MEAI

MEAI (5-methoxy-2-aminoindane or 5-MeO-AI or Chaperon) belongs to the indane family of molecules. It was a recreational drug and binge drinking prevention drug. Its molecular structure was first mentioned implicitly in a markush structure schema appearing in a patent from 1998.[1] It was later explicitly and pharmacologically described in a peer reviewed paper in 2017 by David Nutt et al.,[2] followed by another in February 2018 which detailed the pharmacokinetics, pharmacodynamics and metabolism of MEAI.[3] One year later it was studied an reported on in another peer reviewed paper.[4] The aminoindane family of molecules was, perhaps, first chemically described in 1980.[5][6]

MEAI
Clinical data
Trade namesnone
Other names5-MeO-AI; 2,3-Dihydro-5-methoxy-1H-Inden-2-amine
Routes of
administration		Oral
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityhigh
Metabolismacetyl-aminoindandane
Elimination half-lifenon-linear
Excretionfull
Identifiers
  • 5-Methoxy-2-aminoindane
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H13NO
Molar mass163.220 g·mol−1
3D model (JSmol)
  • COC1=CC2=C(CC(C2)N)C=C1
  • InChI=1S/C10H13NO/c1-12-10-3-2-7-4-9(11)5-8(7)6-10/h2-3,6,9H,4-5,11H2,1H3
  • Key:HLXHCNWEVQNNKA-UHFFFAOYSA-N

MEAI was an early candidate of alcohol replacement drugs that came to market during a late 2010s movement to replace alcohol with less-toxic alternatives spearheaded by British psychopharmacologist David Nutt[7][8][9] rippling to the rest of Europe.[10] In an act of gonzo journalism, Michael Slezak writing for New Scientist, tried and reported on his experience with MEAI.[11] MEAI is currently being prepared for FDA registration by Clearmind Medicine Inc (CSE:CMND).[12][13] The company claims wide Intellectual Property Holding.[14][15][16][17]

See also

References
  1. US5708018A, Haadsma-Svensson, Susanne R.; Andersson, Bengt R. & Sonesson, Clas A. et al., "2-aminoindans as selective dopamine D3 ligands", issued 1998-01-13
  2. Shimshoni JA, Winkler I, Edery N, Golan E, van Wettum R, Nutt D (March 2017). "Toxicological evaluation of 5-methoxy-2-aminoindane (MEAI): Binge mitigating agent in development". Toxicology and Applied Pharmacology. 319: 59–68. doi:10.1016/j.taap.2017.01.018. PMID 28167221. S2CID 205304106.
  3. Shimshoni JA, Sobol E, Golan E, Ben Ari Y, Gal O (March 2018). "Pharmacokinetic and pharmacodynamic evaluation of 5-methoxy-2-aminoindane (MEAI): A new binge-mitigating agent". Toxicology and Applied Pharmacology. 343: 29–39. doi:10.1016/j.taap.2018.02.009. PMID 29458138. S2CID 3879333.
  4. Halberstadt, Adam L.; Brandt, Simon D.; Walther, Donna; Baumann, Michael H. (March 2019). "2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α2-adrenergic receptors". Psychopharmacology. 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746.
  5. Sainsbury PD, Kicman AT, Archer RP, King LA, Braithwaite RA (2011). "Aminoindanes--the next wave of 'legal highs'?". Drug Testing and Analysis. 3 (7–8): 479–82. doi:10.1002/dta.318. PMID 21748859.
  6. Cannon JG, Perez JA, Pease JP, Long JP, Flynn JR, Rusterholz DB, Dryer SE (July 1980). "Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene". Journal of Medicinal Chemistry. 23 (7): 745–9. doi:10.1021/jm00181a009. PMID 7190613.
  7. "David Nutt: Decision making about illegal drugs: time for science to take the lead".
  8. The Lancet - Drug harms in the UK: a multicriteria decision analysis
  9. Forster, Katie (24 September 2016). "Hangover free alcohol is finally here". The Independent. Retrieved 25 March 2022.
  10. "Rauschmittel und gesellschaftliche Probleme | Drug related societal issues". Benedict Wermter (in German). 29 April 2019.
  11. High and Dry - New Scientist
  12. "(CSE:CMND)"
  13. החברה שמנסה להפוך סם פסיכדלי למוצר נגד התמכרות
  14. "放纵行为调节剂" (in Chinese). 15 January 2021.
  15. Alcoholic beverage substitutes
  16. European Patent - Binge Behavior Regulators
  17. Clearmind Medicine Inc.
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