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Substituted mescaline analogue
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<h2 id="list-of-substituted-mescaline-analogues">List of substituted mescaline analogues</h2> <h3>4-Substituted</h3> <ul><li><a href="/facts/Allylescaline/gewRG2eo">Allylescaline</a> (AL) (4-allyloxy-3,5-dimethoxyphenethylamine)</li> <li>Amylescaline (4-<i>n</i>-amyloxy-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/Benzscaline/hTBozDtF">Benzscaline</a> (BZ) (4-benzyloxy-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/Biscaline/lgMpWpzj">Biscaline</a> (4-phenyl-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/Buscaline/IXC1vpoD">Buscaline</a> (B) (4-butoxy-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/Cyclopropylmescaline/93YX79xo">Cyclopropylmescaline</a> (CPM) (4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine)</li> <li>Cycloproscaline (CP) (4-cyclopropoxy-3,5-dimethoxyphenethylamine)</li> <li>4-Desmethylmescaline (DESMETHYL) (4-hydroxy-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/4-Desoxymescaline/HQsgT4eQ">4-Desoxymescaline</a> (4-methyl-3,5-dimethoxyphenethylamine)</li> <li>Difluoroescaline (DFE) (multiple forms)</li> <li>Difluoroisoproscaline (DFIP) (multiple forms)</li> <li>Difluoromescaline (DFM) (4-difluoromethoxy-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/Escaline/pfLhBYe6">Escaline</a> (E) (4-ethoxy-3,5-dimethoxyphenethylamine)</li> <li>Fluoroescaline (FE) (multiple forms)</li> <li>Fluoromescaline (FM) (4-fluoromethoxy-3,5-dimethoxyphenethylamine)</li> <li>Fluoroproscaline (FP) (multiple forms)</li> <li>Hexylescaline (4-<i>n</i>-hexyloxy-3,5-dimethoxyphenethylamine)</li> <li>Isobuscaline (IB) (4-isobutoxy-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/Isoproscaline/YR3HDK1G">Isoproscaline</a> (IP) (4-isopropoxy-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/Methallylescaline/8rvhYFTE">Methallylescaline</a> (MAL) (4-methylallyloxy-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/Phenescaline/LQtoHjhn">Phenescaline</a> (4-phenylethoxy-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/Propynylmescaline/twfUnTxK">Propynylmescaline</a> (4-propynyloxy-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/Proscaline/kYx2rm6G">Proscaline</a> (P) (4-propoxy-3,5-dimethoxyphenethylamine)</li> <li>Septylescaline (4-<i>n</i>-heptyloxy-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/4-Thiobuscaline/qAjg6cYD">4-Thiobuscaline</a> (4-TB) (4-butylthio-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/4-Thioescaline/AkrCYB72">4-Thioescaline</a> (4-TE) (4-ethylthio-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/4-Thiomescaline/QXQt1Srr">4-Thiomescaline</a> (4-TM) (4-methylthio-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/4-Thioproscaline/V7C5wG8T">4-Thioproscaline</a> (4-TP) (4-propylthio-3,5-dimethoxyphenethylamine)</li></ul> <ul><li>Trifluoroescaline (TFE) (multiple forms)</li> <li><a href="/facts/Trifluoromescaline/zaFpAqr5">Trifluoromescaline</a> (TFM) (4-trifluoromethoxy-3,5-dimethoxyphenethylamine)</li> <li>Trifluoroproscaline (TFP) (multiple forms)</li> <li>Viscaline (4-vinyl-3,5-dimethoxyphenethylamine)</li></ul> <h3>3- or 5-Extended</h3> <ul><li><a href="/facts/Asymbescaline/9yUUV0hq">Asymbescaline</a> (ASB) (3,4-diethoxy-5-methoxyphenethylamine)</li> <li>Metadifluoromescaline (MDFM) (3,4-dimethoxy-5-difluoromethoxyphenethylamine)</li> <li><a href="/facts/Metaescaline/kzoN3tmt">Metaescaline</a> (ME) (3-ethoxy-4,5-dimethoxyphenethylamine)</li> <li><a href="/facts/Metaproscaline/2VtLmAvN">Metaproscaline</a> (MP) (3,4-dimethoxy-5-propoxyphenethylamine)</li> <li><a href="/facts/Symbescaline/WNb0DhDU">Symbescaline</a> (SB) (4-methoxy-3,5-diethoxyphenethylamine)</li> <li><a href="/facts/4-Thioasymbescaline/Fbp9PE70">4-Thioasymbescaline</a> (4-TASB) (4-ethylthio-3-ethoxy-5-methoxyphenethylamine)</li> <li><a href="/facts/4-Thiometaescaline/Bst7L7Vo">4-Thiometaescaline</a> (4-TME) (4-methylthio-3-ethoxy-5-methoxyphenethylamine)</li> <li><a href="/facts/4-Thiosymbescaline/pmNg82LY">4-Thiosymbescaline</a> (4-TSB) (4-methylthio-3,5-diethoxyphenethylamine)</li> <li><a href="/facts/4-Thiotrescaline/yIG4R6t7">4-Thiotrescaline</a> (4-T-TRIS; 4-thiotrisescaline) (4-ethylthio-3,5-diethoxyphenethylamine)</li> <li><a href="/facts/Trescaline/3scsAAL2">Trescaline</a> (TRIS; trisescaline) (3,4,5-triethoxyphenethylamine)</li></ul> <h3>3- or 5-Replaced</h3> <ul><li>3-Desmethylmescaline (3-DESMETHYL) (3,4-dimethoxy-5-hydroxyphenethylamine)</li> <li><a href="/facts/3-Thioasymbescaline/Fbp9PE70">3-Thioasymbescaline</a> (3-TASB) (3-ethylthio-4-ethoxy-5-methoxyphenethylamine)</li> <li><a href="/facts/5-Thioasymbescaline/Fbp9PE70">5-Thioasymbescaline</a> (5-TASB) (3,4-diethoxy-5-methylthiophenethylamine)</li> <li><a href="/facts/3-Thioescaline/AkrCYB72">3-Thioescaline</a> (3-TE) (3-methoxy-4-ethoxy-5-methylthiophenethylamine)</li> <li><a href="/facts/3-Thiomescaline/QXQt1Srr">3-Thiomescaline</a> (3-TM) (3,4-dimethoxy-5-methylthiophenethylamine)</li> <li><a href="/facts/3-Thiometaescaline/Bst7L7Vo">3-Thiometaescaline</a> (3-TME) (3-ethylthio-4,5-dimethoxyphenethylamine)</li> <li><a href="/facts/5-Thiometaescaline/Bst7L7Vo">5-Thiometaescaline</a> (5-TME) (3-ethoxy-4-methoxy-5-methylthiophenethylamine)</li> <li><a href="/facts/3-Thiosymbescaline/pmNg82LY">3-Thiosymbescaline</a> (3-TSB) (3-ethoxy-4-methoxy-5-ethylthiophenethylamine)</li> <li><a href="/facts/3-Thiotrescaline/yIG4R6t7">3-Thiotrescaline</a> (3-T-TRIS; 3-thiotrisescaline) (3,4-diethoxy-5-ethylthiophenethylamine)</li> <li><a href="/facts/3,4,5-Trideoxymescaline/cCLAGuzA">3,4,5-Trideoxymescaline</a> (TMePEA) (3,4,5-trimethylphenethylamine)</li></ul> <h3>2- or 6-Substituted</h3> <ul><li><a href="/facts/2-Bromomescaline/qgosRL5Y">2-Bromomescaline</a> (2-Br-M) (2-bromo-3,4,5-trimethoxyphenethylamine)</li> <li>2,3,4,5,6-Pentamethoxyphenethylamine (PeMPEA)</li> <li><a href="/facts/2,3,4,5-Tetramethoxyphenethylamine/49STUr3V">2,3,4,5-Tetramethoxyphenethylamine</a> (TeMPEA; TeMPEA-1)</li> <li>2,3,5,6-Tetramethoxyphenethylamine (TeMPEA-3)</li></ul> <h3><i>N</i>-Substituted</h3> <ul><li><a href="/facts/N-Methylmescaline/kVgCXGqQ"><i>N</i>-Methylmescaline</a> (M-M) (<i>N</i>-methyl-3,4,5-trimethoxyphenethylamine)</li> <li>NBOMe-escaline (<i>N</i>-(2-methoxybenzyl)-4-ethoxy-3,5-dimethoxyphenethylamine)</li> <li><a href="/facts/NBOMe-mescaline/gM2f5EC2">NBOMe-mescaline</a> (<i>N</i>-(2-methoxybenzyl)-3,4,5-trimethoxyphenethylamine)</li> <li><a href="/facts/Trichocereine/8Rszr9pI">Trichocereine</a> (MM-M) (<i>N</i>,<i>N</i>-dimethylmescaline)</li></ul> <h3>α or β-substituted</h3> <p class="note">See also: 3C (psychedelics)</p> <ul><li><a href="/facts/BOM_(psychedelic)/pq4xFegf">BOM</a> (β,3,4,5-tetramethoxyphenethylamine)</li> <li><a href="/facts/%CE%91-Ethylmescaline/xmzlyGYn">α-Ethylmescaline</a> (AEM) (α-ethyl-3,4,5-trimethoxyphenethylamine)</li> <li><a href="/facts/3,4,5-Trimethoxyamphetamine/XsRnGhAY">3,4,5-Trimethoxyamphetamine</a> (3,4,5-TMA; TMA; TMA-1; α-methylmescaline)</li></ul> <h3>Other compounds</h3> <ul><li>3,5-Dimethoxyphenethylamine (3,5-DMPEA; 4-desmethoxymescaline)</li> <li>Flyscaline (mescaline-FLY)</li> <li><a href="/facts/Isomescaline/T95aBcya">Isomescaline</a> (IM) (2,3,4-trimethoxyphenethylamine)</li> <li><a href="/facts/Jimscaline/0LhEaNxD">Jimscaline</a> (1-(4,5,6-trimethoxy-2,3-dihydro-1<i>H</i>-inden-1-yl)methylamine)</li> <li><a href="/facts/Lophophine/NUjPFDdx">Lophophine</a> (3-methoxy-4,5-methylenedioxyphenethylamine)</li> <li><a href="/facts/2-Thioisomescaline/9jHGpLTx">2-Thioisomescaline</a> (2-TIM) (2-methylthio-3,4-dimethoxyphenethylamine)</li> <li><a href="/facts/3-Thioisomescaline/9jHGpLTx">3-Thioisomescaline</a> (3-TIM) (3-methylthio-2,4-dimethoxyphenethylamine)</li> <li><a href="/facts/4-Thioisomescaline/9jHGpLTx">4-Thioisomescaline</a> (4-TIM) (4-methylthio-2,4-dimethoxyphenethylamine)</li> <li>Tomscaline (1-(2,3,4-trimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine)</li></ul> <h2 id="see-also">See also</h2> <ul><li>3C (psychedelics) (4-substituted 3,5-dimethoxyamphetamines)</li> <li><i><a href="/facts/PiHKAL/sAR8owwC">PiHKAL</a></i> (<i>Phenethylamines I Have Known and Loved</i>)</li> <li><i><a href="/facts/The_Shulgin_Index,_Volume_One:_Psychedelic_Phenethylamines_and_Related_Compounds/bevcka9e">The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds</a></i></li></ul> <h2 id="external-links">External links</h2> <ul><li><a href="https://isomerdesign.com/pihkal/home">Isomer Design</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025. <a href="978-0-12-433951-4" target="_blank">978-0-12-433951-4</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978). "Mescaline analogs: substitutions at the 4-position" (PDF). NIDA Res Monogr (22): 27–37. PMID 101882. <a href="https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38" target="_blank">https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795. <a href="https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79" target="_blank">https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. <a href="978-1-4757-0512-6" target="_blank">978-1-4757-0512-6</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Shulgin AT (March 1973). "Mescaline: the chemistry and pharmacology of its analogs". Lloydia. 36 (1): 46–58. PMID 4576313. <a href="https://bitnest.netfirms.com/external/Lloydia/36.1.46" target="_blank">https://bitnest.netfirms.com/external/Lloydia/36.1.46</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Alexander T. Shulgin; Ann Shulgin (1991). PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN 978-0-9630096-0-9. OCLC 25627628. <a href="978-0-9630096-0-9" target="_blank">978-0-9630096-0-9</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. ISBN 978-0-9630096-3-0. OCLC 709667010. <a href="978-0-9630096-3-0" target="_blank">978-0-9630096-3-0</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025. <a href="978-0-12-433951-4" target="_blank">978-0-12-433951-4</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978). "Mescaline analogs: substitutions at the 4-position" (PDF). NIDA Res Monogr (22): 27–37. PMID 101882. <a href="https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38" target="_blank">https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795. <a href="https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79" target="_blank">https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. <a href="978-1-4757-0512-6" target="_blank">978-1-4757-0512-6</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><p>Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025. <a href="978-0-12-433951-4" target="_blank">978-0-12-433951-4</a> <a href="#fnref:12" class="footnote-back-ref">↩</a></p></li> <li id="fn:13"><p>Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978). "Mescaline analogs: substitutions at the 4-position" (PDF). NIDA Res Monogr (22): 27–37. PMID 101882. <a href="https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38" target="_blank">https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38</a> <a href="#fnref:13" class="footnote-back-ref">↩</a></p></li> <li id="fn:14"><p>Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795. <a href="https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79" target="_blank">https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79</a> <a href="#fnref:14" class="footnote-back-ref">↩</a></p></li> <li id="fn:15"><p>Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. <a href="978-1-4757-0512-6" target="_blank">978-1-4757-0512-6</a> <a href="#fnref:15" class="footnote-back-ref">↩</a></p></li> <li id="fn:16"><p>Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2021). "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines". Front Pharmacol. 12: 794254. doi:10.3389/fphar.2021.794254. PMC 8865417. PMID 35222010. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8865417" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8865417</a> <a href="#fnref:16" class="footnote-back-ref">↩</a></p></li> <li id="fn:17"><p>Halberstadt AL, Chatha M, Chapman SJ, Brandt SD (March 2019). "Comparison of the behavioral effects of mescaline analogs using the head twitch response in mice". J Psychopharmacol. 33 (3): 406–414. doi:10.1177/0269881119826610. PMC 6848748. PMID 30789291. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848748" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6848748</a> <a href="#fnref:17" class="footnote-back-ref">↩</a></p></li> <li id="fn:18"><p>Stoeckmann OV, Trachsel D, Liechti ME, Rudin D (21 May 2024). "Supplementum 276: Abstracts of the of the 8th Annual Spring Congress of the Swiss Society of General Internal Medicine: P181. New Mescaline Derivatives: Profiling of Scalines' Potency and Affinity on Different Serotonin Receptor Subtypes". Swiss Medical Weekly. 154 (5): 138S. doi:10.57187/s.3896. ISSN 1424-3997. <a href="https://doi.org/10.57187%2Fs.3896" target="_blank">https://doi.org/10.57187%2Fs.3896</a> <a href="#fnref:18" class="footnote-back-ref">↩</a></p></li> <li id="fn:19"><p>Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Retrieved 1 February 2025. <a href="978-0-12-433951-4" target="_blank">978-0-12-433951-4</a> <a href="#fnref:19" class="footnote-back-ref">↩</a></p></li> <li id="fn:20"><p>Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795. <a href="https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79" target="_blank">https://archives.nida.nih.gov/sites/default/files/monograph146.pdf#page=79</a> <a href="#fnref:20" class="footnote-back-ref">↩</a></p></li> <li id="fn:21"><p>Braun U, Braun G, Jacob P, Nichols DE, Shulgin AT (1978). "Mescaline analogs: substitutions at the 4-position" (PDF). NIDA Res Monogr (22): 27–37. PMID 101882. <a href="https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38" target="_blank">https://archives.nida.nih.gov/sites/default/files/monograph22.pdf#page=38</a> <a href="#fnref:21" class="footnote-back-ref">↩</a></p></li> <li id="fn:22"><p>Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. 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