Bromadoline

Bromadoline

Systematic (IUPAC) name
trans-4-bromo-N-(2-(dimethylamino)cyclohexyl)benzamide
Identifiers
CAS Number	67579-24-2
ATC code	none
PubChem	CID 54753
ChemSpider	49457
UNII	R8DWN01P1M
ChEMBL	CHEMBL2110893
Synonyms	Bromadoline
Chemical data
Formula	C15H21BrN2O
Molar mass	325.244 g/mol
Chirality	Racemic mixture 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 Key:UFDJFJYMMIZKLG-KBPBESRZSA-N
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Bromadoline (U-47931E)^[1] is an opioid analgesic selective for the mu-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] It is presumed that the (1R,2R) isomer is the active opioid, overlaying as it does with many other mu agonists.^[5] Bromadoline is related to AH-7921 and U-47700.^[6]

See also

• AH-7921
• U-47700
• Spiradoline
• U-50488

References

1. Unlisted Drugs. 34–35. Chatham: Pharmaceutical Section, Special Libraries Association. 1982. p. 392. ISBN 978-0-913210-13-0.
2. Hayes AG, Skingle M, Tyers MB (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. U.S. Patent 4,098,904
4. Hayes AG, Sheehan MJ, Tyers MB (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. Cheng J, Liu G, Zhang J, Xu Z, Tang Y (2011). "Insights into subtype selectivity of opioid agonists by ligand-based and structure-based methods". Journal of Molecular Modeling 17 (3): 477–93. doi:10.1007/s00894-010-0745-1. PMID 20499259.
6. Cheney BV, Szmuszkovicz J, Lahti RA, Zichi DA (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.