Allylescaline

Last updated
Allylescaline
Allylescaline.svg
Allylescaline-3d-sticks.png
Clinical data
Other namesAL; Allylmescaline; 4-Allyloxy-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-allyloxyphenethylamine
Routes of
administration 		Oral [1]
Drug class Serotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action 10–50 minutes [1]
Duration of action 8–12 hours [1]
Identifiers
  • {3,5-dimethoxy-4-[(prop-2-en-1-yl)oxy]phenyl}ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C13H19NO3
Molar mass 237.299 g·mol−1
3D model (JSmol)
  • COc1cc(cc(OC)c1OCC=C)CCN
  • InChI=1S/C13H19NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h4,8-9H,1,5-7,14H2,2-3H3 X mark.svgN
  • Key:JNUAYHHGCXYBHX-UHFFFAOYSA-N X mark.svgN
   (verify)

Allylescaline (AL), or allylmescaline, also known as 4-allyloxy-3,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. [1] It is taken orally. [1]

Contents

The drug acts as an agonist of the serotonin 5-HT2 receptors, including the serotonin 5-HT2A receptor. [2] [3] It is closely related to other scalines including mescaline, escaline, and proscaline, among others. [1] [4]

Allylescaline was first described in the scientific literature by Otakar Leminger in 1972. [5] Subsequently, it was further described by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). [1] It was encountered as a novel designer drug in 2013. [6] [7]

Use and effects

According to Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, the dose range of allylescaline is 20 to 35 mg and its duration is 8 to 12 hours. [1] [8] [9] Its onset ranged from 10 minutes to 50 minutes, with peak effects occurring at around 1 to 1.25 hours. [1] The drug has been described as having a very gradual onset, an unusually long plateau of effects, a very gradual descent, and some effects persisting past 12 hours or even into the middle of the next day. [1] [5] Allylescaline is about 10 times as potent as mescaline, which has a listed dose range of 200 to 400 mg. [1] [8] [9] It was the most potent scaline (mescaline analogue) of all those described. [1] [8] [9]

The effects of allylescaline have been reported to include perceptual changes, warmer and enhanced colors, objects looking different or more "plastic", colorful hallucinations in the dark, surroundings being much more interesting than usual, no sharpening of the senses including visual, auditory, or olfactory, pleasantly and abundantly increased energy, creative and free-flowing thoughts, clearheadedness, unusual ease of free association, everything feeling funny and laughter, feelings of inner excitement and enjoyment, desire to move, simultaneous positive and negative feelings, working through and being freed of depression, feelings of dissociation and being disconnected from one's thoughts, wholly social and no requirement of withdrawal, religious feelings and connection, slight vertigo, light drunkenness, restless sleep and unusual and difficult dreams during sleep, and next-day hangover such as lethargy. [1] [5]

Interactions

Pharmacology

Pharmacodynamics

Allylescaline acts as a potent agonist of the serotonin 5-HT2 receptors, including the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors. [2] [3] It also possesses other activities, such as weak interactions with dopamine D2-like receptors. [2] A 2021 study evaluated the pharmacodynamics of many scalines, but did not include allylescaline. [4] However, a subsequent 2025 study comprehensively assessed and reported the drug's pharmacodynamics. [2]

Chemistry

Synthesis

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

Analogues

Analogues of allylescaline include mescaline, escaline, proscaline, methallylescaline, cyclopropylmescaline, and 3C-AL, among others. [1] [4]

History

Allylescaline was first synthesized and studied by Otakar Leminger in 1972. [5] 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. [6] [7]

Society and culture

Sweden

Allylescaline is illegal in Sweden as of January 2016. [10]

United States

Allylescaline is not directly 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.[ citation needed ]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 AL Entry in PiHKAL
  2. 1 2 3 4 Jain MK, Gumpper RH, Slocum ST, Schmitz GP, Madsen JS, Tummino TA, Suomivuori CM, Huang XP, Shub L, DiBerto JF, Kim K, DeLeon C, Krumm BE, Fay JF, Keiser M, Hauser AS, Dror RO, Shoichet B, Gloriam DE, Nichols DE, Roth BL (July 2025). "The polypharmacology of psychedelics reveals multiple targets for potential therapeutics" (PDF). Neuron. 113 (19): 3129–3142.e9. doi:10.1016/j.neuron.2025.06.012. PMID   40683247.
  3. 1 2 Åstrand A, Guerrieri D, Vikingsson S, Kronstrand R, Green H (December 2020). "In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT1A, and 5-HT2A receptors-On-target receptor potency and efficacy, and off-target effects". Forensic Sci Int. 317 110553. doi:10.1016/j.forsciint.2020.110553. PMID   33160102.
  4. 1 2 3 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.
  5. 1 2 3 4 Leminger, Otakar (1972). "The Chemistry of Alkoxylated Phenethylamines – Part 2". Chemický Průmysl. 22: 553.
  6. 1 2 King LA (2014). "New phenethylamines in Europe". Drug Test Anal. 6 (7–8): 808–818. doi:10.1002/dta.1570. PMID   24574327.
  7. 1 2 "EMCDDA–Europol 2013 Annual Report on the implementation of Council Decision 2005/387/JHA". www.euda.europa.eu. 2 July 2024. Retrieved 16 October 2025.
  8. 1 2 3 Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Res Monogr. 146: 74–91. PMID   8742795.
  9. 1 2 3 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.
  10. ↑ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.
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