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3C-AL

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3C-AL
Clinical data
Other names4-Allyloxy-3,5-dimethoxyamphetamine; 3,5-Dimethoxy-4-allyloxyamphetamine; α-Methylallylescaline; 3C-Allylescaline
Routes of
administration		Oral[1][2]
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Pharmacokinetic data
Duration of action8–12 hours[1][2]
Identifiers
  • 1-[3,5-dimethoxy-4-[(prop-2-en-1-yl)oxy]phenyl]propan-2-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H21NO3
Molar mass251.326 g·mol−1
3D model (JSmol)
Melting point180 to 181 °C (356 to 358 °F)
  • C=CCOc1c(OC)cc(cc1OC)CC(N)C
  • InChI=1S/C14H21NO3/c1-5-6-18-14-12(16-3)8-11(7-10(2)15)9-13(14)17-4/h5,8-10H,1,6-7,15H2,2-4H3
  • Key:ROINMNZLTKSBPR-UHFFFAOYSA-N

3C-AL, also known as 4-allyloxy-3,5-dimethoxyamphetamine or as α-methylallylescaline (3C-allylescaline), is a psychedelic drug of the phenethylamine, amphetamine, and 3C families related to 3,4,5-trimethoxyamphetamine (TMA).[3][1][2] It is the amphetamine (3C) analogue of allylescaline.[3][1][2] The drug has a dose range of 15 to 30 mg orally and a duration of 8 to 12 hours.[1][2] Its effects have been described as more visual than those of allylescaline.[1] The drug is a potent partial agonist of the serotonin 5-HT2A receptor and also interacts with other serotonin receptors and targets.[2] The chemical synthesis of 3C-AL has been described.[3][4] 3C-AL was described by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved), but he did not synthesize or test 3C-AL.[3] Instead, Daniel Trachsel synthesized 3C-AL in 2002[4] and described its properties and effects in 2013.[1] The pharmacology of 3C-AL was studied in greater detail in 2021.[2]

See also

References

  1. ^ a b c d e f g Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 642–643, 736–737. ISBN 978-3-03788-700-4. OCLC 858805226. Retrieved 31 January 2025.
  2. ^ a b c d e f g 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.
  3. ^ a b c d Shulgin A. "AL". PiHKAL.
  4. ^ a b Trachsel D (2002). "Synthesis of novel (phenylalkyl)amines for the investigation of structure-activity relationships. Part 1. Mescalin derivatives". Helvetica Chimica Acta. 85 (9): 3019–3026. doi:10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4.
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