Proscaline
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| Other names | 4-Propoxy-3,5-dimethoxyphenethylamine; 4-Propoxy-3,5-DMPEA |
| Routes of administration | Oral[1] |
| Drug class | Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen |
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| Pharmacokinetic data | |
| Duration of action | 8–12 hours[1] |
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| Chemical and physical data | |
| Formula | C13H21NO3 |
| Molar mass | 239.315 g·mol−1 |
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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
[edit]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
[edit]Pharmacology
[edit]Pharmacodynamics
[edit]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
[edit]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
[edit]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
[edit]The chemical synthesis of proscaline has been described.[1]
Analogues
[edit]Analogues of proscaline include mescaline, escaline, isoproscaline, allylescaline, methallylescaline, cyclopropylmescaline, cycloproscaline, fluoroproscaline, and 3C-P, among others.[1][10][11]
History
[edit]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
[edit]Legal status
[edit]United Kingdom
[edit]Proscaline is a Class A controlled substance in the United Kingdom.[citation needed]
United States
[edit]Proscaline is not directly scheduled under the Controlled Substances Act in the United States. However, due to its structural similarities with mescaline, a Schedule I drug, it could potentially be subject to the same control measures and penalties for possession and manufacture under the Federal Analogue Act.[citation needed]
See also
[edit]References
[edit]- ^ a b c d e f g h i j k l m n o Proscaline entry in PiHKAL
- ^ a b c d Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (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. [...]
- ^ a b Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Res Monogr. 146: 74–91. PMID 8742795.
- ^ a b 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.
- ^ Alexander T. Shulgin (1980). "Hallucinogens". In Burger A, Wolf ME (eds.). Burger's Medicinal Chemistry. Vol. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627.
- ^ Shulgin AT (1982). "Chemistry of Psychotomimetics". In Hoffmeister F, Stille G (eds.). Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. Vol. 55 / 3. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916.
- ^ a b c d Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun. 14 (1) 8221. Bibcode:2023NatCo..14.8221W. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.
- ^ 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) - ^ a b c 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.
- ^ Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Test Anal. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
- ^ 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.
- ^ Leminger, Otakar (1972). "The Chemistry of Alkoxylated Phenethylamines – Part 2". Chemický Průmysl. 22: 553.
- ^ King LA (2014). "New phenethylamines in Europe". Drug Test Anal. 6 (7–8): 808–818. doi:10.1002/dta.1570. PMID 24574327.
- ^ https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2013