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== Entheogenic use ==
== Entheogenic use ==


2C-B is used as [[entheogen]] by the [[Sangoma]] people over their traditional plants, they refer to the chemical as ''Ubulawu Nomathotholo'', which roughly translates to "Medicine of the Singing Ancestors".<ref>{{cite web|url=http://www.tacethno.com/info/2cb/2cbhistory.html#South%20Africa |title=2CB chosen over traditional entheogen's by South African healers. |publisher=Tacethno.com |date= |accessdate=2012-05-15}}</ref>
2C-B is used as [[entheogen]] by the [[Sangoma]] people over their traditional plants, they refer to the chemical as ''[[Ubulawu Nomathotholo]]'', which roughly translates to "Medicine of the Singing Ancestors".<ref>{{cite web|url=http://www.tacethno.com/info/2cb/2cbhistory.html#South%20Africa |title=2CB chosen over traditional entheogen's by South African healers. |publisher=Tacethno.com |date= |accessdate=2012-05-15}}</ref> <ref>{{cite web|url=http://tribes.tribe.net/bioregionalanimism/thread/e77f48a7-7cea-42d3-9d12-bb6f50d65f6c |title=Ubulawu Nomathotholo: Entheogens aiding in transrational animist relationship dynamics |publisher=Tribes.tribe.net |date= |accessdate=2012-08-22}}</ref>


==Legal status and scheduling==
==Legal status and scheduling==

Revision as of 04:18, 23 August 2012

2C-B
Names
IUPAC name
2-(4-bromo-2,5-dimethoxyphenyl)ethanamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.164.088 Edit this at Wikidata
  • InChI=1S/C10H14BrNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 checkY
    Key: YMHOBZXQZVXHBM-UHFFFAOYSA-N checkY
  • InChI=1/C10H14BrNO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3
    Key: YMHOBZXQZVXHBM-UHFFFAOYAK
  • COc1cc(c(cc1Br)OC)CCN
Properties
C10H14BrNO2
Molar mass 260.13 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

4-bromo-2,5-dimethoxyphenethylamine (2C-B) 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 to on the street as 'Bees' or 'Nexus'. The drug is usually taken orally, but can also be insufflated or vaporised.

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 smart shops 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, which led to the replacement of 2C-B by other phenethylamine psychedelics like 2C-I, 2C-T-2 and 2C-T-7 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). [1]

Internationally, 2C-B is a Schedule II drug under the Convention on Psychotropic Substances.[2] 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 on July 2, 1995.

Patterns of Use

2C-B first became popularized in the United States as a legal substitute for Ecstasy when MDMA became illegal in 1985. Though 2C-B is still used in the rave subculture, commonly mistaken for and/or sold under the name of Ecstasy (MDMA), intentional use has become more common. Street prices range between $10–35 per tablet in the United States when bought in small quantities and between $100 to $500 per gram when sold in bulk. 2C-B tends to be consumed by a relatively small and knowledgeable group of users.[3]

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.[4] The common oral recreational dose is around 15–25 mg,[5] 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.[6]

When sold as "Ecstasy", tablets containing 2C-B often contain about 5mg of the drug, an amount which produces stimulatory effects that mimick the effects of MDMA; in contast, tablets marketed as 2C-B have larger quantities of the drug (10-20mg) which cause hallucinogenic effects.[1] Street purity of 2C-B, when tested, has been found to be relatively high.[7] 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".[8] 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.[1]

Effects

1000 Milligrams (1g) of 2C-B
2C-B pill with heart logo.

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[citation needed], 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.

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 (5–10 mg).
  • At 5–10 mg, experiments with young chickens have shown it to produce effects similar to a low dosage of amphetamines.[9]
  • 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 (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, hypertension and hyperthermia.[10]

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 10 mg
Moderate

15–20 mg

Strong

21–35 mg

Extremely Intense

>35 mg

LD50

Unknown

Duration

2-7 Hours

Insufflated (Snorted) Dosage
ED50 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 reports a dose of 100 mg (oral)[11] taken without apparent harm.

Pharmacology

Unlike most hallucinogens, 2C-B has been shown to be a low efficacy serotonin 5-HT2A receptor partial agonist[12] or even full antagonist.[13] 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.[12] The rank order of receptor antagonist 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.[citation needed]

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.[14] 2C-B also reduces aggressor responses in drugged rats.[15]

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.[16] 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.[17]

Entheogenic use

2C-B is used as entheogen by the Sangoma people over their traditional plants, they refer to the chemical as Ubulawu Nomathotholo, which roughly translates to "Medicine of the Singing Ancestors".[18] [19]

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.[20] 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 or 2C-T-2.[21]
  • 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[22] as "4-Bromo-2,5-dimethoxybenzeneethanamine and any salt, isomer or salt of isomer thereof".
  • Italy: 2C-B is schedule I (tabella I[23])
  • Japan: Scheduled Summer 1998. Previously marketed as "Performax".
  • Netherlands: Scheduled on July 9, 1997.
  • Norway: Schedule II[24] 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[25] 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

References

  1. ^ a b c de Boer; et al. (1999). "More Data About the New Psychoactive Drug 2C-B" (PDF). Journal of Analytical Toxicology. 23 (3): 227–228. doi:10.1093/jat/23.3.227. Retrieved 16 August 2012. {{cite journal}}: Explicit use of et al. in: |last= (help); Unknown parameter |month= ignored (help)
  2. ^ "List of psychotropic substances under international control" (PDF). Archived from the original (PDF) on 2 March 2007. Retrieved 2007-03-30. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  3. ^ Gahlinger, Paul (2004). Illegal Drugs: A Complete Guide to Their History, Chemistry, Use and Abuse. Penguin. pp. 343–344. ISBN 9780452285057.
  4. ^ "2C-B (Nexus) Reappears on the Club Drug Scene" (Press release). Drug Enforcement Administration. May 2001. Archived from the original on 5 October 2006. Retrieved 2006-10-04. {{cite press release}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  5. ^ "Erowid 2C-B Vault : Dose/Dosage".
  6. ^ Ambrose JB, Bennett HD, Lee HS, Josephson SA (2010). "Cerebral vasculopathy after 4-bromo-2,5-dimethoxyphenethylamine ingestion". The Neurologist. 16 (3): 199–202. doi:10.1097/NRL.0b013e3181a3cb53. PMID 20445431. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  7. ^ Cole; et al. (2002). "4-Bromo-2,5-dimethoxyphenethylamine (2C-B): a review of the public domain literature". Science and Justice. 42 (4): 223–224. doi:10.1016/S1355-0306(05)71668-3. PMID 16686272. Retrieved 16 August 2012. {{cite journal}}: Explicit use of et al. in: |last= (help); Unknown parameter |month= ignored (help)
  8. ^ Caudevilla-Gálligo; et al. (2012). "4-Bromo-2,5-dimethoxyphenethylamine (2C-B): presence in the recreational drug market in Spain, pattern of use and subjective effects". Journal of Psychopharmacology. 26 (7): 1026–1035. doi:10.1177/0269881111431752. Retrieved 16 August 2012. {{cite journal}}: Explicit use of et al. in: |last= (help); Unknown parameter |month= ignored (help)
  9. ^ Bronson ME, Jiang W, DeRuiter J, Clark CR (1995). "A behavioral comparison of Nexus, cathinone, BDB, and MDA". Pharmacol. Biochem. Behav. 51 (2–3): 473–5. doi:10.1016/0091-3057(95)00013-M. PMID 7667371.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  10. ^ Carmo H, Hengstler JG, de Boer D; et al. (2005). "Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human". Toxicology. 206 (1): 75–89. doi:10.1016/j.tox.2004.07.004. PMID 15590110. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  11. ^ "Shulgin, A (1991) ''PIHKAL''". Erowid.org. Retrieved 2012-05-15.
  12. ^ a b Moya, PR; Berg, KA; Gutiérrez-Hernandez, MA; Sáez-Briones, P; Reyes-Parada, M; Cassels, BK; Clarke, WP (2007). "Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors". The Journal of Pharmacology and Experimental Therapeutics. 321 (3): 1054–61. doi:10.1124/jpet.106.117507. PMID 17337633.
  13. ^ Villalobos CA, Bull P, Sáez P, Cassels BK, Huidobro-Toro JP (2004). "4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT2A receptor antagonists in Xenopus laevis oocytes". Br. J. Pharmacol. 141 (7): 1167–74. doi:10.1038/sj.bjp.0705722. PMC 1574890. PMID 15006903. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  14. ^ Carmo H, Hengstler JG, de Boer D; et al. (2005). "Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human". Toxicology. 206 (1): 75–89. doi:10.1016/j.tox.2004.07.004. PMID 15590110. {{cite journal}}: Explicit use of et al. in: |author= (help); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link){
  15. ^ Muehlenkamp F, Lucion A, Vogel WH (1995). "Effects of selective serotonergic agonists on aggressive behavior in rats". Pharmacol. Biochem. Behav. 50 (4): 671–4. doi:10.1016/0091-3057(95)00351-7. PMID 7617717. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  16. ^ Glennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, King A, Herrick-Davis K (1994). "Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines". Journal of Medicinal Chemistry. 37 (13): 1929–35. doi:10.1021/jm00039a004. PMID 8027974. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  17. ^ "Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German)". Diss.fu-berlin.de. 2010-02-28. Retrieved 2012-05-15.
  18. ^ "2CB chosen over traditional entheogen's by South African healers". Tacethno.com. Retrieved 2012-05-15.
  19. ^ "Ubulawu Nomathotholo: Entheogens aiding in transrational animist relationship dynamics". Tribes.tribe.net. Retrieved 2012-08-22.
  20. ^ "Erowid 2C-B page".
  21. ^ "Last Argentina Controlled Drugs List" (PDF). Retrieved 2012-05-15.
  22. ^ "CDSA Schedule II".
  23. ^ "Italy Drug Schedule (Tabella I)".
  24. ^ "Norway Drug Schedule".
  25. ^ "Switzerland Drug Law" (PDF).

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