In his bookPiHKAL (Phenethylamines I Have Known and Loved) and other publications,Alexander Shulgin lists 2C-B's dose range as 12 to 24mgorally and itsduration as 4 to 8hours.[1][30][31] However, in an earlier report, he described an effective dose range of 8 to 10mg orally and a duration of 6 to 8hours.[18][5] Threshold effects occur at a dose of 4mg orally.[18][32] A widerrecreational dose range of 2 to 55mg or more orally has been described as well, with a typical dose estimate of about 20mg.[33][34][2][5][16][9][6] A low dose has been said to be 5 to 15mg, a moderate dose 10 to 25mg, and a high or strong dose 20 to 50mg.[2][8][3] Most people use doses of 20mg or lower.[5] Shulgin and others describe 2C-B as having a steepdose–response curve, such that a small increase in dose can result in an unexpectedly large increase in effects.[1][19][32] Over the 12 to 24mg dose range, every 2mg increment can result in a profound increase or change in effects.[1] Higher doses are said to lead to more intense but not longer-lasting effects.[32] The drug'sonset is about 1.2hours, with a range of 0.3 to 1.5hours, and its time to peak effects is about 2.5hours on average.[5][2][7] Effects on average last about 6hours and are slightly shorter than those ofpsilocybin.[5][8][9] In addition tooral administration, 2C-B may beinsufflated less commonly, with doses being approximately one-third of those of the oral route or in the range of 10 to 30mg and with this route producing more rapid and intense of effects.[2][5][3][6]
The effects of 2C-B were reported by Shulgin to includesensory enhancement, brightened colors, visual richness,mental imagery,psychedelic visuals including kaleidoscopic and organic forms, sound distortion, increased appreciation ofart andmusic,passivity,relaxation,emotional changes,euphoria, increased body awareness,tactile enhancement, feeling like waves of energy are flowing through oneself, feeling like one's body is flooded withorgasms, andsexual enhancement.[1][18][35][36] He has succinctly described 2C-B as having "a luxury of sensory enhancement (visual, sexual, gustatory) with a minimum of introspective demands".[37] The drug was one of his favorite psychedelics.[36] At doses of 8 to 10mg, 2C-B was described as consistently producing substantial sensory enhancement, but as not "superimposing hallucinogenesis" or as having "nohallucinogenic effects", with the state being described as quite distinct from that usually associated with psychedelics.[18][5] It was also said to lack thelassitude that can be associated with psilocybin.[18]
In published reports by other authors, 2C-B has been claimed to produce effects including visual,auditory, andtactile perceptual changes,closed-eyeimagery,LSD-like visuals such as colors and geometric shapes,time dilation,MDMA-likestimulant andentactogenic effects, such as being more in touch with emotions, as well as feelings oflove, enhancedsociability, andempathy, feelings of peace andwell-being,euphoria, a "body high", increased sensitivity to touch, touch feeling pleasurable, and being erotic.[19][6][38][5] The presence of entactogenic effects with 2C-B is said to be unique among most psychedelics, along with certain other atypical psychedelics like5-MeO-DiPT and5-MeO-MiPT.[15][17][16][19] 2C-B's effects are often described as being milder and more easily managed than other psychedelics.[19][6][5][3] For example, it is said to be less incapacitating or impairing, "non-ego-threatening", not "mentally challenging" or confusing, not leading to an "extreme headspace", and leaving the mind "very clear".[19][5] In addition, it is said to produce changes in thought and time perception less frequently.[5] Due to its potential for relatively light effects, the drug has been referred to as the "Diet Coke of psychedelics" or as a "beginner psychedelic".[19] Nonetheless, it has been described as quite visual, with the potential for all of the visuals of LSD but without the head space that LSD and psilocybin produce.[19] However, the visuals are dose-dependent, being mild at lower doses and being more substantial and LSD-like at higher doses.[19] 2C-B is often compared to a mixture of LSD and MDMA or a "candyflip".[19][5] However, it is described as a "clear-headed candyflip", with entactogenic-like effects, LSD-like effects such as visuals, but a very clear head space.[19] In addition, it is said to not have the same kind of forceful positive mood push that MDMA has, and to be a little more unpredictable and capable of causingbad trips or negative head spaces.[19] 2C-B is said to be more of a "party drug", to be morerecreational, and to have less likelihood of challenging, emotional-breakthrough, ormystical-type experiences, relative to psychedelics like psilocybin and LSD.[38][5]
Formalclinical studies have found that 2C-B produces a mixture of psychedelic, some possible entactogen-like, and some stimulant effects.[16][8][9] Specific effects in these studies have included slight hallucinogenic states, perceptual changes,ego dissolution, time dilation, increasedcreativity, stimulation, vigor, happiness or elation, euphoria, feelings of well-being, reducedanger, enhanced sociability and friendliness, increased reactivity tonegative emotional stimuli, decreased ability to recognize expressions ofhappiness, augmentedemotionality in speech,tenseness,confusion, and mildsympathomimetic effects such aspressor effects, among others.[16][8][9] Findings on the entactogen-like effects of 2C-B have been mixed, with some studies reporting that it produces such effects[5][16] but other studies finding no such effects similarly to psilocybin.[9] However, in other research, both psilocybin and MDMA have been found to increaseemotional empathy.[9] Compared to psilocybin in adouble-blind,placebo-controlledclinical trial, 2C-B produced fewer negative mood effects, greater positive mood effects, less intense hallucinogenic effects including overallaltered consciousness,oceanic boundlessness,ego dissolution, experiential depth, and time dilation, and lesscognitive impairment.[9] Conversely, their effects in terms of visual changes and enhanced body perception were equivalent.[9] Besides having more positively valenced mood effects than psilocybin, 2C-B produced MDMA-like positive mood effects with little in the way of negative mood effects.[9] It was concluded that in line withanecdotal reports, 2C-B is non-ego-threatening, lacks the more serious head space of other psychedelics, and has a greater emphasis on visual and tactile changes.[9] It was also remarked that 2C-B may be a more optimal psychedelic for people afraid of thepsychedelic experience or at greater risk for negative experiences such as due to highneuroticism, with this applicable for instance in the context ofpsychedelic-assisted psychotherapy.[9]
2C-B tablets often contain a dose of 5 or 10mg of the drug.[2][8] Low doses of 2C-B like 5 to 10mg orally are said to produce stimulation, entactogen-like effects, and perceptual enhancement, while higher doses like 10 to 20mg orally are said to produce psychedelic and hallucinogenic effects.[7][39][12][3] 2C-B is frequently used at low doses as a substitute for MDMA.[38] It is often used by people who go to electronic music festivals, also known asraves.[38][6] The drug is also frequently used at clubs and parties, at home, or in nature.[5] 2C-B is often combined with other drugs, such as MDMA,alcohol, andcannabis.[5] Besides recreational use, 2C-B has been used in psychedelic-assisted psychotherapy at doses of 15 to 30mg orally.[40]
Severeadverse reactions are rare, but use of 2C-B was linked to significantbrain injury in onecase 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.[41] In a later case report of unknown dose, 2C-B causedserotonin syndrome,seizures, severebrain edema, and severe and long-lastingneurological impairment.[7] There is a case report of acquiredsynesthesia following a single very high dose of 2C-B.[42] There is also a case report of persistentpsychosis following a single dose of 2C-B.[43]
2C-B acts as apotentpartial agonist of theserotonin5-HT2 receptors, including of the serotonin5-HT2A and5-HT2C receptors and to a lesser extent of the serotonin5-HT2B receptor.[20][21][22] In one study, it hadEC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy) values of 1.2nM (101%) at the serotonin 5-HT2A receptor, 13nM (97%) at the serotonin 5-HT2B receptor, and 0.63nM (98%) at the serotonin 5-HT2C receptor.[20] In earlier studies, 2C-B was found to be a low-efficacy serotonin 5-HT2A and 5-HT2C receptor partial agonist or even antagonist.[63][64][3] However, subsequent studies have consistently found higher efficacy of 2C-B at these receptors.[20][21][22] In addition to the serotonin 5-HT2 receptors, 2C-B also shows lower affinity for otherserotonin receptors, such as the serotonin5-HT1A and5-HT1B receptors among others.[22][21][3] However, while 2C-B itself was not assessed, other 2C derivatives showed little activity as serotonin 5-HT1A receptor agonists (EC50 = >3,000nM).[65]
2C-B produces thehead-twitch response, a behavioral proxy of psychedelic effects, in rodents.[20] It also shows potent and efficaciousanti-inflammatory effects in preclinical research.[71]
2C-B appears to have relatively loworalbioavailability.[9] With 30mg 2C-B by orally, itspeak concentrations (mean ± SD) were 5.4ng/mL and itstime to peak concentrations was 2.3hours.[10] In another study, with 20mg 2C-B orally, peak levels were 3.31ng/mL and time to peak levels was 2.43hours.[9]
2C-B appears to undergo substantialfirst-pass metabolism.[9] It has been shown to bemetabolized byliverhepatocytes, resulting indeamination anddemethylation that produces severalproducts.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 byoxidative 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.[49] Deamination of 2C-B is mediated by themonoamine oxidase (MAO)enzymesMAO-A andMAO-B.[4][50][10]
There is species differentiation in the metabolism of 2C-B.[49] Mice hepatocytes produce 4-bromo-2,5-dimethoxyphenol (BDMP), a previously unknown metabolite.[49] 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.[49]
2C-B's metabolites BDMPAA and 4-bromo-2-hydroxy-5-methoxyphenylacetic acid (B-2-HMPAA) in humans occur at peak concentrations 280-fold and 17-fold higher than those of 2C-B withoral administration of 2C-B, respectively.[10]
A variety ofN-substituted derivatives of 2C-B have been tested, includingN-methyl-2C-B,N,N-dimethyl-2C-B,N-ethyl-2C-B andN-benzyl-2C-B.[72] Most simplealkyl derivatives were considerably lesspotent than 2C-B, withN-ethyl-2C-B for instance having a 40times loweraffinity for theserotonin5-HT2A receptor.[72] TheN-benzyl derivative however was found to have higher affinity than 2C-B itself, withN-(4-bromobenzyl)-2C-B binding even more tightly.[72] This initial research did not includefunctional assays of activity, but later led to the development of potent substitutedN-benzyl derivatives such as25B-NBOMe,[73] and25B-NBOH. AnotherN-substituted derivative,2C-B-AN, is anN-benzylphenethylamine-likeprodrug of 2C-B.[24][74][75]
2C-B has been said to have been legally sold inSouthern Africa from 1993 to 1996 and used as anentheogen by theSangoma,Nyanga, andAmagqirha people in place of their traditional plants; they refer to the chemical asUbulawu Nomathotholo, which roughly translates to "Medicine of the Singing Ancestors".[83][84][85]
The drug became acontrolled substance in the United States in 1994.[26][26][4][12][13] It also became a controlled substance in most other countries in the mid-1990s.[5] In addition, 2C-B was placed inSchedule II of theUnited NationsConvention on Psychotropic Substances and hence became an internationally controlled substance in 2001.[3][8] Following 2C-B's restriction, other 2C psychedelics emerged as designer drugs.[4] Nonetheless, 2C-B is the most popular of the 2C psychedelics.[12][13][19][6] Numerous other 2C drugs besides 2C-B have also been made controlled substances.[13] Besides other 2Cs,derivatives of 2C-B such as2C-B-FLY and25B-NBOMe have been developed and emerged as well-known novel designer drugs.[1][23][24]
Brand names and street names of 2C-B include Nexus, Venus, Bromo, Erox, Perfomax, Bees, Toonies, Spectrum, XTC, and Synergy, among others.[4][12][2][86]
Street purity of 2C-B, when tested, has been found to be relatively high.[2] 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".[5] An analysis of street samples in the Netherlands found impurities "in small percentages"; only one of the impurities, theN-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.[39]
In 2011, street prices in the United States ranged between $10 and $30 per tablet when purchased in small quantities.[86] 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 thedarknet in 2020).[87]
2C-B is controlled inAustralia 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 AustraliaPoisons Standard (October 2015), however similar drugs such as2C-T-2 and2C-I are making 2C-B fall under the Australian analogue act.[91]
InCanada, 2C-B is classified underControlled Drugs and Substances Act as Schedule III as "4-bromo-2,5-dimethoxybenzeneethanamine and any salt, isomer or salt of isomer thereof".[92]
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.[93]
Possession of more than 200mg of 2C-B is punishable with a two years jail sentence.[95] Smaller amount is punishable by a fine. The 200mg threshold is merely a guideline which the court can reconsider depending on circumstances.
In theNetherlands, 2C-B was scheduled on July 9, 1997.
In the Netherlands, 2C-B became a list I substance of theOpium 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 ban2C-I,2C-T-2 and2C-T-7 alongside 2C-B.
2C-B is currently classified as Schedule I inSweden.
2C-B was first classified as "health hazard" under the actLagen om förbud mot vissa hälsofarliga varorcode: swe promoted to code: sv (Act on the Prohibition of Certain Goods Dangerous to Health) as of April 1, 1999, under SFS 1999:58[102] that made it illegal to sell or possess. Then it became schedule I as of June 1, 2002, published in LVFS 2002:4[103] but mislabeled "2-CB" in the document. However, this was corrected in a new document, LVFS 2009:22[104] effective December 9, 2009.
All drugs in the 2C family are Class A under theMisuse 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.[106]
In the United States, 2C-B is classified as aSchedule I controlled substance. This became permanent law on June 2, 1995,[107] following a proposal by theDrug Enforcement Administration in December 1994.[108]
^abcdefghijklmCole MD, Lea C, Oxley N (2002)."4-Bromo-2,5-dimethoxyphenethylamine (2C-B): a review of the public domain literature"(PDF).Sci Justice.42 (4):223–224.doi:10.1016/S1355-0306(02)71832-7.PMID12632938.2C-B gained popularity during the mid 1980s as a replacement of choice for LSD and psilocybin [4]. It is encountered by the forensic scientist in powdered and tablet forms. It may be consumed orally, in tablets which typically contain 5 mg, in doses of between 10 and 50 mg. A light dose is considered to be 5–15 mg, a strong dose 20–50 mg [5]. Following an onset period of 20–90 minutes, the effects may last for two to five hours and after-effects may last between two and four hours. It may also be insufflated in powdered form, the doses for this route of administration being approximately one third of the oral dose.
^abcdefghijklmnopqrsNugteren-van Lonkhuyzen JJ, van Riel AJ, Brunt TM, Hondebrink L (December 2015). "Pharmacokinetics, pharmacodynamics and toxicology of new psychoactive substances (NPS): 2C-B, 4-fluoroamphetamine and benzofurans".Drug Alcohol Depend.157:18–27.doi:10.1016/j.drugalcdep.2015.10.011.PMID26530501.Nasal insufflation is rarely practiced, but it produces more rapid and intense effects than oral exposure (Caudevilla-Gálligo et al., 2012; Dean et al., 2013). [...] 2CB was first synthesized in the 1970s for psychotherapeutic use (Shulgin and Carter, 1975; Shulgin and Shulgin, 1991), but was abandoned due to significant gastrointestinal effects and the lack of empathogenic effects (Dean et al., 2013). [...]
^abcdefghijklmnopqDean BV, Stellpflug SJ, Burnett AM, Engebretsen KM (June 2013)."2C or not 2C: phenethylamine designer drug review".J Med Toxicol.9 (2):172–178.doi:10.1007/s13181-013-0295-x.PMC3657019.PMID23494844.In 1974, 4-bromo-2,5-dimethoxyphenethylamine (2C-B), the first of the 2Cs, was synthesized by Alexander Shulgin as he was exploring homologs from 2,5-dimethoxy-4-bromoamphetamine [3]. 2C-B was manufactured in the 1980s and early 1990s under the names Nexus, Erox, Performax, Toonies, Bromo, Spectrum, and Venus and marketed as MDMA's replacement after MDMA became scheduled in the USA [6, 7]. 2C-B was initially intended for psychotherapy use due to its short 1-h duration of action [3]. Due to 2C-B's significant gastrointestinal effects and lack of empathogenic effects as compared to MDMA, it rapidly fell out of favor for psychotherapy. In 1995, 2C-B was placed on Schedule I of the Controlled Substances Act by the Drug Enforcement Agency (DEA) [6, 7]. However, following the scheduling of 2C-B, other 2C analogues were made available by suppliers as legal alternatives [8].
^abcdefghijklmnopqrstuvwxyzaaabCaudevilla-Gálligo F, Riba J, Ventura M, González D, Farré M, Barbanoj MJ, et al. (July 2012)."4-Bromo-2,5-dimethoxyphenethylamine (2C-B): presence in the recreational drug market in Spain, pattern of use and subjective effects"(PDF).Journal of Psychopharmacology.26 (7):1026–1035.doi:10.1177/0269881111431752.PMID22234927.S2CID35535891.4-Bromo-2,5-dimethoxyphenethylamine (2C-B, Nexus, Afro) is one of these synthetic drugs. At the chemical level, 2C-B is structurally related to mescaline and was first synthesized in the mid-1970s (Shulgin and Carter, 1975). It gained certain popularity as a legal substitute for MDMA after its prohibition in 1985 (Bouso et al., 2008). In some European countries 2C-B was legally sold as an aphrodisiac under the brand names Nexus, Erox and Performax in stores specialized in psychoactive products, the so-called smart shops (US Department of Justice, 2001). [...] To date, very little scientific research has been conducted on 2C-B. The drug is known to be orally active and its effects are mediated by its action as a partial 5-HT2A and 5-HT2C receptor agonist. In addition, 2C-B is a substrate and an inhibitor of the serotonin transporter (SERT) (McLean et al., 2006; Montgomery et al., 2007). Regarding its psychotropic properties, 2C-B has been reported to induce 'perceptual enhancement' and euphoria at doses of 8–10mg but to lack hallucinogenic or psychotomimetic effects (Shulgin and Carter, 1975). These authors also stated that the effects last 6–8h and that they are milder than those of classical psychedelics such as lysergic acid diethylamide (LSD).
^abcdefghiMallaroni P, Mason NL, Vinckenbosch FR, Ramaekers JG (June 2022)."The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides".Psychopharmacology (Berl).239 (6):1783–1796.doi:10.1007/s00213-022-06142-4.PMC9166850.PMID35487983.Entheogenic features such as oceanic boundlessness and dread of ego dissolution were rated significantly less for 2C-B than for 4-AcO-DMT and 1P-LSD. Characterised as an entactogen with psychedelic-like effects, observational studies have demonstrated 2C-B only produces mild psychedelic effects. As with other entactogens such as 2C-E, 4-FA and MDMA, its effects are limited to perceptual alterations and pseudohallucinations (Papaseit et al. 2018; Kuypers et al. 2019; Papaseit et al. 2020; Studerus et al. 2021). These descriptions may be exemplified by the absence of dose-dependent effects, endorsement of euphoria as a motivation by 49% of users and its reiterated use at music events (Palamar et al. 2016a, b). Consequently, that what distinguishes certain phenethylamines from tryptamines and lysergamides may not be a question of experience quality, but rather depth.
^abcdSpoelder AS, Louwerens JK, Krens SD, Jager N, LeCouffe NE, de Ruijter W, et al. (November 2019)."Unexpected Serotonin Syndrome, Epileptic Seizures, and Cerebral Edema Following 2,5-dimethoxy-4-bromophenethylamine Ingestion".J Forensic Sci.64 (6):1950–1952.doi:10.1111/1556-4029.14214.PMC6900031.PMID31643086.In low doses, it produces enhanced sensory sensitivity and has stimulating effects similar to those of 3,4-methylenedioxymethamphetamine (MDMA) or "ecstasy." In higher doses, the psychedelic and hallucinogenic effects predominate. [...] After oral ingestion of 10–30 mg 2C-B, the onset of the effect is seen within 30–75 min and generally lasts 4–8 h (6,9). 2C-B displays a dose-response curve with lower doses resulting in stimulating effects with increased visual, auditory and tactile sensations, whereas in higher doses, the hallucinogenic effects prevail (1,10).
^abcdefghijklmnopqrstuvMallaroni P, Mason NL, Reckweg JT, Paci R, Ritscher S, Toennes SW, et al. (August 2023). "Assessment of the Acute Effects of 2C-B vs. Psilocybin on Subjective Experience, Mood, and Cognition".Clin Pharmacol Ther.114 (2):423–433.doi:10.1002/cpt.2958.PMID37253161.
^abcdefghijklmnoWills B, Erickson T (9 March 2012). "Psychoactive Phenethylamine, Piperazine, and Pyrrolidinophenone Derivatives". In Barceloux DG (ed.).Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants. Wiley. pp. 156–192.doi:10.1002/9781118105955.ch10.ISBN978-0-471-72760-6.DOSE EFFECT: Anecdotal data suggests that recreational doses of 2C-B range from 4—30 mg with lower doses (4—10 mg) producing entactogenic effects, whereas high doses (10— 20 mg) cause psychedelic and sympathomimetic effects.
^abVarì MR, Pichini S, Giorgetti R, Busardò FP (2019)."New psychoactive substances—Synthetic stimulants".WIREs Forensic Science.1 (2) e1197.doi:10.1002/wfs2.1197.ISSN2573-9468.In addition, simple variations of mescaline (a natural phenylethylamine occurring in the peyote cactus (Lophophora williamsii (Lem.) J.M. Coult.)) led to the synthesis of powerful hallucinogenic substances, e.g., 4-bromo-2,5-dimethoxyphenethylamine (2C-B), synthesized by Shulgin in 1974.
^abLuethi D, Liechti ME (April 2020)."Designer drugs: mechanism of action and adverse effects"(PDF).Arch Toxicol.94 (4):1085–1133.Bibcode:2020ArTox..94.1085L.doi:10.1007/s00204-020-02693-7.PMC7225206.PMID32249347.In one of the few clinical studies of a designer drug, 4-bromo-2,5-dimethoxyphenylethylamine (2C-B) was shown to induce euphoria, well-being, and changes in perception, and to have mild stimulant properties (González et al. 2015). 2C-B may thus be classified as a psychedelic with entactogenic properties, an effect profile that is similar to various other phenethylamine psychedelics (Shulgin and Shulgin 1995).
^abOeri HE (May 2021)."Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy".J Psychopharmacol.35 (5):512–536.doi:10.1177/0269881120920420.PMC8155739.PMID32909493.While an argument can be made that compounds like 4-bromo-2,5-dimethoxyphenethylamine (2CB) or N,N-diisopropyl-5-methoxytryptamine (5-MeO-DiPT) are also entactogenic, and they have been described as such in the past (González et al., 2015; Palamar and Acosta, 2020; Schifano et al., 2019), they were also excluded due to their high affinity as agonists at post-synaptic 5-HT2 and 5-HT1A receptors (Fantegrossi et al., 2006; Nugteren-van Lonkhuyzen et al., 2015; Taylor et al., 1986; Villalobos et al., 2004), which would indicate that their effects also include a marked psychedelic component.
^abcDuan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants".Chem Rev.124 (1):124–163.doi:10.1021/acs.chemrev.3c00375.PMID38033123.
^abcdefgPoulie CB, Jensen AA, Halberstadt AL, Kristensen JL (December 2020)."DARK Classics in Chemical Neuroscience: NBOMes".ACS Chem Neurosci.11 (23):3860–3869.doi:10.1021/acschemneuro.9b00528.PMC9191638.PMID31657895.However, 2C-B was emergency scheduled by the Drug Enforcement Administration (DEA) in 1994, due to its appearance on the recreational drug market as a replacement for 3,4-methylenedioxy methamphetamine (MDMA) (which had been scheduled in 1985). At that time, 2C-B was still being legally manufactured by the German company Drittewelle under the trade name of Erox and sold in Dutch "head-shops" under the name Nexus. In March 2001, the UN Commission on Narcotic Drugs added 2C-B to Schedule II of the Convention on Psychotropic Substances.
^abPassie T, Brandt SD (2018). "Self-Experiments with Psychoactive Substances: A Historical Perspective".Handb Exp Pharmacol. Handbook of Experimental Pharmacology.252:69–110.doi:10.1007/164_2018_177.ISBN978-3-030-10560-0.PMID30478735.Noteworthy is Shulgin's first synthesis, SE, and description of the subjective effects of 2C-B (Shulgin 1975).
^Shulgin AT, Shulgin LA, Jacob P (May 1986)."A protocol for the evaluation of new psychoactive drugs in man".Methods Find Exp Clin Pharmacol.8 (5):313–320.PMID3724306. Archived fromthe original on 2025-07-12.Somatic sensitizer: In addition to an extensive visual syndrome, the phenethylamine 2-CB (4-bromo-2,5-dimethoxyphenethylamine) (13) produces an intense awareness of physical responses to stimuli: olfactory, auditory, gustatory and sexual.
^ab"Ask Dr. Alexander "Sasha" Shulgin Online".keeping freedom in mind -. 7 February 2003.Dear Dr. Shulgin: What is 2C-B? What are its effects? --Brian [...] And what is its action? It is, in my opinion, one of the most graceful, erotic, sensual, introspective compounds I have ever invented. For most people, it is a short-lived and comfortable psychedelic, with neither toxic side-effects nor next-day hang-over. Its effects are felt very much in the body, as well as in the mind, and thus it has found clinical use as a follow-up to MDMA. Once the MDMA has shown you where your problems are, the 2C-B opens up the emotional, intuitive and archetypal area of your psyche to help you solve them. It was probably one of my favorite drugs, back in those yesteryear days when one could explore one's consciousness with legal immunity.
^abcdSexton JD, Nichols CD, Hendricks PS (2019)."Population Survey Data Informing the Therapeutic Potential of Classic and Novel Phenethylamine, Tryptamine, and Lysergamide Psychedelics".Front Psychiatry.10 896.doi:10.3389/fpsyt.2019.00896.PMC7026018.PMID32116806.In support of this view, 2C-B, the most commonly reported novel phenethylamine, is often substituted for MDMA among electronic music party goers secondary to its purported psychostimulant properties (15, 20, 65). Indeed, novel phenethylamines are often described in terms of psychostimulant effects (20, 29), whereas challenging, emotional breakthrough, and mystical-type experiences appear to underlie the therapeutic outcomes of the classic tryptamine psychedelic psilocybin (16, 66, 67). [...] As noted above, the novel phenethylamine 2C-B may have a reputation as a "party drug, " and thus the associations reported here may reflect the influence of recreational use motives.
^abde Boer D, Gijzels MJ, Bosman IJ, Maes RA (1999)."More data about the new psychoactive drug 2C-B".Journal of Analytical Toxicology.23 (3):227–228.doi:10.1093/jat/23.3.227.PMID10369336.The amount of 2C-B found in Ecstasy tablets is in the range of required dosages, 5–10 mg for stimulating effects and 10–20 mg for hallucinogenic effects.
^Yanakieva S, Luke DP, Jansari A, Terhune DB (July 2019). "Acquired synaesthesia following 2C-B use".Psychopharmacology (Berl).236 (7):2287–2289.doi:10.1007/s00213-019-05242-y.PMID31025060.
^Huang HH, Bai YM (January 2011). "Persistent psychosis after ingestion of a single tablet of '2C-B'".Prog Neuropsychopharmacol Biol Psychiatry.35 (1):293–294.doi:10.1016/j.pnpbp.2010.10.018.PMID21036198.
^McIntyre RS (2023). "Serotonin 5-HT2B receptor agonism and valvular heart disease: implications for the development of psilocybin and related agents".Expert Opin Drug Saf.22 (10):881–883.doi:10.1080/14740338.2023.2248883.PMID37581427.
^Tagen M, Mantuani D, van Heerden L, Holstein A, Klumpers LE, Knowles R (September 2023). "The risk of chronic psychedelic and MDMA microdosing for valvular heart disease".J Psychopharmacol.37 (9):876–890.doi:10.1177/02698811231190865.PMID37572027.
^abcTheobald DS, Maurer HH (January 2007). "Identification of monoamine oxidase and cytochrome P450 isoenzymes involved in the deamination of phenethylamine-derived designer drugs (2C-series)".Biochem Pharmacol.73 (2):287–297.doi:10.1016/j.bcp.2006.09.022.PMID17067556.
^Marcher-Rørsted E, Halberstadt AL, Klein AK, Chatha M, Jademyr S, Jensen AA, et al. (May 2020). "Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists".ACS Chem Neurosci.11 (9):1238–1244.doi:10.1021/acschemneuro.0c00129.PMID32212672.
^Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR (February 2019). "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases".Drug Test Anal.11 (2):318–324.doi:10.1002/dta.2494.PMID30188017.
^Zwartsen A, Verboven AH, van Kleef RG, Wijnolts FM, Westerink RH, Hondebrink L (December 2017). "Measuring inhibition of monoamine reuptake transporters by new psychoactive substances (NPS) in real-time using a high-throughput, fluorescence-based assay".Toxicol in Vitro.45 (Pt 1):60–71.Bibcode:2017ToxVi..45...60Z.doi:10.1016/j.tiv.2017.05.010.PMID28506818.
^Moya PR, Berg KA, Gutiérrez-Hernandez MA, Sáez-Briones P, Reyes-Parada M, Cassels BK, et al. (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):1054–1061.CiteSeerX10.1.1.690.3752.doi:10.1124/jpet.106.117507.PMID17337633.S2CID11651502.
^Potts AJ, Thomas SH, Hill SL (2022). "Pharmacology and toxicology of N-Benzyl-phenylethylamines (25X-NBOMe) hallucinogens".Novel Psychoactive Substances. Elsevier. pp. 279–300.doi:10.1016/b978-0-12-818788-3.00008-5.ISBN978-0-12-818788-3. Retrieved15 November 2025.2C-B, the 2C analogue of 25B-NBOMe, also had a preferential inhibitory effect on hSERT, but with an IC50 ten-times greater (EC50 54 micromolar) than 25B-NBOMe or 25INBOMe. A similar pattern of comparatively weaker interactions with hNET and hDAT (IC50 166 micromolar and 240 micromolar, respectively) was also observed. [42] The IC50 values for 2C-B and 25X-NBOMes were significantly greater than the drug-concentrations identified in human plasma and predicted in human cerebrospinal fluid [42] and therefore the significance of interactions with monoamine transporters in human toxicity is not clear.
^Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain".Eur J Pharmacol.559 (2–3):132–137.doi:10.1016/j.ejphar.2006.11.075.PMID17223101.
^abcGlennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, et al. (June 1994). "Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines".Journal of Medicinal Chemistry.37 (13):1929–1935.doi:10.1021/jm00039a004.PMID8027974.
^Elliott SP, Holdbrook T, Brandt SD (May 2020). "Prodrugs of New Psychoactive Substances (NPS): A New Challenge".Journal of Forensic Sciences.65 (3):913–920.doi:10.1111/1556-4029.14268.PMID31943218.
^Kargbo RB (April 2025). "Innovative Approaches in Psychedelics, AI, and Communication: A Multi-Domain Perspective".ACS Med Chem Lett.16 (4):514–516.doi:10.1021/acsmedchemlett.5c00114.PMC 11995231.PMID40236531.
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