2C-O-4

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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
PubChem CID
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 as 4-isopropoxy-2,5-dimethoxyphenethylamine, is a phenethylamine of the 2C family.[1] It is also a positional isomer of isoproscaline and was probably first synthesized by Alexander Shulgin.[1] It produces hallucinogenic or psychedelic effects.[1] Because of the low potency of 2C-O-4, and the inactivity of 2C-O, Shulgin felt that the 2C-O series would not be an exciting area for research, and did not pursue any further analogues.[1]

Use and effects

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

Toxicity

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

Pharmacology

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

Chemistry

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

Society and culture

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Canada

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

United States

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

See also

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References

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  1. ^ a b c d e f g h i j k l Shulgin, 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.