Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C8H11NO2 |
| Molecular Weight | 153.1784 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC[C@H](O)C1=CC=C(O)C=C1
InChI
InChIKey=QHGUCRYDKWKLMG-QMMMGPOBSA-N
InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2/t8-/m0/s1
| Molecular Formula | C8H11NO2 |
| Molecular Weight | 153.1784 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
(-)-octopamine is an enantiomer of octopamine, a naturally occurring phenolamine acting as a neurotransmitter in invertebrates. Octopamine is considered to be trace amine present in mammalian tissues at very low (nanomolar) concentrations. Generally, the (-)-enantiomers of octopamine are more active than the (+)-enantiomers at adrenergic receptors. However (+)-octopamine is more potent than the (-)-octopamine as an inhibitor of semicarbazide-sensitive amine oxidase.
Originator
Curator's Comment: Preparation of optical isomers of octopamine was performed by Kappe and Armstrong in 1964. The natural occurrence of octopamine was first reported by Erspamer (1952) who identified it as a constituent of extracts of salivary glands of the octopus. https://www.ncbi.nlm.nih.gov/pubmed/14919575
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| PREPARATION OF D- AND L-OCTOPAMINE. | 1964 Jul |
|
| Beta-adrenergic activities of octopamine and synephrine stereoisomers on guinea-pig atria and trachea. | 1987 Sep |
|
| Activities of octopamine and synephrine stereoisomers on alpha-adrenoceptors. | 1988 Feb |
|
| Semicarbazide-sensitive amine oxidase (SSAO) of the rat aorta. Interactions with some naturally occurring amines and their structural analogues. | 1989 May 1 |
|
| Selective inhibition of adenylyl cyclase by octopamine via a human cloned alpha 2A-adrenoceptor. | 1997 Sep |
Sample Use Guides
The phenolamines, octopamine and synephrine were only able to couple the alpha 2A-adrenoceptor to a dose-dependent decrease in cyclic AMP production at concentrations up to 1 mM, with the synephrine isomers being more potent than the corresponding octopamine isomers. The meta-isomers of both phenolamines were more potent than the corresponding para-isomers and the (-)-enantiomers were more potent than the (+)-enantiomers. Thus, (-)-meta-synephrine [(-)-phenylephrine] was the most effective isomer tested with an observable decrease occurring between 100 nM and 1 microM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:19:34 GMT 2023
by
admin
on
Sat Dec 16 09:19:34 GMT 2023
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| Record UNII |
H1P36W1J84
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| Record Status |
Validated (UNII)
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| Record Version |
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440266
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m8118
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RACEMATE -> ENANTIOMER |
