Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C8H11NO2.ClH |
| Molecular Weight | 189.639 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NC[C@@H](O)C1=CC=C(O)C=C1
InChI
InChIKey=PUMZXCBVHLCWQG-DDWIOCJRSA-N
InChI=1S/C8H11NO2.ClH/c9-5-8(11)6-1-3-7(10)4-2-6;/h1-4,8,10-11H,5,9H2;1H/t8-;/m1./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 |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
(+)-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 less 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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1867 |
|||
Target ID: CHEMBL2093864 |
4.68 null [pIC50] | ||
Target ID: CHEMBL1907610 |
2.0 null [pIC50] | ||
Target ID: CHEMBL2095166 |
|||
Target ID: P15101 Gene ID: 280758.0 Gene Symbol: DBH Target Organism: Bos taurus (Bovine) |
|||
Target ID: CHEMBL4592 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
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 09:48:10 GMT 2023
by
admin
on
Sat Dec 16 09:48:10 GMT 2023
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| Record UNII |
V1GXM433TY
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| Record Status |
Validated (UNII)
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| Record Version |
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425366-60-5
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admin on Sat Dec 16 09:48:10 GMT 2023 , Edited by admin on Sat Dec 16 09:48:10 GMT 2023
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