MEAI

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MEAI
Clinical data
Other names5-MeO-AI; 5-MeO-2-AI; 5-Methoxy-2-aminoindane; 5-Methoxy-2-aminoindan; Methoxyaminoindane; Chaperon; Pace; CMND-100; CMND100
Routes of
administration		Oral, Intranasal[1][2][3]
Drug classSerotonin–norepinephrine releasing agent (SNRA); Selective serotonin releasing agent (SSRA); Psychoactive drug; Entactogen
ATC code
  • None
Legal status
Legal status
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, also known as 5-methoxy-2-aminoindane (5-MeO-AI) and by its developmental code name CMND-100, is an entactogen-like psychoactive drug of the 2-aminoindane family.[4][5] It is a cyclized phenethylamine and is the 2-aminoindane analogue of 3-methoxyamphetamine.[6][5] The drug acts as a serotonin–norepinephrine releasing agent (SNRA) or as a modestly selective serotonin releasing agent (SSRA), with about 6-fold preference for induction of serotonin over norepinephrine release.[5] MEAI has been encountered as a novel designer recreational drug.[7][1] It is also under development for potential medical use in the treatment of alcoholism, cocaine use disorder, metabolic syndrome, and obesity.[2][8][3][9]

Use and effects

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When used recreationally, MEAI is reported to produce mild to moderate psychoactive effects, including stimulation and euphoria.[5][1][7] Its dose is said to be 100 to 250 mg orally and 30 to 60 mg intranasally.[1] The drug is sometimes used as an alcohol substitute.[1]

Interactions

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See also: MDMA § Interactions, Trip killer § Antidotes of other hallucinogens, and MDMA/citalopram

Pharmacology

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Pharmacodynamics

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MEAI acts as a monoamine releasing agent (MRA).[5] It is a modestly selective serotonin releasing agent (SSRA), with 6-fold preference for induction of serotonin release over norepinephrine release and 20-fold preference for induction of serotonin release over dopamine release.[5] In addition to inducing monoamine neurotransmitter release, MEAI has moderate affinity for the α2-adrenergic receptor.[5] Based on these findings, MEAI might produce MDMA-like entactogenic and sympathomimetic effects but may be expected to have reduced misuse liability in comparison.[5]

Activities of 2-aminoindanes and amphetamine relatives
Compound Monoamine release (EC50Tooltip half-maximal effective concentration, nM) Ref
Serotonin Norepinephrine Dopamine
2-AI >10,000 86 439 [5]
MDAI 114 117 1,334 [5]
MMAI 31 3,101 >10,000 [5]
MEAI 134 861 2,646 [5]
d-Amphetamine 698–1,765 6.6–7.2 5.8–24.8 [10][11][12][13][14]
MDA 160–162 47–108 106–190 [15][12][16]
MDMA 50–85 54–110 51–278 [10][17][18][15][16]
3-MA ND 58.0 103 [12]
Notes: The smaller the value, the more strongly the compound produces the effect. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: [5]

Chemistry

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MEAI, also known as 5-methoxy-2-aminoindane, is a substituted 2-aminoindane derivative.[6][5] It is a cyclized phenethylamine and is the 2-aminoindane analogue of the amphetamine 3-methoxyamphetamine.[6][5]

History

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MEAI appears to have been first synthesized in 1956.[5][1] The 2-aminoindane family of compounds was perhaps first chemically described in 1980.[19][20] MEAI's molecular structure was first mentioned implicitly in a markush structure schema appearing in a patent from 1998.[21] It was later described by David Nutt and colleagues as a potential preventative against binge drinking in the mid-2010s and thereafter.[7][22][23][24] The drug also emerged as a novel designer recreational drug by the mid-2010s.[7][23][1]

Alcohol substitute

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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 advocated by British psychopharmacologist David Nutt and others.[25][26][27][28]

In an act of gonzo journalism, Michael Slezak writing for New Scientist, tried and reported on his experience with MEAI following an interview.[23] Ezekiel Golan is said to have developed MEAI and originally intended for it to be sold as a legal high, but changed his mind, indicating plans to work with Nutt and his company DrugScience. The goal was to develop MEAI further as a "binge behaviour regulator"[29] and "alcoholic beverage substitute".[30]

In 2018, a company called Diet Alcohol Corporation of the Americas (DACOA) began openly marketing an MEAI-based drink called "Pace" for sale in the United States and Canada. Pace was described as a 50 mL bottle containing 160 mg of MEAI in mineral water. Distribution halted after Health Canada released a warning indicating the substance was considered illegal to market for consumption in Canada due to structural similarity to amphetamine.[31][32] After this, Golan revealed himself to be the developer of Pace.[33] He claimed that the MEAI featured in Pace was "manufactured in India" and "bottled in Delaware".[33] Health Canada provided a statement to CBC News stating "Pace is an illegal and unauthorized product in Canada."[33]

Research

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MEAI, under the developmental code name CMND-100, is under development by Clearmind Medicine for the treatment of alcoholism, cocaine use disorder, metabolic syndrome, and obesity.[2][8][3][9] As of February 2026, it is in phase 1/2 clinical trials for treatment of alcoholism and is in the preclinical stage of development for all other indications.[2][8][3]

See also

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References

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  1. ^ a b c d e f g "5-MeO-AI". АИПСИН (in Russian). Retrieved 1 January 2026.
  2. ^ a b c d "Revolutionary Psychedelics for Treating Addiction & Mental Health". Clearmind. 16 December 2024. Retrieved 16 March 2025.
  3. ^ a b c d "CMND-100 Drug Profile". Ozmosi. 1 January 1900. Retrieved 28 February 2026.
  4. ^ Ekhlasi M, Frytz A, Bassir Nia A (2 December 2025). "The Potential Therapeutic Effects of MEAI in the Treatment of Alcohol Use Disorder". Current Addiction Reports. 12 (1) 88. doi:10.1007/s40429-025-00700-4. ISSN 2196-2952. Retrieved 19 December 2025.
  5. ^ a b c d e f g h i j k l m n o p Halberstadt AL, Brandt SD, Walther D, Baumann MH (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. PMID 30904940.
  6. ^ a b c Nichols DE, Marona-Lewicka D, Huang X, Johnson MP (1993). "Novel serotonergic agents". Drug Design and Discovery. 9 (3–4): 299–312. PMID 8400010.
  7. ^ a b c d 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. Bibcode:2017ToxAP.319...59S. doi:10.1016/j.taap.2017.01.018. PMID 28167221. S2CID 205304106. 5-Methoxy-2-aminoindane (MEAI or Chaperon) is a psychoactive compound of the aminoindane class with a mechanism of action described by one patent as being possibly mediated by binding to the dopamine D3 receptor (Haadsma-Svensson et al., 1994). In recent years MEAI has been recreationally used by many people, mainly in the UK, who report a mild euphoric, alcohol-like tipsy experience (Nutt, 2013; Slezak, 2014). Typically recreational users ingest orally MEAI at doses of up to 1–2 mg/kg body weight in a session and report an onset of effect of up to 4 h with reduced desire to consume alcoholic beverages.
  8. ^ a b c "Delving into the Latest Updates on CMND-100 with Synapse". Synapse. 27 February 2026. Retrieved 28 February 2026.
  9. ^ a b וינרב ג (16 February 2022). "החברה שמנסה להפוך סם פסיכדלי למוצר נגד התמכרות" [The company trying to turn a psychedelic drug into an anti-addiction product]. Globes (in Hebrew).
  10. ^ a b Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, et al. (January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse. 39 (1): 32–41. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707. S2CID 15573624.
  11. ^ Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, et al. (March 2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology. 38 (4): 552–562. doi:10.1038/npp.2012.204. PMC 3572453. PMID 23072836.
  12. ^ a b c Blough B (July 2008). "Dopamine-releasing agents" (PDF). In Trudell ML, Izenwasser S (eds.). Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. OL 18589888W.
  13. ^ Glennon RA, Dukat M (2017). "Structure-Activity Relationships of Synthetic Cathinones". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. Vol. 32. pp. 19–47. doi:10.1007/7854_2016_41. ISBN 978-3-319-52442-9. PMC 5818155. PMID 27830576.
  14. ^ Partilla JS, Dersch CM, Baumann MH, Carroll FI, Rothman RB (1999). "Profiling CNS Stimulants with a High-Throughput Assay for Biogenic Amine Transporter Substrates". Problems of Drug Dependence 1999: Proceedings of the 61st Annual Scientific Meeting, The College on Problems of Drug Dependence, Inc (PDF). NIDA Res Monogr. Vol. 180. pp. 1–476. PMID 11680410. Archived from the original (PDF) on August 5, 2023. RESULTS. Methamphetamine and amphetamine potently released NE (IC50s = 14.3 and 7.0 nM) and DA (IC50s = 40.4 nM and 24.8 nM), and were much less potent releasers of 5-HT (IC50s = 740 nM and 1765 nM). [...]
  15. ^ a b Setola V, Hufeisen SJ, Grande-Allen KJ, Vesely I, Glennon RA, Blough B, et al. (June 2003). "3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro". Molecular Pharmacology. 63 (6): 1223–1229. doi:10.1124/mol.63.6.1223. PMID 12761331. S2CID 839426.
  16. ^ a b Brandt SD, Walters HM, Partilla JS, Blough BE, Kavanagh PV, Baumann MH (December 2020). "The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats". Psychopharmacology. 237 (12): 3703–3714. doi:10.1007/s00213-020-05648-z. PMC 7686291. PMID 32875347.
  17. ^ Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, et al. (April 2012). "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology. 37 (5): 1192–1203. doi:10.1038/npp.2011.304. PMC 3306880. PMID 22169943.
  18. ^ Marusich JA, Antonazzo KR, Blough BE, Brandt SD, Kavanagh PV, Partilla JS, et al. (February 2016). "The new psychoactive substances 5-(2-aminopropyl)indole (5-IT) and 6-(2-aminopropyl)indole (6-IT) interact with monoamine transporters in brain tissue". Neuropharmacology. 101: 68–75. doi:10.1016/j.neuropharm.2015.09.004. PMC 4681602. PMID 26362361.
  19. ^ 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): 479–482. doi:10.1002/dta.318. PMID 21748859.
  20. ^ Cannon JG, Perez JA, Pease JP, Long JP, Flynn JR, Rusterholz DB, et al. (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): 745–749. doi:10.1021/jm00181a009. PMID 7190613.
  21. ^ US 5708018, Haadsma-Svensson SR, Andersson BR, Sonesson CA, Lin CH, Waters RN, Svensson KA, Carlsson PA, Hansson LO, Stjernlof NP, "2-aminoindans as selective dopamine D3 ligands", published 1998-01-13, assigned to Pharmacia & Upjohn Co. 
  22. ^ 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. Bibcode:2018ToxAP.343...29S. doi:10.1016/j.taap.2018.02.009. PMID 29458138. S2CID 3879333.
  23. ^ a b c Slezak M (30 December 2014). "High and dry? Party drug could target excess drinking". New Scientist. Retrieved 2022-10-16.
  24. ^ Nutt D (11 November 2013). "Alcohol without the hangover? It's closer than you think". The Guardian. Retrieved 28 February 2026.
  25. ^ Nutt D (23 October 2013). "Decision making about illegal drugs: time for science to take the lead". Nobel Forum, Karolinska Institutet – via YouTube.
  26. ^ Nutt DJ, King LA, Phillips LD (November 2010). "Drug harms in the UK: a multicriteria decision analysis". Lancet. 376 (9752): 1558–1565. Bibcode:2010Lanc..376.1558N. doi:10.1016/S0140-6736(10)61462-6. PMID 21036393. S2CID 5667719.
  27. ^ Forster K (24 September 2016). "Hangover free alcohol is finally here". The Independent. Retrieved 25 March 2022.
  28. ^ Wermter B (29 April 2019). "Rauschmittel und gesellschaftliche Probleme" [Drug related societal issues]. Benedict Wermter (in German).
  29. ^ US 10406123B2, Golan E, "Binge behavior regulators", issued 2019-09-10 
  30. ^ US 20170360067, Golan E, "Alcoholic beverage substitutes", issued 2017-12-21 
  31. ^ "Advisory - Health Canada warns consumers that Pace, promoted as an alcohol substitute, is unauthorized and may pose serious health risks". Health Canada. 21 December 2018 – via CISION.
  32. ^ Brunet J (24 April 2019). "FACT CHECK: Is Pace, an "Alcohol Alternative," Legal in Canada?". The Walrus. Toronto, Ontario.
  33. ^ a b c Wright J (8 December 2018). "Is this drink really a new 'alcohol alternative'?". Information Morning Saint John. pp. All. Retrieved 15 October 2022.
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