Butopamine

Butopamine
Clinical data
Other names	LY-131126; (R,R)-Ractopamine;
Drug class	Sympathomimetic; β-Adrenergic receptor agonist; Positive inotrope; Positive chronotrope
Identifiers
	IUPAC name 4-[(3R)-3-[[(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]amino]butyl]phenol;
CAS Number	66734-12-1;
PubChem CID	68556;
ChemSpider	61830;
UNII	ZX7907IE2H;
KEGG	D03195;
ChEBI	CHEBI:82648;
ChEMBL	ChEMBL2103767;
CompTox Dashboard (EPA)	DTXSID50216876 ;
Chemical and physical data
Formula	C18H23NO3
Molar mass	301.386 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H](CCC1=CC=C(C=C1)O)NC[C@@H](C2=CC=C(C=C2)O)O;
	InChI InChI=1S/C18H23NO3/c1-13(2-3-14-4-8-16(20)9-5-14)19-12-18(22)15-6-10-17(21)11-7-15/h4-11,13,18-22H,2-3,12H2,1H3/t13-,18+/m1/s1; Key:YJQZYXCXBBCEAQ-ACJLOTCBSA-N;

Butopamine (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name; developmental code name LY-131126; also known as (R,R)-ractopamine) is a sympathomimetic agent, β-adrenergic receptor agonist, and positive inotrope of the phenethylamine family which was studied for treatment of heart failure but was never marketed.^[1]^[2]^[3]^[4] It is an analogue of dobutamine^[3]^[4] and is the (R,R)-enantiomer of ractopamine.^[2] Butopamine is not a catecholamine and is resistant to metabolism by catechol O-methyltransferase (COMT).^[3] In contrast to dobutamine, butopamine is orally active.^[3] In addition to its positive inotropic effects, butopamine has positive chronotropic effects.^[3]

References

^ Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 199. ISBN 978-1-4757-2085-3. Retrieved 27 February 2025.
^ ^a ^b Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 58. ISBN 978-94-011-4439-1. Retrieved 27 February 2025.
^ ^a ^b ^c ^d ^e Hess HJ (1981). Annual Reports in Medicinal Chemistry. Academic Press. p. 96. ISBN 978-0-08-058360-0. Retrieved 27 February 2025.
^ ^a ^b Chatterjee K (March 1985). "Recent advances in the management of chronic heart failure". Prim Care. 12 (1): 117–142. doi:10.1016/S0095-4543(21)01244-6. PMID 3846305.