Isoproscaline

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Wikipedia

Isoproscaline
Clinical data
Other names4-Isopropoxy-3,5-dimethoxyphenethylamine
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action10–16 hours[1]
Identifiers
  • 2-{{#parsoidfragment:1}}{3,5-dimethoxy-4-[(propan-2-yl)oxy]phenyl}ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H21NO3
Molar mass239.315 g·mol−1
3D model (JSmol)
Melting point163 to 164 °C (325 to 327 °F) (hydrochloride)
  • CC(C)Oc1c(cc(cc1OC)CCN)OC
  • InChI=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 checkY
  • Key:UBNHYNYMUORHAM-UHFFFAOYSA-N checkY
  (verify)

Isoproscaline or 4-isopropoxy-3,5-dimethoxyphenethylamine is an analogue of mescaline.[1] It is closely related to proscaline and was first synthesized by David E. Nichols and colleagues.[2] It produces hallucinogenic, psychedelic, and entheogenic effects.

Use and effects

Little is known about the psychopharmacological effects of isoproscaline. In his book PiHKAL, Alexander Shulgin lists a psychedelic dose as being 40–80 mg, with effects lasting 10–16 hours.[1]

Interactions

Pharmacology

Pharmacodynamics

The mechanism that produces the hallucinogenic and entheogenic effects of isoproscaline is most likely to result from action as a 5-HT2A serotonin receptor agonist in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines.

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.

Society and culture

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.

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.

See also

References

  1. 1 2 3 4 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. Isoproscaline entry
  2. ↑ Nichols DE, Dyer DC (February 1977). "Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues". J Med Chem. 20 (2): 299–301. doi:10.1021/jm00212a022. PMID 836502.