Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 2-Bromo-LSD: Difference between pages

{{Short description|Chemical compound}}

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| verifiedrevid = 477212727

| IUPAC_name = (6a''R'',9''R'')-5-bromo-''N'',''N''-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide

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| legal_status = Not scheduled (United States, Canada, Germany, EU precursors)<ref>{{cite web | url = https://biochem.thc-pharm.de/product_info.php?products_id=122 | title = BOL-148 hydrochloride | work = THC Pharm GmbH | access-date = 2019-04-23 | archive-date = 2012-12-17 | archive-url = https://archive.today/20121217223056/https://biochem.thc-pharm.de/product_info.php?products_id=122 | url-status = dead }}</ref><ref>{{cite web | url = https://psilocybinalpha.com/news/betterlife-confirms-non-controlled-status-of-2-bromo-lsd-with-health-canada | title = BetterLife Confirms Non-Controlled Status of 2-bromo-LSD with Health Canada - Psilocybin Alpha | date = 19 January 2021 | work = Psychedelic Alpha }}</ref>

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 478-84-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = JUA77QEU32

| IUPHAR_ligand = 272

| synonyms = 2-Bromolysergic acid diethylamide; BOL-148

| C=20 | H=24 | Br=1 | N=3 | O=1

| SMILES = CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=C(NC4=CC=CC(=C34)C2=C1)Br)C

'''2-Bromo-LSD''', also known as '''BOL-148''', is a derivative of [[lysergic acid]] invented by [[Albert Hofmann]], as part of the original research from which the closely related compound [[LSD]] was also derived.<ref>{{cite journal | vauthors = Troxler F, Hofmann A | title = Substitutionen am Ringsystem der Lysergsäure. III. Halogenierung. 45. Mitteilung über Mutterkornalkaloide | journal = Helvetica Chimica Acta | date = 1957 | volume = 40 | issue = 7 | pages = 2160–2170 | doi = 10.1002/hlca.19570400716 }}</ref>

2-Bromo-LSD was found to be inactive as a [[Psychedelic drug|psychedelic]] and so was comparatively little researched for many years, although its similar behavior in the body made it useful for [[isotopic labeling |radiolabelling]] studies. It was found to bind to many of the same [[Receptor (biochemistry)|receptors]] as LSD, but acting as a [[neutral antagonist]] rather than an agonist.<ref name="pmid13348662">{{cite journal | vauthors = Ginzel KH, Mayer-Gross W | title = Prevention of psychological effects of d-lysergic acid diethylamide (LSD 25) by its 2-brom derivative (BOL 148) | journal = Nature | volume = 178 | issue = 4526 | pages = 210 | date = July 1956 | pmid = 13348662 | doi = 10.1038/178210a0 | s2cid = 4169373 | bibcode = 1956Natur.178..210G | doi-access = free }}</ref><ref name="pmid14405871">{{cite journal | vauthors = Isbell H, Miner EJ, Logan CR | title = Cross tolerance between D-2-brom-lysergic acid diethylamide (BOL-148) and the D-diethylamide of lysergic acid (LSD-25) | journal = Psychopharmacologia | volume = 1 | issue = 2 | pages = 109–116 | date = November 1959 | pmid = 14405871 | doi = 10.1007/bf00409110 | s2cid = 1915318 }}</ref> 2-Bromo-LSD reportedly attenuates the effects of LSD in humans.<ref name="MehtaTricklebank2019">{{cite book| vauthors = Mehta MA, Tricklebank MD |title=The Serotonin System|chapter=Serotonin and the psychedelics|year=2019|pages=193–202|doi=10.1016/B978-0-12-813323-1.00011-6|isbn=9780128133231|s2cid=196510587 }}</ref><ref name="pmid21163816">{{cite journal | vauthors = Tfelt-Hansen P | title = Is BOL-148 hallucinogenic? | journal = Cephalalgia | volume = 31 | issue = 5 | pages = 634; author reply 635-634; author reply 636 | date = April 2011 | pmid = 21163816 | doi = 10.1177/0333102410392069 | s2cid = 12412491 }}</ref>

However its generally similar behavior to LSD in some respects has shown to be very useful in one specific area, the treatment of [[cluster headache]]s.<ref name="pmid20713566">{{cite journal | vauthors = Karst M, Halpern JH, Bernateck M, Passie T | title = The non-hallucinogen 2-bromo-lysergic acid diethylamide as preventative treatment for cluster headache: an open, non-randomized case series | journal = Cephalalgia | volume = 30 | issue = 9 | pages = 1140–1144 | date = September 2010 | pmid = 20713566 | doi = 10.1177/0333102410363490 | s2cid = 33199115 }}</ref> These debilitating attacks have been known for some time to be amenable to treatment with certain hallucinogenic drugs such as LSD and [[psilocybin]], but because of the illegal status of these drugs and the kind of mental changes they induce, research into their medical use has been slow and therapeutic application limited to very specific circumstances under strict supervision. It had been thought that this specific therapeutic action against cluster headaches was limited to hallucinogenic drugs of this type, and would always present a major barrier to their clinical use. However, a serendipitous discovery found that 2-bromo-LSD can also produce this therapeutic effect, despite lacking the other effects of LSD. This has led to a resurgence of interest and research into 2-bromo-LSD and its possible medical uses. Some isolated incidents of hallucinogenic responses have been reported, but as with other non-hallucinogenic LSD analogs such as [[lisuride]], this appears to be a rare side effect occurring only in individuals with an as yet unexplained susceptibility to this reaction.

== References ==

{{Reflist}}

== Further reading ==

{{refbegin}}

* {{cite journal | vauthors = King AR, Martin IL, Melville KA | title = Reversal learning enhanced by lysergic acid diethylamide (LSD): concomitant rise in brain 5-hydroxytryptamine levels | journal = British Journal of Pharmacology | volume = 52 | issue = 3 | pages = 419–426 | date = November 1974 | pmid = 4458849 | pmc = 1777004 | doi = 10.1111/j.1476-5381.1974.tb08611.x }}

* {{cite journal | vauthors = Zivin JA, Venditto JA | title = Experimental CNS ischemia: serotonin antagonists reduce or prevent damage | journal = Neurology | volume = 34 | issue = 4 | pages = 469–474 | date = April 1984 | pmid = 6142430 | doi = 10.1212/wnl.34.4.469 | s2cid = 24926055 }}

* {{cite journal | vauthors = Harvey JA | title = Role of the serotonin 5-HT(2A) receptor in learning | journal = Learning & Memory | volume = 10 | issue = 5 | pages = 355–362 | year = 2003 | pmid = 14557608 | pmc = 218001 | doi = 10.1101/lm.60803 }}

* {{cite journal | vauthors = Dave KD, Harvey JA, Aloyo VJ | title = The time-course for up- and down-regulation of the cortical 5-hydroxytryptamine (5-HT)2A receptor density predicts 5-HT2A receptor-mediated behavior in the rabbit | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 323 | issue = 1 | pages = 327–335 | date = October 2007 | pmid = 17640952 | doi = 10.1124/jpet.107.121707 | s2cid = 13870625 }}

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{{Antimigraine}}

{{Serotonin receptor modulators}}

{{Ergolines}}

[[Category:Antimigraine drugs]]

[[Category:Lysergamides]]

[[Category:Serotonin receptor antagonists]]

[[Category:Bromoarenes]]

[[Category:Diethylamino compounds]]