2C-O-4
Encyclopedia
2C-O-4 or 4-isoprop
oxy
-2,5-dimethoxy
phenethylamine
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 entheogen
ic effects. 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
.
s, and the full chemical name is 2-(4-isopropoxy-2,5-dimethoxyphenyl)ethanamine.
, Shulgin lists the dosage of 2C-O-4 as being >60 mg.
, 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
.
Propyl
In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula -C3H7. It is the substituent form of the alkane propane...
oxy
Oxy
Oxy may refer to:Chemistry* Oxy or oxo is a term used to describe a ketone functional group* Oxy is a slang name for oxygen acetylene welding* Oxy is the name of a character from the Molecularium...
-2,5-dimethoxy
Methoxy
In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether...
phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
is a phenethylamine
Phenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
of the 2C family
2C (psychedelics)
2C is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of the benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolically stable and longer acting...
. It is also a positional isomer of isoproscaline
Isoproscaline
Isoproscaline or 4--propyl-3,5-dimethoxyphenethylamine is an analogue of mescaline. It is closely related to proscaline and was first synthesized by David E. Nichols...
and was probably first synthesized by Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...
. It produces hallucinogenic
Psychedelics, dissociatives and deliriants
This general group of pharmacological agents can be divided into three broad categories: psychedelics, dissociatives, and deliriants. These classes of psychoactive drugs have in common that they can cause subjective changes in perception, thought, emotion and consciousness...
, psychedelic
Psychedelic
The term psychedelic is derived from the Greek words ψυχή and δηλοῦν , translating to "soul-manifesting". A psychedelic experience is characterized by the striking perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly...
, and entheogen
Entheogen
An entheogen , in the strict sense, is a psychoactive substance used in a religious, shamanic, or spiritual context. Historically, entheogens were mostly derived from plant sources and have been used in a variety of traditional religious contexts...
ic effects. Because of the low potency of 2C-O-4, and the inactivity of 2C-O
2C-O
2C-O or 2,4,5-Trimethoxyphenethylamine is a phenethylamine of the 2C family and was first synthesized by Jansen in 1931. It is a positional isomer of the drug mescaline and is structurally similar to the drug 2C-D.-Chemistry:...
, Shulgin felt that the 2C-O series would not be an exciting area for research, and did not pursue any further analogues
Analog (chemistry)
In chemistry, a structural analog , also known as chemical analog or simply analog, is a compound having a structure similar to that of another one, but differing from it in respect of a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced...
.
Chemistry
2C-O-4 is in a class of compounds commonly known as phenethylaminePhenethylamine
Phenylethylamine or phenethylamine is a natural monoamine alkaloid, trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects. Studies suggest that phenylethylamine functions as a neuromodulator or neurotransmitter in the...
s, and the full 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 (Phenethylamines i Have Known And Loved)PiHKAL
PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin which was published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens...
, Shulgin lists the dosage of 2C-O-4 as being >60 mg.
Pharmacology
The mechanism that produces the hallucinogenic and entheogenic effects of 2C-O-4 is unknown.Legality
2C-O-4 is unscheduled and unregulated in the United StatesUnited States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...
, however because of its close similarity in structure and effects to mescaline
Mescaline
Mescaline or 3,4,5-trimethoxyphenethylamine is a naturally occurring psychedelic alkaloid of the phenethylamine class used mainly as an entheogen....
and 2C-T-7
2C-T-7
2C-T-7 is a psychedelic phenethylamine of the 2C family. In his book PiHKAL: A Chemical Love Story, Alexander Shulgin lists the dosage range as 10 to 30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic effects that last 8 to 15 hours...
, possession and sale of 2C-O-4 may be subject to prosecution under the Federal Analog Act
Federal Analog Act
The Federal Analog Act, , is a controversial section of the United States Controlled Substances Act which allowed any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were also listed in those schedules, but only if intended for human...
.