Details
| Stereochemistry | EPIMERIC |
| Molecular Formula | C8H11NO2.C4H6O6 |
| Molecular Weight | 303.2653 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O.NCC(O)C1=CC=C(O)C=C1
InChI
InChIKey=SEYAYFMQVRHSQR-LREBCSMRSA-N
InChI=1S/C8H11NO2.C4H6O6/c9-5-8(11)6-1-3-7(10)4-2-6;5-1(3(7)8)2(6)4(9)10/h1-4,8,10-11H,5,9H2;1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1
| 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 | ( + / - ) |
| Molecular Formula | C4H6O6 |
| Molecular Weight | 150.0868 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
39.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4277715/ |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
OCTOPAMINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
213 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4277715/ |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
OCTOPAMINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
243 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4277715/ |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
OCTOPAMINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
175 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4277715/ |
8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered: |
OCTOPAMINE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
67% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4277715/ |
OCTOPAMINE serum | Homo sapiens |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| inconclusive [IC50 0.1096 uM] | ||||
| inconclusive | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes [Inhibition 10 uM] | ||||
| yes [Inhibition 10 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
Page: 157 | 158 |
no | |||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Molecular and functional characterization of an octopamine receptor from honeybee (Apis mellifera) brain. | 2003-08 |
|
| HPLC electrochemical detection of trace amines in human plasma and platelets and expression of mRNA transcripts of trace amine receptors in circulating leukocytes. | 2003-07-31 |
|
| Octopaminergic modulation of synaptic transmission between an identified sensory afferent and flight motoneuron in the locust. | 2003-07-14 |
|
| Presynaptic impairment of synaptic transmission in Drosophila embryos lacking Gs(alpha). | 2003-07-02 |
|
| The control of vascular resistance in the southern rock lobster, Jasus edwardsii (Decapoda: Palinuridae). | 2003-07 |
|
| Modulation of early olfactory processing by an octopaminergic reinforcement pathway in the honeybee. | 2003-06-15 |
|
| Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase. | 2003-06 |
|
| To swim or not to swim: regional effects of serotonin, octopamine and amine mixtures in the medicinal leech. | 2003-06 |
|
| B96Bom encodes a Bombyx mori tyramine receptor negatively coupled to adenylate cyclase. | 2003-06 |
|
| Hygienic behavior in the honey bee (Apis mellifera L.) and the modulatory role of octopamine. | 2003-06 |
|
| Elusive amines and primary headaches: historical background and prospectives. | 2003-05 |
|
| Metabolic flux analysis of the phenylpropanoid pathway in wound-healing potato tuber tissue using stable isotope-labeled tracer and LC-MS spectroscopy. | 2003-05 |
|
| Synaptic facilitation by ectopic octopamine and 5-HT receptors in Aplysia. | 2003-04-15 |
|
| The effect of octopamine on behavioral responses of free-foraging bumblebees to a change in food source profitability. | 2003-04 |
|
| Agonist-specific coupling of a cloned human alpha1A-adrenoceptor to different second messenger pathways. | 2003-04 |
|
| Early multiple organ failure after recurrent endotoxemia in the presence of vasoconstrictor-masked hypovolemia. | 2003-03 |
|
| Central modulatory neurons control fuel selection in flight muscle of migratory locust. | 2003-02-15 |
|
| Biogenic amines in the antennal lobes and the initiation and maintenance of foraging behavior in honey bees. | 2003-02-05 |
|
| Octopamine modulates spermathecal muscle contractions in Locusta migratoria. | 2003-02 |
|
| Functionally distinct dopamine and octopamine transporters in the CNS of the cabbage looper moth. | 2003-02 |
|
| Site-directed mutagenesis studies on the Drosophila octopamine/tyramine receptor. | 2003-02 |
|
| Neurohormonal and glutamatergic neuronal control of the cardioarterial valves in the isopod crustacean Bathynomus doederleini. | 2003-02 |
|
| Three-dimensional pharmacophore hypotheses of octopamine/tyramine agonists which inhibit [1-14C]acetate incorporation in Plodia interpunctella. | 2003-01-02 |
|
| Positive and negative modulation of Bombyx mori adenylate cyclase by 5-phenyloxazoles: identification of octopamine and tyramine receptor agonists. | 2003-01 |
|
| Serotonin regulates repolarization of the C. elegans pharyngeal muscle. | 2003-01 |
|
| Unusual genetic architecture of natural variation affecting drug resistance in Drosophila melanogaster. | 2002-12 |
|
| Behavioural pharmacology of octopamine, tyramine and dopamine in honey bees. | 2002-11-15 |
|
| Immunoreactivity against choline acetyltransferase, gamma-aminobutyric acid, histamine, octopamine, and serotonin in the larval chemosensory system of Dosophila melanogaster. | 2002-11-11 |
|
| Serotonin precursor (5-hydroxytryptophan) has a profound effect on the post-copulatory time-fixed sexually refractory stage in the male cricket, Gryllus bimaculatus DeGeer. | 2002-11 |
|
| Three-dimensional common-feature hypotheses of inhibitors of calling behaviour and in vitro [14C]acetate incorporation by pheromone glands of Plodia interpunctella. | 2002-11 |
|
| Activation of octopaminergic receptors by essential oil constituents isolated from aromatic plants: possible mode of action against insect pests. | 2002-11 |
|
| Biogenic amines evoke heartbeat reversal in larvae of the sweet potato hornworm, Agrius convolvuli. | 2002-11 |
|
| Central regulation of photosensitive membrane turnover in the lateral eye of Limulus. I. Octopamine primes the retina for daily transient rhabdom shedding. | 2002-10-24 |
|
| Phylogenetic analysis of 277 human G-protein-coupled receptors as a tool for the prediction of orphan receptor ligands. | 2002-10-17 |
|
| Three-dimensional common-feature hypotheses for octopamine agonist arylethanolamines. | 2002-10 |
|
| Stress response in Drosophila melanogaster strain inactive with decreased tyramine and octopamine contents. | 2002-10 |
|
| A trace amine, tyramine, functions as a neuromodulator in Drosophila melanogaster. | 2002-09-06 |
|
| Juvenile hormone and octopamine in the regulation of division of labor in honey bee colonies. | 2002-09 |
|
| Octopamine enhances moth olfactory responses to pheromones, but not those to general odorants. | 2002-09 |
|
| Octopamine modulates responsiveness to foraging-related stimuli in honey bees (Apis mellifera). | 2002-09 |
|
| Characterization of a tyramine receptor from Caenorhabditis elegans. | 2002-09 |
|
| Determination of adrenergic agonists from extracts and herbal products of Citrus aurantium L. var. amara by LC. | 2002-08-01 |
|
| Ingestion of double-stranded RNA by preparasitic juvenile cyst nematodes leads to RNA interference. | 2002-08 |
|
| Intracerebroventricular administration of octopamine stimulates food intake of chicks through alpha(2)-adrenoceptor. | 2002-08 |
|
| Neurochemical fine tuning of a peripheral tissue: peptidergic and aminergic regulation of fluid secretion by Malpighian tubules in the tobacco hawkmoth M. sexta. | 2002-07 |
|
| Are monoaminergic systems involved in the lethargy induced by a parasitoid wasp in the cockroach prey? | 2002-05 |
|
| 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 |
|
| Heterosynaptic modulation by the octopaminergic OC interneurons increases the synaptic outputs of protraction phase interneurons (SO, N1L) in the feeding system of Lymnaea stagnalis. | 2002 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:38:54 GMT 2025
by
admin
on
Mon Mar 31 22:38:54 GMT 2025
|
| Record UNII |
5GQV08V31D
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
81098-58-0
Created by
admin on Mon Mar 31 22:38:54 GMT 2025 , Edited by admin on Mon Mar 31 22:38:54 GMT 2025
|
PRIMARY | |||
|
5GQV08V31D
Created by
admin on Mon Mar 31 22:38:54 GMT 2025 , Edited by admin on Mon Mar 31 22:38:54 GMT 2025
|
PRIMARY | |||
|
44151651
Created by
admin on Mon Mar 31 22:38:54 GMT 2025 , Edited by admin on Mon Mar 31 22:38:54 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |