Proscaline

Clinical data
Other names	4-Propoxy-3,5-dimethoxyphenethylamine; 4-Propoxy-3,5-DMPEA
Routes of administration	Oral[1]
Drug class	Serotonin5-HT2 receptoragonist;Serotonergic psychedelic;Hallucinogen
ATC code	None
Pharmacokinetic data
Duration of action	8–12 hours[1]
Identifiers
IUPAC name 2-(3,5-dimethoxy-4-propoxyphenyl)ethan-1-amine
CAS Number	39201-78-0 Y[EPA]
PubChemCID	15102790
ChemSpider	10439596 Y
UNII	99G781N5IO
ChEMBL	ChEMBL340765 Y
CompTox Dashboard(EPA)	DTXSID00192454
Chemical and physical data
Formula	C13H21NO3
Molar mass	239.315 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1cc(cc(OC)c1OCCC)CCN
InChI InChI=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 Y Key:HYWLMSUAZVDUFW-UHFFFAOYSA-N Y
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Proscaline, also known as4-propoxy-3,5-dimethoxyphenethylamine, is apsychedelic drug of thephenethylamine andscaline families related tomescaline.^[1] It is takenorally.^[1][2]

In his bookPiHKAL (Phenethylamines I Have Known and Loved) and other publications,Alexander Shulgin reports that a dose of 30 to 60 mgorally produces effects lasting 8 to 12 hours.^[1][3][4][2] Theonset was not described, but peak effects occurred after about 2 hours.^[1] A typical dose estimate is 45 mg.^[2] Doses as high as 80 mg have also been explored.^[1] The drug has approximately 6 or 7 times thepotency of mescaline, which itself has a listed dose range of 200 to 400 mg.^{[1][3][4][5][6]}

The effects of proscaline have been reported to include insignificantclosed-eye visuals, sharpening of thesenses,hyperawareness,relaxation and feeling at ease, deep feelings of peace and contentment,euphoria, no enhanced clarity or deep realizations, feelings of uninhibitederoticism,pain relief,drowsiness,intoxication andfeeling drunk,irritability,restlessness,tremors,insomnia, difficulty withdreams, long-lasting residual effects, and no next-dayhangover.^[1]

Proscaline is aserotonin5-HT₂ receptoragonist, including of the serotonin5-HT_2A,5-HT_2B, and5-HT_2C receptors.^[7][8] Activation of the serotonin 5-HT_2A receptor is thought to be responsible for itspsychedelic effects.^[7] The drug is much morepotent as an agonist of the serotonin 5-HT_2C receptor than as an agonist of the serotonin 5-HT_2A or 5-HT_2B receptors.^[7]

It produces thehead-twitch response, a behavioral proxy of psychedelic effects, in rodents.^[7][9][2]

Proscaline, also known as 4-propoxy-3,5-dimethoxyphenethylamine, is asubstituted phenethylamine andscaline (4-substituted 3,5-dimethoxyphenethylamine)derivative related tomescaline (3,4,5-trimethoxyphenethylamine).^[1] It is the 4-propoxyhomologue of mescaline.^[1]

Proscaline is much morelipophilic thanmescaline orescaline (log P = 1.70, 0.78, and 1.11, respectively), which is expected to be more optimal and advantageous in terms ofdrug-like properties such asblood–brain barrierpermeability.^[9]

Thechemical synthesis of proscaline has been described.^[1]

Analogues of proscaline includemescaline,escaline,isoproscaline,allylescaline,methallylescaline,cyclopropylmescaline,cycloproscaline,fluoroproscaline, and3C-P, among others.^[1][10][11]

Proscaline was firstsynthesized and studied by Otakar Leminger in 1972.^[12][1] The drug was later synthesized byAlexander Shulgin and further described in his 1991 bookPiHKAL (Phenethylamines I Have Known and Loved).^[1] It was encountered as a noveldesigner drug inEurope in 2013.^[13][14][9]

Proscaline is aClass A controlled substance in theUnited Kingdom.^{[citation needed]}

Proscaline is not directly scheduled under theControlled Substances Act in theUnited States. 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.^{[citation needed]}

• Substituted mescaline analogue

• Proscaline - Isomer Design
• Proscaline - PsychonautWiki
• P (Proscaline) - PiHKAL - Erowid
• P (Proscaline) - PiHKAL - Isomer Design
• The Big & Dandy Proscaline Thread - Bluelight
• Leminger's Scalines - countyourculture

• Drugs not assigned an ATC code
• 5-HT2A agonists
• 5-HT2B agonists
• 5-HT2C agonists
• Designer drugs
• Methoxy compounds
• Phenol ethers
• PiHKAL
• Propoxy compounds
• Psychedelic phenethylamines
• Scalines

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