Isoproscaline

Isoproscaline
Names
Preferred IUPAC name
2-{{#parsoidfragment:0}}{3,5-Dimethoxy-4-[(propan-2-yl)oxy]phenyl}ethan-1-amine
Other names
2-(4-Isopropoxy-3,5-dimethoxyphenyl)ethanamine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
InChI
  • 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
  • InChI=1/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
    Key: UBNHYNYMUORHAM-UHFFFAOYAL
SMILES
  • CC(C)Oc1c(cc(cc1OC)CCN)OC
Properties
Chemical formula
 C13H21NO3
Molar mass 239.31 g/mol
Melting point 163 to 164 °C (325 to 327 °F; 436 to 437 K) (hydrochloride)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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

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. ↑ 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.
  2. ↑ Isoproscaline entry in PiHKAL
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