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-QRPNPIFTSA-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-;/m0./s1
(-)-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
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.
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23724773
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19462-08-9
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56N63J1TK4
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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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SUBSTANCE RECORD
