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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H23NO3
Molecular Weight 301.3801
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTOPAMINE

SMILES

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

InChI

InChIKey=YJQZYXCXBBCEAQ-ACJLOTCBSA-N
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

HIDE SMILES / InChI

Molecular Formula C18H23NO3
Molecular Weight 301.3801
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.alma.alberta.ca/cs/groups/alma/documents/document/mdaw/mda5/~edisp/agucmint-009415.pdf and http://www.google.com/patents/US8383685

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 Butopamine was prepared by Tuttle et al (unpublished data) and has a structure similar to dobutamine.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.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Hemodynamic effects of intravenous butopamine in congestive heart failure.
1980 Sep
Patents

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
Created
by admin
on Fri Dec 15 16:11:34 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:34 GMT 2023
Record UNII
ZX7907IE2H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUTOPAMINE
INN   USAN  
INN   USAN  
Official Name English
BUTOPAMINE [USAN]
Common Name English
RACTOPAMINE R,R-FORM
Common Name English
LY-131126
Code English
COMPOUND LY-131126
Code English
COMPOUND LY 131126
Code English
butopamine [INN]
Common Name English
(R)-P-HYDROXY-.ALPHA.-((((R)-3-(P-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)METHYL)BENZYL ALCOHOL
Common Name English
BENZENEMETHANOL, 4-HYDROXY-.ALPHA.-(((3-(4-HYDROXYPHENYL)-1-METHYLPROPYL)AMINO)METHYL)-, (R-(R*,R*))
Common Name English
COMPOUND-LY-131126
Code English
Classification Tree Code System Code
NCI_THESAURUS C48149
Created by admin on Fri Dec 15 16:11:34 GMT 2023 , Edited by admin on Fri Dec 15 16:11:34 GMT 2023
Code System Code Type Description
INN
4619
Created by admin on Fri Dec 15 16:11:34 GMT 2023 , Edited by admin on Fri Dec 15 16:11:34 GMT 2023
PRIMARY
CHEBI
82648
Created by admin on Fri Dec 15 16:11:34 GMT 2023 , Edited by admin on Fri Dec 15 16:11:34 GMT 2023
PRIMARY
EPA CompTox
DTXSID50216876
Created by admin on Fri Dec 15 16:11:34 GMT 2023 , Edited by admin on Fri Dec 15 16:11:34 GMT 2023
PRIMARY
CAS
66734-12-1
Created by admin on Fri Dec 15 16:11:34 GMT 2023 , Edited by admin on Fri Dec 15 16:11:34 GMT 2023
PRIMARY
ChEMBL
CHEMBL2103767
Created by admin on Fri Dec 15 16:11:34 GMT 2023 , Edited by admin on Fri Dec 15 16:11:34 GMT 2023
PRIMARY
NCI_THESAURUS
C81649
Created by admin on Fri Dec 15 16:11:34 GMT 2023 , Edited by admin on Fri Dec 15 16:11:34 GMT 2023
PRIMARY
FDA UNII
ZX7907IE2H
Created by admin on Fri Dec 15 16:11:34 GMT 2023 , Edited by admin on Fri Dec 15 16:11:34 GMT 2023
PRIMARY
MESH
C026597
Created by admin on Fri Dec 15 16:11:34 GMT 2023 , Edited by admin on Fri Dec 15 16:11:34 GMT 2023
PRIMARY
EVMPD
SUB06031MIG
Created by admin on Fri Dec 15 16:11:34 GMT 2023 , Edited by admin on Fri Dec 15 16:11:34 GMT 2023
PRIMARY
SMS_ID
100000081565
Created by admin on Fri Dec 15 16:11:34 GMT 2023 , Edited by admin on Fri Dec 15 16:11:34 GMT 2023
PRIMARY
PUBCHEM
68556
Created by admin on Fri Dec 15 16:11:34 GMT 2023 , Edited by admin on Fri Dec 15 16:11:34 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY