2C-B

Last updated
2C-B
2C-B.svg
Clinical data
Routes of
administration 		Oral, insufflation, rectal
Legal status
Legal status
Pharmacokinetic data
Onset of action 20–40 min. (Oral)
Elimination half-life 2.48 ± 3.20 h [1]
Duration of action 4–12 hours depending on route of administration
Identifiers
  • 2-(4-Bromo-2,5-dimethoxyphenyl)ethanamine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.164.088 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C10H14BrNO2
Molar mass 260.131 g·mol−1
3D model (JSmol)
  • COc1cc(CCN)c(OC)cc1Br
  • 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
  • Key:YMHOBZXQZVXHBM-UHFFFAOYSA-N

2C-B (4-bromo-2,5-dimethoxyphenethylamine) is a synthetic psychedelic drug of the 2C family, mainly used as a recreational drug. [2] The substance was first synthesized by Alexander Shulgin in 1974, and gained an initial reputation for potential psychotherapeutic use, but its use has been limited to mainly recreational use. To date, there is limited scientific information regarding the drug's pharmacokinetics and pharmacological effects in humans. The existing studies primarily classify 2C-B as a stimulant, and hallucinogen, and less commonly as an entactogen, and empathogen. [3]

Contents

2C-B, also referred to by a number of slang names, is known to circulate in the illicit market in multiple forms: [4] [5] most commonly as a powder, and less commonly in capsules or pills. For recreational use, the substance is generally consumed orally or nasally. In Shulgin's book PiHKAL , the dosage range is listed as 12–24 mg. [6]

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.[ citation needed ] 2C-B was first sold commercially as a purported aphrodisiac [7] under the trade name "Erox", which was manufactured by the German pharmaceutical company Drittewelle. [8] For several years, it was available as tablets in Dutch smart shops under the name "Nexus" and "B-Dub".[ citation needed ]

Patterns of use

2C-B first became popularized in the United States as a short-lived substitute for the street drug ecstasy (MDMA) when the latter became illegal in 1985. [9] Many 2C-B users are young adults who attend raves. [4] 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 the 2000s. [10]

In 2011, street prices in the United States ranged between $10 and $30 per tablet when purchased in small quantities. [4] Larger retail purchases cost between $200 and $500 per gram. Wholesale purchases of 2C-B would lower the price ($100 to $300 per gram in 2001, $30 to $100 on the darknet in 2020). [7]

Toxicity and dosage

The September 1998 issue of 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. [7] The common oral recreational dose is around 15–25 mg, [11] at which visual and auditory effects are experienced. Severe adverse reactions are extremely rare, but use of 2C-B was linked to significant brain injury in one case report; the alleged "2C-B" was never actually discovered by testing so the only evidence suggesting 2C-B was the cause was the victim's own words, without taking into consideration that adulteration and impurities are very common in illicit drugs. [12]

OralInsufflated
ED50 10 mg4–6 mg
Moderate15–25 mg5–9 mg
Strong26–35 mg10–20 mg
Extremely Intense>35 mg>20 mg
Duration4–8 hours2–4 hours

The lethal dosage is unknown. It was reported in PiHKAL , by Alexander Shulgin, that a psychologist had accidentally taken a 100 mg dose orally without apparent harm. [6]

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 (10–20 mg) which cause hallucinogenic effects. [13] Street purity of 2C-B, when tested, has been found to be relatively high. [14] 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". [15] 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. [13]

Effects

2C-B pill with heart logo 2cb pill.jpg
2C-B pill with heart logo

Little 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; [16] [17] it is often compared to a mixture of a serotonergic psychedelic and MDMA. [15] At 5–10 mg, experiments with young chickens have shown it to produce effects similar to a low dosage of amphetamines. [18]

The anecdotal effects of 2C-B that have been reported by users on online discussion forums include: [19] [20] [21]

Side effects

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 route of administration, dose, and other factors. [19]

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. [16] 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 psychedelics, 2C-B has been shown to be a low efficacy human serotonin 5-HT2A and 5-HT2C receptor partial agonist. [25] This suggests that activation of the 5-HT2A-coupled phospholipase D pathway [25] or functional antagonism of 5-HT2A may also play a role. The rank order of 5-HT2A receptor antagonist potency for this family of drugs in Xenopus is 2C-I > 2C-B > 2C-D > 2C-H. [26]

Research suggests that 2C-B increases dopamine levels in the brains of rats, which may contribute to its psychoactivity. [27]

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 (BDMPE) and 4-bromo-2,5-dimethoxyphenylacetic acid (BDMPAA) metabolites. Additionally, 4-bromo-2,5-dimethoxybenzoic acid (BDMBA) can also be produced 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. [23]

There is species differentiation in the metabolism of 2C-B. Mice hepatocytes produce 4-bromo-2,5-dimethoxy-phenol (BDMP), a previously unknown metabolite. Meanwhile, human, monkey and rabbit hepatocytes produce 2-(4-bromo-2-hydroxy-5-methoxyphenyl)-ethanol (B-2-HMPE), but dog, rat and mouse hepatocytes do not. [23] 2C-B also reduces aggressive responses in drugged rats. [28]

Analogues and derivatives

Analogues and derivatives of 2C-B:

25-N:

25-NB:

25-NM:

Substituted benzofurans:

N-(2C)-fentanyl:

Other:

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 a 40 times lower affinity for 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. [33] 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, [34] and 25B-NBOH.

Entheogenic use

1000mg of 4-bromo-2,5-dimethoxyphenethylamine 4-bromo-2,5-dimethoxyphenethylamine.jpg
1000mg of 4-bromo-2,5-dimethoxyphenethylamine

2C-B was used as entheogen by the Sangoma, Nyanga, and Amagqirha people in place of their traditional plants; they refer to the chemical as Ubulawu Nomathotholo, which roughly translates to "Medicine of the Singing Ancestors". [35] [36] [37]

Reagent results

Exposing compounds to the reagents gives a colour change which is indicative of the compound under test.

MarquisMeckeMandelinLiebermannFroehdeRobadope
Yellow to greenYellow to olive brownishgreenYellow to blackYellow to greenSlow pink
EhrlichHofmannSimon'sScottFolin
No reactionNo reactionNo reactionNo reaction(Light) purple

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. [38]

2C-B is a scheduled drug in most jurisdictions. [39] The following is a partial list of territories where the substance has been scheduled.

Countries

Argentina

2C-B is controlled under the List 1, as well as similar substances like 2C-I or 2C-T-2. [40]

Australia

2C-B is controlled in Australia and on the list of substances subject to import and export controls (Appendix B). It was 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. Alexander Shulgin came to Australia to testify on behalf of the defense, to no avail.

2C-B is not specifically listed in the Australia Poisons Standard (October 2015), however similar drugs such as 2C-T-2 and 2C-I are making 2C-B fall under the Australian analogue act. [41]

Belgium

In Belgium, 2C-B is a controlled substance making production, distribution, and possession illegal.

Brazil

In Brazil, 2C-B is a controlled substance making production, distribution, and possession illegal.

Canada

In Canada, 2C-B is classified under Controlled Drugs and Substances Act as Schedule III as "4-bromo-2,5-dimethoxybenzeneethanamine and any salt, isomer or salt of isomer thereof". [42]

2C-B has been rescheduled (Schedule III), in a new amendment, taking effect on October 31, 2016. This is to include the other 2C-x analogues. [43]

Chile

In August 2007, 2C-B, along with many other psychologically active substances, [44] was added to Ley 20.000, known as the Ley de Drogas  [ es ].

Czech Republic

Possession of more than 200 mg of 2C-B is punishable with a two years jail sentence. [45] Smaller amount is punishable by a fine. The 200 mg threshold is merely a guideline which the court can reconsider depending on circumstances.

Denmark

In Denmark, 2C-B is listed as a category B drug. [46]

Estonia

In Estonia, 2C-B is classified as Schedule I.

Germany

In Germany, 2C-B is controlled in the Betäubungsmittelgesetz (BtMG) Anlage I as "Bromdimethoxyphenethylamin" (BDMPEA).

Italy

2C-B is schedule I (tabella I). [47]

Japan

In Japan, 2C-B was scheduled in 1998. It was previously marketed as "Performax".

Luxembourg

In Luxembourg, 2C-B is a prohibited substance since 2001. [48]

Netherlands

In the Netherlands, 2C-B was scheduled on July 9, 1997.

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.

Norway

In Norway, 2C-B was classified as Schedule II on March 22, 2004, listed as 4-bromo-2,5-dimethoxyphenethylamine. [49]

Poland

2C-B is schedule I (I-P group) in Poland.

Russia

Banned as a narcotic drug with a criminal penalty for possession of at least 10 mg. [50]

Spain

In Spain, 2C-B was added to Category 2 prohibited substances in 2002.

Sweden

2C-B is currently classified as Schedule I in Sweden.

2C-B was first classified as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor  [ sv ] (Act on the Prohibition of Certain Goods Dangerous to Health) as of April 1, 1999, under SFS 1999:58 [51] that made it illegal to sell or possess. Then it became schedule I as of June 1, 2002, published in LVFS 2002:4 [52] but mislabeled "2-CB" in the document. However, this was corrected in a new document, LVFS 2009:22 [53] effective December 9, 2009.

Switzerland

In Switzerland, 2C-B is listed in Anhang D of the DetMV and is illegal to possess. [54]

UK

All drugs in the 2C family are Class A under the 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. [55]

United States

In the United States, 2C-B is classified as CSA Schedule I Section (d) Subsection (3) 4-Bromo-2,5-dimethoxyphenethylamine.

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 (DEA) proposed to place 4-bromo-2,5-DMPEA into Schedule I, making 2C-B illegal in the United States. [56] This became permanent law on July 2, 1995. [57]

Related Research Articles

<span class="mw-page-title-main">2C-I</span> Chemical compound

2C-I (2,5-Dimethoxy-4-iodophenethylamine) is a phenethylamine of the 2C family with psychedelic properties. It was first synthesized by Alexander Shulgin and described in his 1991 book PiHKAL. The drug has been used recreationally as psychedelic and other reported effects and was sometimes confused with the more potent chemical cousin 25I-NBOMe, nicknamed "Smiles," in the media.

<span class="mw-page-title-main">2C-T-7</span> Psychedelic phenthylamine drug

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 10–30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic effects that last 8 to 15 hours. Up until Operation Web Tryp and three deaths, two of which involved the use of other drugs in addition to 2C-T-7, and one which involved an excessive insufflated dose, 2C-T-7 was sold commercially in Dutch and Japanese smartshops and online. It is known on the streets as Blue Mystic or 7th Heaven. There has been little real research done on this chemical other than Shulgin's comments in PiHKAL and a few small animal studies mostly aimed at detecting metabolites.

<span class="mw-page-title-main">2C-C</span> Chemical compound

2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. In his book PiHKAL , Shulgin lists the dosage range as 20–40 mg. 2C-C is usually taken orally, but may also be insufflated. 2C-C is schedule I of section 202(c) of the Controlled Substances Act in the United States, signed into law as of July, 2012 under the Food and Drug Administration Safety and Innovation Act.

<span class="mw-page-title-main">2C-D</span> Chemical compound

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. In his book PiHKAL, Shulgin lists the dosage range as being from 20 to 60 mg. Lower doses of 10 mg or less have been explored for microdosing.

<span class="mw-page-title-main">2C-T-21</span> Psychedelic phenethylamine drug

2C-T-21 is a psychedelic phenethylamine of the 2C family sometimes used as an entheogen. It was first synthesized by Alexander Shulgin.

<span class="mw-page-title-main">2,5-Dimethoxy-4-methylamphetamine</span> Chemical compound

2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine. It was first synthesized by Alexander Shulgin, and later reported in his book PiHKAL: A Chemical Love Story. DOM is classified as a Schedule I substance in the United States, and is similarly controlled in other parts of the world. Internationally, it is a Schedule I drug under the Convention on Psychotropic Substances. It is generally taken orally.

<span class="mw-page-title-main">2,5-Dimethoxy-4-bromoamphetamine</span> Chemical compound

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INN) and bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967. Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.

<span class="mw-page-title-main">2C-T-8</span> Chemical compound

2C-T-8 is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen.

<span class="mw-page-title-main">2,5-Dimethoxy-4-iodoamphetamine</span> Chemical compound

2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine. Unlike many other substituted amphetamines, however, it is not primarily a stimulant. DOI has a stereocenter and R-(−)-DOI is the more active stereoisomer. In neuroscience research, [125I]-R-(−)-DOI is used as a radioligand and indicator of the presence of 5-HT2A serotonin receptors. DOI's effects have been compared to LSD, although there are differences that experienced users can distinguish. Besides the longer duration, the trip tends to be more energetic than an LSD trip, with more body load and a different subjective visual experience. The after effects include residual stimulation and difficulty sleeping, which, depending on the dose, may persist for days. While rare, it is sometimes sold as a substitute for LSD, or even sold falsely as LSD, which may be dangerous because DOI does not have the same established safety profile as LSD.

<span class="mw-page-title-main">2C-B-FLY</span> Psychedelic designer drug

2C-BFLY is a psychedelic phenethylamine and designer drug of the 2C family. It was first synthesized in 1996 by Aaron Monte, Professor of Chemistry at UW-La Crosse.

<span class="mw-page-title-main">25I-NBOMe</span> Synthetic hallucinogen

25I-NBOMe is a novel synthetic psychoactive substance with strong hallucinogenic properties, synthesized in 2003 for research purposes. Since 2010, it has circulated in the recreational drug scene, often misrepresented as LSD. The recreational usage of 25I is associated with severe intoxication and deaths in humans.

<span class="mw-page-title-main">2CBCB-NBOMe</span> Chemical compound

2CBCB-NBOMe (NBOMe-TCB-2) is a compound indirectly derived from the phenethylamine series of hallucinogens, which was discovered in 2007 at Purdue University as part of the ongoing research program of the team led by David Nichols focusing on the mapping of the specific amino acid residues responsible for ligand binding to the 5HT2A receptor. 2CBCB-NBOMe acts as a potent and selective agonist for the 5-HT2A and 5-HT2C receptors, with a Ki of 0.27 nM at the human 5-HT2A receptor, a similar potency to other agonists such as TCB-2, NBOMe-2C-I and Bromo-DragonFLY.

<span class="mw-page-title-main">2CBFly-NBOMe</span> Chemical compound

2CBFly-NBOMe is a compound indirectly derived from the phenethylamine hallucinogen 2C-B, and related to benzodifurans like 2C-B-FLY and N-benzylphenethylamines like 25I-NBOMe. It was discovered in 2002, and further researched by Ralf Heim at the Free University of Berlin, and subsequently investigated in more detail by a team at Purdue University led by David E. Nichols. It acts as a potent partial agonist for the 5-HT2A serotonin receptor subtype.

<span class="mw-page-title-main">25B-NBOMe</span> Chemical compound

25B-NBOMe is a derivative of the phenethylamine psychedelic 2C-B, discovered in 2004 by Ralf Heim at the Free University of Berlin. It acts as a potent full agonist for the 5HT2A receptor. Anecdotal reports from users suggest 25B-NBOMe to be an active hallucinogen at a dose of as little as 250–500 μg, making it a similar potency to other phenethylamine derived hallucinogens such as Bromo-DragonFLY. Duration of effects lasts about 12–16 hours, although the parent compound is rapidly cleared from the blood when used in the radiolabeled form in tracer doses. Recently, Custodio et al. (2019) evaluated the potential involvement of dysregulated dopaminergic system, neuroadaptation, and brain wave changes which may contribute to the rewarding and reinforcing properties of 25B-NBOMe in rodents.

<span class="mw-page-title-main">2CB-Ind</span> Chemical compound

2CB-Ind is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, discovered in 1974 by Alexander Shulgin. It acts as a moderately potent and selective agonist for the 5-HT2A and 5-HT2C receptors, but unlike the corresponding benzocyclobutene derivative TCB-2 which is considerably more potent than the parent compound 2C-B, 2CB-Ind is several times weaker, with racemic 2CB-Ind having a Ki of 47nM at the human 5-HT2A receptor, only slightly more potent than the mescaline analogue (R)-jimscaline.

<span class="mw-page-title-main">25C-NBOMe</span> Psychedelic drug

25C-NBOMe is a psychedelic drug and derivative of the psychedelic phenethylamine 2C-C. 25C-NBOMe appeared on online vendor sites in 2010 but was not reported in the literature until 2011. It acts as a potent agonist of the 5-HT2A receptor, and has been studied in its 11C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET). Multiple deaths have occurred from usage of 25C-NBOMe due to the ease of accidental overdose. The long-term toxic effects of the drug have not been researched.

<span class="mw-page-title-main">25B-NBOH</span> Chemical compound

25B-NBOH is a derivative of the phenethylamine derived hallucinogen 2C-B which has been sold as a designer drug. It acts as a potent serotonin receptor agonist with similar affinity to the better-known compound 25B-NBOMe at 5-HT2A and 5-HT2C receptors with pKis values of 8.3 and 9.4, respectively.

<span class="mw-page-title-main">2C-B-BUTTERFLY</span> Chemical compound

2C-B-BUTTERFLY is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, which was discovered in 1999 by Michael S. Whiteside and Aaron Monte. It is a ring-expanded homologue of the better known compound 2C-B-FLY, and has similar properties as an agonist for serotonin receptors, but with more selectivity for 5-HT2C over 5-HT2A.

<span class="mw-page-title-main">25B-NBF</span> Chemical compound

25B-NBF is a derivative of the phenethylamine hallucinogen 2C-B, which acts as a highly potent partial agonist for the human 5-HT2A receptor.

<span class="mw-page-title-main">25G-NBOMe</span> Chemical compound

25G-NBOMe (NBOMe-2C-G) is a derivative of the phenethylamine hallucinogen 2C-G, which acts as a highly potent agonist for the human 5-HT2A receptor.

References

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  24. ↑ "Erowid 2C-B Vault : FAQ v1.0". erowid.org.
  25. 1 2 Moya PR, Berg KA, Gutiérrez-Hernandez MA, Sáez-Briones P, Reyes-Parada M, Cassels BK, Clarke WP (June 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. CiteSeerX   10.1.1.690.3752 . doi:10.1124/jpet.106.117507. PMID   17337633. S2CID   11651502.
  26. ↑ Villalobos CA, Bull P, Sáez P, Cassels BK, Huidobro-Toro JP (April 2004). "4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 4-HT2A receptor antagonists in Xenopus laevis oocytes". British Journal of Pharmacology. 141 (7): 1167–74. doi:10.1038/sj.bjp.0705722. PMC   1574890 . PMID   15006903.
  27. ↑ Páleníček T, Fujáková M, et al. (January 2013). "Behavioral, neurochemical and pharmaco-EEG profiles of the psychedelic drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in rats". Psychopharmacology. 225 (1): 75–93. doi:10.1007/s00213-012-2797-7. PMID   22842791. S2CID   10771354.
  28. ↑ Muehlenkamp F, Lucion A, Vogel WH (April 1995). "Effects of selective serotonergic agonists on aggressive behavior in rats". Pharmacology Biochemistry and Behavior. 50 (4): 671–4. doi:10.1016/0091-3057(95)00351-7. PMID   7617717. S2CID   12774131.
  29. ↑ "Explore N-(2C-B)-Fentanyl | PiHKAL · info". isomerdesign.com.
  30. ↑ "Explore N-(2C-FLY)-Fentanyl | PiHKAL · info". isomerdesign.com.
  31. ↑ Glennon, Richard A.; Bondarev, Mikhail L.; Khorana, Nantaka; Young, Richard; May, Jesse A.; Hellberg, Mark R.; McLaughlin, Marsha A.; Sharif, Najam A. (November 2004). "β-Oxygenated Analogues of the 5-HT2ASerotonin Receptor Agonist 1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–6041. doi:10.1021/jm040082s. ISSN   0022-2623. PMID   15537358.
  32. ↑ Beta-hydroxyphenylalkylamines and their use for treating glaucoma
  33. ↑ Glennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, King A, Herrick-Davis K (June 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.
  34. ↑ Heim R (March 19, 2004). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur: Entwicklung eines neuen Struktur-Wirkungskonzepts [Synthesis and pharmacology of potent 5-HT2A receptor agonists which have a partial N-2-methoxybenzyl structure: Development of a new structure-activity concept] (Thesis) (in German). Free University of Berlin . Retrieved August 1, 2014.
  35. ↑ "2CB chosen over traditional entheogen's by South African healers". Tacethno.com. 2008-03-27. Retrieved May 15, 2012.
  36. ↑ The Nexus Factor - An Introduction to 2C-B Erowid
  37. ↑ Ubulawu Nomathotholo Pack Photo by Erowid. © 2002 Erowid.org
  38. ↑ "List of psychotropic substances under international control" (PDF). Green List (23rd ed.). International Narcotics Control Board. August 2003. Archived from the original (PDF) on 2 March 2007.
  39. ↑ "Erowid 2C-B page".
  40. ↑ "Last Argentina Controlled Drugs List" (PDF). Retrieved May 15, 2012.
  41. ↑ Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534
  42. ↑ "CDSA Schedule II". Archived from the original on 2020-07-25. Retrieved 2008-06-13.
  43. ↑ "Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". Canada Gazette. Government of Canada, Public Works and Government Services Canada, Public Services and Procurement Canada, Integrated Services Branch, Canada. 2016-05-04.
  44. ↑ "APRUEBA REGLAMENTO DE LA LEY Nº 20.000 QUE SANCIONA EL TRÁFICO ILÍCITO DE ESTUPEFACIENTES Y SUSTANCIAS SICOTRÓPICAS Y SUSTITUYE LA LEY Nº 19.366" (PDF).
  45. ↑ "Erowid Psychoactive Vaults : Drug Laws : Czech Republic". erowid.org.
  46. ↑ "Bekendtgørelse om euforiserende stoffer" (in Danish). 2008-07-01. Retrieved 2013-10-01.
  47. ↑ "Italy Drug Schedule (Tabella I)". Archived from the original on 2011-06-27.
  48. ↑ Règlement grand-ducal du 14 décembre 2001 modifiant l'annexe du règlement grand-ducal modifié du 4 mars 1974 concernant certaines substances toxiques.
  49. ↑ "Norway Drug Schedule".
  50. ↑ "Постановление Правительства РФ от 01.10.2012 N 1002 "Об утверждении значительного, крупного и особо крупного размеров наркотических средств и психотропных веществ, а также значительного, крупного и особо крупного размеров для растений, содержащих наркотические средства или психотропные вещества, либо их частей, содержащих наркотические средства или психотропные вещества, для целей статей 228, 228.1, 229 и 229.1 Уголовного кодекса Российской Федерации" (с изменениями и дополнениями)". base.garant.ru.
  51. ↑ "Förordning (1999:58) om förbud mot vissa hälsofarliga varo" (in Swedish). 1999-02-25. Archived from the original on 2013-10-04. Retrieved 2013-10-01.
  52. ↑ "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997:12) om förteckningar över narkotika: LVFS 2002:4" (PDF) (in Swedish). Archived from the original (PDF) on 2013-10-04. Retrieved 2013-09-14.
  53. ↑ "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997:12) om förteckningar över narkotika: LVFS 2009:22" (PDF) (in Swedish). Archived from the original (PDF) on 2018-09-16. Retrieved 2013-09-14.
  54. ↑ "Verzeichnis aller betäubungsmittelhaltigen Stoffe" [Directory of all narcotics-containing substances]. Swissmedic (in German). Swiss Agency for Therapeutic Products. 2011-08-18. p. 2. Archived from the original (PDF) on 2012-03-15. Retrieved 2013-11-30.
  55. ↑ "BBC - Advice - 2CB". BBC . Retrieved 2013-10-01.
  56. ↑ "Schedules of Controlled Substances; Proposed Placement of 4-bromo-2,5-dimethoxyphenethylamine into Schedule I" (PDF). Federal Register. 59 (243): 65521. 20 December 1994. Retrieved 2013-09-26.
  57. ↑ "Erowid 2C-B Vault : DEA Ruling on Scheduling". erowid.org. Retrieved 2021-07-25.
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