Isoproscaline

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.

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	64778-72-9 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL126203 Y
ChemSpider	10439597 Y
PubChem CID	15102787
UNII	7W67II88GC Y
CompTox Dashboard (EPA)	DTXSID70215088
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 Y Key: UBNHYNYMUORHAM-UHFFFAOYSA-N Y 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). Y verify (what is YN ?) Infobox references

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

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

The mechanism that produces the hallucinogenic and entheogenic effects of isoproscaline is most likely to result from action as a 5-HT_2A 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

Legal status

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

• Substituted mescaline analogue
• Proscaline