Chemistry:2-Bromo-LSD

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Short description: Chemical compound
2-Bromo-LSD
2-bromo-LSD structure.svg
Clinical data
Other names2-Bromolysergic acid diethylamide; BOL-148
Legal status
Legal status
  • Not scheduled (United States, Canada, Germany, EU precursors)[1][2]
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC20H24BrN3O
Molar mass402.336 g·mol−1
3D model (JSmol)
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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.[3]

2-Bromo-LSD was found to be inactive as a psychedelic and so was comparatively little researched for many years, although its similar behavior in the body made it useful for radiolabelling studies. It was found to bind to many of the same receptors as LSD, but acting as a neutral antagonist rather than an agonist.[4][5] 2-Bromo-LSD reportedly attenuates the effects of LSD in humans.[6][7]

However its generally similar behavior to LSD in some respects has shown to be very useful in one specific area, the treatment of cluster headaches.[8] 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

  1. ↑ "BOL-148 hydrochloride". THC Pharm GmbH. https://biochem.thc-pharm.de/product_info.php?products_id=122. 
  2. ↑ "BetterLife Confirms Non-Controlled Status of 2-bromo-LSD with Health Canada - Psilocybin Alpha". Psychedelic Alpha. 19 January 2021. https://psilocybinalpha.com/news/betterlife-confirms-non-controlled-status-of-2-bromo-lsd-with-health-canada. 
  3. ↑ "Substitutionen am Ringsystem der Lysergsäure. III. Halogenierung. 45. Mitteilung über Mutterkornalkaloide". Helvetica Chimica Acta 40 (7): 2160–2170. 1957. doi:10.1002/hlca.19570400716. 
  4. ↑ "Prevention of psychological effects of d-lysergic acid diethylamide (LSD 25) by its 2-brom derivative (BOL 148)". Nature 178 (4526): 210. July 1956. doi:10.1038/178210a0. PMID 13348662. Bibcode: 1956Natur.178..210G. 
  5. ↑ "Cross tolerance between D-2-brom-lysergic acid diethylamide (BOL-148) and the D-diethylamide of lysergic acid (LSD-25)". Psychopharmacologia 1 (2): 109–116. November 1959. doi:10.1007/bf00409110. PMID 14405871. 
  6. ↑ "Serotonin and the psychedelics". The Serotonin System. 2019. pp. 193–202. doi:10.1016/B978-0-12-813323-1.00011-6. ISBN 9780128133231. 
  7. ↑ "Is BOL-148 hallucinogenic?". Cephalalgia 31 (5): 634; author reply 635-634; author reply 636. April 2011. doi:10.1177/0333102410392069. PMID 21163816. 
  8. ↑ "The non-hallucinogen 2-bromo-lysergic acid diethylamide as preventative treatment for cluster headache: an open, non-randomized case series". Cephalalgia 30 (9): 1140–1144. September 2010. doi:10.1177/0333102410363490. PMID 20713566. 

Further reading



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