2C-I
Encyclopedia
2C-I or 2,5-dimethoxy-4-iodophenethylamine is a psychedelic
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...

 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 was 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 was described in Shulgin’s book PiHKAL: A Chemical Love Story
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...

. The drug is used recreationally for its psychedelic
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...

 and entactogenic
Empathogen-entactogen
The terms empathogen and entactogen are used to describe a class of psychoactive drugs that produce distinctive emotional and social effects similar to those of MDMA. Putative members of this class include 2C-B, 2C-I, MDMA, MDA, MDEA, MBDB, 2C-T-7, and 2C-T-2, among others...

 effects. 2C-I is commonly sold in its hydrochloride
Hydrochloride
In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base . This is also known as muriate, derived from hydrochloric acid's other name: muriatic acid....

 salt
Salt
In chemistry, salts are ionic compounds that result from the neutralization reaction of an acid and a base. They are composed of cations and anions so that the product is electrically neutral...

 form, which is a fluffy, sparkling-white powder, which has also been pressed into tablet
Tablet
A tablet is a pharmaceutical dosage form. It comprises a mixture of active substances and excipients, usually in powder form, pressed or compacted from a powder into a solid dose...

 form, and is commonly known as 'India' on the street.

Recreational use

In the early 2000s, 2C-I was sold in Dutch smart shop
Smart shop
A smart shop is a retail establishment that specializes in the sales of psychoactive substances, usually including psychedelics, as well as related literature and paraphernalia...

s, after 2C-B
2C-B
2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps and is referred...

, which was previously sold, was banned. In April 2008, 2C-I was also banned in the Netherlands, along with three other 2C-x phenethylamines previously sold in Dutch smartshops for short periods of time. During the same period, 2C-I also became available in powder form from several online
ONLINE
ONLINE is a magazine for information systems first published in 1977. The publisher Online, Inc. was founded the year before. In May 2002, Information Today, Inc. acquired the assets of Online Inc....

 vendors of research chemicals in the United States
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...

, Asia
Asia
Asia is the world's largest and most populous continent, located primarily in the eastern and northern hemispheres. It covers 8.7% of the Earth's total surface area and with approximately 3.879 billion people, it hosts 60% of the world's current human population...

, and Western Europe. In 2002 and 2003, tablet
Tablet
A tablet is a pharmaceutical dosage form. It comprises a mixture of active substances and excipients, usually in powder form, pressed or compacted from a powder into a solid dose...

s of 2C-I were being sold in nightclubs and at raves in Denmark
Denmark
Denmark is a Scandinavian country in Northern Europe. The countries of Denmark and Greenland, as well as the Faroe Islands, constitute the Kingdom of Denmark . It is the southernmost of the Nordic countries, southwest of Sweden and south of Norway, and bordered to the south by Germany. Denmark...

 and in the United Kingdom
United Kingdom
The United Kingdom of Great Britain and Northern IrelandIn the United Kingdom and Dependencies, other languages have been officially recognised as legitimate autochthonous languages under the European Charter for Regional or Minority Languages...

 as a club drug
Club drug
Club drugs are a loosely-defined category of recreational drugs which are associated with discothèques in the 1970s and dance clubs, parties, and raves in the 1980s to the 2000s...

.

It is often misrepresented as mescaline
Mescaline
Mescaline or 3,4,5-trimethoxyphenethylamine is a naturally occurring psychedelic alkaloid of the phenethylamine class used mainly as an entheogen....

 in US street sale of singular dosages, as it shares some level of similarity in psychological effect. Both chemicals are members of the psychedelic 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...

 class of drugs, except 2C-I is an analog of mescaline in the 2C-x series
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...

. A major difference between the research chemicals in the 2C-x series, and mescaline is a much greater potency by weight and thus also a steeper dose-response in the newer synthetic drugs. 2C-I's effective dosage range per milligram is approximately 10-fold less than mescaline. This means that a small carrier material, such as a small candy or pressed pill, is suitable for 2C-I. That type of small carrier material has an insufficiently small holding capacity to contain a large enough quantity of mescaline to produce a substantial psychoactive effect. In addition, mescaline sounds inherently less dangerous to consume to the lay-man rather than a relatively obscure compound of modern innovation with less documentation of potential long-term effects in humans. 2C-I also lacks the more appealing ancient predecessor, mescaline, with a history of natural use as a cactus-derived psychedelic with continued ethnobotanical use in the spiritual traditions of some cultures.

In general, 2C-I is taken orally, although it can also be insufflated (though 2C-I often causes considerable pain upon insufflation
Insufflation (medicine)
Insufflation is the practice of inhaling a substance. Insufflation has limited medical use, but is a common route of administration with many respiratory drugs used to treat conditions in the lungs and paranasal sinus .The technique is common for many recreational drugs and is also used for some...

) or administered rectally as well. It is also possible to smoke or vaporize it, although the dose required is higher. There have also been a few reports of intramuscular and intravenous injections. Intravenous doses should not be self-administered due to the immediate onset of hallucinations and strong physical stimulation before the needle's plunger is fully depressed. An oral recreational dose of 2C-I is commonly between 10 mg and 25 mg, although doses as low as 2 mg have been reported to be active.

Effects

The onset of effects usually occurs within two hours, and the effects of the drug typically last somewhere in the range of 4 to 12 hours (depending on the dose). The effects of the drug at small dosages (less than 12 mg) has been reported as more mental and less sensory than those of 2C-B
2C-B
2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps and is referred...

. Users of 2C-I do, however, tend to report a physical stimulant
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...

 effect, often quite strong and clean. The effects of the drug at larger dosages (12-30+ mg) are often described as combining 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...

 or 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...

 effects typical of drugs such as LSD
LSD
Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...

 with the empathogenic
Empathogen-entactogen
The terms empathogen and entactogen are used to describe a class of psychoactive drugs that produce distinctive emotional and social effects similar to those of MDMA. Putative members of this class include 2C-B, 2C-I, MDMA, MDA, MDEA, MBDB, 2C-T-7, and 2C-T-2, among others...

 or entactogenic effects of drugs such as MDMA (ecstasy). Although unpleasant physical side-effects such as muscle tension, nausea
Nausea
Nausea , is a sensation of unease and discomfort in the upper stomach with an involuntary urge to vomit. It often, but not always, precedes vomiting...

, and vomiting have been reported, their incidence with the use of 2C-I appears to be less common than with some closely related 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...

s such as 2C-T-2
2C-T-2
2C-T-2, or 2,5-dimethoxy-4-ethylthiophenethylamine is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin. The drug has structural and pharmacodynamic properties similar to the drug 2C-T-7 .-Dosage:In Alexander Shulgin's book...

 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...

. Some physical effects include dilated pupils, high energy, and muscle relaxation. Users report feeling light and sometimes giddy or excited during the first two hours. Users also report that heavy music, usually electronic, and other auditory stimulation is enjoyable.

Dosage

Oral Dosage
ED50
Effective dose (pharmacology)
An effective dose in pharmacology is the dose or amount of drug that produces a therapeutic response or desired effect in some fraction of the subjects taking it....

 
2–5 mg
light
5–10 mg
Common
10–20 mg
Strong
20–30 mg
LD50
Lethal dose
A lethal dose is an indication of the lethality of a given substance or type of radiation. Because resistance varies from one individual to another, the 'lethal dose' represents a dose at which a given percentage of subjects will die...

 

Unknown
Duration
4-12 Hours
Insufflated (Snorted) Dosage
ED50
Effective dose (pharmacology)
An effective dose in pharmacology is the dose or amount of drug that produces a therapeutic response or desired effect in some fraction of the subjects taking it....

 
0.5–2 mg
Moderate 5–10 mg
Strong 10+ mg
Duration
4-8 Hours


The lethal dosage is unknown.

Side-effects

One death was falsely attributed to 2C-I on March 17, 2011. It was later thought to be that the drug was in fact 2C-E
2C-E
2C-E is a psychedelic and phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. 2C-E is typically found as a white crystalline powder....

, and not 2C-I. It is possible that this is another one of the several cases in which Bromo-DragonFLY
Bromo-DragonFLY
Bromo-DragonFLY is a psychedelic hallucinogenic drug related to the phenethylamine family. Bromo-DragonFLY is considered an extremely potent hallucinogen, only slightly less potent than LSD with a normal dose in the region of 200 μg to 800 μg, and it has an extremely long duration of action up to...

 was mislabeled as 2C-E. There have been no reports of physical dependence or addiction
Substance use disorder
Substance use disorders include substance abuse and substance dependence. In DSM-IV, the conditions are formally diagnosed as one or the other, but it has been proposed that DSM-5 combine the two into a single condition called "Substance-use disorder"....

, which is characteristic of compounds that have similar chemical structure. If currently on drugs for hyperthyroidism, patients must continue with caution because 2C-I may interact negatively with them. Large doses of 2C-I (>45 mg), like other phenethylamines, may result in undesirable psychological effects, the persistence and severity of which are largely undocumented.

Law

There is currently a bill that is proposing to ban many chemicals from the 2c series, including 2c-i, in the United States. 2,5-dimethoxyphenethylamine (2c-h) is also being banned because it is considered a precursor to some of the other 2c-x chemicals.

2C-C
2C-C
2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. The full name of the chemical is 2,5-dimethoxy-4-chlorophenethylamine. In his book PiHKAL , Shulgin lists the dosage range as 20–40 mg. 2C-C is usually taken orally,...

, 2C-D
2C-D
2C-D is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, and its activity was subsequently investigated in humans by Alexander Shulgin. The full name of the chemical is...

, 2C-E
2C-E
2C-E is a psychedelic and phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. 2C-E is typically found as a white crystalline powder....

, 2C-P
2C-P
2C-P is a psychedelic phenethylamine and 2C compound first synthesized by Alexander Shulgin.-Chemistry:2C-P is 2,5-dimethoxy-4--propylphenethylamine. The full name of the chemical is 2-ethanamine.-Dosage:...

, 2C-N
2C-N
2C-N, or 2,5-Dimethoxy-4-nitrophenethylamine, is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin.-Chemistry:The full name of the chemical is 2-ethanamine....

, 2C-H
2C-H
2C-H, or 2,5-dimethoxyphenethylamine, is a lesser-known chemical of the 2C family. 2C-H was first synthesized by Alexander Shulgin. In his book PiHKAL , the dosage and duration are both unknown...

, 2c-t-2
2C-T-2
2C-T-2, or 2,5-dimethoxy-4-ethylthiophenethylamine is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin. The drug has structural and pharmacodynamic properties similar to the drug 2C-T-7 .-Dosage:In Alexander Shulgin's book...

, and 2c-t-4
2C-T-4
2C-T-4 or 2,5-dimethoxy-4-isopropylthiophenethylamine is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen.-Chemistry:...

 are all being targeted through this bill. 2C-B
2C-B
2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps and is referred...

 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...

 are already illegal in the US.
2C-I is an illegal, controlled substance in several European nations, including Denmark
Denmark
Denmark is a Scandinavian country in Northern Europe. The countries of Denmark and Greenland, as well as the Faroe Islands, constitute the Kingdom of Denmark . It is the southernmost of the Nordic countries, southwest of Sweden and south of Norway, and bordered to the south by Germany. Denmark...

, Germany
Germany
Germany , officially the Federal Republic of Germany , is a federal parliamentary republic in Europe. The country consists of 16 states while the capital and largest city is Berlin. Germany covers an area of 357,021 km2 and has a largely temperate seasonal climate...

, Greece
Greece
Greece , officially the Hellenic Republic , and historically Hellas or the Republic of Greece in English, is a country in southeastern Europe....

, Ireland
Ireland
Ireland is an island to the northwest of continental Europe. It is the third-largest island in Europe and the twentieth-largest island on Earth...

, Italy
Italy
Italy , officially the Italian Republic languages]] under the European Charter for Regional or Minority Languages. In each of these, Italy's official name is as follows:;;;;;;;;), is a unitary parliamentary republic in South-Central Europe. To the north it borders France, Switzerland, Austria and...

, the Netherlands
Netherlands
The Netherlands is a constituent country of the Kingdom of the Netherlands, located mainly in North-West Europe and with several islands in the Caribbean. Mainland Netherlands borders the North Sea to the north and west, Belgium to the south, and Germany to the east, and shares maritime borders...

, Poland
Poland
Poland , officially the Republic of Poland , is a country in Central Europe bordered by Germany to the west; the Czech Republic and Slovakia to the south; Ukraine, Belarus and Lithuania to the east; and the Baltic Sea and Kaliningrad Oblast, a Russian exclave, to the north...

, Spain
Spain
Spain , officially the Kingdom of Spain languages]] under the European Charter for Regional or Minority Languages. In each of these, Spain's official name is as follows:;;;;;;), is a country and member state of the European Union located in southwestern Europe on the Iberian Peninsula...

, and the United Kingdom
United Kingdom
The United Kingdom of Great Britain and Northern IrelandIn the United Kingdom and Dependencies, other languages have been officially recognised as legitimate autochthonous languages under the European Charter for Regional or Minority Languages...

. In December 2003, the European Council
European Council
The European Council is an institution of the European Union. It comprises the heads of state or government of the EU member states, along with the President of the European Commission and the President of the European Council, currently Herman Van Rompuy...

 issued a binding order compelling all EU
European Union
The European Union is an economic and political union of 27 independent member states which are located primarily in Europe. The EU traces its origins from the European Coal and Steel Community and the European Economic Community , formed by six countries in 1958...

 member states to ban 2C-I within three months. 2C-I is unscheduled and unregulated in the United States
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...

, but is a potential analog of 2C-B
2C-B
2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps and is referred...

 (which is Schedule I), and as such sale for human consumption or possession to ingest or use for illicit non-medical or industrial intents and purposes could be prosecuted as crimes 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...

. It is also a controlled substance in Argentina
Argentina
Argentina , officially the Argentine Republic , is the second largest country in South America by land area, after Brazil. It is constituted as a federation of 23 provinces and an autonomous city, Buenos Aires...

 as well as 2C-B
2C-B
2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps and is referred...

 and 2C-T-2
2C-T-2
2C-T-2, or 2,5-dimethoxy-4-ethylthiophenethylamine is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin. The drug has structural and pharmacodynamic properties similar to the drug 2C-T-7 .-Dosage:In Alexander Shulgin's book...

.

See also

  • Empathogen-entactogen
    Empathogen-entactogen
    The terms empathogen and entactogen are used to describe a class of psychoactive drugs that produce distinctive emotional and social effects similar to those of MDMA. Putative members of this class include 2C-B, 2C-I, MDMA, MDA, MDEA, MBDB, 2C-T-7, and 2C-T-2, among others...

  • 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...

  • 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...

  • Recreational drug use
    Recreational drug use
    Recreational drug use is the use of a drug, usually psychoactive, with the intention of creating or enhancing recreational experience. Such use is controversial, however, often being considered to be also drug abuse, and it is often illegal...

  • 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...

  • 2C family

External links

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