BU-48

BU-48 is a drug that is used in scientific research. It is from the oripavine family, related to better-known drugs such as etorphine and buprenorphine.

BU-48
Identifiers
IUPAC name
  • N-Cyclopropylmethyl-[7α,8α,2',3']-cyclohexano-1'[S]-hydroxy-6,14-endo-ethenotetrahydronororipavine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC27H33NO4
Molar mass435.564 g·mol−1
3D model (JSmol)
SMILES
  • CO[C@]12C=C[C@@]3([C@H]4[C@@H]1[C@H](CCC4)O)[C@H]5Cc6ccc(c7c6[C@]3([C@H]2O7)CCN5CC8CC8)O
InChI
  • InChI=1S/C27H33NO4/c1-31-27-10-9-25(17-3-2-4-18(29)22(17)27)20-13-16-7-8-19(30)23-21(16)26(25,24(27)32-23)11-12-28(20)14-15-5-6-15/h7-10,15,17-18,20,22,24,29-30H,2-6,11-14H2,1H3/t17-,18+,20-,22-,24-,25-,26+,27-/m1/s1
  • Key:LMFRYUPWVALVRA-QDFTYCMYSA-N
  (verify)

The parent compound from which BU-48 was derived (with N-methyl rather than methylcyclopropyl on the nitrogen and lacking the aliphatic hydroxyl group) is a powerful μ-opioid agonist 1000 times more potent than morphine,[1] but in contrast BU-48 has only weak analgesic effects and instead acts primarily as a δ-opioid agonist. Its main effects are to produce convulsions,[2] but it may also have antidepressant effects.[3]

See also

References
  1. Lewis JW, Bentley KW, Cowan A (1971). "Narcotic analgesics and antagonists". Annual Review of Pharmacology. 11: 241–70. doi:10.1146/annurev.pa.11.040171.001325. PMID 4948499.
  2. Broom DC, Guo L, Coop A, Husbands SM, Lewis JW, Woods JH, Traynor JR (September 2000). "BU48: a novel buprenorphine analog that exhibits delta-opioid-mediated convulsions but not delta-opioid-mediated antinociception in mice". The Journal of Pharmacology and Experimental Therapeutics. 294 (3): 1195–200. PMID 10945877.
  3. Broom DC, Jutkiewicz EM, Rice KC, Traynor JR, Woods JH (September 2002). "Behavioral effects of delta-opioid receptor agonists: potential antidepressants?". Japanese Journal of Pharmacology. 90 (1): 1–6. doi:10.1254/jjp.90.1. PMID 12396021.
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