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Isoproscaline

From Wikipedia, the free encyclopedia
Pharmaceutical compound
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-{3,5-dimethoxy-4-[(propan-2-yl)oxy]phenyl}ethan-1-amine
CAS Number
PubChemCID
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 or4-isopropoxy-3,5-dimethoxyphenethylamine is ananalogue ofmescaline.[1] It is closely related toproscaline and was first synthesized byDavid E. Nichols and colleagues.[2] It producespsychedelic effects.

Use and effects

[edit]

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

Interactions

[edit]
See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Pharmacology

[edit]

Pharmacodynamics

[edit]

The mechanism that produces the hallucinogenic and entheogenic effects of isoproscaline is most likely to result from action as a5-HT2Aserotonin receptoragonist in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines andphenethylamines.

Chemistry

[edit]

Isoproscaline is in a class of compounds commonly known asphenethylamines, and the full chemical name is 2-(4-isopropoxy-3,5-dimethoxyphenyl)ethanamine.

Society and culture

[edit]

Legal status

[edit]

Isoproscaline is unscheduled in theUnited States; however, because of its close similarity in structure and effects tomescaline, possession and sale of isoproscaline may be subject to prosecution under theFederal 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

[edit]

References

[edit]
  1. ^abcdShulgin, 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.
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