MEAI

MEAI
Clinical data
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;
Identifiers
	IUPAC name 5-Methoxy-2-aminoindane;
CAS Number	81593-54-6;
PubChem CID	12147687;
CompTox Dashboard (EPA)	DTXSID80478566 ;
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) is a recreational drug and binge-drinking prevention drug, first chemically described in 1980,[1][2] and first pharmacologically described in a peer reviewed paper in 2017 by David Nutt et al.,[3] followed by another in February 2018 which detailed pharmacokinetics, pharmacodynamics and metabolism of MEAI.[4] In 2018, a company in the United States began offering an MEAI-based drink called "Pace".[5]

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. Though MEAI was made commercially available online in the United States as "Pace", Nutt's commercial efforts moved away from direct marketing of MEAI in favor of Alcarelle.[6]

References

Sainsbury, P.D.; Kicman, A.T.; Archer, R.P.; King, L.A.; Braithwaite, R.A. (2011). "Aminoindanes-the next wave of 'legal highs'?". Drug Testing and Analysis. 3 (7–8): 479–482. doi:10.1002/dta.318. PMID 21748859.
Cannon, Joseph G.; Perez, Julio A.; Pease, Jonathan P.; Long, John Paul; Flynn, Jan R.; Rusterholz, David B.; Dryer, Stuart E. (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.
Shimshoni, Jakob A.; Winkler, Ilan; Edery, Nir; Golan, Ezekiel; Van Wettum, René; Nutt, David (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. ISSN 1096-0333. PMID 28167221.
Shimshoni, Jakob A.; Sobol, Eyal; Golan, Ezekiel; Ben Ari, Yulius; Gal, Orit (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.
Pace, Drink. "Pace by DACOA". Pace. DACOA. Retrieved 12 August 2018.
"Alcarelle".

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[1] Sainsbury, P.D.; Kicman, A.T.; Archer, R.P.; King, L.A.; Braithwaite, R.A. (2011). "Aminoindanes-the next wave of 'legal highs'?". Drug Testing and Analysis. 3 (7–8): 479–482. doi:10.1002/dta.318. PMID 21748859.

[2] Cannon, Joseph G.; Perez, Julio A.; Pease, Jonathan P.; Long, John Paul; Flynn, Jan R.; Rusterholz, David B.; Dryer, Stuart E. (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.

[3] Shimshoni, Jakob A.; Winkler, Ilan; Edery, Nir; Golan, Ezekiel; Van Wettum, René; Nutt, David (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. ISSN 1096-0333. PMID 28167221.

[4] Shimshoni, Jakob A.; Sobol, Eyal; Golan, Ezekiel; Ben Ari, Yulius; Gal, Orit (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.

[5] Pace, Drink. "Pace by DACOA". Pace. DACOA. Retrieved 12 August 2018.

[6] "Alcarelle".