2C-B

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2C-B's dose range as 12 to 24mg orally and its duration as 4 to 8hours. However, in an earlier report, he described an effective dose range of 8 to 10mg orally and a duration of 6 to 8hours. A wider recreational dose range of 2 to 55mg or more orally has been described as well, with a typical dose estimate of about 20mg. He has succinctly described 2C-B as having "a luxury of sensory enhancement (visual, sexual, gustatory) with a minimum of introspective demands". The drug was one of his favorite psychedelics Specific effects in these studies have included slight hallucinogenic states, perceptual changes, ego dissolution, time dilation, increased creativity, stimulation, vigor, happiness or elation, euphoria, feelings of well-being, reduced anger, enhanced sociability and friendliness, increased reactivity to negative emotional stimuli, decreased ability to recognize expressions of happiness, augmented emotionality in speech, tenseness, confusion, and mild sympathomimetic effects such as pressor effects, among others. It is often used by people who go to electronic music festivals, also known as raves. ==Contraindications==

The adverse effects of 2C-B have been studied. In a later case report of unknown dose, 2C-B caused serotonin syndrome, seizures, severe brain edema, and severe and long-lasting neurological impairment. There is a case report of acquired synesthesia following a single very high dose of 2C-B. There is also a case report of persistent psychosis following a single dose of 2C-B. Tolerance Tolerance is said to build to the effects of 2C-B analogously to the case of other psychedelics. Long-term effects 2C-B is a potent serotonin 5-HT2B receptor agonist similarly to many other serotonergic psychedelics and hence may pose a risk of cardiac valvulopathy and other complications with frequent long-term use. ==Overdose==

At doses over 20 or 30mg orally, frightening hallucinations, as well as tachycardia, hypertension, and hyperthermia, may occur. It was reported by Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) that a psychologist had accidentally taken a 100mg dose orally without apparent harm. There are three case reports of 2C-B intoxication in the scientific literature as of 2015 and no deaths have been attributed to 2C-B alone as of 2018. == Interactions ==

2C-B is metabolized by the monoamine oxidase (MAO) enzymes MAO-A and MAO-B. Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-B. 2C-B may also have interactions with other medications and drugs. ==Pharmacology==

Pharmacodynamics 2C-B acts as a potent partial agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A and 5-HT2C receptors and to a lesser extent of the serotonin 5-HT2B receptor. Although 2C-B itself was not evaluated, other closely related members of the 2C series, including 2C-C, 2C-D, 2C-E, 2C-I, and 2C-T-2, all showed no activity as monoamine releasing agents of serotonin, norepinephrine, or dopamine ( = >100,000nM or "inactive"). 2C-B produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. Pharmacokinetics Absorption 2C-B appears to have relatively low oral bioavailability. Distribution The volume of distribution and plasma protein binding of 2C-B are unknown. This compound is active and has similarly potency as a serotonin 5-HT2A receptor agonist as 2C-B itself in vitro. Elimination The elimination half-life of 2C-B in humans is 1.2 to 2.5hours. ==Chemistry==

2C-B, also known as 4-bromo-2,5-dimethoxyphenethylamine, is a substituted phenethylamine of the 2C family, also known as the 4-substituted 2,5-dimethoxyphenethylamines. A variety of N-substituted derivatives of 2C-B have been tested, including N-methyl-2C-B, N,N-dimethyl-2C-B, N-ethyl-2C-B and N-benzyl-2C-B. 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, and 25B-NBOH. Another N-substituted derivative, 2C-B-AN, is an N-benzylphenethylamine-like prodrug of 2C-B. 2C-DB (6-bromo-2C-B) is a ring-substituted derivative of 2C-B. FLY derivatives of 2C-B like 2C-B-FLY, 2C-B-DRAGONFLY, and 2C-B-BUTTERFLY are analogues in which the methoxy groups of 2C-B on the phenyl ring have been cyclized into furan or other rings to form benzodifuran and other tricyclic compounds. Other related cyclized compounds, while not technically phenethylamines or 2C-B derivatives, include 2C-B-BZP and 2C-B-PP. A notable positional isomer of 2C-B is the scaline and mescaline analogue 4-bromomescaline (4-Br-3,5-DMPEA). }} ==History==

2C-B was first synthesized and evaluated by American chemist Alexander Shulgin in 1974. Shulgin proposed 2C-B and 2C-D for use in psychedelic-assisted psychotherapy. 2C-B was legitimately marketed and sold as an over-the-counter sexual enhancer under brand names like Erox in several European countries such as Germany in the 1980s and early 1990s. It was manufactured by the German pharmaceutical company Drittewelle and was sold in adult stores, smart shops, and some nightclubs. In addition, 2C-B was sold in Dutch smart shops as an ecstasy-like legal high under names like Nexus. The drug became a controlled substance in the United States in 1994. ==Society and culture==

Names Brand names and street names of 2C-B include Nexus, Venus, Bromo, Erox, Perfomax, Bees, Toonies, Spectrum, XTC, and Synergy, among others. Illicit forms logo. Street purity of 2C-B, when tested, has been found to be relatively high. Legal status United Nations The UN Commission on Narcotic Drugs added 2C-B to Schedule II of the Convention on Psychotropic Substances in March 2001. 2C-B is a scheduled drug in most jurisdictions. The following is a partial list of territories where the substance has been scheduled. Argentina 2C-B is controlled under the List 1, as well as similar substances like 2C-I or 2C-T-2. 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. 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". 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. Chile In August 2007, 2C-B, along with many other psychologically active substances, was added to Ley 20.000, known as the Ley de drogas. Czech Republic Possession of more than 200mg of 2C-B is punishable with a two years jail sentence. Smaller amount is punishable by a fine. The 200mg 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. Estonia In Estonia, 2C-B is classified as Schedule I. Finland Scheduled in the "government decree on substances, preparations and plants considered to be narcotic drugs". Germany In Germany, 2C-B is controlled in the Betäubungsmittelgesetz (BtMG) Anlage I as "Bromdimethoxyphenethylamin" (BDMPEA). Italy 2C-B is schedule I (tabella I). 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. 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. 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 10mg. 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 (Act on the Prohibition of Certain Goods Dangerous to Health) as of April 1, 1999, under SFS 1999:58 that made it illegal to sell or possess. Then it became schedule I as of June 1, 2002, published in LVFS 2002:4 but mislabeled "2-CB" in the document. However, this was corrected in a new document, LVFS 2009:22 effective December 9, 2009. Switzerland In Switzerland, 2C-B is listed in Anhang D of the DetMV and is illegal to possess. United Kingdom 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. United States In the United States, 2C-B is classified as a Schedule I controlled substance. This became permanent law on June 2, 1995, following a proposal by the Drug Enforcement Administration in December 1994. ==Research==

2C-B has been studied and suggested for more widespread use in psychedelic-assisted psychotherapy. == See also ==