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
Molecular Formula | C8H11NO2 |
Molecular Weight | 153.1784 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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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Selective activation of beta3-adrenoceptors by octopamine: comparative studies in mammalian fat cells. | 1999 Apr |
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Distribution and action of some putative neurotransmitters in the stomatogastric nervous system of the earthworm, Eisenia fetida (Oligochaeta, Annelida). | 2001 Apr |
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Oscillations of the transepithelial potential of moth olfactory sensilla are influenced by octopamine and serotonin. | 2001 Aug |
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Synthesis of lipids in the fat body of Gryllus bimaculatus: age-dependency and regulation by adipokinetic hormone. | 2001 Aug |
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Functional expression of a locust tyramine receptor in murine erythroleukaemia cells. | 2001 Dec |
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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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Octopamine influences division of labor in honey bee colonies. | 2001 Feb |
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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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Effects of catecholamines on calvarial bone resorption in vitro. | 2001 Jul |
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Trace amines: identification of a family of mammalian G protein-coupled receptors. | 2001 Jul 31 |
|
An in vitro method for recording the electrical activity of the isolated heart of the adult Drosophila melanogaster. | 2001 Jul-Aug |
|
Nitric oxide and the control of firefly flashing. | 2001 Jun 29 |
|
Cloning and characterization of a hydroxycinnamoyl-CoA:tyramine N-(hydroxycinnamoyl)transferase induced in response to UV-C and wounding from Capsicum annuum. | 2001 May |
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Mixtures of octopamine and serotonin have nonadditive effects on the CNS of the medicinal leech. | 2001 May |
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Substituent-dependent, positive and negative modulation of Bombyx mori adenylate cyclase by synthetic octopamine/tyramine analogues. | 2001 May |
|
Apolipophorin-III in the greater wax moth, Galleria mellonella (Lepidoptera: Pyralidae). | 2001 Nov |
|
Ontogeny of neurohormonal regulation of the cardiovascular system in the crayfish Procambarus clarkii. | 2001 Oct |
|
[Interaction of hormones in controlling reproductive function of Drosophila females under stressful conditions is genetically determined]. | 2001 Sep |
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A role for octopamine in honey bee division of labor. | 2002 |
|
Metamodulation of the biogenic amines: second-order modulation by steroid hormones and amine cocktails. | 2002 |
|
Is Na(+) required for the binding of dopamine, amphetamine, tyramine, and octopamine to the human dopamine transporter? | 2002 Apr |
|
In vivo alpha(1)-adrenergic lipolytic activity in subcutaneous adipose tissue of obese subjects. | 2002 Apr |
|
Determination of adrenergic agonists from extracts and herbal products of Citrus aurantium L. var. amara by LC. | 2002 Aug 1 |
|
Modulation by 5-hydroxytryptamine of nicotinic acetylcholine responses recorded from an identified cockroach (Periplaneta americana) motoneuron. | 2002 Feb |
|
Neurotransmitters and neuropeptides in the brain of the locust. | 2002 Feb 1 |
|
Comparative effects of dehydropirlindole and other compounds on rat brain monoamine oxidase type A. | 2002 Jan |
|
Fictive locomotion induced by octopamine in the earthworm. | 2002 Jan |
|
Distribution and development of dopamine- and octopamine-synthesizing neurons in the medicinal leech. | 2002 Jan 7 |
|
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 |
|
A high-affinity octopamine transporter cloned from the central nervous system of cabbage looper Trichoplusia ni. | 2002 Mar 1 |
|
Are monoaminergic systems involved in the lethargy induced by a parasitoid wasp in the cockroach prey? | 2002 May |
|
Drosophila as a new model organism for the neurobiology of aggression? | 2002 May |
|
Central regulation of photosensitive membrane turnover in the lateral eye of Limulus. I. Octopamine primes the retina for daily transient rhabdom shedding. | 2002 May-Jun |
|
Three-dimensional common-feature hypotheses of inhibitors of calling behaviour and in vitro [14C]acetate incorporation by pheromone glands of Plodia interpunctella. | 2002 Nov |
|
Biogenic amines evoke heartbeat reversal in larvae of the sweet potato hornworm, Agrius convolvuli. | 2002 Nov |
|
Immunoreactivity against choline acetyltransferase, gamma-aminobutyric acid, histamine, octopamine, and serotonin in the larval chemosensory system of Dosophila melanogaster. | 2002 Nov 11 |
|
Stress response in Drosophila melanogaster strain inactive with decreased tyramine and octopamine contents. | 2002 Oct |
|
Phylogenetic analysis of 277 human G-protein-coupled receptors as a tool for the prediction of orphan receptor ligands. | 2002 Oct 17 |
|
Juvenile hormone and octopamine in the regulation of division of labor in honey bee colonies. | 2002 Sep |
|
Synaptic facilitation by ectopic octopamine and 5-HT receptors in Aplysia. | 2003 Apr 15 |
|
Functionally distinct dopamine and octopamine transporters in the CNS of the cabbage looper moth. | 2003 Feb |
|
Site-directed mutagenesis studies on the Drosophila octopamine/tyramine receptor. | 2003 Feb |
|
Central modulatory neurons control fuel selection in flight muscle of migratory locust. | 2003 Feb 15 |
|
Positive and negative modulation of Bombyx mori adenylate cyclase by 5-phenyloxazoles: identification of octopamine and tyramine receptor agonists. | 2003 Jan |
|
Presynaptic impairment of synaptic transmission in Drosophila embryos lacking Gs(alpha). | 2003 Jul 2 |
|
To swim or not to swim: regional effects of serotonin, octopamine and amine mixtures in the medicinal leech. | 2003 Jun |
|
Hygienic behavior in the honey bee (Apis mellifera L.) and the modulatory role of octopamine. | 2003 Jun |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:47:57 GMT 2023
by
admin
on
Sat Dec 16 17:47:57 GMT 2023
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Record UNII |
14O50WS8JD
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Record Status |
Validated (UNII)
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Record Version |
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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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17134
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104-14-3
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14O50WS8JD
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3653
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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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PRIMARY | RxNorm |
Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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PARENT -> IMPURITY |
limits for Ractopamine Hydrochloride Suspension
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |