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2-Bromo-LSD

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2-Bromo-LSD
Clinical data
Other names2-Bromolysergic acid diethylamide; 2-Bromo-LSD; 2-Br-LSD; BOL-148; BOL148; Bromolysergide; BETR-001; TD-0148A; NYPRG-101
Legal status
Legal status
  • Not scheduled (United States, Canada, Germany, EU precursors)[1][2]
Identifiers
  • (6aR,9R)-5-bromo-N,N-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H24BrN3O
Molar mass402.336 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=C(NC4=CC=CC(=C34)C2=C1)Br)C
  • InChI=1S/C20H24BrN3O/c1-4-24(5-2)20(25)12-9-14-13-7-6-8-16-18(13)15(19(21)22-16)10-17(14)23(3)11-12/h6-9,12,17,22H,4-5,10-11H2,1-3H3/t12-,17-/m1/s1 checkY
  • Key:VKRAXSZEDRWLAG-SJKOYZFVSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.

In 2023, 2-bromo-LSD was characterized as a non-hallucinogenic serotonin 5-HT2A receptor biased partial agonist and as a serotonin 5-HT2B receptor antagonist.[9] Similarly to LSD, it was also found to interact with numerous other serotonin receptors and targets.[9]

2-Bromo-LSD, under the developmental code name BETR-001 (previously TD-0148A), is under development by BetterLife Pharma for the treatment of cluster headaches and other indications.[10][11]

References

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  1. ^ "BOL-148 hydrochloride". THC Pharm GmbH. Archived from the original on 2012-12-17. Retrieved 2019-04-23.
  2. ^ "BetterLife Confirms Non-Controlled Status of 2-bromo-LSD with Health Canada - Psilocybin Alpha". Psychedelic Alpha. 19 January 2021.
  3. ^ Troxler F, Hofmann A (1957). "Substitutionen am Ringsystem der Lysergsäure. III. Halogenierung. 45. Mitteilung über Mutterkornalkaloide". Helvetica Chimica Acta. 40 (7): 2160–2170. doi:10.1002/hlca.19570400716.
  4. ^ Ginzel KH, Mayer-Gross W (July 1956). "Prevention of psychological effects of d-lysergic acid diethylamide (LSD 25) by its 2-brom derivative (BOL 148)". Nature. 178 (4526): 210. Bibcode:1956Natur.178..210G. doi:10.1038/178210a0. PMID 13348662. S2CID 4169373.
  5. ^ Isbell H, Miner EJ, Logan CR (November 1959). "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. doi:10.1007/bf00409110. PMID 14405871. S2CID 1915318.
  6. ^ Mehta MA, Tricklebank MD (2019). "Serotonin and the psychedelics". The Serotonin System. pp. 193–202. doi:10.1016/B978-0-12-813323-1.00011-6. ISBN 9780128133231. S2CID 196510587.
  7. ^ Tfelt-Hansen P (April 2011). "Is BOL-148 hallucinogenic?". Cephalalgia. 31 (5): 634, author reply 635-634, author reply 636. doi:10.1177/0333102410392069. PMID 21163816. S2CID 12412491.
  8. ^ Karst M, Halpern JH, Bernateck M, Passie T (September 2010). "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. doi:10.1177/0333102410363490. PMID 20713566. S2CID 33199115.
  9. ^ a b Lewis V, Bonniwell EM, Lanham JK, Ghaffari A, Sheshbaradaran H, Cao AB, Calkins MM, Bautista-Carro MA, Arsenault E, Telfer A, Taghavi-Abkuh FF, Malcolm NJ, El Sayegh F, Abizaid A, Schmid Y, Morton K, Halberstadt AL, Aguilar-Valles A, McCorvy JD (March 2023). "A non-hallucinogenic LSD analog with therapeutic potential for mood disorders". Cell Rep. 42 (3): 112203. doi:10.1016/j.celrep.2023.112203. PMC 10112881. PMID 36884348.
  10. ^ "BETR 001". AdisInsight. 29 August 2024. Retrieved 24 October 2024.
  11. ^ "Delving into the Latest Updates on Bromolysergide with Synapse". Synapse. 14 October 2024. Retrieved 24 October 2024.

Further reading

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