Substituted mescaline analogue

A substituted mescaline analogue, also known as a scaline and typically but not always a 4-substituted 3,5-dimethoxyphenethylamine, is an analogue of the phenethylamine serotonergic psychedelic mescaline (3,4,5-trimethoxyphenethylamine).[1][2][3][4][5][6][7]

Other related compounds include the 2C (4-substituted 2,5-dimethoxyphenethylamine) and DOx (4-substituted 2,5-dimethoxyamphetamine) compounds as well as 3,4,5-trimethoxyamphetamine (TMA) and other 4-substituted 3,5-dimethoxyamphetamines (3C drugs).[1][2][3][4] They are also mescaline analogues, but the 2C and DOx drugs have a third methoxy group in the 2 position instead of the 3 position while TMA is an amphetamine rather than a phenethylamine.[1][2][3][4]

The pharmacology of mescaline analogues has been studied.[8][9][10] Mescaline analogues, or 4-substituted 3,5-dimethoxyphenethylamines specifically, tend to be much less potent than the 2C and DOx drugs.[1][3][2] This relates to the fact that the 2,4,5-substitution pattern tends to be optimal in terms of receptor affinity and potency.[1][11] However, mescaline analogues are frequently much more potent than mescaline.[1][3]

Substituted mescaline analogues have been extensively characterized by Alexander Shulgin and described in his books such as PiHKAL (Phenethylamines I Have Known and Loved)[6] and The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds[7] as well as in his literature reviews.[1][3][4][5] They have also been studied by David E. Nichols[12][13][14] and Daniel Trachsel,[15][8][10] among other researchers.

List of substituted mescaline analogues

4-Substituted

  • 4-D (4-trideuteromethoxy-3,5-methoxyphenethylamine)
  • Allylescaline (AL) (4-allyloxy-3,5-dimethoxyphenethylamine)
  • Amylescaline (4-n-amyloxy-3,5-dimethoxyphenethylamine)
  • Benzscaline (BZ) (4-benzyloxy-3,5-dimethoxyphenethylamine)
  • Biscaline (4-phenyl-3,5-dimethoxyphenethylamine)
  • Buscaline (B) (4-butoxy-3,5-dimethoxyphenethylamine)
  • Cyclopropylmescaline (CPM) (4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine)
  • Cycloproscaline (CP) (4-cyclopropoxy-3,5-dimethoxyphenethylamine)
  • 4-Desmethylmescaline (DESMETHYL) (4-hydroxy-3,5-dimethoxyphenethylamine)
  • 4-Desoxymescaline (4-methyl-3,5-dimethoxyphenethylamine)
  • Difluoroescaline (DFE) (multiple forms)
  • Difluoroisoproscaline (DFIP) (multiple forms)
  • Difluoromescaline (DFM) (4-difluoromethoxy-3,5-dimethoxyphenethylamine)
  • Escaline (E) (4-ethoxy-3,5-dimethoxyphenethylamine)
  • Fluoroescaline (FE) (multiple forms)
  • Fluoromescaline (FM) (4-fluoromethoxy-3,5-dimethoxyphenethylamine)
  • Fluoroproscaline (FP) (multiple forms)
  • Hexylescaline (4-n-hexyloxy-3,5-dimethoxyphenethylamine)
  • Isobuscaline (IB) (4-isobutoxy-3,5-dimethoxyphenethylamine)
  • Isoproscaline (IP) (4-isopropoxy-3,5-dimethoxyphenethylamine)
  • Methallylescaline (MAL) (4-methylallyloxy-3,5-dimethoxyphenethylamine)
  • Phenescaline (4-phenylethoxy-3,5-dimethoxyphenethylamine)
  • Propynylmescaline (4-propynyloxy-3,5-dimethoxyphenethylamine)
  • Proscaline (P) (4-propoxy-3,5-dimethoxyphenethylamine)
  • Septylescaline (4-n-heptyloxy-3,5-dimethoxyphenethylamine)
  • 4-Thiobuscaline (4-TB) (4-butylthio-3,5-dimethoxyphenethylamine)
  • 4-Thioescaline (4-TE) (4-ethylthio-3,5-dimethoxyphenethylamine)
  • 4-Thiomescaline (4-TM) (4-methylthio-3,5-dimethoxyphenethylamine)
  • 4-Thioproscaline (4-TP) (4-propylthio-3,5-dimethoxyphenethylamine)
  • Trifluoroescaline (TFE) (multiple forms)
  • Trifluoromescaline (TFM) (4-trifluoromethoxy-3,5-dimethoxyphenethylamine)
  • Trifluoroproscaline (TFP) (multiple forms)
  • Viscaline (4-vinyl-3,5-dimethoxyphenethylamine)

3- or 5-Extended

  • Asymbescaline (ASB) (3,4-diethoxy-5-methoxyphenethylamine)
  • Metadifluoromescaline (MDFM) (3,4-dimethoxy-5-difluoromethoxyphenethylamine)
  • Metaescaline (ME) (3-ethoxy-4,5-dimethoxyphenethylamine)
  • Metaproscaline (MP) (3,4-dimethoxy-5-propoxyphenethylamine)
  • Symbescaline (SB) (4-methoxy-3,5-diethoxyphenethylamine)
  • 4-Thioasymbescaline (4-TASB) (4-ethylthio-3-ethoxy-5-methoxyphenethylamine)
  • 4-Thiometaescaline (4-TME) (4-methylthio-3-ethoxy-5-methoxyphenethylamine)
  • 4-Thiosymbescaline (4-TSB) (4-methylthio-3,5-diethoxyphenethylamine)
  • 4-Thiotrescaline (4-T-TRIS; 4-thiotrisescaline) (4-ethylthio-3,5-diethoxyphenethylamine)
  • Trescaline (TRIS; trisescaline) (3,4,5-triethoxyphenethylamine)

3- or 5-Replaced

2- or 6-Substituted

N-Substituted

α- or β-substituted

See also: 3C (psychedelics)

Other compounds

  • 3,5-Dimethoxyphenethylamine (3,5-DMPEA; 4-desmethoxymescaline)
  • Beta-D (3,4,5-trimethoxy-β-dideuterophenethylamine; β-dideuteromescaline)
  • Bromojimscaline (1-(7-bromo-4,5,6-trimethoxy-2,3-dihydro-1H-inden-1-yl)methanamine)
  • Bromotomscaline (1-(5-bromo-2,3,4-trimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methanamine)
  • Flyscaline (mescaline-FLY)
  • Isomescaline (IM) (2,3,4-trimethoxyphenethylamine)
  • Jimscaline (1-(4,5,6-trimethoxy-2,3-dihydro-1H-inden-1-yl)methylamine)
  • Lophophine (3-methoxy-4,5-methylenedioxyphenethylamine)
  • 2-Thioisomescaline (2-TIM) (2-methylthio-3,4-dimethoxyphenethylamine)
  • 3-Thioisomescaline (3-TIM) (3-methylthio-2,4-dimethoxyphenethylamine)
  • 4-Thioisomescaline (4-TIM) (4-methylthio-2,4-dimethoxyphenethylamine)
  • Tomscaline (1-(2,3,4-trimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl)methylamine)

See also

References

  1. ^ a b c d e f g 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.
  2. ^ a b c d 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.
  3. ^ a b c d e f Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795.
  4. ^ a b c d 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.
  5. ^ a b Shulgin AT (March 1973). "Mescaline: the chemistry and pharmacology of its analogs". Lloydia. 36 (1): 46–58. PMID 4576313.
  6. ^ a b 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.
  7. ^ a b 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.
  8. ^ a b 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.
  9. ^ 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.
  10. ^ a b Stoeckmann OV, Trachsel D, Liechti ME, Rudin D (21 May 2024). "Supplementum 276: Abstracts 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.
  11. ^ Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA (August 2000). "1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists". Journal of Medicinal Chemistry. 43 (16): 3074–3084. doi:10.1021/jm9906062. PMID 10956215.
  12. ^ Nichols DE, Dyer DC (February 1977). "Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues". J Med Chem. 20 (2): 299–301. doi:10.1021/jm00212a022. PMID 836502.
  13. ^ Monte AP, Waldman SR, Marona-Lewicka D, Wainscott DB, Nelson DL, Sanders-Bush E, Nichols DE (September 1997). "Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives". J Med Chem. 40 (19): 2997–3008. doi:10.1021/jm970219x. PMID 9301661.
  14. ^ McLean TH, Chambers JJ, Parrish JC, Braden MR, Marona-Lewicka D, Kurrasch-Orbaugh D, Nichols DE (July 2006). "C-(4,5,6-trimethoxyindan-1-yl)methanamine: a mescaline analogue designed using a homology model of the 5-HT2A receptor". J Med Chem. 49 (14): 4269–4274. doi:10.1021/jm060272y. PMID 16821786.
  15. ^ Trachsel, D.; Lehmann, D.; Enzensperger, C. (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Retrieved 31 January 2025.
  16. ^ "PiHKAL·info". 2-Chloromescaline. 1 April 2025. Retrieved 29 May 2025.
  17. ^ "PiHKAL·info". Dibromomescaline. 1 April 2025. Retrieved 29 May 2025.
  18. ^ "PiHKAL·info". 2,6-Dichloromescaline. 1 April 2025. Retrieved 29 May 2025.


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