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<!--Clinical data-->
<!--Clinical data-->
| tradename = Pace
| tradename = none
| pregnancy_category =
| pregnancy_category =
| legal_DE = NpSG
| legal_DE = NpSG
Line 13: Line 13:


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
| bioavailability = high
| bioavailability = High{{Citation needed|date=October 2024}}
| protein_bound =
| metabolism = acetyl-aminoindandane
| metabolism = Acetyl-aminoindandane{{Citation needed|date=October 2024}}
| elimination_half-life =
| elimination_half-life = Non-linear{{Citation needed|date=October 2024}}
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
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| PubChem = 12147687
| PubChem = 12147687
| ChemSpiderID = 11591017
| ChemSpiderID = 11591017
| synonyms = 5-MeO-AI; 2,3-Dihydro-5-methoxy-1''H''-Inden-2-amine
| synonyms = 5-MeO-AI; 5-MeO-2-AI; 5-Methoxy-2-aminoindane; 5-Methoxy-2-aminoindan; Chaperon; CMND-100; CMND100


<!--Chemical data-->
<!--Chemical data-->
| C=10|H=13|N=1|O=1
| C=10|H=13|N=1|O=1
| smiles = COC1=CC2=C(CC(C2)N)C=C1
| SMILES = COC1=CC2=C(CC(C2)N)C=C1
| StdInChI = 1S/C10H13NO/c1-12-10-3-2-7-4-9(11)5-8(7)6-10/h2-3,6,9H,4-5,11H2,1H3
| StdInChI = 1S/C10H13NO/c1-12-10-3-2-7-4-9(11)5-8(7)6-10/h2-3,6,9H,4-5,11H2,1H3
| StdInChIKey = HLXHCNWEVQNNKA-UHFFFAOYSA-N
| StdInChIKey = HLXHCNWEVQNNKA-UHFFFAOYSA-N
}}
}}
MEAI was an early candidate of [[alcohol (drug)|alcohol]] replacement drugs that came to market during a late 2010s movement to replace alcohol with less-toxic alternatives spearheaded by British [[Psychopharmacology|psychopharmacologist]] [[David Nutt]]<ref>{{cite web |title=David Nutt: Decision making about illegal drugs: time for science to take the lead |url=https://www.youtube.com/watch?v=mDo09IBVHZw |language=en}}</ref><ref>[https://www.thelancet.com/journals/lancet/article/PIIS0140-6736(10)61462-6/fulltext The Lancet - Drug harms in the UK: a multicriteria decision analysis]</ref><ref>{{cite news |last1=Forster |first1=Katie |title=Hangover free alcohol is finally here |url=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 |access-date=25 March 2022 |publisher=The Independent |date=24 September 2016 |language=en}}</ref> rippling to the rest of Europe.<ref>{{cite web |title=Rauschmittel und gesellschaftliche Probleme {{!}} Drug related societal issues |url=https://benedictwermter.com/gesellschaftliche-probleme-und-rauschmittel-drug-related-societal-issues/ |website=Benedict Wermter |language=de-DE |date=29 April 2019}}</ref> In an act of [[gonzo journalism]], Michael Slezak writing for [[New Scientist]], tried and reported on his experience with MEAI.<ref>[https://www.newscientist.com/article/mg22530022-900-high-and-dry-party-drug-could-target-excess-drinking/ High and Dry - New Scientist]</ref> MEAI is currently being prepared for [[FDA]] registration by Clearmind Medicine Inc (CSE:CMND).<ref>[https://www.thecse.com/en/listings/life-sciences/clearmind-medicine-inc "(CSE:CMND)"]</ref><ref>[https://www.globes.co.il/news/article.aspx?did=1001402418 החברה שמנסה להפוך סם פסיכדלי למוצר נגד התמכרות]</ref> The company claims wide Intellectual Property Holding.<ref>{{cite web |title=放纵行为调节剂 |url=https://patents.google.com/patent/CN107406369B/en?q=binge+behavior+golan&oq=binge+behavior+golan |language=zh |date=15 January 2021}}</ref><ref>[https://patents.google.com/patent/US20170360067A1/en?q=alcoholic+beverage+substitutes+Golan&oq=alcoholic+beverage+substitutes+Golan Alcoholic beverage substitutes]</ref><ref>[https://patents.google.com/patent/EP3230255B1/en?q=golan+binge+brhavior&oq=golan+binge+brhavior European Patent - Binge Behavior Regulators]</ref><ref>[https://www.clearmindmedicine.com/ Clearmind Medicine Inc.]</ref>


'''MEAI''', also known as '''5-methoxy-2-aminoindane''' ('''5-MeO-AI'''), is a [[monoamine releasing agent]] of the [[2-aminoindane]] group.<ref name="HalberstadtBrandtWalther2019" /> It specifically acts as a [[selective serotonin releasing agent]] (SSRA).<ref name="HalberstadtBrandtWalther2019" /> The drug is under development for the treatment of [[alcoholism]], [[cocaine use disorder]], [[metabolic syndrome]], and [[obesity]] under the developmental code name '''CMND-100'''.<ref name="AdisInsight" />
⚫
'''MEAI''' ('''5-methoxy-2-aminoindane''' or '''5-MeO-AI''' or '''Chaperon''') belongs to the [[indane]] family of molecules. It was a [[recreational drug use|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.<ref>{{Cite patent|number=US5708018A|title=2-aminoindans as selective dopamine D3 ligands|gdate=1998-01-13|invent1=Haadsma-Svensson|invent2=Andersson|invent3=Sonesson|invent4=Lin|inventor1-first=Susanne R.|inventor2-first=Bengt R.|inventor3-first=Clas A.|inventor4-first=Chiu-Hong|url=https://patents.google.com/patent/US5708018/en}}</ref> It was later explicitly and pharmacologically described in a peer reviewed paper in 2017 by [[David Nutt]] et al.,<ref>{{cite journal | vauthors = Shimshoni JA, Winkler I, Edery N, Golan E, van Wettum R, Nutt D | title = Toxicological evaluation of 5-methoxy-2-aminoindane (MEAI): Binge mitigating agent in development | journal = Toxicology and Applied Pharmacology | volume = 319 | pages = 59–68 | date = March 2017 | pmid = 28167221 | doi = 10.1016/j.taap.2017.01.018 | s2cid = 205304106 }}</ref> followed by another in February 2018 which detailed the [[pharmacokinetics]], [[pharmacodynamics]] and metabolism of MEAI.<ref>{{cite journal | vauthors = Shimshoni JA, Sobol E, Golan E, Ben Ari Y, Gal O | title = Pharmacokinetic and pharmacodynamic evaluation of 5-methoxy-2-aminoindane (MEAI): A new binge-mitigating agent | journal = Toxicology and Applied Pharmacology | volume = 343 | pages = 29–39 | date = March 2018 | pmid = 29458138 | doi = 10.1016/j.taap.2018.02.009 | s2cid = 3879333 }}</ref> One year later it was studied an reported on in another peer reviewed paper.<ref>{{cite journal |last1=Halberstadt |first1=Adam L. |last2=Brandt |first2=Simon D. |last3=Walther |first3=Donna |last4=Baumann |first4=Michael H. |title=2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α2-adrenergic receptors |journal=Psychopharmacology |date=March 2019 |volume=236 |issue=3 |pages=989–999 |doi= 10.1007/s00213-019-05207-1| pmc=6848746}}</ref> In 2018, a company in the United States began offering an MEAI-based drink called "Pace".<ref>{{cite web |title=Alcohol Alternative {{!}} Redlands {{!}} Pacedrink.com |url=https://alcoholfutures.com |website=pacedrink |access-date=1 March 2022 |language=en}}</ref><ref>[https://www.youtube.com/watch?v=qxhaFw7QmVs Promotional Video for Pace]</ref> The aminoindane family of molecules was, perhaps, first chemically described in 1980.<ref>{{cite journal|vauthors=Sainsbury PD, Kicman AT, Archer RP, King LA, Braithwaite RA|year=2011|title=Aminoindanes--the next wave of 'legal highs'?|journal=Drug Testing and Analysis|volume=3|issue=7–8|pages=479–82|doi=10.1002/dta.318|pmid=21748859}}</ref><ref>{{cite journal|vauthors=Cannon JG, Perez JA, Pease JP, Long JP, Flynn JR, Rusterholz DB, Dryer SE|date=July 1980|title=Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene|journal=Journal of Medicinal Chemistry|volume=23|issue=7|pages=745–9|doi=10.1021/jm00181a009|pmid=7190613}}</ref>

==Effects==
When used [[recreational drug|recreationally]], MEAI is reported to produce mild [[psychoactive drug|psychoactive]] effects and [[euphoriant|euphoria]].<ref name="HalberstadtBrandtWalther2019" />

==Pharmacology==
MEAI is a [[monoamine releasing agent]].<ref name="HalberstadtBrandtWalther2019">{{cite journal | vauthors = Halberstadt AL, Brandt SD, Walther D, Baumann MH | title = 2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α2-adrenergic receptors | journal = Psychopharmacology (Berl) | volume = 236 | issue = 3 | pages = 989–999 | date = March 2019 | pmid = 30904940 | pmc = 6848746 | doi = 10.1007/s00213-019-05207-1 | url = }}</ref> It is a modestly [[binding selectivity|selective]] [[serotonin releasing agent]], with 6-fold preference for induction of [[serotonin]] release over [[norepinephrine]] release and 20-fold preference for induction of serotonin release over [[dopamine]] release.<ref name="HalberstadtBrandtWalther2019" /> In addition to inducing [[monoamine neurotransmitter]] release, MEAI has moderate [[affinity (pharmacology)|affinity]] for the [[alpha-2 adrenergic receptor|α<sub>2</sub>-adrenergic receptor]].<ref name="HalberstadtBrandtWalther2019" /> Based on these findings, MEAI might produce [[MDMA]]-like [[entactogen]]ic and [[sympathomimetic]] effects but may be expected to have reduced [[misuse liability]] in comparison.<ref name="HalberstadtBrandtWalther2019" />

==History==
MEAI appears to have been first [[chemical synthesis|synthesized]] in 1956.<ref name="HalberstadtBrandtWalther2019" />
⚫
Its molecular structure was first mentioned implicitly in a [[markush structure]] schema appearing in a patent from 1998.<ref>{{cite patent|country=US|number=5708018|title=2-aminoindans as selective dopamine D3 ligands|pubdate=1998-01-13|inventor= Haadsma-Svensson SR, Andersson BR, Sonesson CA, Lin CH, Waters RN, Svensson KA, Carlsson PA, Hansson LO, Stjernlof NP |assign1=[[Pharmacia_%26_Upjohn|Pharmacia & Upjohn Co.]]}}</ref> It was later explicitly and pharmacologically described in a peer reviewed paper in 2017 by [[David Nutt]] and Ezekiel Golan et al.<ref>{{cite journal | vauthors = Shimshoni JA, Winkler I, Edery N, Golan E, van Wettum R, Nutt D | title = Toxicological evaluation of 5-methoxy-2-aminoindane (MEAI): Binge mitigating agent in development | journal = Toxicology and Applied Pharmacology | volume = 319 | pages = 59–68 | date = March 2017 | pmid = 28167221 | doi = 10.1016/j.taap.2017.01.018 | bibcode = 2017ToxAP.319...59S | s2cid = 205304106 }}</ref> followed by another in February 2018 which detailed the [[pharmacokinetics]], [[pharmacodynamics]] and metabolism of MEAI by Shimshoni, David Nutt, Ezekiel Golan et al.<ref>{{cite journal | vauthors = Shimshoni JA, Sobol E, Golan E, Ben Ari Y, Gal O | title = Pharmacokinetic and pharmacodynamic evaluation of 5-methoxy-2-aminoindane (MEAI): A new binge-mitigating agent | journal = Toxicology and Applied Pharmacology | volume = 343 | pages = 29–39 | date = March 2018 | pmid = 29458138 | doi = 10.1016/j.taap.2018.02.009 | bibcode = 2018ToxAP.343...29S | s2cid = 3879333 }}</ref> One year later it was studied and reported on in another peer reviewed paper by Halberstadt et al.<ref>{{cite journal | vauthors = Halberstadt AL, Brandt SD, Walther D, Baumann MH | title = 2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α<sub>2</sub>-adrenergic receptors | journal = Psychopharmacology | volume = 236 | issue = 3 | pages = 989–999 | date = March 2019 | pmid = 30904940 | pmc = 6848746 | doi = 10.1007/s00213-019-05207-1 }}</ref> The aminoindane family of molecules was, perhaps, first chemically described in 1980.<ref>{{cite journal | vauthors = Sainsbury PD, Kicman AT, Archer RP, King LA, Braithwaite RA | title = Aminoindanes--the next wave of 'legal highs'? | journal = Drug Testing and Analysis | volume = 3 | issue = 7–8 | pages = 479–482 | year = 2011 | pmid = 21748859 | doi = 10.1002/dta.318 }}</ref><ref>{{cite journal | vauthors = Cannon JG, Perez JA, Pease JP, Long JP, Flynn JR, Rusterholz DB, Dryer SE | title = Comparison of biological effects of N-alkylated congeners of beta-phenethylamine derived from 2-aminotetralin, 2-aminoindan, and 6-aminobenzocycloheptene | journal = Journal of Medicinal Chemistry | volume = 23 | issue = 7 | pages = 745–749 | date = July 1980 | pmid = 7190613 | doi = 10.1021/jm00181a009 }}</ref>

==Alcohol substitute==
MEAI was an early candidate of [[alcohol (drug)|alcohol]] replacement drugs that came to market during a late 2010s movement to replace alcohol with less-toxic alternatives spearheaded by British [[Psychopharmacology|psychopharmacologist]] [[David Nutt]]<ref>{{cite web | vauthors = Nutt D | title = Decision making about illegal drugs: time for science to take the lead | work = Nobel Forum, Karolinska Institutet | date = 23 October 2013 | via=[[YouTube]] |url=https://www.youtube.com/watch?v=mDo09IBVHZw |language=en}}</ref><ref name="pmid21036393">{{cite journal | vauthors = Nutt DJ, King LA, Phillips LD | title = Drug harms in the UK: a multicriteria decision analysis | journal = Lancet | location = London, England | volume = 376 | issue = 9752 | pages = 1558–65 | date = November 2010 | pmid = 21036393 | doi = 10.1016/S0140-6736(10)61462-6 | s2cid = 5667719 }}</ref><ref>{{cite news | vauthors = Forster K |title=Hangover free alcohol is finally here |url=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 |access-date=25 March 2022 |work=The Independent |date=24 September 2016 |language=en}}</ref> rippling to the rest of Europe.<ref>{{cite web |title=Rauschmittel und gesellschaftliche Probleme | trans-title = Drug related societal issues |url=https://benedictwermter.com/gesellschaftliche-probleme-und-rauschmittel-drug-related-societal-issues/ |website=Benedict Wermter | vauthors = Wermter B |language=de-DE |date=29 April 2019}}</ref>

In an act of [[gonzo journalism]], Michael Slezak writing for [[New Scientist]], tried and reported on his experience with MEAI<ref name=":0" /> after being provided with it by Dr Zee<ref>{{cite news | vauthors = Slezak M |date=9 August 2014 |title= An Interview with Dr Z |pages=1–3 |work=New Scientist |url= https://www.drzee.org/_files/ugd/7ca39c_857476e79f6947d3befecdd31deaa83f.pdf |access-date=16 October 2022}}</ref> (Ezekiel Golan) after an interview<ref name=":0">{{cite web | vauthors = Slezak M |date=30 December 2014 |title=High and dry? Party drug could target excess drinking |url=https://www.newscientist.com/article/mg22530022-900-high-and-dry-party-drug-could-target-excess-drinking/ |access-date=2022-10-16 |website=New Scientist |language=en-US}}</ref> 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"<ref>{{cite patent | country = US |number= 10406123B2|title=Binge behavior regulators|gdate=2019-09-10|inventor= Golan E |url=https://patents.google.com/patent/US10406123B2/en}}</ref> and "alcoholic beverage substitute".<ref>{{cite patent | country = US |number= 20170360067 |title=Alcoholic beverage substitutes |gdate=2017-12-21 |inventor = Golan E |url= https://patents.google.com/patent/US20170360067A1/en?q=golan+alcoholic+beverage+substitutes&oq=golan+alcoholic+beverage+substitutes }}</ref>

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.<ref>{{cite web | url=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 | title=Advisory - Health Canada warns consumers that Pace, promoted as an alcohol substitute, is unauthorized and may pose serious health risks | work = Health Canada | via = CISION | date = 21 December 2018 }}</ref><ref>{{cite web | vauthors = Brunet J | date = 24 April 2019 | url=https://www.thewalrus-factchecking.com/post/fact-check-is-pace-an-alcohol-alternative-legal-in-canada | title=FACT CHECK: Is Pace, an "Alcohol Alternative," Legal in Canada? | work = The Walrus | location = Toronto, Ontario }}</ref> 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.<ref name = "Wright_2018">{{cite news | vauthors = Wright J |date=8 December 2018 |title=Is this drink really a new 'alcohol alternative'? |pages=All |work=Information Morning Saint John |url=https://www.cbc.ca/news/canada/new-brunswick/pace-drink-alcohol-alternative-binge-drinking-canada-1.4933533 |access-date=15 October 2022}}</ref> Golan claimed the MEAI featured in Pace was "manufactured in India" and "bottled in Delaware".<ref name = "Wright_2018" /> [[Health Canada]] provided a statement to CBC News stating "Pace is an illegal and unauthorized product in Canada." Both [[Chemistry World]]<ref>{{cite web | vauthors = Extance A | date = 6 September 2017 |title=The rising tide of 'legal highs' |url=https://www.chemistryworld.com/features/the-rising-tide-of-legal-highs/3007738.article |access-date=2022-10-17 |website=Chemistry World |language=en}}</ref> and The [[BBC]] have dubbed Ezekiel Golan as "the man who invents legal highs".<ref>{{cite web |date=23 January 2018 |title=Meet Dr. Zee - the man who invented legal highs |url=https://www.bbc.co.uk/bbcthree/clip/0e5fa0a1-6305-40f9-ab11-f1fa512328fc | work = BBC }}</ref> [[The Guardian]] called him "the godfather of legal highs"<ref>{{cite web | vauthors = Jonze T |date=24 May 2016 |title=Dr Zee, the godfather of legal highs: 'I test everything on myself' |url=https://www.theguardian.com/tv-and-radio/2016/may/24/dr-zee-the-godfather-of-legal-highs-i-test-everything-on-myself |website=[[TheGuardian.com]]}}</ref> for his contribution in reintroducing [[substituted cathinone]] based drugs commonly sold as [[Bath salts (drug)]] including [[Mephedrone]]

==Pharmaceutical development==
On May 26, 2022, MEAI was prepared for [[FDA]] registration by Clearmind Medicine Inc.;<ref>{{cite web |title=Clearmind Medicine |url=https://www.clearmindmedicine.com/news-release/clearmind-announces-successful-pre-ind-meeting-with-u-s-fda-for-cmnd-100-for-alcohol-use-disorder |website=www.clearmindmedicine.com}}</ref><ref>{{cite web | title = Clearmind Medicine Inc. | url = https://www.thecse.com/en/listings/life-sciences/clearmind-medicine-inc | work = CSE:CMND }}</ref><ref>{{cite news | url = https://www.globes.co.il/news/article.aspx?did=1001402418 | title = החברה שמנסה להפוך סם פסיכדלי למוצר נגד התמכרות | trans-title = The company trying to turn a psychedelic drug into an anti-addiction product | work = Globes | date = 16 February 2022 | language = Hebrew | last1 = וינרב | first1 = גלי }}</ref> Clearmind Medicine claims wide intellectual property holdings to Ezekiel Golan's patents.<ref>{{cite patent|country=US|number=10137096|pubdate=2018-11-27|title=Binge behavior regulators|inventor = Golan E }}</ref><ref>{{cite patent|country=EP|number=3230256|pubdate=2019-11-13|title=Alcoholic beverage substitutes|inventor = Golan E }}</ref><ref>{{cite patent|country=EP|number=3230255|pubdate=2017-10-18|title=Binge behavior regulators|inventor = Golan E }}</ref><ref>{{cite web | url=https://www.clearmindmedicine.com/science-and-ip | title=The Science and IP Behind our Treatments | work = Clearmind }}</ref> In March 2022 Clearmind Medicine announced supportive evidence from animal studies in mice attesting to suppression of alcohol consumption.<ref>{{cite web |title=Clearmind Medicine |url=https://www.clearmindmedicine.com/news-release/clearmind-medicine-announces-positive-results-on-cmnd-100-trials |website=www.clearmindmedicine.com}}</ref> In June 2022 Clearmind Medicine announced promising results from animal studies that showed promise for treating cocaine addiction with MEAI.<ref>{{cite web |title=Clearmind Medicine |url=https://www.clearmindmedicine.com/news-release/clearmind-medicine-announces-positive-pre-clinical-results-for-cocaine-addiction-treatment |website=www.clearmindmedicine.com |access-date=14 August 2022}}</ref><ref>{{cite web |title=Clearmind Medicine |url=https://www.clearmindmedicine.com/news-release/clearmind-medicine-announces-additional-positive-pre-clinical-results-for-its-cocaine-addiction-treatment |access-date=2022-10-16 |website=www.clearmindmedicine.com}}</ref>

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]].<ref name="AdisInsight">{{cite web | title=5-Methoxy 2-aminoindane | website=AdisInsight | date=16 October 2024 | url=https://adisinsight.springer.com/drugs/800065665 | access-date=24 October 2024}}</ref> As of October 2024, it is in the [[preclinical research|preclinical stage of development]] for these indications.<ref name="AdisInsight" />


== See also ==
== See also ==
* [[MMAI]]
* [[MMAI]]
* [[5-IAI]]
* [[MDAI]]
* [[MDMAI]]
* [[NM-2-AI]]
* [[Trifluoromethylaminoindane|TAI]]
* [[Pagoclone]]
* [[Pagoclone]]
*[[Acamprosate]]
*[[Naltrexone]]
*[[Alcoholism]]


== References ==
== References ==
{{Reflist|2}}
{{Reflist}}

== External links ==
* [https://www.drzee.org/post/late-nite-psycho-video Information Video About Alcohol Consumption]

{{Entactogens}}
{{Monoamine releasing agents}}


⚫
[[Category:Designer drugs]]
[[Category:2-Aminoindanes]]
[[Category:2-Aminoindanes]]
⚫
[[Category:Designer drugs]]
[[Category:Entactogens and empathogens]]
[[Category:Experimental entactogens]]
[[Category:Experimental psychiatric drugs]]
[[Category:Monoamine releasing agents]]
[[Category:Phenol ethers]]
[[Category:Phenol ethers]]

Latest revision as of 02:34, 2 January 2025

MEAI
Clinical data
Trade namesnone
Other names5-MeO-AI; 5-MeO-2-AI; 5-Methoxy-2-aminoindane; 5-Methoxy-2-aminoindan; Chaperon; CMND-100; CMND100
Routes of
administration		Oral
Legal status
Legal status
Pharmacokinetic data
BioavailabilityHigh[citation needed]
MetabolismAcetyl-aminoindandane[citation needed]
Elimination half-lifeNon-linear[citation needed]
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), is a monoamine releasing agent of the 2-aminoindane group.[1] It specifically acts as a selective serotonin releasing agent (SSRA).[1] The drug is under development for the treatment of alcoholism, cocaine use disorder, metabolic syndrome, and obesity under the developmental code name CMND-100.[2]

Effects

[edit]

When used recreationally, MEAI is reported to produce mild psychoactive effects and euphoria.[1]

Pharmacology

[edit]

MEAI is a monoamine releasing agent.[1] It is a modestly selective serotonin releasing agent, with 6-fold preference for induction of serotonin release over norepinephrine release and 20-fold preference for induction of serotonin release over dopamine release.[1] In addition to inducing monoamine neurotransmitter release, MEAI has moderate affinity for the α2-adrenergic receptor.[1] Based on these findings, MEAI might produce MDMA-like entactogenic and sympathomimetic effects but may be expected to have reduced misuse liability in comparison.[1]

History

[edit]

MEAI appears to have been first synthesized in 1956.[1] Its molecular structure was first mentioned implicitly in a markush structure schema appearing in a patent from 1998.[3] It was later explicitly and pharmacologically described in a peer reviewed paper in 2017 by David Nutt and Ezekiel Golan et al.[4] followed by another in February 2018 which detailed the pharmacokinetics, pharmacodynamics and metabolism of MEAI by Shimshoni, David Nutt, Ezekiel Golan et al.[5] One year later it was studied and reported on in another peer reviewed paper by Halberstadt et al.[6] The aminoindane family of molecules was, perhaps, first chemically described in 1980.[7][8]

Alcohol substitute

[edit]

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[9][10][11] rippling to the rest of Europe.[12]

In an act of gonzo journalism, Michael Slezak writing for New Scientist, tried and reported on his experience with MEAI[13] after being provided with it by Dr Zee[14] (Ezekiel Golan) after an interview[13] 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"[15] and "alcoholic beverage substitute".[16]

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.[17][18] 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.[19] Golan claimed the MEAI featured in Pace was "manufactured in India" and "bottled in Delaware".[19] Health Canada provided a statement to CBC News stating "Pace is an illegal and unauthorized product in Canada." Both Chemistry World[20] and The BBC have dubbed Ezekiel Golan as "the man who invents legal highs".[21] The Guardian called him "the godfather of legal highs"[22] for his contribution in reintroducing substituted cathinone based drugs commonly sold as Bath salts (drug) including Mephedrone

Pharmaceutical development

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On May 26, 2022, MEAI was prepared for FDA registration by Clearmind Medicine Inc.;[23][24][25] Clearmind Medicine claims wide intellectual property holdings to Ezekiel Golan's patents.[26][27][28][29] In March 2022 Clearmind Medicine announced supportive evidence from animal studies in mice attesting to suppression of alcohol consumption.[30] In June 2022 Clearmind Medicine announced promising results from animal studies that showed promise for treating cocaine addiction with MEAI.[31][32]

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] As of October 2024, it is in the preclinical stage of development for these indications.[2]

See also

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References

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  1. ^ a b c d e f g h 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 (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940.
  2. ^ a b c "5-Methoxy 2-aminoindane". AdisInsight. 16 October 2024. Retrieved 24 October 2024.
  3. ^ 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. 
  4. ^ 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. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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): 745–749. doi:10.1021/jm00181a009. PMID 7190613.
  9. ^ Nutt D (23 October 2013). "Decision making about illegal drugs: time for science to take the lead". Nobel Forum, Karolinska Institutet – via YouTube.
  10. ^ Nutt DJ, King LA, Phillips LD (November 2010). "Drug harms in the UK: a multicriteria decision analysis". Lancet. 376 (9752). London, England: 1558–65. doi:10.1016/S0140-6736(10)61462-6. PMID 21036393. S2CID 5667719.
  11. ^ Forster K (24 September 2016). "Hangover free alcohol is finally here". The Independent. Retrieved 25 March 2022.
  12. ^ Wermter B (29 April 2019). "Rauschmittel und gesellschaftliche Probleme" [Drug related societal issues]. Benedict Wermter (in German).
  13. ^ a b Slezak M (30 December 2014). "High and dry? Party drug could target excess drinking". New Scientist. Retrieved 2022-10-16.
  14. ^ Slezak M (9 August 2014). "An Interview with Dr Z" (PDF). New Scientist. pp. 1–3. Retrieved 16 October 2022.
  15. ^ US 10406123B2, Golan E, "Binge behavior regulators", issued 2019-09-10 
  16. ^ US 20170360067, Golan E, "Alcoholic beverage substitutes", issued 2017-12-21 
  17. ^ "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.
  18. ^ Brunet J (24 April 2019). "FACT CHECK: Is Pace, an "Alcohol Alternative," Legal in Canada?". The Walrus. Toronto, Ontario.
  19. ^ a b Wright J (8 December 2018). "Is this drink really a new 'alcohol alternative'?". Information Morning Saint John. pp. All. Retrieved 15 October 2022.
  20. ^ Extance A (6 September 2017). "The rising tide of 'legal highs'". Chemistry World. Retrieved 2022-10-17.
  21. ^ "Meet Dr. Zee - the man who invented legal highs". BBC. 23 January 2018.
  22. ^ Jonze T (24 May 2016). "Dr Zee, the godfather of legal highs: 'I test everything on myself'". TheGuardian.com.
  23. ^ "Clearmind Medicine". www.clearmindmedicine.com.
  24. ^ "Clearmind Medicine Inc". CSE:CMND.
  25. ^ וינרב, גלי (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).
  26. ^ US 10137096, Golan E, "Binge behavior regulators", published 2018-11-27 
  27. ^ EP 3230256, Golan E, "Alcoholic beverage substitutes", published 2019-11-13 
  28. ^ EP 3230255, Golan E, "Binge behavior regulators", published 2017-10-18 
  29. ^ "The Science and IP Behind our Treatments". Clearmind.
  30. ^ "Clearmind Medicine". www.clearmindmedicine.com.
  31. ^ "Clearmind Medicine". www.clearmindmedicine.com. Retrieved 14 August 2022.
  32. ^ "Clearmind Medicine". www.clearmindmedicine.com. Retrieved 2022-10-16.
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