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MEAI
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<h2 id="effects">Effects</h2> <p>When used <a href="/facts/Recreational_drug/eoBD3vKn">recreationally</a>, MEAI is reported to produce mild <a href="/facts/Psychoactive_drug/dNXrUmsx">psychoactive</a> effects and <a href="/facts/Euphoriant/u4cnbWC4">euphoria</a>.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p> <h2 id="pharmacology">Pharmacology</h2> <h3>Pharmacodynamics</h3> <p>MEAI is a <a href="/facts/Monoamine_releasing_agent/JwSvmyR8">monoamine releasing agent</a> (MRA).<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> It is a modestly <a href="/facts/Binding_selectivity/RryTsdGv">selective</a> <a href="/facts/Serotonin_releasing_agent/p19Sjpqx">serotonin releasing agent</a> (SSRA), with 6-fold preference for induction of <a href="/facts/Serotonin/EzY58q4a">serotonin</a> release over <a href="/facts/Norepinephrine/AjTIC9ox">norepinephrine</a> release and 20-fold preference for induction of serotonin release over <a href="/facts/Dopamine/5gNy8Xkd">dopamine</a> release.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> In addition to inducing <a href="/facts/Monoamine_neurotransmitter/TduN5yes">monoamine neurotransmitter</a> release, MEAI has moderate <a href="/facts/Affinity_(pharmacology)/44QLL4eU">affinity</a> for the <a href="/facts/Alpha-2_adrenergic_receptor/QmUrvvYn">α2-adrenergic receptor</a>.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> Based on these findings, MEAI might produce <a href="/facts/MDMA/WYDACxGN">MDMA</a>-like <a href="/facts/Entactogen/hxo3LqDS">entactogenic</a> and <a href="/facts/Sympathomimetic/IEYU5ERW">sympathomimetic</a> effects but may be expected to have reduced <a href="/facts/Misuse_liability/e3jLXFsF">misuse liability</a> in comparison.<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a> </p> Activities of 2-aminoindanes and amphetamine relatives<table><tbody><tr><th rowspan="2">Compound</th><th colspan="3"><a href="/facts/Monoamine_releasing_agent/JwSvmyR8">Monoamine release</a> (<a href="/facts/Half-maximal_effective_concentration/x7oD7ITx">EC50</a>Tooltip half-maximal effective concentration, nM)</th><th rowspan="2">Ref</th></tr><tr><th><a href="/facts/Serotonin_releasing_agent/p19Sjpqx">Serotonin</a></th><th><a href="/facts/Norepinephrine_releasing_agent/Ua8s5KKG">Norepinephrine</a></th><th><a href="/facts/Dopamine_releasing_agent/D5HpE1aR">Dopamine</a></th></tr><tr><td><a href="/facts/2-Aminoindane/54to7A9k">2-AI</a></td><td>>10,000</td><td>86</td><td>439</td><td><a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a></td></tr><tr><td><a href="/facts/5,6-Methylenedioxy-2-aminoindane/oVIsAj3Y">MDAI</a></td><td>114</td><td>117</td><td>1,334</td><td><a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a></td></tr><tr><td><a href="/facts/5-Methoxy-6-methyl-2-aminoindane/sdVjK4b1">MMAI</a></td><td>31</td><td>3,101</td><td>>10,000</td><td><a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a></td></tr><tr><td>MEAI</td><td>134</td><td>861</td><td>2,646</td><td><a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a></td></tr><tr><td><a href="/facts/Dextroamphetamine/SoVP3mKN"><i>d</i>-Amphetamine</a></td><td>698–1,765</td><td>6.6–7.2</td><td>5.8–24.8</td><td><a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a><a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a><a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a><a class="footnote-ref" id="fnref:16" href="#fn:16"><sup>16</sup></a><a class="footnote-ref" id="fnref:17" href="#fn:17"><sup>17</sup></a></td></tr><tr><td><a href="/facts/Methylenedioxyamphetamine/VY3nE55f">MDA</a></td><td>160–162</td><td>47–108</td><td>106–190</td><td><a class="footnote-ref" id="fnref:18" href="#fn:18"><sup>18</sup></a><a class="footnote-ref" id="fnref:19" href="#fn:19"><sup>19</sup></a><a class="footnote-ref" id="fnref:20" href="#fn:20"><sup>20</sup></a></td></tr><tr><td><a href="/facts/Methylenedioxymethamphetamine/WYDACxGN">MDMA</a></td><td>50–85</td><td>54–110</td><td>51–278</td><td><a class="footnote-ref" id="fnref:21" href="#fn:21"><sup>21</sup></a><a class="footnote-ref" id="fnref:22" href="#fn:22"><sup>22</sup></a><a class="footnote-ref" id="fnref:23" href="#fn:23"><sup>23</sup></a><a class="footnote-ref" id="fnref:24" href="#fn:24"><sup>24</sup></a><a class="footnote-ref" id="fnref:25" href="#fn:25"><sup>25</sup></a></td></tr><tr><td><a href="/facts/3-Methoxyamphetamine/oyhb5Ecf">3-MA</a></td><td>ND</td><td>58.0</td><td>103</td><td><a class="footnote-ref" id="fnref:26" href="#fn:26"><sup>26</sup></a></td></tr><tr><td colspan="5">Notes: The smaller the value, the more strongly the compound produces the effect. The <a href="/facts/Bioassay/hRM3LIJn">assays</a> were done in rat brain <a href="/facts/Synaptosome/VTwyaNB1">synaptosomes</a> and human <a href="/facts/Potency_(pharmacology)/D38FDyPh">potencies</a> may be different. See also <a href="/facts/Monoamine_releasing_agent/JwSvmyR8">Monoamine releasing agent § Activity profiles</a> for a larger table with more compounds. Refs: <a class="footnote-ref" id="fnref:27" href="#fn:27"><sup>27</sup></a></td></tr></tbody></table> <h2 id="chemistry">Chemistry</h2> <p>MEAI, also known as 5-methoxy-2-aminoindane, is a <a href="/facts/2-aminoindane/54to7A9k">2-aminoindane</a> <a href="/facts/Chemical_derivative/JYcbLkbm">derivative</a>.<a class="footnote-ref" id="fnref:28" href="#fn:28"><sup>28</sup></a> It is the 2-aminoindane <a href="/facts/Structural_analog/3aysWSVG">analogue</a> of the <a href="/facts/Substituted_amphetamine/KlmrodPb">amphetamine</a> <a href="/facts/3-methoxyamphetamine/oyhb5Ecf">3-methoxyamphetamine</a>.<a class="footnote-ref" id="fnref:29" href="#fn:29"><sup>29</sup></a> </p> <h2 id="history">History</h2> <p>MEAI appears to have been first <a href="/facts/Chemical_synthesis/3KXsVVwC">synthesized</a> in 1956.<a class="footnote-ref" id="fnref:30" href="#fn:30"><sup>30</sup></a> Its molecular structure was first mentioned implicitly in a <a href="/facts/Markush_structure/qQgk7fCM">markush structure</a> schema appearing in a patent from 1998.<a class="footnote-ref" id="fnref:31" href="#fn:31"><sup>31</sup></a> It was later explicitly and pharmacologically described in a peer reviewed paper in 2017 by <a href="/facts/David_Nutt/xfzPGomS">David Nutt</a> and Ezekiel Golan et al.<a class="footnote-ref" id="fnref:32" href="#fn:32"><sup>32</sup></a> followed by another in February 2018 which detailed the <a href="/facts/Pharmacokinetics/x4CUUnle">pharmacokinetics</a>, <a href="/facts/Pharmacodynamics/zdvfFshl">pharmacodynamics</a> and metabolism of MEAI by Shimshoni, David Nutt, Ezekiel Golan et al.<a class="footnote-ref" id="fnref:33" href="#fn:33"><sup>33</sup></a> One year later it was studied and reported on in another peer reviewed paper by Halberstadt et al.<a class="footnote-ref" id="fnref:34" href="#fn:34"><sup>34</sup></a> The aminoindane family of molecules was, perhaps, first chemically described in 1980.<a class="footnote-ref" id="fnref:35" href="#fn:35"><sup>35</sup></a><a class="footnote-ref" id="fnref:36" href="#fn:36"><sup>36</sup></a> </p> <h2 id="alcohol-substitute">Alcohol substitute</h2> <p>MEAI was an early candidate of <a href="/facts/Alcohol_(drug)/IeK2fVd5">alcohol</a> replacement drugs that came to market during a late 2010s movement to replace alcohol with less-toxic alternatives spearheaded by British <a href="/facts/Psychopharmacology/INVubgKI">psychopharmacologist</a> <a href="/facts/David_Nutt/xfzPGomS">David Nutt</a><a class="footnote-ref" id="fnref:37" href="#fn:37"><sup>37</sup></a><a class="footnote-ref" id="fnref:38" href="#fn:38"><sup>38</sup></a><a class="footnote-ref" id="fnref:39" href="#fn:39"><sup>39</sup></a> rippling to the rest of Europe.<a class="footnote-ref" id="fnref:40" href="#fn:40"><sup>40</sup></a> </p><p>In an act of <a href="/facts/Gonzo_journalism/zLAjEHUt">gonzo journalism</a>, Michael Slezak writing for <a href="/facts/New_Scientist/GE0SBrn0">New Scientist</a>, tried and reported on his experience with MEAI<a class="footnote-ref" id="fnref:41" href="#fn:41"><sup>41</sup></a> after being provided with it by Dr Zee (Ezekiel Golan)<a class="footnote-ref" id="fnref:42" href="#fn:42"><sup>42</sup></a> following an interview.<a class="footnote-ref" id="fnref:43" href="#fn:43"><sup>43</sup></a> 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 <a href="https://www.drugscience.org.uk/">DrugScience</a>. The goal was to develop MEAI further based on Golan's patents as a "binge behaviour regulator"<a class="footnote-ref" id="fnref:44" href="#fn:44"><sup>44</sup></a> and "alcoholic beverage substitute".<a class="footnote-ref" id="fnref:45" href="#fn:45"><sup>45</sup></a> </p><p>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 <a href="/facts/Health_Canada/BV8TuL14">Health Canada</a> released a warning indicating the substance was considered illegal to market for consumption in Canada due to structural similarity to amphetamine.<a class="footnote-ref" id="fnref:46" href="#fn:46"><sup>46</sup></a><a class="footnote-ref" id="fnref:47" href="#fn:47"><sup>47</sup></a> In a December 2018 article by <a href="/facts/CBC_News/SjnXrBxY">CBC News</a>, 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.<a class="footnote-ref" id="fnref:48" href="#fn:48"><sup>48</sup></a> Golan claimed the MEAI featured in Pace was "manufactured in India" and "bottled in Delaware".<a class="footnote-ref" id="fnref:49" href="#fn:49"><sup>49</sup></a> <a href="/facts/Health_Canada/BV8TuL14">Health Canada</a> provided a statement to CBC News stating "Pace is an illegal and unauthorized product in Canada." </p> <h2 id="pharmaceutical-development">Pharmaceutical development</h2> <p>On May 26, 2022, MEAI was prepared for <a href="/facts/FDA/fMfdaRAa">FDA</a> registration by <a href="https://www.clearmindmedicine.com/">Clearmind Medicine Inc.</a>;<a class="footnote-ref" id="fnref:50" href="#fn:50"><sup>50</sup></a><a class="footnote-ref" id="fnref:51" href="#fn:51"><sup>51</sup></a><a class="footnote-ref" id="fnref:52" href="#fn:52"><sup>52</sup></a> Clearmind Medicine claims wide intellectual property holdings to Ezekiel Golan's patents.<a class="footnote-ref" id="fnref:53" href="#fn:53"><sup>53</sup></a><a class="footnote-ref" id="fnref:54" href="#fn:54"><sup>54</sup></a><a class="footnote-ref" id="fnref:55" href="#fn:55"><sup>55</sup></a><a class="footnote-ref" id="fnref:56" href="#fn:56"><sup>56</sup></a> In March 2022 Clearmind Medicine announced supportive evidence from animal studies in mice attesting to suppression of alcohol consumption.<a class="footnote-ref" id="fnref:57" href="#fn:57"><sup>57</sup></a> In June 2022 Clearmind Medicine announced promising results from animal studies that showed promise for treating cocaine addiction with MEAI.<a class="footnote-ref" id="fnref:58" href="#fn:58"><sup>58</sup></a><a class="footnote-ref" id="fnref:59" href="#fn:59"><sup>59</sup></a> </p><p>MEAI, under the developmental code name CMND-100, is under development by Clearmind Medicine for the treatment of <a href="/facts/Alcoholism/KGPzpChp">alcoholism</a>, <a href="/facts/Cocaine_use_disorder/z5YAhpIM">cocaine use disorder</a>, <a href="/facts/Metabolic_syndrome/jI70tRBv">metabolic syndrome</a>, and <a href="/facts/Obesity/RBF9y5Vl">obesity</a>.<a class="footnote-ref" id="fnref:60" href="#fn:60"><sup>60</sup></a> As of October 2024, it is in the <a href="/facts/Preclinical_research/WSI14rnq">preclinical stage of development</a> for these indications.<a class="footnote-ref" id="fnref:61" href="#fn:61"><sup>61</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/MMAI/sdVjK4b1">MMAI</a></li> <li><a href="/facts/5-IAI/GNcM693u">5-IAI</a></li> <li><a href="/facts/MDAI/oVIsAj3Y">MDAI</a></li> <li><a href="/facts/MDMAI/VrSgFg0Q">MDMAI</a></li> <li><a href="/facts/NM-2-AI/uYgXjPV9">NM-2-AI</a></li> <li><a href="/facts/Trifluoromethylaminoindane/8upXuCMQ">TAI</a></li> <li><a href="/facts/Pagoclone/vmzK8au9">Pagoclone</a></li></ul> <h2 id="external-links">External links</h2> <ul><li><a href="https://www.drzee.org/post/late-nite-psycho-video">Information Video About Alcohol Consumption</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><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 (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><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 (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>"Revolutionary Psychedelics for Treating Addiction & Mental Health". Clearmind. 16 December 2024. Retrieved 16 March 2025.{{cite web}}: CS1 maint: url-status (link) <a href="https://www.clearmindmedicine.com/news-release/clearmind-medicine-announces-irb-approval-for-fda-first-in-human-clinical-trial-of-cmnd-100-at-second-clinical-site" target="_blank">https://www.clearmindmedicine.com/news-release/clearmind-medicine-announces-irb-approval-for-fda-first-in-human-clinical-trial-of-cmnd-100-at-second-clinical-site</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><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 (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><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 (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><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 (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><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 (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><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 (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><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 (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><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 (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><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 (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><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 (Berl). 236 (3): 989–999. doi:10.1007/s00213-019-05207-1. PMC 6848746. PMID 30904940. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848746</a> <a href="#fnref:12" class="footnote-back-ref">↩</a></p></li> <li id="fn:13"><p>Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS (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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:13" class="footnote-back-ref">↩</a></p></li> <li id="fn:14"><p>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 (March 2013). 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