Bromadoline

Bromadoline
Clinical data
Other names	Bromadoline
ATC code	none;
Identifiers
	IUPAC name 4-bromo-N-[(1R,2R)-2-(dimethylamino)cyclohexyl]benzamide;
CAS Number	; 2418521-61-4; 67579-24-2 (mixture of trans isomers);
PubChem CID	6328449;
UNII	R8DWN01P1M;
CompTox Dashboard (EPA)	DTXSID40217897 ;
Chemical and physical data
Formula	C15H21BrN2O
Molar mass	325.250 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)[C@@H]1CCCC[C@H]1NC(=O)C2=CC=C(C=C2)Br;
	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-/m1/s1; Key:UFDJFJYMMIZKLG-ZIAGYGMSSA-N;
	(verify)

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]

References

^ Unlisted Drugs. Vol. 34–35. Chatham: Pharmaceutical Section, Special Libraries Association. 1982. p. 392. ISBN 978-0-913210-13-0.
^ 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.
^ Jacob Szmuszkovicz (4 July 1978). "Patent US4098904 - Analgesic N-(2-aminocycloaliphatic)benzamides". The Upjohn Company.
^ 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.
^ 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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