2C-AL

{{Short description|Chemical compound}}

{{drugbox

| drug_name = 2C-AL

| image = 2C-AL_structure.png

| legal_UK =

| legal_DE =

| C = 13 | H = 19 | N = 1 | O = 2

| IUPAC_name = 2-(2,5-dimethoxy-4-prop-2-enylphenyl)ethanamine

| CAS_number = 2756686-02-7

| ChemSpiderID =

| PubChem = 162430125

| UNII =

| smiles = COC1=CC(=C(C=C1CCN)OC)CC=C

| StdInChI = 1S/C13H19NO2/c1-4-5-10-8-13(16-3)11(6-7-14)9-12(10)15-2/h4,8-9H,1,5-7,14H2,2-3H3

| StdInChIKey = QNVPDGCJKPQARD-UHFFFAOYSA-N

}}

2C-AL is a drug from the substituted phenethylamine family which acts as an agonist of the 5-HT_2A receptor, with an EC₅₀ of 2.15nM at 5-HT_2A vs 77.71nM at 5-HT_2B, and produces a head-twitch response in animal studies. It was first discussed as a hypothetical compound in Daniel Trachsel's 2013 review of the field after his successful synthesis of the related compounds 2C-V and 2C-YN,{{Cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C | title = Phenethylamine Von der Struktur zur Funktion | page = 768 | publisher = Nachtschatten Verlag AG | date = 2013 | isbn = 978-3-03788-700-4}} and finally synthesised by a team at Gilgamesh Pharmaceuticals in 2020 using a different synthetic route from that employed by Trachsel.{{cite patent | url = https://patentscope.wipo.int/search/docs2/pct/WO2022006186/pdf/Z6QRYQjRUoLeRiOeDWcMFqiVKf3MMTkWXfeRv-Yhpxk| inventor = Kruegel AC | title = Phenalkylamines and Methods of Treating Mood Disorders | country = WO | number = 2022/006186 |pubdate=2022-01-06}} Retrieved 2025-05-12