Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C8H11NO2.ClH |
| Molecular Weight | 189.639 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NCC(O)C1=CC=C(O)C=C1
InChI
InChIKey=PUMZXCBVHLCWQG-UHFFFAOYSA-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
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 |
|---|---|---|
| Distribution and action of some putative neurotransmitters in the stomatogastric nervous system of the earthworm, Eisenia fetida (Oligochaeta, Annelida). | 2001 Apr |
|
| Functional expression of a locust tyramine receptor in murine erythroleukaemia cells. | 2001 Dec |
|
| Modulating the modulators: parasites, neuromodulators and host behavioral change. | 2002 |
|
| 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 |
|
| Ingestion of double-stranded RNA by preparasitic juvenile cyst nematodes leads to RNA interference. | 2002 Aug |
|
| Intracerebroventricular administration of octopamine stimulates food intake of chicks through alpha(2)-adrenoceptor. | 2002 Aug |
|
| Determination of adrenergic agonists from extracts and herbal products of Citrus aurantium L. var. amara by LC. | 2002 Aug 1 |
|
| Unusual genetic architecture of natural variation affecting drug resistance in Drosophila melanogaster. | 2002 Dec |
|
| 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 |
|
| 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 |
|
| Dual signalling by different octopamine receptors converges on adenylate cyclase in Sf9 cells. | 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 |
|
| Serotonin precursor (5-hydroxytryptophan) has a profound effect on the post-copulatory time-fixed sexually refractory stage in the male cricket, Gryllus bimaculatus DeGeer. | 2002 Nov |
|
| Three-dimensional common-feature hypotheses of inhibitors of calling behaviour and in vitro [14C]acetate incorporation by pheromone glands of Plodia interpunctella. | 2002 Nov |
|
| Activation of octopaminergic receptors by essential oil constituents isolated from aromatic plants: possible mode of action against insect pests. | 2002 Nov |
|
| Biogenic amines evoke heartbeat reversal in larvae of the sweet potato hornworm, Agrius convolvuli. | 2002 Nov |
|
| Stress response in Drosophila melanogaster strain inactive with decreased tyramine and octopamine contents. | 2002 Oct |
|
| Juvenile hormone and octopamine in the regulation of division of labor in honey bee colonies. | 2002 Sep |
|
| Octopamine enhances moth olfactory responses to pheromones, but not those to general odorants. | 2002 Sep |
|
| A trace amine, tyramine, functions as a neuromodulator in Drosophila melanogaster. | 2002 Sep 6 |
|
| The effect of octopamine on behavioral responses of free-foraging bumblebees to a change in food source profitability. | 2003 Apr |
|
| Synaptic facilitation by ectopic octopamine and 5-HT receptors in Aplysia. | 2003 Apr 15 |
|
| Molecular and functional characterization of an octopamine receptor from honeybee (Apis mellifera) brain. | 2003 Aug |
|
| Octopamine modulates spermathecal muscle contractions in Locusta migratoria. | 2003 Feb |
|
| 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 |
|
| Neurohormonal and glutamatergic neuronal control of the cardioarterial valves in the isopod crustacean Bathynomus doederleini. | 2003 Feb |
|
| Central modulatory neurons control fuel selection in flight muscle of migratory locust. | 2003 Feb 15 |
|
| Biogenic amines in the antennal lobes and the initiation and maintenance of foraging behavior in honey bees. | 2003 Feb 5 |
|
| Positive and negative modulation of Bombyx mori adenylate cyclase by 5-phenyloxazoles: identification of octopamine and tyramine receptor agonists. | 2003 Jan |
|
| Serotonin regulates repolarization of the C. elegans pharyngeal muscle. | 2003 Jan |
|
| Three-dimensional pharmacophore hypotheses of octopamine/tyramine agonists which inhibit [1-14C]acetate incorporation in Plodia interpunctella. | 2003 Jan 2 |
|
| Octopaminergic modulation of synaptic transmission between an identified sensory afferent and flight motoneuron in the locust. | 2003 Jul 14 |
|
| Presynaptic impairment of synaptic transmission in Drosophila embryos lacking Gs(alpha). | 2003 Jul 2 |
|
| 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 |
|
| To swim or not to swim: regional effects of serotonin, octopamine and amine mixtures in the medicinal leech. | 2003 Jun |
|
| B96Bom encodes a Bombyx mori tyramine receptor negatively coupled to adenylate cyclase. | 2003 Jun |
|
| Hygienic behavior in the honey bee (Apis mellifera L.) and the modulatory role of octopamine. | 2003 Jun |
|
| Modulation of early olfactory processing by an octopaminergic reinforcement pathway in the honeybee. | 2003 Jun 15 |
|
| Elusive amines and primary headaches: historical background and prospectives. | 2003 May |
|
| Metabolic flux analysis of the phenylpropanoid pathway in wound-healing potato tuber tissue using stable isotope-labeled tracer and LC-MS spectroscopy. | 2003 May |
Patents
Sample Use Guides
In Vivo Use Guide
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
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ACTIVE MOIETY
SUBSTANCE RECORD
