Chemistry:Proscaline

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Proscaline, also known as 4-propoxy-3,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline.[1] It is taken orally.[1][2]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin reports that a dose of 30 to 60 mg orally produces effects lasting 8 to 12 hours.[1][3][4][2] The onset was not described, but peak effects occurred after about 2 hours.[1] A typical dose estimate is 45 mg.[2] Doses as high as 80 mg have also been explored.[1] The drug has approximately 6 or 7 times the potency of mescaline, which itself has a listed dose range of 200 to 400 mg.[1][3][4][5][6]

The effects of proscaline have been reported to include insignificant closed-eye visuals, sharpening of the senses, hyperawareness, relaxation and feeling at ease, deep feelings of peace and contentment, euphoria, no enhanced clarity or deep realizations, feelings of uninhibited eroticism, pain relief, drowsiness, intoxication and feeling drunk, irritability, restlessness, tremors, insomnia, difficulty with dreams, long-lasting residual effects, and no next-day hangover.[1]

Interactions

Pharmacology

Pharmacodynamics

Proscaline is a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.[7][8] Activation of the serotonin 5-HT2A receptor is thought to be responsible for its psychedelic effects.[7] The drug is much more potent as an agonist of the serotonin 5-HT2C receptor than as an agonist of the serotonin 5-HT2A or 5-HT2B receptors.[7]

It produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[7][9][2]

Chemistry

Proscaline, also known as 4-propoxy-3,5-dimethoxyphenethylamine, is a substituted phenethylamine and scaline (4-substituted 3,5-dimethoxyphenethylamine) derivative related to mescaline (3,4,5-trimethoxyphenethylamine).[1] It is the 4-propoxy homologue of mescaline.[1]

Properties

Proscaline is much more lipophilic than mescaline or escaline (log P = 1.70, 0.78, and 1.11, respectively), which is expected to be more optimal and advantageous in terms of drug-like properties such as blood–brain barrier permeability.[9]

Synthesis

The chemical synthesis of proscaline has been described.[1]

Analogues

Analogues of proscaline include mescaline, escaline, isoproscaline, allylescaline, methallylescaline, cyclopropylmescaline, cycloproscaline, fluoroproscaline, and 3C-P, among others.[1][10][11]

History

Proscaline was first synthesized and studied by Otakar Leminger in 1972.[12][1] The drug was later synthesized by Alexander Shulgin and further described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1] It was encountered as a novel designer drug in Europe in 2013.[13][14][9]

Society and culture

United Kingdom

United States

See also

  • Substituted mescaline analogue

References

  1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 Proscaline entry in PiHKAL
  2. ↑ 2.0 2.1 2.2 2.3 "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology 167. May 2020. doi:10.1016/j.neuropharm.2019.107933. PMID 31917152. PMC 9191653. http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf. "Table 4 Human potency data for selected hallucinogens. [...]". 
  3. ↑ 3.0 3.1 "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Res Monogr 146: 74–91. 1994. PMID 8742795. https://bitnest.netfirms.com/external/Books/NIDA146.74. 
  4. ↑ 4.0 4.1 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6. 
  5. ↑ Alexander T. Shulgin (1980). "Hallucinogens". Burger's Medicinal Chemistry. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5. 
  6. ↑ "Chemistry of Psychotomimetics". Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. 55 / 3. Berlin: Springer Berlin Heidelberg. 1982. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916. https://bitnest.netfirms.com/external/10.1007/978-3-642-67770-0_1. 
  7. ↑ 7.0 7.1 7.2 7.3 "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun 14 (1). December 2023. doi:10.1038/s41467-023-44016-1. PMID 38102107. Bibcode: 2023NatCo..14.8221W. 
  8. ↑ McCorvy JD (16 January 2013). Mapping the binding site of the 5-HT2A receptor using mutagenesis and ligand libraries: Insights into the molecular actions of psychedelics (Ph.D. thesis). Purdue University. Archived from the original on 15 May 2025. Retrieved 27 May 2025 – via Purdue e-Pubs.{{cite thesis}}: CS1 maint: bot: original URL status unknown (link)
  9. ↑ 9.0 9.1 9.2 "Comparison of the behavioral effects of mescaline analogs using the head twitch response in mice". J Psychopharmacol 33 (3): 406–414. March 2019. doi:10.1177/0269881119826610. PMID 30789291. 
  10. ↑ "Fluorine in psychedelic phenethylamines". Drug Test Anal 4 (7–8): 577–590. 2012. doi:10.1002/dta.413. PMID 22374819. 
  11. ↑ "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines". Front Pharmacol 12. 2021. doi:10.3389/fphar.2021.794254. PMID 35222010. 
  12. ↑ Leminger, Otakar (1972). "The Chemistry of Alkoxylated Phenethylamines – Part 2". Chemický Průmysl 22: 553. http://www.erowid.org/archive/rhodium/chemistry/leminger.html. 
  13. ↑ "New phenethylamines in Europe". Drug Test Anal 6 (7–8): 808–818. 2014. doi:10.1002/dta.1570. PMID 24574327. 
  14. ↑ https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2013

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