{{Infobox drug | Watchedfields = changed | verifiedrevid = 415669304 | drug_name = | image = Isoproscaline2DACS.svg | image_class = skin-invert-image | width = 250px | image2 = Isoproscaline ball-and-stick structure.png | image_class2 = bg-transparent | width2 = 225px
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral<ref name="PiHKAL" /> | class = Serotonin receptor modulator; Serotonin 5-HT<sub>2A</sub> receptor agonist; Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = 2 hours<ref name="PiHKAL" /> | elimination_half-life = | duration_of_action = 10–16 hours<ref name="PiHKAL" /> | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 64778-72-9 | CAS_supplemental = | PubChem = 15102787 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 10439597 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 7W67II88GC | KEGG = | ChEBI = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 126203 | NIAID_ChemDB = | PDB_ligand = | synonyms = IP; 4-Isopropoxy-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-isopropoxyphenethylamine
<!-- Chemical data --> | IUPAC_name = 2-<nowiki/>{3,5-dimethoxy-4-[(propan-2-yl)oxy]phenyl}ethan-1-amine | C=13 | H=21 | N=1 | O=3 | SMILES = CC(C)Oc1c(cc(cc1OC)CCN)OC | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C13H21NO3/c1-9(2)17-13-11(15-3)7-10(5-6-14)8-12(13)16-4/h7-9H,5-6,14H2,1-4H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = UBNHYNYMUORHAM-UHFFFAOYSA-N
<!-- Physical data --> | melting_point = 163 | melting_high = 164 | melting_notes = (hydrochloride) }}
'''Isoproscaline''', also known as '''4-isopropoxy-3,5-dimethoxyphenethylamine''', is a psychedelic drug of the phenethylamine and scaline families related to mescaline.<ref name="PiHKAL" /> It is closely related to proscaline and was first synthesized by David E. Nichols and colleagues.<ref name="NicholsDyer1977">{{cite journal | vauthors = Nichols DE, Dyer DC | title = Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues | journal = J Med Chem | volume = 20 | issue = 2 | pages = 299–301 | date = February 1977 | pmid = 836502 | doi = 10.1021/jm00212a022 | url = }}</ref> The drug is taken orally.<ref name="PiHKAL" />
==Use and effects== In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved''), Alexander Shulgin lists isoproscaline's dose as 40 to 80{{nbsp}}mg orally and its duration as 10 to 16{{nbsp}}hours.<ref name="PiHKAL">{{CitePiHKAL}} [http://www.erowid.org/library/books_online/pihkal/pihkal092.shtml Isoproscaline entry]</ref> The onset was described as slow and about 2{{nbsp}}hours and the descent very slow and gradual and starting at about 6 or 7{{nbsp}}hours.<ref name="PiHKAL" /> The effects of isoproscaline included enhanced emotions, desire to move and dance, feelings of energy flow and freedom in the body, feelings of ecstasy, euphoria, meaningfulness, mental rejuvenation, enhanced sociability and conversation, body load, queasiness, nausea, discomfort, insomnia, and slight next-day irritability.<ref name="PiHKAL" /> No visual changes or other sensory effects were mentioned.<ref name="PiHKAL" /> Shulgin described isoproscaline as a "completely fascinating phenethylamine".<ref name="PiHKAL" />
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Pharmacology== ===Pharmacodynamics=== Isoproscaline shows affinity for the serotonin 5-HT<sub>2</sub> receptors and acts as an agonist of the serotonin 5-HT<sub>2A</sub> receptor.<ref name="KolaczynskaLuethiTrachsel2021">{{cite journal | vauthors = Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME | title = Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines | journal = Front Pharmacol | volume = 12 | issue = | article-number = 794254 | date = 2021 | pmid = 35222010 | pmc = 8865417 | doi = 10.3389/fphar.2021.794254 | doi-access = free | url = }}</ref>
==Chemistry== Isoproscaline is in a class of compounds commonly known as phenethylamines, and the full chemical name is 2-(4-isopropoxy-3,5-dimethoxyphenyl)ethanamine.<ref name="PiHKAL" />
===Synthesis=== The chemical synthesis of isoproscaline has been described.<ref name="PiHKAL" />
===Analogues=== Analogues of isoproscaline include mescaline, escaline, proscaline, allylescaline, and methallylescaline, among others.<ref name="PiHKAL" />
==Society and culture== ===Legal status=== ====Canada==== Isoproscaline is not a controlled substance in Canada as of 2025.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>
====United Kingdom==== In the UK, its highly likely that this compound would be covered by the "phenylethylamine amendment" to the misuse of drugs act likely rendering it a Class A controlled drug.
====United States==== Isoproscaline is unscheduled in the United States;<ref name="OrangeBook2026">{{citation | title = Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) | date = January 2026 | publisher = U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division | location = United States | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf}}</ref> however, because of its close similarity in structure and effects to mescaline, possession and sale of isoproscaline may be subject to prosecution under the Federal Analog Act.
==See also== * Scaline
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/92 Isoproscaline - Isomer Design] * [https://erowid.org/library/books_online/pihkal/pihkal092.shtml Isoproscaline - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/92 Isoproscaline - PiHKAL - Isomer Design]
{{Psychedelics}} {{Serotonin receptor modulators}} {{Phenethylamines}}
Category:5-HT2A agonists Category:David E. Nichols Category:Designer drugs Category:Isopropoxy compounds Category:Phenol ethers Category:PiHKAL Category:Psychedelic phenethylamines Category:Scalines Category:Serotonin receptor modulators