2C-B
Encyclopedia
2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug
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...

 of the 2C family. 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...

 in 1974. In Shulgin's book PiHKAL
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 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 to on the street 'Bees' or 'Nexus'. The drug is usually taken orally, but can also be insufflated
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...

.

History

2C-B was synthesized from 2,5-dimethoxybenzaldehyde
2,5-Dimethoxybenzaldehyde
2,5-Dimethoxybenzaldehyde is an organic compound and a benzaldehyde derivative. One of its uses is the production of 2,5-dimethoxyphenethylamine also known as 2C-H. 2C-H is used to produce many other psychoactive drugs, such as 2C-B, 2C-I and 2C-C....

 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...

 in 1974. It first saw use among the psychiatric community as an aid during therapy. It was considered one of the best drugs for this purpose because of its short duration, relative absence of side effects, and comparably mild nature. Shortly after becoming popular in the medical community, it became popular recreationally. 2C-B was first sold commercially as an aphrodisiac
Aphrodisiac
An aphrodisiac is a substance that increases sexual desire. The name comes from Aphrodite, the Greek goddess of sexuality and love. Throughout history, many foods, drinks, and behaviors have had a reputation for making sex more attainable and/or pleasurable...

 under the trade name "Eros", which was manufactured by the German pharmaceutical company Drittewelle. For several years, it was available 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 under the name "Nexus" as predosed tablets, however, it was placed on List I of the Opium Law
Opium Law
The Opium Law is the section of the Dutch law which covers nearly all psychotropic drugs. All non-psychotropic, but prescription-only drugs are covered by the Medicine Act.- Origin and history :...

 after being sold without any incidents occurring, which led to the replacement of 2C-B by other phenethylamine psychedelics like 2C-I
2C-I
2C-I or 2,5-dimethoxy-4-iodophenethylamine is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. It was described in Shulgin’s book PiHKAL: A Chemical Love Story. The drug is used recreationally for its psychedelic and entactogenic effects...

, 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...

 that were not controlled substances in the Netherlands at the time (but were banned later by the Dutch government, after being sold in smartshops for short periods).

Internationally, 2C-B is a Schedule II drug under the Convention on Psychotropic Substances
Convention on Psychotropic Substances
The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, benzodiazepines, and psychedelics signed at Vienna on February 21, 1971...

. In the Netherlands, 2C-B became a list I substance of the Opium Law, after being legally sold in smartshops, and which led to the follow-up by other, at that time, legal phenethylamines. The Netherlands was the first country in the world to subsequently ban 2C-B (as well as 2C-I, 2C-T-2 and 2C-T-7). In the United States
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...

, a notice of proposed rulemaking published on December 20, 1994 in the Federal Register
Federal Register
The Federal Register , abbreviated FR, or sometimes Fed. Reg.) is the official journal of the federal government of the United States that contains most routine publications and public notices of government agencies...

(59 FR 65521) and after a review of relevant data, the Deputy Administrator of the Drug Enforcement Administration
Drug Enforcement Administration
The Drug Enforcement Administration is a federal law enforcement agency under the United States Department of Justice, tasked with combating drug smuggling and use within the United States...

 (DEA) proposed to place 4-bromo-2,5-DMPEA
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...

 into Schedule I, making 2C-B illegal in the United States. This became permanent law on July 2, 1995.

It is used in the rave
Rave
Rave, rave dance, and rave party are parties that originated mostly from acid house parties, which featured fast-paced electronic music and light shows. At these parties people dance and socialize to dance music played by disc jockeys and occasionally live performers...

 subculture
Subculture
In sociology, anthropology and cultural studies, a subculture is a group of people with a culture which differentiates them from the larger culture to which they belong.- Definition :...

, commonly mistaken for and/or sold under the name of ecstasy (MDMA). Street prices range between $20–25 per tablet in the United States when bought in small quantities.

Toxicity and dosage

The September 1998 Journal of Analytical Toxicology reported that very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-B. The relationship between its use and death are unknown. The common oral recreational dose is around 15–25 mg, at which visual and auditory effects are experienced. Severe adverse reactions are rare, but use of 2C-B has been linked to significant injury in some cases.

Effects

The effects of 2C-B include:
  • When insufflated, the onset, or ‘coming up’, happens very rapidly, usually reaching the peak at about 20–40 minutes lasting anywhere from 30 minutes to a few hours depending on dosage. When orally consumed, 2C-B has a much longer delay before the onset of effects than when it is insufflated. Oral ingestion generally takes roughly 30–90 minutes for the effects to be felt; while with insufflation the onset may be immediate. 2C-B is also considered one of the most painful drugs to insufflate, with users almost always reporting intense nasal burning lasting as long as 5 minutes.

  • This radical change is not usually overwhelming to most users, but the intensity of the experience can make them nauseated and/or frightened. Plateau effects are reached in about 20-40 min and last for about 2–3 hours, but this also depends on the method of ingestion: with insufflation the effects are more abrupt and intense but have a significantly shorter duration, while oral usage will result in a milder longer experience. The ‘rush’ that users feel off MDMA and grinding of teeth is often reported in less experienced users. There have been cases where 2C-B has been reported to be more intense than LSD with extremely high doses.

The visuals ‘waver’ or come and go in a carousel-like pattern meaning that when the effect is strong then dies down, users may feel that the trip is over, only for it to come back stronger. The duration as a whole, though is only about 2–5 hours depending on dosage.
  • Some users report aphrodisiac
    Aphrodisiac
    An aphrodisiac is a substance that increases sexual desire. The name comes from Aphrodite, the Greek goddess of sexuality and love. Throughout history, many foods, drinks, and behaviors have had a reputation for making sex more attainable and/or pleasurable...

     effects at lower doses (5–10 mg).
  • At 5–10 mg, laboratory results have shown it to produce effects similar to a low dosage of amphetamines.
  • At higher dosages (greater than 15 mg) some users consider the hallucinations a “turn-off” or distracting.
  • The hallucinations have a tendency to decrease and then increase in intensity, giving the users a sense of “waves” or even glowing. These are popularly described as “clichéd ’70s visuals” or objects taking on "water color" like textures. Other users have noted DMT-like "brain movies".
  • While the effects of the drug often render users unable to concentrate deeply on anything in particular, some can become engrossed in an activity such as watching a movie or playing a video game, distracting themselves from the visual and auditory effects of the drug.
  • Excessive giggling or smiling is common, as is a tendency for deeper “belly laughs”. Some users report mild “jitters” (body tremors), shuddering breath, and/or mild muscle spasms after snorting (not immediate). Whether or not these effects are enjoyable depends on the user.
  • Some users say that the effects are more intense when listening to music and report that they can see sounds and noises.
  • Some users experience a decrease in visual acuity, although others report sharper vision.
  • At low doses the experience may shift in intensity from engaging to mild/undetectable. Experienced users report the ability to take control of the effects and switch from engaged to sober at will.
  • Increased awareness of one’s body; attention may be brought to perceived ‘imperfections’ or internal body processes.
  • Possible side effects include: mild diarrhea, gas, and nausea. Some users have said to experience a slight irritability for roughly a day or so after use. However, these effects are rare and the drug is generally easier on the body than MDMA
    Methylenedioxymethamphetamine
    MDMA is an entactogenic drug of the phenethylamine and amphetamine class of drugs. In popular culture, MDMA has become widely known as "ecstasy" , usually referring to its street pill form, although this term may also include the presence of possible adulterants...

     (Ecstasy).
  • Severe headaches after coming down from large doses have been reported. However, many users report a lack of “comedown” or “crash”, instead noting a gradual return to sobriety. There are reports of hangover effects, especially when the drug is combined with alcohol.
  • At doses over 30/40 mg the user may experience frightening hallucinations inducing tachycardia
    Tachycardia
    Tachycardia comes from the Greek words tachys and kardia . Tachycardia typically refers to a heart rate that exceeds the normal range for a resting heart rate...

    , hypertension
    Hypertension
    Hypertension or high blood pressure is a cardiac chronic medical condition in which the systemic arterial blood pressure is elevated. What that means is that the heart is having to work harder than it should to pump the blood around the body. Blood pressure involves two measurements, systolic and...

     and hyperthermia
    Hyperthermia
    Hyperthermia is an elevated body temperature due to failed thermoregulation. Hyperthermia occurs when the body produces or absorbs more heat than it can dissipate...

    .


The following effects are highly dose-dependent.
  • Open eye visuals (OEVs), such as cartoon-like distortions and red or green halos around objects. Closed eye visuals (CEVs) are more common than OEVs.
  • Affects and alters ability to communicate, engage in deep thought, or maintain attention span.
  • Some users report experiencing frightening or fearful effects during the experience. Users describe feeling frigid or cold on reaching a plateau, while others feel wrapped in comfortable blankets/ultimate pleasure.
  • Coordination may be affected, some users lose balance or have perceptual distinction problems.
  • Effects last roughly 2–5 hours.

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....

 
10 mg
Moderate
15–20 mg
Strong
21–35 mg
Extremely Intense
>35 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
2-7 Hours
Insufflated (Snorted) Dosage
ED50
Effective dose
Effective dose may refer to:*Effective dose the dose of pharmacologic agent which will have a therapeutic effect in some fraction of the population receiving the drug...

 
7–10 mg
Moderate
13–19 mg
Strong
20–30 mg
Extremely Intense
>31 mg
Duration
2-5 Hours


The lethal dosage is unknown. It is worth noting that 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...

 reports a dose of 100 mg (oral) taken without apparent harm.

Pharmacology

Unlike most hallucinogens, 2C-B has been shown to be a low efficacy serotonin
Serotonin
Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...

 5-HT2A receptor
5-HT2A receptor
The mammalian 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor . This is the main excitatory receptor subtype among the GPCRs for serotonin , although 5-HT2A may also have an inhibitory effect on certain areas such...

 partial agonist
Partial agonist
Partial agonists bind and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist...

 or even full antagonist. This suggests that the 5-HT2C receptor
5-HT2C receptor
The 5-HT2C receptor is a subtype of 5-HT receptor that binds the endogenous neurotransmitter serotonin . It is a G protein-coupled receptor that is coupled to Gq/G11 and mediates excitatory neurotransmission. HTR2C denotes the human gene encoding for the receptor, that in humans is located at the...

 is primarily responsible for mediating the effects experienced by users of 2-CB, although functional antagonism of 5-HT2A or activation of the 5-HT2A-coupled phospholipase D
Phospholipase D
Phospholipase D is an enzyme which is located in the plasma membrane and catalyzes the hydrolysis of phosphatidylcholine to form phosphatidic acid , releasing the soluble choline headgroup into the cytosol...

 pathway may also play a role. The rank order of receptor antagonist
Antagonist
An antagonist is a character, group of characters, or institution, that represents the opposition against which the protagonist must contend...

 potency for this family of drugs is 2C-I>2C-B>2C-D>2C-H.

2C-B has been shown to be metabolized by liver hepatocytes resulting in deamination and demethylation that produces several products. Oxidative deamination results in the 2-(4-bromo-2,5-dimethoxyphenyl)-ethanol (BDMPE) and 4-bromo-2,5-dimethoxyphenylacetic acid (BDMPAA) metabolites. Additionally, 4-bromo-2,5-dimethoxybenzoic acid (BDMBA) can be produced also by oxidative deamination. Further metabolism of BDMPE and BDMPAA may occur by demethylation. Alternatively, the later metabolites can be generated by demethylation of 2C-B followed by oxidative deamination.

There is species differentiation in the metabolism of 2C-B. Mice hepatocytes produce 4-bromo-2,5-dimethoxy-phenol (BDMP) a previously unknown metabolite. 2-(4-bromo-2-hydroxy-5-methoxyphenyl)-ethanol (B-2-HMPE) was produced by hepatocytes from human, monkey and rabbit but not by dog, rat and mouse. 2C-B also reduces aggressor responses in drugged rats.

N-substituted derivatives

A variety of N-substituted derivatives of 2CB have been tested, including N-methyl-2CB, N,N-dimethyl-2CB, N-ethyl-2CB and N-benzyl-2CB. Most simple alkyl derivatives were considerably less potent than 2CB, with N-ethyl-2CB for instance having around 40x lower affinity at the 5-HT2A receptor. The N-benzyl derivative however was found to have higher binding affinity than 2CB itself, with N-(4-bromobenzyl)-2CB binding even more tightly again. This initial research did not include functional assays of activity, but later led to the development of potent substituted N-benzyl derivatives such as NBOMe-2CB.

Legal status and scheduling

The UN
United Nations
The United Nations is an international organization whose stated aims are facilitating cooperation in international law, international security, economic development, social progress, human rights, and achievement of world peace...

 Commission on Narcotic Drugs
Commission on Narcotic Drugs
The Commission on Narcotic Drugs is the central drug policy-making body within the United Nations system. Its predecessor, the Advisory Committee on the Traffic in Opium and Other Dangerous Drugs, was established by the first Assembly of the League of Nations on December 15, 1920...

 added 2C-B to Schedule II of the Convention on Psychotropic Substances
Convention on Psychotropic Substances
The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, benzodiazepines, and psychedelics signed at Vienna on February 21, 1971...

 in March 2001. LSD, psilocybin, and mescaline are in the more restrictive Schedule I.

Although still available through online stores in some countries as a "research chemical" not for human consumption, 2C-B is scheduled as a drug in most jurisdictions. The following is a partial list of territories where the substance has been scheduled.
  • Argentina: It is controlled under the List 1, as well as other substances like 2C-I
    2C-I
    2C-I or 2,5-dimethoxy-4-iodophenethylamine is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. It was described in Shulgin’s book PiHKAL: A Chemical Love Story. The drug is used recreationally for its psychedelic and entactogenic effects...

     or 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...

    .
  • Australia: Controlled and on the list of substances subject to import and export controls (Appendix B:). Placed on Schedule One of the Drugs Misuse and Trafficking Act when it first came to notice in 1994, when in a showcase legal battle Chemist R.Simpson was charged with manufacturing the substance in Sydney NSW. Alexander Shulgin came to Australia to testify on behalf of the defense.(to no avail).
  • Brazil: Controlled substance, making production, distribution, or possession illegal.
  • Estonia: Schedule I.
  • Canada: CDSA Schedule III as "4-Bromo-2,5-dimethoxybenzeneethanamine and any salt, isomer or salt of isomer thereof".
  • Italy: 2C-B is schedule I (tabella I)
  • Japan: Scheduled Summer 1998. Previously marketed as "Performax".
  • Netherlands: Scheduled on July 9, 1997.
  • Norway: Schedule II as of March 22, 2004. Listed as 4-bromo-2,5-dimethoxyphenethylamine.
  • Poland: 2C-B is schedule I (I-P group) in Poland.
  • Spain: Added to Category 2 prohibited substances in 2002.
  • Sweden: Schedule I in Sweden on Jun 13, 2002.
  • Switzerland: Listed in Anhang D of the DetMV and is illegal to possess.
  • USA: CSA Schedule I Section (d) Subsection (3) 4-Bromo-2,5-dimethoxyphenethylamine.
  • UK: All drugs in the 2C family are Class A under the 1971 Misuse of Drugs Act which means they are illegal to produce, supply or possess in any form.

See also

  • 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...

  • Psychedelics, dissociatives and deliriants
    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...

  • PiHKAL
    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...

  • DOI
    2,5-Dimethoxy-4-iodoamphetamine
    2,5-dimethoxy-4-iodoamphetamine is a psychedelic drug and a substituted amphetamine of the phenethylamine family. It is also a powerful anti-inflammatory that is effective at doses on the order of 100 micrograms in humans, far below its effective dose as a psychedelic. Despite being a substituted...

  • DOB
    2,5-Dimethoxy-4-bromoamphetamine
    DOB, also known as Brolamfetamine and Bromo-DMA, is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. DOB was first synthesized by Alexander Shulgin in 1967...


External links

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