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2C-O-4

From Wikipedia, the free encyclopedia
Pharmaceutical compound
2C-O-4
Clinical data
Other names4-Isopropoxy-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-isopropoxyphenethylamine
Routes of
administration
Oral[1]
ATC code
  • None
Pharmacokinetic data
Duration of actionA few hours[1]
Identifiers
  • 2-{2,5-Dimethoxy-4-[(propan-2-yl)oxy]phenyl}ethan-1-amine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC13H21NO3
Molar mass239.315 g·mol−1
3D model (JSmol)
  • CC(C)Oc1cc(OC)c(cc1OC)CCN
  • InChI=1S/C13H21NO3/c1-9(2)17-13-8-11(15-3)10(5-6-14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3 checkY
  • Key:KAKXJLWAEMHHTL-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

2C-O-4, also known as4-isopropoxy-2,5-dimethoxyphenethylamine, is aphenethylamine of the2C family.[1] It is also apositional isomer ofisoproscaline and was probably firstsynthesized byAlexander Shulgin.[1] It produceshallucinogenic orpsychedelic effects.[1] Because of the lowpotency of 2C-O-4, and the inactivity of2C-O, Shulgin felt that the 2C-O series would not be an exciting area for research, and did not pursue any furtheranalogues.[1]

Use and effects

[edit]

Little is known about thepsychopharmacological effects of 2C-O-4.[1] Based on the one report available in his bookPiHKAL, Shulgin lists the dose of 2C-O-4 as being >60 mg.[1] At 60 mg, thresholdpsychoactive effects occurred.[1] These included awareness of something in the front part of the head,yawning,physiological changes, and a generalexhilaration andexcitement.[1] The effects lasted a few hours and were rated as a +1 on theShulgin Rating Scale.[1] The drug was regarded as remaining to be fully explored.[1]

Toxicity

[edit]

The toxicity of 2C-O-4 is not known.

Pharmacology

[edit]

Thepharmacology of 2C-O-4 has been studied.[2]

Chemistry

[edit]

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

Society and culture

[edit]

Legal status

[edit]

Canada

[edit]

As of October 31, 2016, 2C-O-4 is a controlled substance (Schedule III) in Canada.[3]

United States

[edit]

2C-O-4 is unscheduled and unregulated in theUnited States; however, because of its close similarity in structure and effects tomescaline and2C-T-7, possession and sale of 2C-O-4 may be subject to prosecution under theFederal Analog Act.

See also

[edit]

References

[edit]
  1. ^abcdefghijklShulgin, Alexander;Shulgin, Ann (September 1991).PiHKAL: A Chemical Love Story.Berkeley, California:Transform Press.ISBN 0-9630096-0-5.OCLC 25627628.2C-O-4 Entry in PiHKAL
  2. ^Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2019)."Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines".Front Pharmacol.10: 1423.doi:10.3389/fphar.2019.01423.PMC 6893898.PMID 31849671.
  3. ^"Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". 4 May 2016.


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