Methallylescaline

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists the dose range of methallylescaline as 40 to 65mg and its duration as 12 to 16hours. As such, its dose range is relatively narrow. Moreover, the drug has been reported to have an unusually steep dose–response curve, such that a small increase in dose can result in an unexpectedly large increase in effects. Methallylescaline has about 6times the potency of mescaline, which has a much higher listed dose range of 200 to 400mg. Its onset is within 1hour and peak effects occur within 2hours.

Shulgin has described methallylescaline as a "mixed bag" in terms of experience reports. Its effects have been reported to include closed-eye visuals, "visual theater", open-eye visuals including visual distortions, visual depth and movement effects, kaleidoscopic neon colors, watercolors, fantasy, mental imagery, feelings of unreality, easy childhood memory recall, self-connectedness, eroticism, initial discomfort, overload, feeling overwhelmed, shades of possible amnesia, loss of contact, extreme restlessness, trouble sleeping, and enhanced dreams. It was also reported to produce quite strong body effects, diuretic effects, and slightly reduced heart rate. Some found it unpleasant and said that they would not repeat the experience, whereas others were impressed by it, found it enjoyable, and called it "beautiful". Many expressed that the dose they tried was too strong for them and that a lower dose would be better. Methallylescaline has been described as having relatively more visual imagery than other scalines like cyclopropylmescaline and allylescaline.

Others have noted that methallylescaline has strong visual effects, as well as prominent nausea, vomiting, and body load, including feeling "overstimulated. The drug is frequently compared to mescaline.

Interactions

Pharmacology

Pharmacodynamics

Methallylescaline acts as a potent agonist of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors, among other actions. It was inactive serotonin 5-HT2B receptor agonist in one study, but was a potent agonist in another study. The comprehensive receptor interactions of methallylescaline have been studied.

The drug produces the head-twitch response (HTR), a behavioral proxy of psychedelic effects, in rodents. Surprisingly, the HTR induced by methallylescaline was blocked by the selective serotonin 5-HT2C receptor antagonist SB-242084 but not by the serotonin 5-HT2A receptor antagonist ketanserin.

In addition to its psychedelic-like effects, methallylescaline produces hyperlocomotion (a stimulant-like effect), conditioned place preference (CPP; a rewarding effect), and modest self-administration (a reinforcing effect) in rodents, among other effects.

Methallylescaline, along with BOD and DOI, has been reported to produce serotonergic neurotoxicity in rodents at high doses given repeatedly. Other psychedelics have also been found to produce neurotoxicity in preclinical research.

Pharmacokinetics

The metabolism of methallylescaline has been studied.

Chemistry

Methallylescaline, also known as 4-methylallyloxy-3,5-dimethoxyphenethylamine, is a substituted phenethylamine and scaline. It is a synthetic derivative of mescaline (3,4,5-trimethoxyphenethylamine) with a methallyloxy group instead of methoxy group at the 4 position.

Synthesis

The chemical synthesis of methallylescaline has been described.

Analogues

Analogues of methallylescaline include mescaline, escaline, allylescaline, and cyclopropylmescaline, among others. Some other analogues include 3C-MAL, 2C-T-3, 2C-O-3, and MMALM.

History

Methallylescaline was first described in the literature by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). It was first tried by Shulgin in 1981 and its hallucinogenic effects were discovered by him in 1982. The drug has an entry in PiHKAL, but not in Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. It was encountered as a novel designer drug in Europe by 2013. Methallylescaline's pharmacology was described by Matthias Liechti and Daniel Trachsel and colleagues in 2021. Discussion of methallylescaline online began increasing in late 2023.

Society and culture

Names

Alexander Shulgin described the name of methallylescaline (MAL) as "completely unsound". This was because there was no union of a methallyl group with escaline. Instead, methallylescaline is mescaline with a 2-propene group attached to the methyl of the methoxy group at the 4 position. However, Shulgin expressed that there is no way of naming the compound in that manner. The only corresponding proper name would be 4-methylallyldesmethylmescaline (MAD). However, Shulgin found the acronym MAD to be disagreeable and ultimately preferred MAL.

Legal status

Canada

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

Sweden

Methallylescaline is illegal in Sweden as of 26 January 2016.

United States

Methallylescaline is not explicitly scheduled under the Controlled Substances Act. However, due to its structural similarities with mescaline, it could potentially be prosecuted under the Federal Analogue Act if sold for human consumption.

References

References

1. Anvisa. (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
2. (2011). "[[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]]". Transform Press.
3. "Methallylescaline". PiHKAL.
4. (10 May 2024). "Weekly Briefing Issue 181".
5. "SATA Early Warning System of the Americas".
6. (2003). "Hallucinogens: A Forensic Drug Handbook". Elsevier Science.
7. (2021). "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines". Frontiers in Pharmacology.
8. (March 2023). "Structure-Activity Relationship and Evaluation of Phenethylamine and Tryptamine Derivatives for Affinity towards 5-Hydroxytryptamine Type 2A Receptor". Biomolecules & Therapeutics.
9. (October 2025). "The polypharmacology of psychedelics reveals multiple targets for potential therapeutics". Neuron.
10. (July 2025). "Serotonin 2C receptors are also important in head-twitch responses in male mice". Psychopharmacology.
11. (September 2020). "Two newly-emerging substituted phenethylamines MAL and BOD induce differential psychopharmacological effects in rodents". Journal of Psychopharmacology.
12. (September 2021). "Molecular and clinical aspects of potential neurotoxicity induced by new psychoactive stimulants and psychedelics". Experimental Neurology.
13. (2006). "Ecstasy-induced cell death in cortical neuronal cultures is serotonin 2A-receptor-dependent and potentiated under hyperthermia". Neuroscience.
14. (June 2009). "Molecular and cellular mechanisms of ecstasy-induced neurotoxicity: an overview". Molecular Neurobiology.
15. (June 2025). "Metabolism study of two phenethylamine - derived new psychoactive substances using in silico, in vivo, and in vitro approaches". Archives of Toxicology.
16. (30 September 2018). "In vitro Metabolism of Methallylescaline in Human Hepatocytes Using Liquid Chromatography-High Resolution Mass Spectrometry". Mass Spectrometry Letters.
17. (2013). "Phenethylamine: von der Struktur zur Funktion". Nachtschatten-Verlag.
18. (1994). "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Research Monograph.
19. Alexander Shulgin. (1981). "Pharmacology Lab Notes #4".
20. (2014). "New phenethylamines in Europe". Drug Testing and Analysis.
21. (2 July 2024). "EMCDDA–Europol 2013 Annual Report on the implementation of Council Decision 2005/387/JHA".
22. (July 2015). "Rapid detection of NBOME's and other NPS on blotter papers by direct ATR-FTIR spectrometry". Forensic Science International.
23. "Controlled Drugs and Substances Act".
24. (November 2015). "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara". Folkhälsomyndigheten.
25. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.