:2C-O-4

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| ImageFile = 2C-O-4-Chemdraw.png

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| ImageFile2 = 2C-O-4 animation.gif

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| PIN = 2-{2,5-Dimethoxy-4-[(propan-2-yl)oxy]phenyl}ethan-1-amine

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|Section1={{Chembox Identifiers

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| ChemSpiderID = 21106225

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| StdInChI = 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

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| StdInChIKey = KAKXJLWAEMHHTL-UHFFFAOYSA-N

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| CASNo = 952006-65-4

| PubChem = 44719510

| UNII = 1GFL65O0VB

| SMILES = CC(C)Oc1cc(OC)c(cc1OC)CCN

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|Section2={{Chembox Properties

| Formula =

| C=13 | H=21 | N=1 | O=3

| MolarMass = 239.31 g/mol

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2C-O-4, also known as 4-isopropoxy-2,5-dimethoxyphenethylamine, is a phenethylamine of the 2C family. It is also a positional isomer of isoproscaline and was probably first synthesized by Alexander Shulgin. It produces hallucinogenic, psychedelic, and entheogenic effects.{{CitePiHKAL}} [http://www.erowid.org/library/books_online/pihkal/pihkal035.shtml 2C-O-4 Entry in PiHKAL] 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.

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.

Effects

Little is known about the psychopharmacological effects of 2C-O-4. Based on the one report available in his book PiHKAL, Shulgin lists the dosage of 2C-O-4 as being >60 mg.

Pharmacology

The pharmacology of 2C-O-4 has been studied.{{cite journal | vauthors = Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME | title = Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines | journal = Front Pharmacol | volume = 10 | issue = | pages = 1423 | date = 2019 | pmid = 31849671 | pmc = 6893898 | doi = 10.3389/fphar.2019.01423 | doi-access = free | url = }}

Dangers

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

Legality

=Canada=

As of October 31, 2016, 2C-O-4 is a controlled substance (Schedule III) in Canada.{{Cite web|url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php|title = Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)|date = 4 May 2016}}

=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

References