-Amphetamine/dl-Amphetamine} {02-Dextroamphetamine} {03-Dextromethamphetamine}
no ATC code: {4-FMP} {4-MTA} {Benzphetamine} {MDMA} {MDA} {MDEA} {Paramethoxyamphetamine}
Aleph, 2C-B, 2C-B-FLY, 2C-C, 2C-D, 2C-E, 2C-F, 2C-G, 2C-I, 2C-N, 2C-O, 2C-O-4, 2C-P, 2C-T, 2C-T-2, 2C-T-4, 2C-T-7, 2C-T-8, 2C-T-9, 2C-T-13, 2C-T-15. 2C-T-17, 2C-T-21, 2C-TFM, 3C-E, 3C-P, Br-DFLY, DESOXY, DMMDA-2, DOB, DOC, DOET, DOI, DOM, DON, Escaline, Ganesha, HOT-2, HOT-7, HOT-17, Isoproscaline, Lophophine, MDA, MMDA, MMDA-2, MMDA-3a, MMDMA, Macromerine, Mescaline, Proscaline, TMA
AEM, AL, Aleph, Aleph-2, Aleph-4, Aleph-6, Aleph-7, Ariadne, Asymbescaline, Buscaline, Beatrice, Bis-TOM, BOB, BOD, BOH, BOHD, BOM, 4-bromo-3,5-dimethoxyamphetamine, 2-bromo-4,5-methylenedioxyamphetamine, 2C-B, 3C-BZ, 2C-C, 2C-D, 2C-E, 3C-E, 2C-F, 2C-G, 2C-G-3, 2C-G-4, 2C-G-5, 2C-G-N, 2C-H, 2C-I, 2C-N, 2C-O-4, 2C-P, CPM, 2C-SE, 2C-T, 2C-T-2, 2C-T-4, psi-2C-T-4, 2C-T-7, 2C-T-8, 2C-T-9, 2C-T-13, 2C-T-15, 2C-T-17, 2C-T-21, 4-D, beta-D, DESOXY, 2,4-DMA, 2,5-DMA, 3,4-DMA, DMCPA, DME, DMMDA, DMMDA-2, DMPEA, DOAM, DOB, DOBU, DOC, DOEF, DOET, DOI, DOM, psi-DOM, DON, DOPR, Escaline, EEE, EEM, EME, EMM, Ethyl-J, Ethyl-K, F-2, F-22, Flea, 3C-G-3, 3C-G-4, 3C-G-5, 3C-G-N, Ganesha, HOT-2, HOT-7, HOT-17, IDNNA, Isomescaline, Isoproscaline, Iris, J/BDB, Lophophine, Mescaline, 4-MA, Madam-6, Methallylescaline, MDA, MDAL, MDBU, MDBZ, MDCPM, MDDM, MDE, MDHOET, MDIP, MDMA, MDMC/EDMA, MDMEO, MDMEOET, MDMP, MDOH, MDPEA, MDPH, MDPL, MDPR, Metaescaline, MEDA, MEE, MEM, MEPEA, Meta-DOB, Meta-DOT, Methyl-DMA, Methyl-DOB, Methyl-J/MBDB, Methyl-K, Methyl-MA, Methyl-MMDA-2, MMDA, MMDA-2, MMDA-3a, MMDA-3b, MME, MP, MPM, Ortho-DOT Proscaline, Phenescaline, Phenethylamine, Propynyl, Symbescaline, 2,3,4,5-tetramethoxyamphetamine, 3-TASB, 4-TASB, 5-TASB, Thiobuscaline, 3-TE, 4-TE, 3-TIM, 4-TIM, 5-TIM, 3-TM, 4-TM, TMA, TMA-2, TMA-3, TMA-4, TMA-5, TMA-6, 3-TME, 4-TME, 5-TME, 2T-MMDA-3a, 4T-MMDA-2, TMPEA, 2-TOET, 5-TOET, 2-TOM, 5-TOM, TOMSO, Thioproscaline, Trisescaline, 3-TSB, 4-TSB, 3-T-Trisescaline, 4-T-Trisescaline
