MDAI
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MDAI (5,6-methylenedioxy-2-aminoindane) is a
Chemistry
The
ring system, which changes its pharmacological properties substantially.MDAI can be produced from 3-(3,4-methylenedioxyphenyl)propionic acid[2] which is converted to the acid chloride and then heated to produce 5,6-Methylenedioxy-1-indanone. Treatment of the indanone with amyl nitrite in methanol with HCl afforded the hydroxyimino ketone. This is reduced to the 2-aminoindan following a modification of Nichols' earlier method from a paper discussing DOM analogues,[3] using a Pd/C catalyst in glacial acetic acid with catalytic H2SO4.
Pharmacology
MDAI has been shown to inhibit the reuptake of serotonin, dopamine, and norepinephrine with IC50 values of 512 nM, 5,920 nM, and 1,426 nM, respectively. This demonstrates that MDAI has selective affinity for the serotonin transporter (SERT). In animals treated with reserpine and MDAI, greater extracellular concentrations of monoamine neural transmitters resulted, most significantly serotonin. This result indicates that MDAI is a potent releaser of serotonin, while effectively inhibiting the reuptake of serotonin. For comparison, MDAI is similar in potency with releasing serotonin to MDA but significantly less potent than MDMA.[4]
Effects
The family of drugs typified by MDMA produce their effects through multiple mechanisms of action in the body, and consequently produce three distinct cues which animals can be trained to respond to: a stimulant cue typified by drugs such as methamphetamine, a psychedelic cue typified by drugs such as LSD and DOM, and an "entactogen-like" cue which is produced by drugs such as MDAI and MBDB. These drugs cause drug-appropriate responses in animals trained to recognize the effects of MDMA, but do not produce responses in animals trained selectively to respond to stimulants or hallucinogens. Because these compounds selectively release serotonin in the brain but have little effect on dopamine or noradrenaline levels, they can produce empathogenic effects but without any stimulant action, instead being somewhat sedating.[5][6][7][8][9][10][11]
Very high doses can be fatal in rats with a 50% fatality rate for those subcutaneously injected with 28 mg/kg of MDAI. This is a result of the way serotonin release interferes with thermoregulation.[12]
Use in scientific research
MDAI and other similar drugs have been widely used in scientific research, as they are able to replicate many of the effects of MDMA, but without causing the neurotoxicity which may be associated with MDMA and some related drugs. No tests have been performed on cardiovascular toxicity.[2][13][14][15][16][17][18]
Use as a recreational drug
MDAI has been advertised as a designer drug. It started to be sold online from around 2007, but reached peak popularity between about 2010–2012, after bans on mephedrone came into effect in various countries. Internet-sourced products claimed to be MDAI have been shown variously to contain mephedrone or other substituted cathinone derivatives, and mixed compositions of inorganic substances, while generally containing no MDAI. The number of internet searches for MDAI has been considerably higher in the UK compared to Germany and the USA.[19] MDAI is only non-neurotoxic in isolation but may become neurotoxic when mixed with other drugs.[20] Three deaths were linked to MDAI use in the UK during 2011–2012, all involving symptoms consistent with serotonin syndrome. Two of these also involved other drugs while one death appeared to be from MDAI alone.[21]
Legal Status
As of October 2015 MDAI is a controlled substance in China.[22]
MDAI is illegal in Denmark as of September 2015.[23]
As of December 2011 MDAI is a controlled substance in Switzerland [24]
See also
References
- ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
- ^ PMID 1967651.
- PMID 4809251.
- PMID 1685125.
- PMID 2886126.
- S2CID 19664637.
- PMID 2880944.
- PMID 1979813.
- S2CID 19069907. PMID
- PMID 7925587.
- S2CID 28388528.
- S2CID 33032545.
- S2CID 20485505.
- PMID 1674539.
- S2CID 7199902.
- PMID 8400010.
- PMID 8937435.
- S2CID 41048219.
- S2CID 205924978.
- S2CID 20354123.
- S2CID 12322724.
- ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.
- ^ "Lists of euphoriant substances subject to control in Denmark". The Danish Medicines Agency. September 2015.
- ^ "812.121.11" (PDF). Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien (Regulation of the EDI about the directories of drugs, psychotropic substances, precursors and auxiliary chemicals) (in German). Das Eidgenössische Departement des Innern (EDI). December 2011.