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Allylescaline
Psychedelic drug
Psychedelic drug
| Field | Value | |||
|---|---|---|---|---|
| Verifiedfields | verified | |||
| Watchedfields | verified | |||
| verifiedrevid | 477348333 | |||
| image | Allylescaline.svg | |||
| image_class | skin-invert-image | |||
| width | 250px | |||
| image2 | Allylescaline-3d-sticks.png | |||
| image_class2 | bg-transparent | |||
| width2 | 250px | |||
| routes_of_administration | Oral | |||
| class | Serotonin [5-HT2 receptor](5-ht2-receptor) agonist; Serotonin [5-HT2A receptor](5-ht2a-receptor) agonist; Serotonergic psychedelic; Hallucinogen | |||
| ATC_prefix | None | |||
| onset | 10–50 minutes | |||
| duration_of_action | 8–12 hours | |||
| CAS_number_Ref | ||||
| CAS_number | 39201-75-7 | |||
| PubChem | 44719469 | |||
| ChemSpiderID_Ref | ||||
| ChemSpiderID | 21106254 | |||
| UNII_Ref | ||||
| UNII | J39IWS08EN | |||
| ChEMBL_Ref | ||||
| ChEMBL | 126803 | |||
| synonyms | AL; Allylmescaline; 4-Allyloxy-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-allyloxyphenethylamine | |||
| IUPAC_name | {3,5-dimethoxy-4-[(prop-2-en-1-yl)oxy]phenyl}ethan-1-amine | |||
| C | 13 | H=19 | N=1 | O=3 |
| SMILES | COc1cc(cc(OC)c1OCC=C)CCN | |||
| StdInChI_Ref | ||||
| StdInChI | 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 | |||
| StdInChIKey_Ref | ||||
| StdInChIKey | JNUAYHHGCXYBHX-UHFFFAOYSA-N |
| Drugs.com =
| elimination_half-life =
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. It is taken orally.
The drug acts as an agonist of the serotonin 5-HT2 receptors, including the serotonin 5-HT2A receptor. It is closely related to other scalines including mescaline, escaline, and proscaline, among others.
Allylescaline was first described in the scientific literature by Otakar Leminger in 1972. Subsequently, it was further described by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). It was encountered as a novel designer drug in 2013.
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 35mg and its duration is 8 to 12hours. Its onset ranged from 10minutes to 50minutes, with peak effects occurring at around 1 to 1.25hours. 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 12hours or even into the middle of the next day. Allylescaline is about 10times as potent as mescaline, which has a listed dose range of 200 to 400mg. It was the most potent scaline (mescaline analogue) of all those described.
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.
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. It also possesses other activities, such as weak interactions with dopamine D2-like receptors. A 2021 study evaluated the pharmacodynamics of many scalines, but did not include allylescaline. However, a subsequent 2025 study comprehensively assessed and reported the drug's pharmacodynamics.
Chemistry
Synthesis
The chemical synthesis of allylescaline has been described.
Analogues
Analogues of allylescaline include mescaline, escaline, proscaline, methallylescaline, cyclopropylmescaline, and 3C-AL, among others.
History
Allylescaline was first synthesized and studied by Otakar Leminger in 1972. The drug was later synthesized by Alexander Shulgin and further described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). It was encountered as a novel designer drug in Europe in 2013.
Society and culture
Legal status
Canada
Allylescaline is not a controlled substance in Canada as of 2025.
Sweden
Allylescaline is illegal in Sweden as of January 2016.
United States
Allylescaline is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.
References
References
- (1994). "Structure-activity relationships of the classic hallucinogens and their analogs". NIDA Res Monogr.
- (2003). "Hallucinogens: A Forensic Drug Handbook". Elsevier Science.
- (July 2025). "The polypharmacology of psychedelics reveals multiple targets for potential therapeutics". Neuron.
- (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.
- (2021). "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines". Front Pharmacol.
- Leminger, Otakar. (1972). "The Chemistry of Alkoxylated Phenethylamines – Part 2". Chemický Průmysl.
- [http://www.erowid.org/library/books_online/pihkal/pihkal002.shtml AL Entry in ''PiHKAL'']
- (2014). "New phenethylamines in Europe". Drug Test Anal.
- (2 July 2024). "EMCDDA–Europol 2013 Annual Report on the implementation of Council Decision 2005/387/JHA".
- "Controlled Drugs and Substances Act".
- (November 2015). "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara". Folkhälsomyndigheten.
- (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.
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