Menu
Home
People
Places
Arts
History
Plants & Animals
Science
Life & Culture
Technology
Reference.org
NBOMe-mescaline
open-in-new
<h2 id="history">History</h2> <p>NBOMe-mescaline and NBOMe-escaline were first reported in 1999 resulting from research performed at <a href="/facts/Free_University_of_Berlin/SmAKBFQn">Free University of Berlin</a> concerning their activity as partial agonists at rat vascular 5-HT2A receptors.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> NBOMe-mescaline was first reported in September 2008 to have been self administered by humans as a <a href="/facts/Psychedelic_drug/aj9GNANW">psychedelic drug</a> at some unspecified point prior.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> It first became available as a commodity in the research chemical market in May 2010 several months after a few 25x-<a href="/facts/NBOMe/dgahclhS">NBOMes</a> became available. </p> <h2 id="properties-and-chemistry">Properties and chemistry</h2> <p>Solubility of the <a href="/facts/Hydrochloride_salt/7Sdqua4a">hydrochloride salt</a>: ~5 mg/ml in Phosphate Buffered Saline (PBS) @ <a href="/facts/PH/RnSv8D7y">pH</a> 7.2; ~10 mg/ml in <a href="/facts/Ethanol/3lCLfBSP">ethanol</a> & <a href="/facts/Dimethylformamide/wjI8UfB4">DMF</a>; ~20 mg/ml in <a href="/facts/DMSO/T4HSYfuC">DMSO</a>.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p> <h3>Synthesis</h3> <p>NBOMe-mescaline can be synthesized from <a href="/facts/Mescaline/Y6gXHD9T">mescaline</a> and 2-methoxybenzaldehyde, via reductive <a href="/facts/Alkylation/1rd5SNbt">alkylation</a>. That can be done stepwise by first making the <a href="/facts/Imine/yK72z07j">imine</a> and then reducing the formed imine with <a href="/facts/Sodium_borohydride/D2Hwts5x">sodium borohydride</a>, or by direct reaction with <a href="/facts/Sodium_triacetoxyborohydride/endKhBtu">sodium triacetoxyborohydride</a>. An alternative production method which removes the need to obtain the illegal compound mescaline as an isolated precursor can be achieved via a <a href="/facts/One-pot_reaction/6CgQGt4D">one-pot reaction</a> utilizing 3,4,5-trimethoxy<a href="/facts/Phenylacetonitrile/PY6qMHBa">phenylacetonitrile</a> with <a href="/facts/Lithium_Aluminium_Hydride/QMMhdqEy">Lithium Aluminium Hydride</a> as a reducing agent. </p> <h2 id="legal-status">Legal status</h2> <p>NBOMe-mescaline is not listed in the schedules set out by the <a href="/facts/United_Nations/fgXLnmgT">United Nations</a>' <a href="/facts/Single_Convention_on_Narcotic_Drugs/HDX96jtX">Single Convention on Narcotic Drugs</a> from 1961 nor their <a href="/facts/Convention_on_Psychotropic_Substances/GsXhIsRg">Convention on Psychotropic Substances</a> from 1971,<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> so the signatory countries to these international drug control treaties are not required by said treaties to control NBOMe-mescaline. </p> <h3>United States</h3> <p>NBOMe-mescaline is not listed in the <a href="/facts/List_of_Schedule_I_drugs_(US)/FG3jg7la">list of scheduled controlled substances</a> in the USA.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a> It is therefore not <a href="/facts/Controlled_Substances_Act/8laeNsgD">scheduled</a> at the <a href="/facts/Federal_government_of_the_United_States/VJCxUaf7">federal level</a> in the <a href="/facts/United_States/P0sCdLe5">United States</a>, but it is possible that NBOMe-mescaline could legally be considered an <a href="/facts/Structural_analog/3aysWSVG">analog</a> of <a href="/facts/Mescaline/Y6gXHD9T">mescaline</a>, and therefore sales or <a href="/facts/Drug_possession/35xLkxmQ">possession</a> could potentially be prosecuted under the <a href="/facts/Federal_Analogue_Act/TjlKpUsG">Federal Analogue Act</a>.<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a> </p> <h3>United Kingdom</h3> <p>This substance is a <a href="/facts/Class_A_drug/SVEfw54x">Class A drug</a> in the United Kingdom as a result of the <i>N</i>-benzylphenethylamine catch-all clause in the <a href="/facts/Misuse_of_Drugs_Act_1971/nKQyQ4c5">Misuse of Drugs Act 1971</a>.<a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Substituted_mescaline_analogue/q6pwfRts">Substituted mescaline analogue</a></li> <li><a href="/facts/Mescaline/Y6gXHD9T">Mescaline</a></li> <li><a href="/facts/2-Bromomescaline/qgosRL5Y">2-Bromomescaline</a></li> <li><a href="/facts/Trifluoromescaline/zaFpAqr5">Trifluoromescaline</a></li> <li><a href="/facts/25I-NBOMe/eA2kwDRN">25I-NBOMe</a></li></ul> <h2 id="external-links">External links</h2> <ul><li><a href="https://isomerdesign.com/PiHKAL/explore.php?domain=pk&id=403">NBOMe-mescaline @ IsomerDesign</a></li> <li><a href="https://www.bluelight.org/vb/threads/505420-The-Big-amp-Dandy-NBOMe-Mescaline-Thread">The Big & Dandy NBOMe-Mescaline Thread @ BlueLight.org</a></li> <li><a href="https://www.erowid.org/experiences/subs/exp_MescalineNBOMe.shtml">Erowid Experience Vaults: Mescaline-NBOMe (also 345-NBOMe)</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Pertz HH, Rheineck A, Elz S (1999). "N-Benzylated derivatives of the hallucinogenic drugs mescaline and escaline as partial agonists at rat vascular 5-HT2A receptors". Naunyn-Schmiedeberg's Arch Pharmacol. 359 (Suppl 3): R29. Archived from the original on September 25, 2015. <a href="https://web.archive.org/web/20150925085048/http://bitnest.ca/external.php?id=%2502%257F%2505J%2516%251A%2509%2504%2504e%255C%25258%2522UV%2508%2507N%2501Q%2540i%251Ec%250B7kq" target="_blank">https://web.archive.org/web/20150925085048/http://bitnest.ca/external.php?id=%2502%257F%2505J%2516%251A%2509%2504%2504e%255C%25258%2522UV%2508%2507N%2501Q%2540i%251Ec%250B7kq</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Rickli A, Luethi D, Reinisch J, Buchy D, Hoener MC, Liechti ME (December 2015). "Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)" (PDF). Neuropharmacology. 99: 546–53. doi:10.1016/j.neuropharm.2015.08.034. PMID 26318099. S2CID 10382311. <a href="http://edoc.unibas.ch/56163/1/20170921163006_59c3cceeb8e5d.pdf" target="_blank">http://edoc.unibas.ch/56163/1/20170921163006_59c3cceeb8e5d.pdf</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Pertz HH, Rheineck A, Elz S (1999). "N-Benzylated derivatives of the hallucinogenic drugs mescaline and escaline as partial agonists at rat vascular 5-HT2A receptors". Naunyn-Schmiedeberg's Arch Pharmacol. 359 (Suppl 3): R29. Archived from the original on September 25, 2015. <a href="https://web.archive.org/web/20150925085048/http://bitnest.ca/external.php?id=%2502%257F%2505J%2516%251A%2509%2504%2504e%255C%25258%2522UV%2508%2507N%2501Q%2540i%251Ec%250B7kq" target="_blank">https://web.archive.org/web/20150925085048/http://bitnest.ca/external.php?id=%2502%257F%2505J%2516%251A%2509%2504%2504e%255C%25258%2522UV%2508%2507N%2501Q%2540i%251Ec%250B7kq</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>25B-NB (n-Benzyl-2C-B) @ BlueLight.org <a href="https://www.bluelight.org/vb/threads/388351-25B-NB-%28n-Benzyl-2C-B%29" target="_blank">https://www.bluelight.org/vb/threads/388351-25B-NB-%28n-Benzyl-2C-B%29</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Cayman Chemical's Mescaline NBOMe HCl MSDS <a href="https://www.caymanchem.com/msdss/9001990m.pdf" target="_blank">https://www.caymanchem.com/msdss/9001990m.pdf</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>"UN International Drug Control Conventions". Archived from the original on 2014-03-17. Retrieved 2015-09-29. <a href="https://web.archive.org/web/20140317082038/http://www.unodc.org/unodc/en/commissions/CND/conventions.html" target="_blank">https://web.archive.org/web/20140317082038/http://www.unodc.org/unodc/en/commissions/CND/conventions.html</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>"§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2015-09-21. <a href="https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm" target="_blank">https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary <a href="https://www.erowid.org/psychoactives/law/analog/analog_info1.shtml" target="_blank">https://www.erowid.org/psychoactives/law/analog/analog_info1.shtml</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>"The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk. <a href="http://www.legislation.gov.uk/uksi/2014/1106/made" target="_blank">http://www.legislation.gov.uk/uksi/2014/1106/made</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> </ol>