Escaline

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists the dose range of escaline as 40 to 60mg of the hydrochloride salt taken orally. The duration is stated to be 8 to 12hours, whereas the onset is not described. Escaline is approximately 5- to 8-fold more potent than mescaline.

The effects of escaline have been described relatively limitedly but have been reported to include sensory enhancement without an intellectual component, little synthesis of external sensory inputs like music or visual stimuli, easy fantasy, rational thinking and insight, pleasantness, powerful and complex intoxication, pain relief, muscle tension, motor incoordination to the extent of not being able to walk or tie one's shoelaces, body tension that outweighed the desired psychoactive effects, tachycardia, dehydration, nightmares, and next-day hangover symptoms such as tiredness and low energy.

Interactions

Pharmacology

Pharmacodynamics

The receptor interactions of escaline and analogues have been described.

Escaline produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents. It partially substitutes for LSD in rodent drug discrimination tests.

Chemistry

Synthesis

The chemical synthesis of escaline has been described.

Analogues

Analogues of escaline include mescaline, proscaline, allylescaline, methallylescaline, and 3C-E, among others.

History

Escaline was first described in the scientific literature by George S. Grace in 1934. Subsequently, it was also described by F. Benington and colleagues in 1954. It was later re-examined in the laboratory of David E. Nichols, who prepared a series of mescaline analogues that included escaline, proscaline, and isoproscaline and published their work in 1977.

Society and culture

Legal status

Canada

Escaline is not a controlled substance in Canada as of 2025.

Sweden

Escaline is illegal in Sweden as of 26 January 2016.

United States

Escaline is a Schedule I controlled substance (DEA #7930) in the United States with the reason cited being that it is a positional isomer of 3,4,5-trimethoxyamphetamine (TMA).

References

References

1. "E (Эскалин) (Escaline)".
2. "Erowid Online Books : "PIHKAL" - #72 E".
3. (September 2008). "Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT(2A) receptors". ChemMedChem.
4. (2021). "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines". Frontiers in Pharmacology.
5. (July 2025). "The polypharmacology of psychedelics reveals multiple targets for potential therapeutics". Neuron.
6. (March 2019). "Comparison of the behavioral effects of mescaline analogs using the head twitch response in mice". Journal of Psychopharmacology.
7. (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology.
8. (October 2018). "Dark Classics in Chemical Neuroscience: Mescaline". ACS Chemical Neuroscience.
9. Grace, George S.. (1934). "The Action of Mescaline and Some Related Compounds". The Journal of Pharmacology and Experimental Therapeutics.
10. (1954). "Synthesis of 4-Hydroxy- and 4-Ethoxy-3,5-dimethoxy-β-phenethylamines 1". Journal of the American Chemical Society.
11. (February 1977). "Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues". Journal of Medicinal Chemistry.
12. (August 1977). "Directional lipophilic character in a series of psychotomimetic phenethylamine derivatives". Life Sciences.
13. "Controlled Drugs and Substances Act".
14. (November 2015). "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara". Folkhälsomyndigheten.
15. (December 2024). "Controlled Substances - Alphabetical Order". U.S. Department of Justice.
16. [[Drug Enforcement Administration]]. (3 December 2007). "Definition of “Positional Isomer” as It Pertains to the Control of Schedule I Controlled Substances".