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Substituted mescaline analogue

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Mescaline.

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.

Use and effects

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Doses and durations of scalines
Compound Chemical name Dose Duration
β,β-Dideuteromescaline (β-D) 3,4,5-Trimethoxy-β,β-dideuterophenethylamine 200–400 mg 12 hours
4-Desoxymescaline (DESOXY) 4-Methyl-3,5-dimethoxyphenethylamine 40–120 mg 6–8 hours
4-O-Desmethylmescaline (DESMETHYL) 4-Hydroxy-3,5-dimethoxyphenethylamine Unknown Unknown
4-Trideuteromescaline (4-D) 4-Trideuteromethoxy-3,5-dimethoxyphenethylamine 200–400 mg 12 hours
Allylescaline (AL) 4-Allyloxy-3,5-dimethoxyphenethylamine 20–35 mg 8–12 hours
Asymbescaline (ASB) 3,4-Diethoxy-5-methoxyphenethylamine 200–280 mg 10–15 hours
Benzscaline (BZ) 4-Benzyloxy-3,5-dimethoxyphenethylamine Unknown Unknown
Biscaline (BI) 4-Phenyl-3,5-dimethoxyphenethylamine Unknown Unknown
Buscaline (B) 4-Butoxy-3,5-dimethoxyphenethylamine >150 mg Several hours
Cyclopropylmescaline (CPM) 4-Cyclopropylmethoxy-3,5-dimethoxyphenethylamine 60–80 mg 12–18 hours
Cycloproscaline (CP) 4-Cyclopropoxy-3,5-dimethoxyphenethylamine ≥60 mg ≥6 hours
Difluoroescaline (DFE) 4-(2,2-Difluoroethoxy)-3,5-dimethoxyphenethylamine 40–80 mg 6–12 hours
Difluoroisoproscaline (DFIP) 4-(1,3-Difluoropropoxy)-3,5-dimethoxyphenethylamine Unknown Unknown
Difluoromescaline (DFM) 4-Difluoromethoxy-3,5-dimethoxyphenethylamine 50–100 mg 12–18 hours
Escaline (E) 4-Ethoxy-3,5-dimethoxyphenethylamine 40–60 mg 8–12 hours
Fluoroescaline (FE) 4-(2-Fluoroethoxy)-3,5-dimethoxyphenethylamine ≥75 mg ~6 hours
Fluoroisoproscaline (FIP) 4-(1-Fluoroisopropoxy)-3,5-dimethoxyphenethylamine Unknown Unknown
Fluoromescaline (FM) 4-Fluoromethoxy-3,5-dimethoxyphenethylamine Unknown Unknown
Fluoroproscaline (FP) 4-(3-Fluoropropoxy)-3,5-dimethoxyphenethylamine 60–150 mg 3–5 hours
Isobuscaline (IB) 4-Isobutoxy-3,5-dimethoxyphenethylamine 60–100 mg 10–14 hours
Isomescaline (IM) 2,3,4-Trimethoxyphenethylamine >400 mg Unknown
Isoproscaline (IP) 4-Isopropoxy-3,5-dimethoxyphenethylamine 40–80 mg 10–16 hours
Mescaline (M) 3,4,5-Trimethoxyphenethylamine 200–400 (50–800) mg 10–12 (6–14) hours
Metadifluoromescaline (MDFM) 3-(Difluoromethoxy)-4,5-dimethoxyphenylethylamine ≥85 mg ~8 hours
Metatrifluoromescaline (MTFM) 3,4-Dimethoxy-5-(trifluoroisopropoxy)phenethylamine Unknown Unknown
Metaescaline (ME) 3-Ethoxy-4,5-dimethoxyphenethylamine 200–350 mg 8–12 hours
Metaproscaline (MP) 3,4-Dimethoxy-5-propoxyphenethylamine >240 mg Unknown
Methallylescaline (MAL) 4-Methallyloxy-3,5-dimethoxyphenethylamine 40–65 mg 12–16 hours
Phenescaline (PE) 4-Phenethyloxy-3,5-dimethoxyphenethylamine >150 mg Unknown
Phescaline (PH) 4-Phenoxy-3,5-dimethoxyphenethylamine Unknown Unknown
Propynylmescaline 4-Propynyloxy-3,5-dimethoxyphenethylamine ≥80 mg 8–12 hours
Proscaline (P) 4-Propoxy-3,5-dimethoxyphenethylamine 30–60 mg 8–12 hours
sec-Buscaline (SBU) 4-sec-Butoxy-3,5-dimethoxyphenethylamine Unknown Unknown
Symbescaline (SB) 4-Methoxy-3,5-diethoxyphenethylamine >240 mg Unknown
tert-Buscaline (TBU) 4-tert-Butoxy-3,5-dimethoxyphenethylamine Unknown Unknown
Thioasymbescaline (TASB) 3-Ethoxy-4-ethylthio-5-methoxyphenethylamine 60–100 mg 10–15 hours
Thiobuscaline (TB) 4-Butylthio-3,5-dimethoxyphenethylamine 60–120 mg ~8 hours
Thioescaline (TE) 4-Ethylthio-3,5-dimethoxyphenethylamine 20–30 mg 9–12 hours
Thioisomescaline (TIM) 2,3-Dimethoxy-4-methylthiophenethylamine >240 mg Unknown
Thiomescaline (TM) 4-Methylthio-3,5-dimethoxyphenethylamine 20–40 mg 10–15 hours
Thiometaescaline (TME) 3-Ethoxy-4-methylthio-5-methoxyphenethylamine 60–100 mg 10–15 hours
Thioproscaline (TP) 4-Propylthio-3,5-dimethoxyphenethylamine 20–25 mg 10–15 hours
Thiosymbescaline (TSB) 4-Methylthio-3,5-diethoxyphenethylamine >240 mg Unknown
Thiotrescaline (T-TRIS) 4-Ethylthio-3,5-diethoxyphenethylamine >200 mg Unknown
Trescaline (TRIS) 3,4,5-Triethoxyphenethylamine >240 mg Unknown
Trifluoroescaline (TFE) 4-(2,2,2-Trifluoroethoxy)-3,5-dimethoxyphenethylamine 35–65 mg 12–18 hours
Trifluoroisoproscaline (TFIP) 4-(1,1,1-Trifluoroisopropoxy)-3,5-dimethoxyphenethylamine Unknown Unknown
Trifluoromescaline (TFM) 4-(Trifluoromethoxy)-3,5-dimethoxyphenethylamine 15–40 mg 14–24 hours
Trifluoroproscaline (TFP) 4-(3,3,3-Trifluoropropoxy)-3,5-dimethoxyphenethylamine ≥60 mg Unknown
Viscaline (V) 4-Vinyl-3,5-dimethoxyphenethylamine Unknown Unknown
Refs: [1][3][16][7][17][18][15][19][8]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

List of substituted mescaline analogues

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4-Substituted

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3- or 5-Extended

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3- or 5-Replaced

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2- or 6-Substituted

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N-Substituted

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α- or β-substituted

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See also: 3C (psychedelics)

Other compounds

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See also

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References

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  1. ^ a b c d e f g h 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. Archived from the original (PDF) on August 5, 2023.
  3. ^ a b c d e f g Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID 8742795. Archived from the original (PDF) on August 5, 2023.
  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 c 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 c 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. ^ a b 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. ^ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  17. ^ Halberstadt, Adam L.; Chatha, Muhammad; Klein, Adam K.; Wallach, Jason; Brandt, Simon D. (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152. Table 4 Human potency data for selected hallucinogens. [...]
  18. ^ Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Test Anal. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
  19. ^ Luethi D, Liechti ME (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol. 21 (10): 926–931. doi:10.1093/ijnp/pyy047. PMID 29850881.
  20. ^ "PiHKAL·info". 2-Chloromescaline. 1 April 2025. Retrieved 29 May 2025.
  21. ^ "PiHKAL·info". Dibromomescaline. 1 April 2025. Retrieved 29 May 2025.
  22. ^ "PiHKAL·info". 2,6-Dichloromescaline. 1 April 2025. Retrieved 29 May 2025.
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