Details
Stereochemistry | RACEMIC |
Molecular Formula | C8H11NO2 |
Molecular Weight | 153.1784 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NCC(O)C1=CC=C(O)C=C1
InChI
InChIKey=QHGUCRYDKWKLMG-UHFFFAOYSA-N
InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2
Octopamine is an organic chemical closely related to norepinephrine. In many types of invertebrates it functions as a neurotransmitter. Octopamine is known to exert adrenergic effects in mammals although specific octopamine receptors have been cloned only in invertebrates. It has been shown that octopamine can stimulate alpha(2)-adrenoceptors (ARs) in Chinese hamster ovary cells transfected with human alpha(2)-ARs. Octopamine stimulates lipolysis through beta(3)-rather than beta(1)-or beta(2)-AR activation in white adipocytes from different mammalian species. Octopamine activates only beta(3)-ARs and is devoid of alpha(2)-adrenergic agonism. Thus, octopamine could be considered as an endogenous selective beta(3)-AR agonist. In humans Octopamine is a trace amine found endogenously in the human brain where it interacts with signalling of catecholamines; it is structurally similar to synephrine and tyramine, being a metabolite of the latter (via dopamine β-hydroxylase) and substrate for the synthesis of the former (via phenethanolamine N-methyltransferase[3]) while being perhaps the closest in structure to noradrenaline. Octopamine is found in the bitter orange similar to many biogenic amines related to L-tyrosine that are used as dietary supplements, this includes synephrine and hordenine. p-Octopamine HCl (Norphen) was studied in the late
1960’s and 1970’s as a drug for the treatment of hypotensive
regulatory and circulatory disorders. Octopamine was used as a nootropic. All optical isomers (enantiomers) of octopamine are on the
World Anti-Doping Agency (WADA) 2014 list of substances
prohibited in competition.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10515667 | https://www.ncbi.nlm.nih.gov/pubmed/24654910
Curator's Comment: Octopamine (OA), a biogenic monoamine structurally related to noradrenaline, acts as a neurohormone, a neuromodulator and a neurotransmitter in invertebrates. The known actions of OA in the central nervous system include desensitization of sensory inputs, influence on learning and memory, or regulation of the 'mood' of the animal. In vertebrates p-Octopamine is considered to be a CNS stimulant in spite of the fact that it binds poorly to adrenergic receptors.
Approval Year
PubMed
Title | Date | PubMed |
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Amine modulation of the transient potassium current in identified cells of the lobster stomatogastric ganglion. | 2001 Dec |
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Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor. | 2001 Dec |
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Hormonal stimulation of proline synthesis in the fat body of the fruit beetle, Pachnoda sinuata, is calcium dependent. | 2001 Dec |
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Inositol trisphosphate mediates the action of hypertrehalosemic hormone on fat body of the American cockroach, Periplaneta americana. | 2001 Dec |
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Dopamine-synthesizing neurons include the putative H-cell homologue in the moth Manduca sexta. | 2001 Feb 19 |
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Quantitative trait loci for the monoamine-related traits heart rate and headless behavior in Drosophila melanogaster. | 2001 Jan |
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An in vitro method for recording the electrical activity of the isolated heart of the adult Drosophila melanogaster. | 2001 Jul-Aug |
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Serotonergic and octopaminergic systems in the squat lobster Munida quadrispina (Anomura, Galatheidae). | 2001 Oct 29 |
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Neurochemical fine tuning of a peripheral tissue: peptidergic and aminergic regulation of fluid secretion by Malpighian tubules in the tobacco hawkmoth M. sexta. | 2002 Jul |
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Biogenic amines evoke heartbeat reversal in larvae of the sweet potato hornworm, Agrius convolvuli. | 2002 Nov |
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The effect of octopamine on behavioral responses of free-foraging bumblebees to a change in food source profitability. | 2003 Apr |
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Synaptic facilitation by ectopic octopamine and 5-HT receptors in Aplysia. | 2003 Apr 15 |
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Molecular and functional characterization of an octopamine receptor from honeybee (Apis mellifera) brain. | 2003 Aug |
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Presynaptic impairment of synaptic transmission in Drosophila embryos lacking Gs(alpha). | 2003 Jul 2 |
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HPLC electrochemical detection of trace amines in human plasma and platelets and expression of mRNA transcripts of trace amine receptors in circulating leukocytes. | 2003 Jul 31 |
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Modulation of early olfactory processing by an octopaminergic reinforcement pathway in the honeybee. | 2003 Jun 15 |
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Elusive amines and primary headaches: historical background and prospectives. | 2003 May |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24654910
Curator's Comment: Also was used orally In a study using a 150 mg octopamine sustained release
tablet to treat hypotension, the author recommended one or
two tablets before arising, and another tablet at night as
needed (Stucke, 1972). In a similar study (Braasch et al.,
1971), subjects received the octopamine sustained release
tablet three times daily. In both cases under the described
conditions, the product was reported to raise systolic blood
pressure by approximately 6 to14 mm Hg.
When 500 mg p-octopamine was infused intravenously over 30–40
minutes into human subjects, systolic blood pressure
increases of about 15 mm Hg were observed within 10
minutes. Intramuscular administration of
50 mg of a depo (slow release) form of p-octopamine into
humans resulted in similar increases in systolic blood pressure.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24654910
In isolated adipocytes from rats, the concentrations of 0.01–
0.10 nmol p-octopamine activated b-3 adrenergic receptors
to lower glucose uptake into adipocytes and increase cAMP.
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Classification Tree | Code System | Code | ||
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LOINC |
2672-4
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WHO-VATC |
QC01CA18
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DSLD |
2862 (Number of products:99)
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WHO-ATC |
C01CA18
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NCI_THESAURUS |
C29709
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58025
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CHEMBL53929
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14O50WS8JD
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DB13251
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100000083847
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OCTOPAMINE
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4581
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D009655
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44715
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17134
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104-14-3
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203-179-5
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m8118
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C75043
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3396
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DTXSID7043873
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757399
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SUB09415MIG
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1311141
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)