Isoproscaline

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Isoproscaline
Isoproscaline2DACS.svg
Isoproscaline ball-and-stick structure.png
Clinical data
Other namesIP; 4-Isopropoxy-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-isopropoxyphenethylamine
Routes of
administration 		Oral [1]
Drug class Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of action 2 hours [1]
Duration of action 10–16 hours [1]
Identifiers
  • 2-{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
Formula C13H21NO3
Molar mass 239.315 g·mol−1
3D model (JSmol)
Melting point 163 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 Yes check.svgY
  • Key:UBNHYNYMUORHAM-UHFFFAOYSA-N Yes check.svgY
   (verify)

Isoproscaline or 4-isopropoxy-3,5-dimethoxyphenethylamine is a psychedelic drug of the phenethylamine and scaline families related to mescaline. [1] It is closely related to proscaline and was first synthesized by David E. Nichols and colleagues. [2] The drug is taken orally. [1]

Contents

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists isoproscaline's dose as 40 to 80 mg orally and its duration as 10 to 16 hours. [1] The onset was described as slow and about 2 hours and the descent very slow and gradual and starting at about 6 or 7 hours. [1] The effects of isoproscaline included enhanced emotions, desire to move and dance, feelings of energy flow and freedom in the body, feelings of ecstasy, euphoria, meaningfulness, mental rejuvenation, enhanced sociability and conversation, body load, queasiness, nausea, discomfort, insomnia, and slight next-day irritability. [1] No visual changes or other sensory effects were mentioned. [1] Shulgin described isoproscaline as a "completely fascinating phenethylamine". [1]

Interactions

Pharmacology

Pharmacodynamics

Isoproscaline shows affinity for the serotonin 5-HT2 receptors and acts as an agonist of the serotonin 5-HT2A receptor. [3]

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. [1]

Synthesis

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

Analogues

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

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 5 6 7 8 9 10 11 12 13 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.
  3. ↑ Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2021). "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines". Front Pharmacol. 12 794254. doi: 10.3389/fphar.2021.794254 . PMC   8865417 . PMID   35222010.
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