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Isoproscaline


FieldValue
Watchedfieldschanged
verifiedrevid415669304
imageIsoproscaline2DACS.svg
image_classskin-invert-image
width225px
image2Isoproscaline ball-and-stick structure.png
image_class2bg-transparent
width2200px
routes_of_administrationOral
classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC_prefixNone
onset2 hours
duration_of_action10–16 hours
CAS_number_Ref
CAS_number64778-72-9
PubChem15102787
ChemSpiderID_Ref
ChemSpiderID10439597
UNII_Ref
UNII7W67II88GC
ChEMBL_Ref
ChEMBL126203
synonymsIP; 4-Isopropoxy-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-isopropoxyphenethylamine
IUPAC_name2-{3,5-dimethoxy-4-[(propan-2-yl)oxy]phenyl}ethan-1-amine
C13H=21N=1O=3
SMILESCC(C)Oc1c(cc(cc1OC)CCN)OC
StdInChI_Ref
StdInChI1S/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
StdInChIKeyUBNHYNYMUORHAM-UHFFFAOYSA-N
melting_point163
melting_high164
melting_notes(hydrochloride)

| Drugs.com =

| elimination_half-life =

Isoproscaline or 4-isopropoxy-3,5-dimethoxyphenethylamine is a psychedelic drug of the phenethylamine and scaline families related to mescaline. It is closely related to proscaline and was first synthesized by David E. Nichols and colleagues. The drug is taken orally.

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists isoproscaline's dose as 40 to 80mg orally and its duration as 10 to 16hours. The onset was described as slow and about 2hours and the descent very slow and gradual and starting at about 6 or 7hours. 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. No visual changes or other sensory effects were mentioned. Shulgin described isoproscaline as a "completely fascinating phenethylamine".

Interactions

Pharmacology

Pharmacodynamics

Isoproscaline shows affinity for the serotonin 5-HT2 receptors and acts as an agonist of the serotonin 5-HT2A receptor.

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.

Synthesis

The chemical synthesis of isoproscaline has been described.

Analogues

Analogues of isoproscaline include mescaline, escaline, proscaline, allylescaline, and methallylescaline, among others.

Society and culture

Canada

Isoproscaline is not a controlled substance in Canada as of 2025.

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; 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.

References

References

  1. (February 1977). "Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues". J Med Chem.
  2. {{CitePiHKAL [http://www.erowid.org/library/books_online/pihkal/pihkal092.shtml Isoproscaline entry]
  3. (2021). "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines". Front Pharmacol.
  4. "Controlled Drugs and Substances Act".
  5. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

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