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Description

MDAI Also known as:

  • 5,6-Methylenedioxy-2-aminoindane
  • 5H-Indeno(5,6-d)-1,3-dioxol-6-amine, 6,7-dihydro-
  • 5H-Indeno[5,6-d]-1,3-dioxol-6-amine, 6,7-dihydro-[ACD/Index Name]
  • 6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-amine
  • 6,7-Dihydro-5H-indeno(5,6-d)-1,3-dioxol-6-amine
  • 6,7-Dihydro-5H-indeno[5,6-d][1,3]dioxol-6-amin[German][ACD/IUPAC Name]
  • 6,7-Dihydro-5H-indeno[5,6-d][1,3]dioxol-6-amine[ACD/IUPAC Name]
  • 6,7-Dihydro-5H-indéno[5,6-d][1,3]dioxol-6-amine[French][ACD/IUPAC Name]
  • [132741-81-2]
  • 2H,5H,6H,7H-INDENO[5,6-D][1,3]DIOXOL-6-AMINE
  • 2H-indano[5,6-d]1,3-dioxolene-6-ylamine
  • 5,6-methylenedioxy-2-amineoindanee[ACD/IUPAC Name]
  • 5,6-Methylenedioxy-2-aminoindan
  • 5H-Indeno[5,6-d]-1,3-dioxol-6-amine,6,7-dihydro-
  • 6,7-dihydro-5H-cyclopenta[f][1,3]benzodioxol-6-ylamine
  • 6,7-dihydro-5H-indeno [5,6-d][1,3] dioxol-6-amine[ACD/IUPAC Name]
  • 6,7-Dihydro-5H-indeno[5,6-d][1,3]dioxol-6-ylamine
  • MDAI (5,6-Methylenedioxy-2-aminoindane)
  • MDAI (5,6-Methylenedioxy-2-aminoindane) 1.0 mg/ml in Acetonitrile
  • MFCD12755989

A selective serotonin releasing agent which is rarely used without a stimulant to obtain desirable effects. Previously believed not to be neuruotoxic, however MDAI has been implicated in several lethal and non-lethal intoxications, and as such may pose more of a risk to health than previously believed.

Summary

Notably, this compound primarily produces the non-stimulating effects of prototypical entactogens like MDMA such as sedation, muscle relaxation, and tactile enhancement. MDAI was developed in the 1990s by a team led by David E. Nichols at Purdue University.

It acts as a putatively non-neurotoxic and highly selective serotonin releasing agent (SSRA) with neglible effects on dopamine and norepinephrine. This reportedly limits its potential at producing overtly invigorating, prosocial or euphoric effects. MDAI has been marketed alongside research chemical entactogens like 5-MAPB, 5-APB, and 6-APB as a legal, grey-market alternative to MDMA.

Very little data exists about the pharmacological properties, metabolism, and toxicity of MDAI, and it has a limited history of human use. It is highly advised to use harm reduction practices if using this substance.

Chemistry

This creates an indane group, a bicyclic moeity containing a benzene ring fused to a pentane ring. MDAI contains an amino group NH2 bound to R2 of the indane ring.

MDAI also contains two oxygen substitutions at R5 and R6 joined by a methylene bridge to form a methylenedioxy group. MDAI is structurally related to 2-AI, differing by a methylenedioxy ring.

Common NameMDAI
Systematic nameMDAI
FormulaC_{10}H_{11}NO_{2}
SMILESc1c2c(cc3c1OCO3)CC(C2)N
Std. InChiInChI=1S/C10H11NO2/c11-8-1-6-3-9-10(13-5-12-9)4-7(6)2-8/h3-4,8H,1-2,5,11H2
Std. InChiKeyFQDRMHHCWZAXJM-UHFFFAOYSA-N
Avg. Mass177.1998 Da
Molecular Weight177.1998
Monoisotopic Mass177.078979 Da
Nominal Mass177
ChemSpider ID111694

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Dose Chart

Oral
Threshold20-40mg
Light40-100mg
Common100-150mg
Heavy150-300mg+

Duration Chart

MDAI Duration Data
Onset30-60 minutes
Duration4-6 hours
After-effects1-8 hours

Interactions

Caution

  1. Mushrooms
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  2. LSD
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  3. DMT
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  4. Mescaline
    • The focus and anxiety caused by stimulants is magnified by psychedelics and results in an increased risk of thought loops
  5. 2C-x
    • The anxiogenic and focusing effects of stimulants increase the chance of unpleasant thought loops. The combination is generally uneccessary because of the stimulating effects of psychedelics. Combination of the stimulating effects may be uncomfortable.
  6. Cannabis
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences
  7. Ketamine
    • No unexpected interactions, though likely to increase blood pressure but not an issue with sensible doses. Moving around on high doses of this combination may be ill advised due to risk of physical injury.
  8. MXE
    • Risk of tachycardia, hypertension, and manic states
  9. Cocaine
    • This combination of stimulants will increase strain on the heart. It is not generally worth it as cocaine has a mild blocking effect on dopamine releasers like amphetamine
  10. Caffeine
    • This combination of stimulants is not generally necessary and may increase strain on the heart, as well as potentially causing anxiety and greater physical discomfort.
  11. Alcohol
    • Drinking on stimulants is risky because the sedative effects of the alcohol are reduced, and these are what the body uses to gauge drunkenness. This typically leads to excessive drinking with greatly reduced inhibitions, high risk of liver damage and increased dehydration. They will also allow you to drink past a point where you might normally pass out, increasing the risk. If you do decide to do this then you should set a limit of how much you will drink each hour and stick to it, bearing in mind that you will feel the alcohol and the stimulant less. Extended release formulations may severely impede sleep, further worsening the hangover.
  12. GHB/GBL
    • Stimulants increase respiration rate allowing a higher dose of sedatives. If the stimulant wears off first then the opiate may overcome the patient and cause respiratory arrest.
  13. Opioids
    • Stimulants increase respiration rate allowing a higher dose of opiates. If the stimulant wears off first then the opiate may overcome the patient and cause respiratory arrest.

Dangerous

  1. DOx
    • The combined stimulating effects of the two can lead to an uncomfortable body-load, while the focusing effects of amphetamine can easily lead to thought loops. Coming down from amphetamines while the DOx is still active can be quite anxiogenic.
  2. NBOMes
    • Amphetamines and NBOMes both provide considerable stimulation. When combined they can result in tachycardia, hypertension, vasoconstriction and in extreme cases heart failure. The anxiogenic and focusing effects of stimulants are also not good in combination with psychedelics as they can lead to unpleasant thought loops. NBOMes are known to cause seizures and stimulants can increase this risk.
  3. 2C-T-x
    • Stimulants increase anxiety levels and the risk of thought loops which can lead to negative experiences. In extreme cases, they can result in severe vasoconstriction, tachycardia, hypertension, and in extreme cases heart failure.
  4. 5-MeO-xxT
    • The anxiogenic and focusing effects of stimulants increase the chance of unpleasant thought loops. The combination is generally unnecessary because of the stimulating effects of psychedelics.
  5. DXM
    • Both substances raise heart rate, in extreme cases, panic attacks caused by these drugs have led to more serious heart issues.
  6. PCP
    • This combination can easily lead to hypermanic states

Low Synergy

  1. Benzodiazepines
    • Both can dull each other's effects, so if one wears off before the other it's possible to overdose due to the lack of counteraction

No Synergy

  1. SSRIs

High Synergy

  1. N2O
  2. MDMA
    • Amphetamines increase the neurotoxic effects of MDMA

Legal Status

  • Austria: MDAI is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).
  • Brazil: MDAI is illegal to possess, produce and sell under Portaria SVS/MS nº 344.
  • China: As of October 2015, MDAI is a controlled substance in China.
  • Denmark: MDAI is illegal in Denmark as of September 2015.
  • Germany: MDAI is controlled under the NpSG (New Psychoactive Substances Act) as of November 26, 2016. Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.
  • Switzerland: MDAI is a controlled substance in Switzerland as of December 2011.
  • United Kingdom: MDAI is illegal to produce, supply, or import under the Psychoactive Substance Act, which came into effect on May 26th, 2016.

    • Sources

    References

    1. Johnson MP, Conarty PF, Nichols DE. [3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogs. Eur J Pharmacol. 1991 Jul 23;200(1):9-16. PMID 1685125
    2. Nichols DE, Brewster WK, Johnson MP, Oberlender R, Riggs RM. Nonneurotoxic tetralin and indan analogs of 3,4-(methylenedioxy)amphetamine (MDA). Journal of Medicinal Chemistry. 1990 Feb;33(2):703-10. PMID 1967651
    3. Nichols DE, Johnson MP, Oberlender R. 5-Iodo-2-aminoindan, a non-neurotoxic analog of p-iodoamphetamine. Pharmacology, Biochemistry and Behaviour. 1991 Jan;38(1):135-9. PMID 1826785
    4. Johnson MP, Frescas SP, Oberlender R, Nichols DE. Synthesis and Pharmacological Examination of 1-(3-Methoxy-4-methylphenyl)-2-aminopropane and 5-Methoxy-6-methyl-2-aminoindan: Similarities to 3,4-(Methylenedioxy)methamphetamine (MDMA). Journal of Medicinal Chemistry 1991;34:1662-1668.
    5. Johnson MP, Huang XM, Nichols DE. Serotonin neurotoxicity in rats after combined treatment with a dopaminergic agent followed by a non-neurotoxic 3,4-methylenedioxymethamphetamine (MDMA) analog. Pharmacology, Biochemistry and Behaviour. 1991 Dec;40(4):915-22. PMID 1726189
    6. Nichols DE, Marona-Lewicka D, Huang X, Johnson MP. Novel serotonergic agents. Drug Design and Discovery. 1993;9(3-4):299-312. PMID 8400010
    7. Sprague JE, Johnson MP, Schmidt CJ, Nichols DE. Studies on the mechanism of p-chloroamphetamine neurotoxicity. Biochemical Pharmacology. 1996 Oct 25;52(8):1271-7. PMID 8937435
    8. Cozzi NV, Frescas S, Marona-Lewicka D, Huang X, Nichols DE. Indan analogs of fenfluramine and norfenfluramine have reduced neurotoxic potential. Pharmacology, Biochemistry and Behaviour. 1998 Mar;59(3):709-15. PMID 9512076
    9. Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of Medical Toxicology, 5(2), 63-67. https://doi.org/10.1007/BF03161089
    10. Gillman, P. K. (2005). Monoamine oxidase inhibitors, opioid analgesics and serotonin toxicity. British Journal of Anaesthesia, 95(4), 434-441. https://doi.org/10.1093/bja/aei210
    11. http://portal.anvisa.gov.br/documents/10181/3115436/(1)RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7
    12. 关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | http://www.sfda.gov.cn/WS01/CL0056/130753.html
    13. "Lists of euphoriant substances subject to control in Denmark". The Danish Medicines Agency. September 2015. | http://laegemiddelstyrelsen.dk/en/licensing/company-authorisations-and-registrations/euphoriant-substances/lists
    14. "Anlage NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 15, 2019.
    15. "Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe" (PDF) (in German). Bundesanzeiger Verlag. Retrieved December 15, 2019.
    16. "§ 4 NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 15, 2019.
    17. "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (PDF) (in German). Das Eidgenössische Departement des Innern. Retrieved December 15, 2019.
    18. Psychoactive Substances Act 2016 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted

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    3. PubChem National Center for Bio Informatics
    4. Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
    5. Wikipedia

    Additional APIs were used to construct this information. Thanks to ChemSpider, NCBI, PubChem etc.

    Data is constantly updated so please check back later to see if there is any more available information on this substance.