:Proscaline

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| verifiedrevid = 464217897

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| ImageFile = Proscaline.svg

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| PIN = 2-(3,5-Dimethoxy-4-propoxyphenyl)ethan-1-amine

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| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 10439596

| InChI = 1/C13H21NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h8-9H,4-7,14H2,1-3H3

| InChIKey = HYWLMSUAZVDUFW-UHFFFAOYAZ

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 340765

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 99G781N5IO

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| StdInChI = 1S/C13H21NO3/c1-4-7-17-13-11(15-2)8-10(5-6-14)9-12(13)16-3/h8-9H,4-7,14H2,1-3H3

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| StdInChIKey = HYWLMSUAZVDUFW-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|EPA}}

| CASNo = 39201-78-0

| PubChem = 15102790

| SMILES = COc1cc(cc(OC)c1OCCC)CCN

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| Section2 = {{Chembox Properties

| C=13

| H=21

| N=1

| O=3

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Proscaline (4-propoxy-3,5-dimethoxyphenethylamine or 4-propoxy-3,5-DMPEA) is a psychedelic and hallucinogenic drug. It has structural properties similar to the drugs mescaline, isoproscaline, and escaline. In PiHKAL, Alexander Shulgin reports that a dose of 30–60 mg produces effects lasting 8–12 hours.[http://www.erowid.org/library/books_online/pihkal/pihkal140.shtml Proscaline entry in PiHKAL]{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD | title = Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species | journal = Neuropharmacology | volume = 167 | issue = | pages = 107933 | date = May 2020 | pmid = 31917152 | pmc = 9191653 | doi = 10.1016/j.neuropharm.2019.107933 | url = http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf | quote = Table 4 Human potency data for selected hallucinogens. [...] }}

Pharmacology

Proscaline is a serotonin 5-HT₂ receptor agonist.{{cite journal | vauthors = Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD | title = Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential | journal = Nat Commun | volume = 14 | issue = 1 | pages = 8221 | date = December 2023 | pmid = 38102107 | pmc = 10724237 | doi = 10.1038/s41467-023-44016-1 | url = https://bitnest.netfirms.com/external/10.1038/s41467-023-44016-1}} This is thought to be responsible for its psychedelic effects.

Chemistry

Proscaline is in a class of compounds commonly known as phenethylamines, and is the 4-propoxy homolog of mescaline. The full name of the chemical is 4-propoxy-3,5-dimethoxyphenethylamine.

Legality

= United Kingdom =

Proscaline is a Class A controlled substance in the UK.

= United States =

Proscaline is not directly scheduled under the Controlled Substances Act. However, due to its structural similarities with mescaline, a Schedule I drug, it could potentially be subject to the same control measures and penalties for possession and manufacture under the Federal Analogue Act.