MEAI

Short description: Chemical compound

MEAI

Clinical data
Trade names| none
Other names| 5-MeO-AI; 2,3-Dihydro-5-methoxy-1H-Inden-2-amine
Routes of
administration| Oral
Legal status
Legal status|

* DE: NpSG (Industrial and scientific use only)
* UK: Under Psychoactive Substances Act
* In general: unscheduled

Pharmacokinetic data
Bioavailability| high
Metabolism| acetyl-aminoindandane
Elimination half-life| non-linear
Excretion| full
Identifiers

IUPAC name

* 5-Methoxy-2-aminoindane

CAS Number|

* 73305-09-6 Y

PubChem CID|

* 12147687

ChemSpider|

* 11591017

UNII|

* AD8S15863A

Chemical and physical data
Formula| C10H13NO
Molar mass| 163.220 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* COC1=CC2=C(CC(C2)N)C=C1

InChI

* 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 (5-methoxy-2-aminoindane or 5-MeO-AI or Chaperon) belongs to the indane family of molecules. 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 and Ezekiel Golan et al.[2] followed by another in February 2018 which detailed the pharmacokinetics, pharmacodynamics and metabolism of MEAI by Shimshoni, David Nutt, Ezekiel Golan et al.[3] One year later it was studied and reported on in another peer reviewed paper by Halberstadt et al.[4] The aminoindane family of molecules was, perhaps, first chemically described in 1980.[5][6]

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] after being provided with it by Dr Zee[12] (Ezekiel Golan) after an interview[11] Golan claimed he invented MEAI and originally intended MEAI to be sold as a legal high but instead indicated plans to work with David Nutt and his company DrugScience to develop MEAI further based on Golan's patents as a "binge behaviour regulator"[13] and "alcoholic beverage substitute".[14]

In 2018, a company named Diet Alcohol Corporation of the Americas (DACOA) began openly marketing an MEAI-based drink called "Pace" for sale in the USA and Canada. Pace was described as a 50ml bottle containing 160mg 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.[15][16] In a December 2018 article by CBC News, Ezekiel Golan (Dr Z/Dr Zee) was interviewed and publicly came out as the "lead scientist" of Pace claiming "tens of thousands" of bottles were already sold in Canada.[17] Golan claimed the MEAI featured in Pace was "manufactured in India" and "bottled in Delaware".[17] Health Canada provided a statement to CBC News stating "Pace is an illegal and unauthorized product in Canada." Both Chemistry World[18] and The BBC have dubbed Ezekiel Golan as "the man who invents legal highs".[19] The Guardian called him "the godfather of legal highs"[20] for his contribution in reintroducing substituted cathinone based drugs commonly sold as Bath salts (drug) including Mephedrone

On May 26, 2022, MEAI was prepared for FDA registration by Clearmind Medicine Inc.;[21][22][23] Clearmind Medicine claims wide intellectual property holdings to Ezekiel Golan's patents.[24][25][26][27] In March 2022 Clearmind Medicine announced supportive evidence from animal studies in mice attesting to suppression of alcohol consumption.[28] In June 2022 Clearmind Medicine announced promising results from animal studies that showed promise for treating cocaine addiction with MEAI.[29][30]

## See also

* MMAI
* 5-IAI
* MDAI
* MDMAI
* NM-2-AI
* TAI
* Pagoclone

## References

1. ↑ 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", US patent 5708018, published 1998-01-13, assigned to Pharmacia & Upjohn Co.
2. ↑ "Toxicological evaluation of 5-methoxy-2-aminoindane (MEAI): Binge mitigating agent in development". Toxicology and Applied Pharmacology 319: 59–68. March 2017. doi:10.1016/j.taap.2017.01.018. PMID 28167221.
3. ↑ "Pharmacokinetic and pharmacodynamic evaluation of 5-methoxy-2-aminoindane (MEAI): A new binge-mitigating agent". Toxicology and Applied Pharmacology 343: 29–39. March 2018. doi:10.1016/j.taap.2018.02.009. PMID 29458138.
4. ↑ "2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α2-adrenergic receptors". Psychopharmacology 236 (3): 989–999. March 2019. doi:10.1007/s00213-019-05207-1. PMID 30904940.
5. ↑ "Aminoindanes--the next wave of 'legal highs'?". Drug Testing and Analysis 3 (7–8): 479–482. 2011. doi:10.1002/dta.318. PMID 21748859.
6. ↑ "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. July 1980. doi:10.1021/jm00181a009. PMID 7190613.
7. ↑ "Decision making about illegal drugs: time for science to take the lead" (in en). Nobel Forum, Karolinska Institutet. 23 October 2013. https://www.youtube.com/watch?v=mDo09IBVHZw.
8. ↑ "Drug harms in the UK: a multicriteria decision analysis". Lancet (London, England) 376 (9752): 1558–65. November 2010. doi:10.1016/S0140-6736(10)61462-6. PMID 21036393.
9. ↑ "Hangover free alcohol is finally here" (in en). The Independent. 24 September 2016. https://www.independent.co.uk/life-style/health-and-families/health-news/hangover-free-alcohol-david-nutt-alcosynth-nhs-postive-effects-benzodiazepine-guy-bentley-a7324076.html.
10. ↑ "Rauschmittel und gesellschaftliche Probleme" (in de-DE). 29 April 2019. https://benedictwermter.com/gesellschaftliche-probleme-und-rauschmittel-drug-related-societal-issues/.
11. ↑ 11.0 11.1 "High and dry? Party drug could target excess drinking" (in en-US). 30 December 2014. https://www.newscientist.com/article/mg22530022-900-high-and-dry-party-drug-could-target-excess-drinking/.
12. ↑ "An Interview with Dr Z". New Scientist: pp. 1–3. 9 August 2014. https://www.drzee.org/_files/ugd/7ca39c_857476e79f6947d3befecdd31deaa83f.pdf.
13. ↑ Golan E, "Binge behavior regulators", US patent 10406123B2, issued 2019-09-10
14. ↑ Golan E, "Alcoholic beverage substitutes", US patent 20170360067, issued 2017-12-21
15. ↑ "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. https://www.newswire.ca/news-releases/advisory
health-canada-warns-consumers-that-pace-promoted-as-an-alcohol-substitute--is-unauthorized-and-may-pose-serious-health-risks-703346102.html.
16. ↑ "FACT CHECK: Is Pace, an "Alcohol Alternative," Legal in Canada?". The Walrus. Toronto, Ontario. 24 April 2019. https://www.thewalrus-factchecking.com/post/fact-check-is-pace-an-alcohol-alternative-legal-in-canada.
17. ↑ 17.0 17.1 "Is this drink really a new 'alcohol alternative'?". Information Morning Saint John: pp. All. 8 December 2018. https://www.cbc.ca/news/canada/new-brunswick/pace-drink-alcohol-alternative-binge-drinking-canada-1.4933533.
18. ↑ "The rising tide of 'legal highs'" (in en). 6 September 2017. https://www.chemistryworld.com/features/the-rising-tide-of-legal-highs/3007738.article.
19. ↑ "Meet Dr. Zee - the man who invented legal highs". BBC. 23 January 2018. https://www.bbc.co.uk/bbcthree/clip/0e5fa0a1-6305-40f9-ab11-f1fa512328fc.
20. ↑ "Dr Zee, the godfather of legal highs: 'I test everything on myself'". 24 May 2016. https://www.theguardian.com/tv-and-radio/2016/may/24/dr-zee-the-godfather-of-legal-highs-i-test-everything-on-myself.
21. ↑ "Clearmind Medicine". https://www.clearmindmedicine.com/news-release/clearmind-announces-successful-pre-ind-meeting-with-u-s-fda-for-cmnd-100-for-alcohol-use-disorder.
22. ↑ "Clearmind Medicine Inc.". CSE:CMND. https://www.thecse.com/en/listings/life-sciences/clearmind-medicine-inc.
23. ↑ וינרב, גלי (16 February 2022). "החברה שמנסה להפוך סם פסיכדלי למוצר נגד התמכרות" (in Hebrew). Globes. https://www.globes.co.il/news/article.aspx?did=1001402418.
24. ↑ Golan E, "Binge behavior regulators", US patent 10137096, published 2018-11-27
25. ↑ Golan E, "Alcoholic beverage substitutes", EP patent 3230256, published 2019-11-13
26. ↑ Golan E, "Binge behavior regulators", EP patent 3230255, published 2017-10-18
27. ↑ "The Science and IP Behind our Treatments". Clearmind. https://www.clearmindmedicine.com/science-and-ip.
28. ↑ "Clearmind Medicine". https://www.clearmindmedicine.com/news-release/clearmind-medicine-announces-positive-results-on-cmnd-100-trials.
29. ↑ "Clearmind Medicine". https://www.clearmindmedicine.com/news-release/clearmind-medicine-announces-positive-pre-clinical-results-for-cocaine-addiction-treatment.
30. ↑ "Clearmind Medicine". https://www.clearmindmedicine.com/news-release/clearmind-medicine-announces-additional-positive-pre-clinical-results-for-its-cocaine-addiction-treatment.

## External links

* Information Video About Alcohol Consumption

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*[DE]: Germany
*[UK]: United Kingdom
*[CID]: Compound ID