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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H23NO3.ClH
Molecular Weight 337.841
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTOPAMINE HYDROCHLORIDE

SMILES

Cl.C[C@H](CCC1=CC=C(O)C=C1)NC[C@H](O)C2=CC=C(O)C=C2

InChI

InChIKey=JHGSLSLUFMZUMK-WJKBNZMCSA-N
InChI=1S/C18H23NO3.ClH/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;1H/t13-,18+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C18H23NO3
Molecular Weight 301.3801
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Ractopamine hydrochloride, a beta-adrenoceptor agonist, is a phenethanolamine salt approved for use as a feed additive. Recently published studies indicate that the RR-isomer (butopamine) is the stereoisomer with the most activity at the beta-adrenoceptor. Butopamine was shown to be a non-selective ligand at the beta1 and beta2-adrenoceptors, but signal transduction is more efficiently coupled through the b2-adrenoceptor than the beta1 adrenoceptor. Therefore, the RR-isomer of ractopamine is considered to be a full agonist at the beta2-adrenoceptor and a partial agonist at the beta1¬adrenoceptor. These results are consistent with the pharmacological characterization of racemic ractopamine in isolated cardiac (atria) and smooth muscle (costo-uterine, vas deferens, trachea), which shows a maximal response at beta2- and a submaximal response at beta1¬adrenoceptors when compared with the full beta1 and beta2-adrenoceptor agonist isoproterenol. Butopamine is chemically similar to dobutamine but, unlike dobutamine, it is not a catecholamine. Butopamine induces a positive inotropic response in patients with congestive heart failure but for equal increments in cardiac output, butopamine increases heart rate more than dobutamine. Butopamine inproved cardiac performance in patients with ventricular dysfunction and congestive heart failure. Butopamine was prepared by Tuttle et al (unpublished data) and has a structure similar to dobutamine. This compound is refractory to the action of catechol-O-methyl transferase and thus it is orally active and has a longlasting action. Clinical findings in acute heart failure cases have been reported by Thompson et al. Intravenous administration produced an increase in the cardiac index and heart rate and shortening of systolic time intervals. A few patients experienced ventricular ectopy, especially with the higher doses used. No data pertaining to oral administration are available.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
25.0 nM [Kd]
25.0 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Progressive dose-response protocol ranged from 0.02 to 0.17 mcg/kg/min.
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
8XI60IX48K
Record Status Validated (UNII)
Record Version