Methallylescaline

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Methallylescaline
Methallylescaline.svg
Methallylescaline 3D.png
Clinical data
Other namesMAL; 4-Methylallyloxy-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-methylallyloxyphenethylamine; 4-Methylallyl-desmethylmescaline; MAD
Routes of
administration 		Oral [1]
Drug class Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Onset of action ≤1 hour [1]
Duration of action 12–16 hours [1]
Identifiers
  • 2-{{#parsoidfragment:2}}{3,5-Dimethoxy-4-[(2-methylprop-2-en-1-yl)oxy]phenyl}ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C14H21NO3
Molar mass 251.326 g·mol−1
3D model (JSmol)
  • CC(=C)COc1c(cc(cc1OC)CCN)OC
  • InChI=1S/C14H21NO3/c1-10(2)9-18-14-12(16-3)7-11(5-6-15)8-13(14)17-4/h7-8H,1,5-6,9,15H2,2-4H3 Yes check.svgY
  • Key:FOXJFBFFGULACD-UHFFFAOYSA-N Yes check.svgY
   (verify)

Methallylescaline (MAL), also known as 4-methylallyloxy-3,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. [1] [3] It is taken orally. [1] [3]

Contents

The drug acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor. [4] It is closely structurally related to mescaline and to other scalines like escaline and allylescaline. [4]

Methallylescaline was first described by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). [3] [1] It was encountered as a novel designer drug by 2013. [5] [6] [7]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists the dose range of methallylescaline as 40 to 65 mg and its duration as 12 to 16 hours. [1] [8] [9] As such, its dose range is relatively narrow. [1] [8] [9] 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. [10] Methallylescaline has about 6 times the potency of mescaline, which has a much higher listed dose range of 200 to 400 mg. [8] [9] [1] Its onset is within 1 hour and peak effects occur within 2 hours. [1]

Shulgin has described methallylescaline as a "mixed bag" in terms of experience reports. [1] 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. [1] It was also reported to produce quite strong body effects, diuretic effects, and slightly reduced heart rate. [1] 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". [1] Many expressed that the dose they tried was too strong for them and that a lower dose would be better. [1] Methallylescaline has been described as having relatively more visual imagery than other scalines like cyclopropylmescaline and allylescaline. [1]

Interactions

Pharmacology

Pharmacodynamics

Methallylescaline acts as a potent agonist of the serotonin 5-HT2A receptor. [4] It also interacts with certain other targets, such as the serotonin 5-HT2C receptor. [4]

Chemistry

Methallylescaline, also known as 4-methylallyloxy-3,5-dimethoxyphenethylamine, is a substituted phenethylamine and scaline. [1] [3] [8] [9] It is a synthetic derivative of mescaline (3,4,5-trimethoxyphenethylamine) with a meth allyl oxy group instead of methoxy group at the 4 position. [1] [3] [8] [9]

Synthesis

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

Analogues

Analogues of methallylescaline include mescaline, escaline, allylescaline, and cyclopropylmescaline, among others. [1] [3] [8] [9]

History

Methallylescaline was first described in the literature by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). [3] [1] [8] It was first tried by Shulgin in 1981 and its hallucinogenic effects were discovered by him in 1982. [11] [9] The drug has an entry in PiHKAL, but not in Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . [3] It was encountered as a novel designer drug in Europe by 2013. [5] [6] [7] Methallylescaline's pharmacology was described by Matthias Liechti and Daniel Trachsel and colleagues in 2021. [4]

Society and culture

Names

Alexander Shulgin described the name of methallylescaline (MAL) as "completely unsound". [1] This was because there was no union of a meth allyl group with escaline. [1] Instead, methallylescaline is mescaline with a 2-propene group attached to the methyl of the methoxy group at the 4 position. [1] However, Shulgin expressed that there is no way of naming the compound in that manner. [1] The only corresponding proper name would be 4-methylallyldesmethylmescaline (MAD). [1] However, Shulgin found the acronym MAD to be disagreeable and ultimately preferred MAL. [1]

Sweden

Methallylescaline is illegal in Sweden as of 26 January 2016. [12]

United States

Methallylescaline 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.

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 "Methallylescaline". PiHKAL.
  2. ↑ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  3. 1 2 3 4 5 6 7 8 Shulgin A, Manning T, Daley PF (2011). "#91. Mescaline". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley, CA: Transform Press. pp. 212–225 (217). ISBN   978-0-9630096-3-0. OCLC   709667010. [...] Homologues and Analogues [...] Name: MAL. CAS #: [207740-41-8]. Ref: (30,31). [...] (30) Synthesis (Shulgin and Shulgin, 1991). (31) Orally active in humans at 40-65 mg; duration 12-16 hours (Shulgin and Shulgin, 1991).
  4. 1 2 3 4 5 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 King LA (2014). "New phenethylamines in Europe". Drug Test Anal. 6 (7–8): 808–818. doi:10.1002/dta.1570. PMID   24574327.
  6. 1 2 "EMCDDA–Europol 2013 Annual Report on the implementation of Council Decision 2005/387/JHA". www.euda.europa.eu. 2 July 2024. Retrieved 9 October 2025.
  7. 1 2 Coelho Neto J (July 2015). "Rapid detection of NBOME's and other NPS on blotter papers by direct ATR-FTIR spectrometry". Forensic Science International. 252: 87–92. doi:10.1016/j.forsciint.2015.04.025. PMID   25965305.
  8. 1 2 3 4 5 6 7 Jacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs" (PDF). NIDA Res Monogr. 146: 74–91. PMID   8742795. Archived from the original (PDF) on August 5, 2023.
  9. 1 2 3 4 5 6 7 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 . Retrieved 1 February 2025.
  10. ↑ "SATA Early Warning System of the Americas". Archived from the original on 2025-06-19. [United States National Drug Early Warning System (NDEWS)] issued an alert about the substance methallylescaline, a synthetic analog of mescaline and a 5-HT receptor agonist. Discussions in online forums often warn of methallylescaline's steep dose-response curve, where small dosage changes can dramatically alter the experience. Some of the effects discussed are nausea and "body load". Those who experiment with polysubstance use, combine methallylescaline with other substances, such as etizolam.
  11. ↑ Alexander Shulgin (1981), Pharmacology Lab Notes #4 (PDF)
  12. ↑ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.
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