2C-O-4

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]

2C-O-4

Clinical data
Other names	4-Isopropoxy-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-isopropoxyphenethylamine
Routes of administration	Oral[1]
ATC code	None
Pharmacokinetic data
Duration of action	A few hours[1]
Identifiers
IUPAC name 2-{2,5-Dimethoxy-4-[(propan-2-yl)oxy]phenyl}ethan-1-amine
CAS Number	952006-65-4 N
PubChem CID	44719510
ChemSpider	21106225 Y
UNII	1GFL65O0VB
CompTox Dashboard (EPA)	DTXSID70894771
Chemical and physical data
Formula	C13H21NO3
Molar mass	239.315 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)Oc1cc(OC)c(cc1OC)CCN
InChI 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 Y Key:KAKXJLWAEMHHTL-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Use and effects

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

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

Pharmacology

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

Chemistry

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

Legal status

Canada

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

United States

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

• 2C-O
• 2C-T-4