Isoproscaline

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
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
PubChem CID
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
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 psychedelic effects.

Use and effects

[edit | edit source]

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

[edit | edit source]

Pharmacology

[edit | edit source]

Pharmacodynamics

[edit | edit source]

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.[citation needed]

Chemistry

[edit | edit source]

Isoproscaline is in a class of compounds commonly known as phenethylamines, and the full chemical name is 2-(4-isopropoxy-3,5-dimethoxyphenyl)ethanamine.[1]

Synthesis

[edit | edit source]

The chemical synthesis of isoproscaline has been described.[1]

Analogues

[edit | edit source]

Analogues of isoproscaline include mescaline, escaline, proscaline, allylescaline, and methallylescaline, among others.[1]

Society and culture

[edit | edit source]
[edit | edit source]

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

[edit | edit source]

References

[edit | edit source]
  1. ^ a b c d e f g Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). Isoproscaline entry
  2. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
[edit | edit source]