Bromadoline

Bromadoline (U-47931E)[1] is an opioid analgesic selective for the μ-opioid receptor[2] developed by the Upjohn company in the 1970s.[3] The drug has a potency lying between that of codeine and morphine, being slightly stronger than pentazocine.[4] Bromadoline is related to AH-7921 and U-47700.[5]

Bromadoline
Clinical data
Other namesBromadoline
ATC code
  • none
Identifiers
IUPAC name
  • 4-bromo-N-[(1S,2S)-2-(dimethylamino)cyclohexyl]benzamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H21BrN2O
Molar mass325.250 g·mol−1
3D model (JSmol)
ChiralityRacemate of trans isomers
SMILES
  • CN([C@H]1CCCC[C@@H]1NC(C2=CC=C(C=C2)Br)=O)C
InChI
  • InChI=1S/C15H21BrN2O/c1-18(2)14-6-4-3-5-13(14)17-15(19)11-7-9-12(16)10-8-11/h7-10,13-14H,3-6H2,1-2H3,(H,17,19)/t13-,14-/m0/s1 Y
  • Key:UFDJFJYMMIZKLG-KBPBESRZSA-N Y
  (verify)

See also

References
  1. Unlisted Drugs. Vol. 34–35. Chatham: Pharmaceutical Section, Special Libraries Association. 1982. p. 392. ISBN 978-0-913210-13-0.
  2. Hayes AG, Skingle M, Tyers MB (March 1987). "Evaluation of the receptor selectivities of opioid drugs by investigating the block of their effect on urine output by beta-funaltrexamine". The Journal of Pharmacology and Experimental Therapeutics. 240 (3): 984–8. PMID 3559988.
  3. Jacob Szmuszkovicz (4 July 1978). "Patent US4098904 - Analgesic N-(2-aminocycloaliphatic)benzamides". The Upjohn Company.
  4. Hayes AG, Sheehan MJ, Tyers MB (August 1987). "Differential sensitivity of models of antinociception in the rat, mouse and guinea-pig to mu- and kappa-opioid receptor agonists". British Journal of Pharmacology. 91 (4): 823–32. doi:10.1111/j.1476-5381.1987.tb11281.x. PMC 1853585. PMID 2822190.
  5. Cheney BV, Szmuszkovicz J, Lahti RA, Zichi DA (December 1985). "Factors affecting binding of trans-N-[2-(methylamino)cyclohexyl]benzamides at the primary morphine receptor". Journal of Medicinal Chemistry. 28 (12): 1853–64. doi:10.1021/jm00150a017. PMID 2999404.


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