2C-O, also known as 2,4,5-trimethoxyphenethylamine (2,4,5-TMPEA) or TMPEA-2, is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

and 2C families. It is a

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

mescaline Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...

(3,4,5-trimethoxyphenethylamine) and is the α-

desmethyl In chemical nomenclature, nor- is a prefix to name a structural analog that can be Derivative (chemistry), derived from a parent compound by the removal of one carbon atom along with the accompanying hydrogen atoms. The nor-compound can be derived ...

analogue of 2,4,5-trimethoxyamphetamine (TMA-2). The drug is the

parent compound In chemistry, a parent structure is the structure of an unadorned ion or molecule from which derivatives can be visualized. Parent structures underpin systematic nomenclature and facilitate classification. Fundamental parent structures have one ...

of the 2C-O series of drugs. 2C-O appears to be inactive in terms of

psychoactive A psychoactive drug, psychopharmaceutical, mind-altering drug, consciousness-altering drug, psychoactive substance, or psychotropic substance is a chemical substance that alters psychological functioning by modulating central nervous system acti ...

effects in humans. It was first described by Jansen in 1931.

Chemistry

2C-O is a member of a class of

chemical compounds A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

commonly known as

s. Its full chemical name is 2-(2,4,5-trimethoxyphenyl)ethanamine; it is also known as 2,4,5-trimethoxyphenethylamine and 2,4,5-TMPEA. A variety of

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

s of 2C-O, named 2C-O-2 (4-ethoxy-2,5-dimethoxyphenethylamine) through 2C-O-27, have been developed and studied. One particularly notable derivative is 2C-O-4 (4-isopropoxy-2,5-dimethoxyphenethylamine).

Effects

2C-O at a dose of under 300mg was reported to produce similar

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

effects as mescaline by Jansen in 1931, albeit with more

nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. It can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the throat. Over 30 d ...

and no

euphoria Euphoria ( ) is the experience (or affect) of pleasure or excitement and intense feelings of well-being and happiness. Certain natural rewards and social activities, such as aerobic exercise, laughter, listening to or making music and da ...

. Conversely, in a subsequent report, it was said to be indistinguishable from

placebo A placebo ( ) can be roughly defined as a sham medical treatment. Common placebos include inert tablets (like sugar pills), inert injections (like saline), sham surgery, and other procedures. Placebos are used in randomized clinical trials ...

at a dose of up to 300mg. The present-day consensus appears to be that 2C-O is inactive. In

PiHKAL ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...

, its dosage is listed as greater than 300mg and its duration as unknown. Although 2C-O does not seem to produce effects by itself, 2C-O at a dose of 200mg was reported to strongly potentiate the action of 100mg mescaline when employed as pretreatment 45minutes prior to the administration of mescaline. The apparent inactivity of 2C-O (2,4,5-trimethoxyphenethylamine) has been described as enigmatic, since other 2C drugs are active, since 2C-O's

substituted amphetamine Substituted amphetamines, or simply amphetamines, are a chemical class, class of compounds based upon the amphetamine structure; it includes all derivative (chemistry), derivative compounds which are formed by replacing, or substitution reacti ...

(α-methyl) counterpart 2,4,5-trimethoxyamphetamine (TMA-2) is active, and since its

(3,4,5-trimethoxyphenethylamine) is active.

Dangers

The toxicity of 2C-O is not known.

Pharmacology

2C-O has been found to act as

full agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the agoni ...

of the

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT_2A, 5-HT_2B, and 5-HT_2C receptors. However, it showed more than two orders of magnitude lower

potency Potency may refer to: * Potency (pharmacology), a measure of the activity of a drug in a biological system * Virility * Cell potency, a measure of the differentiation potential of stem cells * In homeopathic dilutions, potency is a measure of ho ...

in activating the serotonin 5-HT_2A receptor than

2C-B 2C-B, also known as 4-bromo-2,5-dimethoxyphenethylamine or by the slang name Nexus, is a synthetic psychedelic drug of the 2C family, mainly used as a recreational drug. It was first synthesized by Alexander Shulgin in 1974 for use in psychoth ...

and

2C-I 2C-I, also known as 2,5-dimethoxy-4-iodophenethylamine, is a phenethylamine of the 2C family with psychedelic effects. It was first synthesized by Alexander Shulgin, and is described in Shulgin's book ''PiHKAL'' (1991). The substance is con ...

. It has been said in the past that it is unclear whether the apparent inactivity of 2C-O is due to strong

metabolism Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...

or low

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...

and/or

efficacy Efficacy is the ability to perform a task to a satisfactory or expected degree. The word comes from the same roots as '' effectiveness'', and it has often been used synonymously, although in pharmacology a distinction is now often made betwee ...

at the serotonin 5-HT_2A receptor. However, an ''

in-vitro ''In vitro'' (meaning ''in glass'', or ''in the glass'') studies are performed with cells or biological molecules outside their normal biological context. Colloquially called " test-tube experiments", these studies in biology and its subdis ...

'' study using

rabbit Rabbits are small mammals in the family Leporidae (which also includes the hares), which is in the order Lagomorpha (which also includes pikas). They are familiar throughout the world as a small herbivore, a prey animal, a domesticated ...

liver The liver is a major metabolic organ (anatomy), organ exclusively found in vertebrates, which performs many essential biological Function (biology), functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of var ...

tissue found that 2C-O was deaminated 25% alone and 25% with the

monoamine oxidase inhibitor Monoamine oxidase inhibitors (MAOIs) are a drug class, class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressa ...

(MAOI)

semicarbazide Semicarbazide is the chemical compound with the formula OC(NH2)(N2H3). It is a water-soluble white solid. It is a derivative of urea. Synthesis The compound prepared by treating urea with hydrazine:Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazi ...

after 1hour whereas

was deaminated 60% alone and 0% with semicarbazide after 1hour. These findings suggest that 2C-O may be less susceptible to metabolism by

monoamine oxidase Monoamine oxidases (MAO) () are a family of enzymes that catalyze the oxidation of monoamines, employing oxygen to clip off their amine group. They are found bound to the outer membrane of mitochondria in most cell types of the body. The fi ...

(MAO) than mescaline. Moreover, it is now known that 2C-O shows far lower potency as a serotonin 5-HT_2A receptor agonist than other 2C drugs. Although 2C-O and certain

s such as 2C-O-4 appear to be inactive or of very low potency in humans, 2C-O derivatives show potent serotonin 5-HT_2A receptor

agonism Agonism (from Greek 'struggle') is a political and social theory that emphasizes the potentially positive aspects of certain forms of conflict. It accepts a permanent place for such conflict in the political sphere, but seeks to show how indivi ...

''in vitro'' and the

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

(α-methyl) analogue TMA-2 as well as derivatives like

MEM Mem (also spelled Meem, Meme, or Mim) is the thirteenth letter of the Semitic abjads, including Hebrew ''mēm'' , Aramaic ''mem'' 𐡌, Syriac ''mīm'' ܡ, Arabic ''mīm'' , and Phoenician ''mēm'' 𐤌. Its sound value is . It is also relate ...

are potent psychedelics in humans.

History

2C-O was first described by Jansen in 1931 and was reported by him to produce psychedelic effects similar to those of

. However, subsequent tests in the 1960s and 1970s suggested that 2C-O is actually inactive as a psychedelic in animals and humans.

Legal status

Canada

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

United States

2C-O is a Schedule I substance, as a positional isomer of

United Kingdom

2C-O and all other compounds featured in

are

Class A drug The Misuse of Drugs Act 1971 (c. 38) is an act of the Parliament of the United Kingdom. It represents action in line with treaty commitments under the Single Convention on Narcotic Drugs, the Convention on Psychotropic Substances, and the ...

s in the United Kingdom.

References

External links

TMPEA (2C-O) - Isomer Design

TMPEA - PiHKAL - Erowid

TMPEA - PiHKAL - Isomer Design
{{DEFAULTSORT:Trimethoxyphenethylamine, 2,4,5- 2,5-Dimethoxyphenethylamines 5-HT2A agonists 5-HT2B agonists 5-HT2C agonists 2C (psychedelics) Methoxy compounds Psychedelic phenethylamines