2C-B

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IUPACName = 2-(4-bromo-2,5-dimethoxy-phenyl)ethanamine
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CASNo = 66142-81-2
PubChem = 98527
SMILES = COC1=CC(=C(C=C1CCN)OC)Br
Section2 = Chembox Properties
Formula = C₁₀H₁₄BrNO₂
MolarMass = 260.13 g/mol
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2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family, an entactogen. It was first synthesized by Alexander Shulgin in 1974. In his book "PiHKAL (Phenethylamines I Have Known And Loved)", the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps. The drug is usually taken orally, but sometimes is insufflated.

Origins and 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 in Dutch smartshops under the name "Nexus" as predosed tablets, however, it was placed on List I of the Opium Law after being sold without any incidents occurring, and which led to the replacement of 2C-B by other phenethylamine psychedelics like 2C-I, 2C-T-2 and 2C-T-7, which weren't controlled substances in the Netherlands at that time (but were banned as well 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 [cite web |url=http://www.incb.org/pdf/e/list/green.pdf |title= List of psychotropic substances under international control |accessdate= 2007-03-30|format=PDF] . 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, a notice of proposed rulemaking published on December 20, 1994 in the "Federal Register" (59 FR 65521) and after a review of relevant data, the Deputy Administrator of the Drug Enforcement Administration (DEA) proposed to place 4-bromo-2,5-DMPEA into Schedule I, making 2C-B illegal in the United States. This became permanent law July 2, 1995.

It is used in the rave subculture, commonly mistaken or sold under the name of ecstasy (MDMA). Street prices range between $10-20 per tablet in the United States when bought in small quantities.Fact|date=April 2008

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 disease and death are unknown. [cite press release|title=2C-B (Nexus) Reappears on the Club Drug Scene|date=May 2001|publisher=Drug Enforcement Administration|url=http://www.usdoj.gov/ndic/pubs0/665/index.htm|accessdate=2006-10-04] At oral doses around 5–15 mg, 2C-B produces an entactogenic effect. But common recreational doses range from 15–40 mg, at which intense visual and auditory effects are experienced. The intensity of the effects increases with dosage. While considered foolhardy, people have survived doses as high as 200mg without negative effects.Fact|date=July 2007 However, doses that high often lead to blackouts and erratic behavior.Fact|date=July 2007

Effects

The effects of 2C-B include:
* The onset, or ‘coming up’, happens very radically, usually reaching the peak at about 20-40 minutes lasting any where from 10-30 minutes depending on dosage. Eating 2C-B takes a considerable amount of time for the onset of effects to start when comparing it to snorting. Eating generally takes roughly 30-90 minutes for the effects to begin; when snorting the onset may begin immediately . In some cases where doses of roughly 35-45mg have been snorted the full effects have been reported to start happening just after 60 seconds or so. 2C-B is also considered one of the most painful drugs to snort, 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 nauseous 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 (snorted or swallowed); with snorting the effects are more abrupt and intense but have a significantly shorter duration while swallowing will be a milder longer trip (occasionally swallowing will significantly increase the effects; depending on dose). The hallucinations are much less intense than LSD with 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 effects at lower doses (5-10mg).
* At 5-10mg, laboratory results have shown to have it produce effects similar to low dosage of amphetamines. [cite web |url=http://www.ncbi.nlm.nih.gov/entrez/queryd.fcgi?itool=pubmed_AbstractPlus&cmd=Retrieve&db=pubmed&list_uids=7667371&dopt=ExternalLink |title= LA behavioral comparison of Nexus, cathinone, BDB, and MDA |accessdate= 2008-05-28]
* At higher dosages (greater than 15mg) 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, and are popularly described as “clichéd ’70s visuals” or objects taking on "water color" like textures. Other users have also noted DMT-like Brain movies.
* While more often than not the effects of the drug render most users unable to concentrate deeply on anything in particular, those that do become engrossed in an activity such as watching a movie or playing a video game have distracted 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 these effects are enjoyable is purely up to the user.
* 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 (Ecstasy).
* Many users report a lack of “comedown” or “crash”, instead noting a gradual return to sobriety. However, there are reports of hangover effects, especially when combined with alcohol.
* At doses over 30/40mg there may be frightening hallucinations and it may induce tachycardia, hypertension and hyperthermia. [cite web |url=http://www.ncbi.nlm.nih.gov/entrez/utils/fref.fcgi?itool=ExternalLink&PrId=3048&uid=15590110&db=pubmed&url=http://linkinghub.elsevier.com/retrieve/pii/S0300-483X(04)00396-8 |title= Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human.|accessdate= 2008-05-28]

"The following effects are highly dose-dependent."
* Open Eye Visuals (OEVs), such as cartoon-like distortions and red or green halos around objects are common. 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

Current Research

Current research into how 2C-B functions within the human body, conducted on rats and oocytes of Xenopus Laevis as well as mammals of various species and via cloning of Human 5-HT2 (serotonin) receptors in cell cultures or in animal subjects that shows that 2C-B activates Human 5-HT2 receptors. Research was conducted with 2C-I, 2C-B, 2C-D and 2C-H, all variants of the same chemical base phenethylamine, therefore react similarly with the central nervous system. However 2C-B as an agonist for 5-HT2a is 30 times less than that of 2C-I. Moreover, the agonization of the receptors was completely reversible in a short amount of time. [cite web |url=http://www.ncbi.nlm.nih.gov/entrez/utils/fref.fcgi?itool=ExternalLink&PrId=3494&uid=15006903&db=pubmed&url=http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pubmed&pubmedid=15006903
title=4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT2A (serotonin) receptor agonists in Xenopus laevis oocytes.|accessdate= 2008-05-28] There is a significant retention of the drug in the brain and lungs after usage. 2C-B and similar PEAs are selective in their stimulation of 5-HT2 receptors, focusing mostly on 5-HT2A, so it may also agonize other receptors in the CNS. 2C-B after metabolized by the liver via deamination and demethylation produces several metabolites: BDMPAA, B-2 HMPAA, BDMBA, BDMPE, B-2-HMPE and BDMP. It is possible that these are metabolized further via demethylation. There may be a higher risk towards metabolization in certain sub-populations of humans. [cite web |url=http://www.ncbi.nlm.nih.gov/entrez/utils/fref.fcgi?itool=ExternalLink&PrId=3048&uid=15590110&db=pubmed&url=http://linkinghub.elsevier.com/retrieve/pii/S0300-483X(04)00396-8
title= Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human. |accessdate= 2008-05-28] . 2C-B also reduces aggressor responses in drugged rats. [cite web |url=http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6T0N-40SFN6V-11&_user=145269&_coverDate=04%2F30%2F1995&_alid=746617046&_rdoc=10&_fmt=high&_orig=mlkt&_cdi=4867&_sort=v&_st=17&_docanchor=&view=c&_ct=139&_acct=C000012078&_version=1&_urlVersion=0&_userid=145269&md5=77fb6d805f2996d8f335bd9f80706ad8
title= Effects of selective serotonergic agonists on aggressive behavior in rats
accessdate= 2008-05-28]

Legal status and scheduling

Although still available through online stores in some countries as a "research chemical" not for human consumption, 2-CB is scheduled as a drug in most jurisdictions [cite web| url=http://www.erowid.org/chemicals/2cb/2cb_law.shtml |title=Erowid 2C-B page] . The following is a partial list of territories where the substance has been scheduled.

*Australia: controlled and on the list of substances subject to import and export controls. Appendix B: Substances Subject to import and export controls
*Brazil: Controlled substance, making production, distribution, or possession illegal.
*Estonia: Schedule I.
*Canada: CDSA Schedule III [cite web |url=http://isomerdesign.com/Cdsa/schedule.php?schedule=3&section=ALL&structure=C |title=CDSA Schedule II] as "4-Bromo-2,5-dimethoxybenzeneethanamine and any salt, isomer or salt of isomer thereof"
*Japan: Scheduled Summer 1998. Previously marketed as "Performax".
*Netherlands: Scheduled on July 9th, 1997.
*Norway: Schedule II [cite web |url=http://www.lovdata.no/ltavd1/lt2004/t2004-1-05-39.html |title=Norway Drug Schedule] 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 [cite web |url=http://www.swissmedic.ch/files/pdf/Verzeichnis_d-D.pdf |title=Switzerland Drug Law|format=PDF] of the DetMV and is illegal to possess.
*US: CSA Schedule I Section (d) Subsection (3) 4-Bromo-2,5-dimethoxyphenethylamine
*UN: U.N. Narcotics Commission added 2C-B added to Schedule II in March 2001.

References

See also

* Phenethylamine
* Psychedelics, dissociatives and deliriants

External links

* [http://www.erowid.org/library/books_online/pihkal/pihkal020.shtml 2C-B Entry in "PiHKAL"]
* [http://www.erowid.org/chemicals/2cb/2cb.shtml Erowid 2C-B vault] —includes reports from users of 2C-B, as well as scientific and government reports
* [http://www.erowid.org/chemicals/2cb/2cb_dose.shtml 2C-B Dosage chart]
* [http://www.tacethno.com/info/2cb/2cbhistory.html 2C-B history]

Categorization