2C-B: Difference between revisions
From Pharmacopedia
More actions
| [checked revision] | [checked revision] |
MDElliottMD (talk | contribs) Repoint CYP2D6/CYP3A4 links to the new Enzyme: namespace |
MDElliottMD (talk | contribs) Repoint receptor links to the new Receptor: namespace |
||
| Line 17: | Line 17: | ||
| legal = Schedule I (United States) | | legal = Schedule I (United States) | ||
| mechanism = 5-HT2A partial agonist | | mechanism = 5-HT2A partial agonist | ||
| intro = 2C-B, chemically 4-bromo-2,5-dimethoxyphenethylamine, is a synthetic psychedelic [[:Category:Phenethylamines|phenethylamine]] first prepared in 1974 by [[Alexander Shulgin]] at his home laboratory in Lafayette, California. It is the founding member of the [[:Category:2C-x series|2C series]], a family of 2,5-dimethoxy-4-substituted phenethylamines that Shulgin and his collaborators developed as variations on the [[Mescaline|mescaline]] skeleton. 2C-B occupies a distinctive position in the psychedelic medicine landscape: a compound with a mescaline-class structural lineage, a [[5-HT2A | | intro = 2C-B, chemically 4-bromo-2,5-dimethoxyphenethylamine, is a synthetic psychedelic [[:Category:Phenethylamines|phenethylamine]] first prepared in 1974 by [[Alexander Shulgin]] at his home laboratory in Lafayette, California. It is the founding member of the [[:Category:2C-x series|2C series]], a family of 2,5-dimethoxy-4-substituted phenethylamines that Shulgin and his collaborators developed as variations on the [[Mescaline|mescaline]] skeleton. 2C-B occupies a distinctive position in the psychedelic medicine landscape: a compound with a mescaline-class structural lineage, a [[Receptor:5-HT2A|5-HT2A]] pharmacology shared with the [[:Category:Psychedelics|classical psychedelics]], and a subjective character that has been described as bridging the [[:Category:Empathogens|entactogenic]] register of [[MDMA]] and the visionary register of the classical psychedelics. It had a brief legal-sale era in the late 1980s and early 1990s before being placed in [[Schedule I]] of the United States [[Controlled Substances Act]], temporarily in 1994 and permanently in 1995, and in Schedule II of the [[Convention on Psychotropic Substances|United Nations Convention on Psychotropic Substances]] in 2001. | ||
| history = The compound that became 2C-B emerged from Shulgin's systematic exploration of the structure-activity relationships of mescaline analogs, a program he had begun in the mid-1960s. Shulgin's hypothesis was that modifications to the trimethoxyphenethylamine skeleton might yield compounds active at lower doses than mescaline's, with subjective profiles that varied in characteristic ways with the substituent at the 4-position of the phenyl ring. 2C-B, with bromine at the 4-position, was one of the most striking results. The first published description appeared in 1975 in Psychopharmacology Communications, the short-lived journal that was one of the few outlets willing to publish Shulgin's work in that era.<ref name="shulgin1975">Shulgin AT, Carter MF. Centrally active phenethylamines. Psychopharmacology Communications. 1975;1(1):93-98.</ref> | | history = The compound that became 2C-B emerged from Shulgin's systematic exploration of the structure-activity relationships of mescaline analogs, a program he had begun in the mid-1960s. Shulgin's hypothesis was that modifications to the trimethoxyphenethylamine skeleton might yield compounds active at lower doses than mescaline's, with subjective profiles that varied in characteristic ways with the substituent at the 4-position of the phenyl ring. 2C-B, with bromine at the 4-position, was one of the most striking results. The first published description appeared in 1975 in Psychopharmacology Communications, the short-lived journal that was one of the few outlets willing to publish Shulgin's work in that era.<ref name="shulgin1975">Shulgin AT, Carter MF. Centrally active phenethylamines. Psychopharmacology Communications. 1975;1(1):93-98.</ref> | ||
| Line 139: | Line 139: | ||
| pk_metabolism = | | pk_metabolism = | ||
| pk_elimination = | | pk_elimination = | ||
| pharmacodynamics = 2C-B is a partial agonist at the serotonin 5-HT2A receptor, with additional activity at [[5-HT2C | | pharmacodynamics = 2C-B is a partial agonist at the serotonin 5-HT2A receptor, with additional activity at [[Receptor:5-HT2C|5-HT2C]] and [[Receptor:5-HT2B|5-HT2B]] and weak inhibition of [[Monoamine transporter|monoamine transporters]].<ref name="nichols2016">Nichols DE. Psychedelics. Pharmacological Reviews. 2016;68(2):264-355. PMID 26841800.</ref> The pharmacological profile is intermediate between the classical 5-HT2A psychedelics such as [[LSD]] and psilocybin and the entactogens such as MDMA. The 5-HT2A action is the principal driver of the psychedelic component; the transporter activity may contribute to the entactogenic character at lower doses. Oral 2C-B has an onset of roughly 45 to 75 minutes and a duration of approximately four to eight hours, which is shorter than psilocybin and considerably shorter than LSD. The compound is structurally a phenethylamine in the mescaline lineage rather than a [[:Category:Tryptamines|tryptamine]]; the 4-bromo substituent on the 2,5-dimethoxyphenethylamine scaffold confers substantially higher 5-HT2A affinity than mescaline's 3,4,5-trimethoxy parent compound, accounting for the dose-potency difference. | ||
{{ShulginsCorner | {{ShulginsCorner | ||