2C-B or 2,5-dimethoxy-4-bromophenethylamine 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 12–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets
or gel caps and is referred to on the street by a number of slang names. The drug is usually
taken orally, but can also be insufflated or vaporized.
History 2C-B was synthesized from 2,5-dimethoxybenzaldehyde
by Alexander Shulgin 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 under the trade name "Eros", which was manufactured
by the German pharmaceutical company Drittewelle. For several years, it was available as tablets
in Dutch smart shops under the name "Nexus". Internationally, 2C-B is a Schedule II drug
under the Convention on Psychotropic Substances. In the Netherlands, 2C-B became a list I substance
of the Opium Law despite no health incidents occurring. Following the ban, other phenethylamines
were sold in place of 2C-B until the Netherlands became the first country in the world to ban
2C-I, 2C-T-2 and 2C-T-7 alongside 2C-B. In the United States, a notice of proposed
rulemaking published on December 20, 1994 in the Federal Register and after a review
of relevant data, the Deputy Administrator of the Drug Enforcement Administration proposed
to place 4-bromo-2,5-DMPEA into Schedule I, making 2C-B illegal in the United States.
This became permanent law on July 2, 1995. Patterns of use
2C-B first became popularized in the United States as a short-lived legal substitute for
the street drug Ecstasy when MDMA became illegal in 1985. Many 2C-B users are young adults
who attend raves. Though 2C-B is still used in the rave subculture, commonly mistaken
for and/or sold as Ecstasy, its intentional use has become more common. In recent years,
2C-B has emerged as the drug of choice for club drug users in Colombia.
Street prices range between $10 and $30 per tablet in the United States when bought in
small quantities. Larger retail purchases cost between $200 and $500 per gram. Wholesale
purchases of 2C-B can lower the price to a range of $100 to $300 per gram.
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 extremely rare, but use of 2C-B has been linked to significant
injury in one case where the dosage is unknown, and the purity/identity of the chemical was
not verified. The lethal dosage is unknown. Alexander Shulgin
reported a 100 mg oral dose taken without apparent harm.
When sold as "Ecstasy", tablets containing 2C-B often contain about 5 mg of the drug,
an amount which produces stimulatory effects that mimic the effects of MDMA; in contrast,
tablets marketed as 2C-B have larger quantities of the drug which cause hallucinogenic effects.
Street purity of 2C-B, when tested, has been found to be relatively high. Researchers in
Spain found that 2C-B samples in the country doubled between 2006 and 2009, switched from
primarily powder form to tablets, and exhibited "low falsification rates". An analysis of
street samples in the Netherlands found impurities "in small percentages"; only one of the impurities,
the N-acetyl derivative of 2C-B, could be identified and comprised 1.3% of the sample.
The authors suggested that this compound was a by-product of 2C-B synthesis.
Effects
Little or no academic research has been conducted on the effects of 2C-B in humans. The information
available is largely anecdotal and limited. Effects are often described as being more
easily managed than other psychedelics; it is often compared to a mixture of a serotonergic
psychedelic and MDMA. The effects of 2C-B include:
At 5–10 mg, experiments with young chickens have shown it to produce effects similar to
a low dosage of amphetamines. 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.
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.
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 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. Increased awareness of one’s body; attention
may be brought to perceived "imperfections" or internal body processes.
The following effects are highly dose-dependent. Open eye visuals, such as cartoon-like distortions
and red or green halos around objects. Closed eye visuals 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.
Use as an aphrodisiac Before it was scheduled, 2C-B was sold in
small doses as an aphrodisiac. Some users report aphrodisiac effects at lower doses
but consider the hallucinations a "turn-off" or distracting at higher dosages.
Side effects Some users report mild "jitters", shuddering
breath, and/or mild muscle spasms after insufflating 2C-B. Whether or not these effects are enjoyable
depends on the user. Mild diarrhea, gas, nausea, and general gastrointenstinal
discomfort. 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. 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. At doses over 30–40 mg the user may experience
frightening hallucinations, as well as tachycardia, hypertension, and hyperthermia.
Duration 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 45–75 minutes for the effects to be felt, plateau lasts 2–4 hours, and
coming down lasts 1–2 hours. Rectal administration onset varies from 5–20 minutes. Insufflated
onset takes 1–10 minutes for effects to be felt. The duration can last from 4 to 12
hours depending on ROA, dose, and other factors. With insufflation the effects are more abrupt
and intense but have a significantly shorter duration, while oral usage results in a milder,
longer experience. When insufflated, the onset happens very rapidly, usually reaching the
peak at about 20–40 minutes and plateauing for 2–3 hours. 2C-B is also considered one
of the most painful drugs to insufflate, with users reporting intense nasal burning lasting
as long as 30 minutes. The sudden intensity of the experience combined with the pain can
often start the experience with a negative imprint and nausea is also increased with
insufflation, compounding the issue. Pharmacology
Unlike most hallucinogens, 2C-B has been shown to be a low efficacy serotonin 5-HT2A receptor
partial agonist or even full antagonist. This suggests that the 5-HT2C receptor is primarily
responsible for mediating the effects experienced by users of 2C-B, although functional antagonism
of 5-HT2A or activation of the 5-HT2A-coupled phospholipase D pathway may also play a role.
The rank order of receptor antagonist potency for this family of drugs is 2C-I > 2C-B > 2C-D
> 2C-H. Research suggests that 2C-B increases dopamine
levels in the brains of rats, which may contribute to its psychoactivity.
Metabolism 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 and 4-bromo-2,5-dimethoxyphenylacetic acid
metabolites. Additionally, 4-bromo-2,5-dimethoxybenzoic acid 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
a previously unknown metabolite. 2-(4-bromo-2-hydroxy-5-methoxyphenyl)-ethanol 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 2C-B 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 2C-B, with N-ethyl-2CB for instance having around 40× lower affinity
at the 5-HT2A receptor. The N-benzyl derivative however was found to have higher binding affinity
than 2C-B 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 25B-NBOMe.
Entheogenic use 2C-B is used as entheogen by the Sangoma,
Nyanga, and Amagqirha people over their traditional plants; they refer to the chemical as Ubulawu
Nomathotholo, which roughly translates to "Medicine of the Singing Ancestors".
Drug prohibition laws United Nations
The UN Commission on Narcotic Drugs added 2C-B to Schedule II of the Convention on Psychotropic
Substances 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. Countries
Argentina It is controlled under the List 1, as well
as other substances like 2C-I or 2C-T-2. Australia
Controlled and on the list of substances subject to import and export controls. 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.
Brazil Controlled substance, making production, distribution,
or possession illegal. Canada
CDSA Schedule III as "4-Bromo-2,5-dimethoxybenzeneethanamine and any salt, isomer or salt of isomer thereof".
Denmark 2C-B is listed as a category B drug.
Estonia Schedule I.
Italy 2C-B is schedule 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 in Poland.
Spain Added to Category 2 prohibited substances
in 2002. Sweden
Schedule I in Sweden on Jun 1, 2002. 2C-B was first classified as "health hazard" under
the act Lagen om förbud mot vissa hälsofarliga varor as of April 1, 1999 under SFS 1999:58
that made it illegal to sell or possess. Then it became schedule I as of June 1, 2002, publicated
in LVFS 2002:4 but mislabeled "2-CB" in the document. However, this was corrected in a
new document, LVFS 2009:22 effective December 9, 2009.
Switzerland Listed in Anhang D of the DetMV and is illegal
to possess. 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. Possession carries a maximum sentence of seven
years imprisonment while supply is punishable by life imprisonment and an unlimited fine.
USA CSA Schedule I Section Subsection 4-Bromo-2,5-dimethoxyphenethylamine.
See also Phenethylamine
βk-2C-B 2C-B-FLY
DOB Bromo-DragonFLY
BOB References
External links 2C-B Entry in PiHKAL
2C-B Entry in PiHKAL • info Erowid 2C-B vault—includes reports from
users of 2C-B, as well as scientific and government reports
2C-B Dosage chart