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MEAI
Chemical compound
Chemical compound
| Field | Value | |||
|---|---|---|---|---|
| image | 5-Methoxy-2-indanamine.svg | |||
| image_class | skin-invert-image | |||
| width | 250px | |||
| routes_of_administration | Oral, Intranasal | |||
| class | Serotonin–norepinephrine releasing agent; Entactogen | |||
| ATC_prefix | None | |||
| legal_DE | NpSG | |||
| legal_UK | PSA | |||
| legal_status | Unscheduled | |||
| bioavailability | High | |||
| metabolism | Acetyl-aminoindandane | |||
| elimination_half-life | Non-linear | |||
| CAS_number_Ref | ||||
| CAS_number | 73305-09-6 | |||
| UNII_Ref | ||||
| UNII | AD8S15863A | |||
| PubChem | 12147687 | |||
| ChemSpiderID | 11591017 | |||
| synonyms | 5-MeO-AI; 5-MeO-2-AI; 5-Methoxy-2-aminoindane; 5-Methoxy-2-aminoindan; Chaperon; CMND-100; CMND100 | |||
| IUPAC_name | 5-Methoxy-2-aminoindane | |||
| C | 10 | H = 13 | N = 1 | O = 1 |
| 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 | |||
| StdInChIKey | HLXHCNWEVQNNKA-UHFFFAOYSA-N |
| elimination_half-life = Non-linear
MEAI, also known as 5-methoxy-2-aminoindane (5-MeO-AI), is a monoamine releasing agent of the 2-aminoindane family. It specifically acts as a selective serotonin releasing agent (SSRA). The drug is under development for the treatment of alcoholism, cocaine use disorder, metabolic syndrome, and obesity under the developmental code name CMND-100. MEAI has been encountered as a novel designer drug.
Use and effects
When used recreationally, MEAI is reported to produce mild to moderate psychoactive effects, including stimulation and euphoria. Its dose is said to be 100 to 250mg orally and 30 to 60mg intranasally. It is sometimes used as an alcohol substitute.
Interactions
Pharmacology
Pharmacodynamics
MEAI is a monoamine releasing agent (MRA). 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. In addition to inducing monoamine neurotransmitter release, MEAI has moderate affinity for the α2-adrenergic receptor. Based on these findings, MEAI might produce MDMA-like entactogenic and sympathomimetic effects but may be expected to have reduced misuse liability in comparison.
| Compound | Monoamine release (, nM) | rowspan="2" | Ref | Serotonin | Norepinephrine | Dopamine | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 2-AI | 10,000 | 86 | 439 | ||||||||||
| MDAI | 114 | 117 | 1,334 | ||||||||||
| MMAI | 31 | 3,101 | 10,000 | ||||||||||
| MEAI | 134 | 861 | 2,646 | ||||||||||
| d-Amphetamine | 698–1,765 | 6.6–7.2 | 5.8–24.8 | vauthors = Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CW | title = Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products | journal = Neuropsychopharmacology | volume = 38 | issue = 4 | pages = 552–562 | date = March 2013 | pmid = 23072836 | pmc = 3572453 | doi = 10.1038/npp.2012.204 }} |
| MDA | 160–162 | 47–108 | 106–190 | ||||||||||
| MDMA | 50–85 | 54–110 | 51–278 | vauthors = Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS | title = Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin | journal = Synapse | volume = 39 | issue = 1 | pages = 32–41 | date = January 2001 | pmid = 11071707 | doi = 10.1002/1098-2396(20010101)39:13.0.CO;2-3 | s2cid = 15573624 }} |
| 3-MA | ND | 58.0 | 103 | ||||||||||
| 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: |
Chemistry
MEAI, also known as 5-methoxy-2-aminoindane, is a substituted 2-aminoindane derivative. It is the 2-aminoindane analogue of the amphetamine 3-methoxyamphetamine.
History
MEAI appears to have been first synthesized in 1956. Its molecular structure was first mentioned implicitly in a markush structure schema appearing in a patent from 1998. It was later explicitly and pharmacologically described in a peer reviewed paper in 2017 by David Nutt and Ezekiel Golan et al. followed by another in February 2018 which detailed the pharmacokinetics, pharmacodynamics and metabolism of MEAI by Shimshoni, David Nutt, Ezekiel Golan et al. One year later it was studied and reported on in another peer reviewed paper by Halberstadt et al. The aminoindane family of molecules was, perhaps, first chemically described in 1980. The drug was encountered as a novel designer drug in Europe in 2018.
Research
Alcohol substitute
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 rippling to the rest of Europe.
In an act of gonzo journalism, Michael Slezak writing for New Scientist, tried and reported on his experience with MEAI after being provided with it by Dr Zee (Ezekiel Golan) following an interview. Golan claimed that he invented 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 based on Golan's patents as a "binge behaviour regulator" and "alcoholic beverage substitute".
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 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. In a December 2018 article by CBC News, Dr Zee (Ezekiel Golan) was interviewed and publicly came out as the "lead scientist" of Pace claiming "tens of thousands" of bottles were already sold in Canada. Golan claimed the MEAI featured in Pace was "manufactured in India" and "bottled in Delaware". Health Canada provided a statement to CBC News stating "Pace is an illegal and unauthorized product in Canada."
Clinical development
On May 26, 2022, MEAI was prepared for FDA registration by Clearmind Medicine Inc.; Clearmind Medicine claims wide intellectual property holdings to Ezekiel Golan's patents. In March 2022 Clearmind Medicine announced supportive evidence from animal studies in mice attesting to suppression of alcohol consumption. In June 2022 Clearmind Medicine announced promising results from animal studies that showed promise for treating cocaine addiction with MEAI.
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. As of October 2024, it is in the preclinical stage of development for these indications.
References
References
- (2 December 2025). "The Potential Therapeutic Effects of MEAI in the Treatment of Alcohol Use Disorder". Current Addiction Reports.
- "5-MeO-AI".
- (March 2019). "2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α2-adrenergic receptors". Psychopharmacology.
- (March 2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology.
- (July 2008). "Dopamine Transporters: Chemistry, Biology and Pharmacology". Wiley.
- (2017). "Neuropharmacology of New Psychoactive Substances (NPS)".
- (1999). "Problems of Drug Dependence 1999: Proceedings of the 61st Annual Scientific Meeting, The College on Problems of Drug Dependence, Inc".
- (January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse.
- (April 2012). "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology.
- (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.
- (June 2003). "3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro". Molecular Pharmacology.
- (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.
- (1993). "Novel serotonergic agents". Drug Design and Discovery.
- "2-aminoindans as selective dopamine D3 ligands".
- (March 2017). "Toxicological evaluation of 5-methoxy-2-aminoindane (MEAI): Binge mitigating agent in development". Toxicology and Applied Pharmacology.
- (March 2018). "Pharmacokinetic and pharmacodynamic evaluation of 5-methoxy-2-aminoindane (MEAI): A new binge-mitigating agent". Toxicology and Applied Pharmacology.
- (March 2019). "2-Aminoindan and its ring-substituted derivatives interact with plasma membrane monoamine transporters and α2-adrenergic receptors". Psychopharmacology.
- (2011). "Aminoindanes--the next wave of 'legal highs'?". Drug Testing and Analysis.
- (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 October 2013). "Decision making about illegal drugs: time for science to take the lead". Nobel Forum, Karolinska Institutet.
- (November 2010). "Drug harms in the UK: a multicriteria decision analysis". Lancet.
- (24 September 2016). "Hangover free alcohol is finally here". The Independent.
- (29 April 2019). "Rauschmittel und gesellschaftliche Probleme".
- (9 August 2014). "An Interview with Dr Z". New Scientist.
- (30 December 2014). "High and dry? Party drug could target excess drinking".
- "Binge behavior regulators".
- "Alcoholic beverage substitutes".
- (21 December 2018). "Advisory - Health Canada warns consumers that Pace, promoted as an alcohol substitute, is unauthorized and may pose serious health risks". Health Canada.
- (24 April 2019). "FACT CHECK: Is Pace, an "Alcohol Alternative," Legal in Canada?". The Walrus.
- (8 December 2018). "Is this drink really a new 'alcohol alternative'?". Information Morning Saint John.
- "Clearmind Medicine".
- "Clearmind Medicine Inc.". CSE:CMND.
- וינרב ג. (16 February 2022). "החברה שמנסה להפוך סם פסיכדלי למוצר נגד התמכרות". Globes.
- "Binge behavior regulators".
- "Alcoholic beverage substitutes".
- "Binge behavior regulators".
- "The Science and IP Behind our Treatments". Clearmind.
- "Clearmind Medicine".
- "Clearmind Medicine".
- "Clearmind Medicine".
- (16 December 2024). "Revolutionary Psychedelics for Treating Addiction & Mental Health".
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