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 |
---|---|---|
Functional expression of a locust tyramine receptor in murine erythroleukaemia cells. | 2001 Dec |
|
Amine modulation of the transient potassium current in identified cells of the lobster stomatogastric ganglion. | 2001 Dec |
|
Hormonal stimulation of proline synthesis in the fat body of the fruit beetle, Pachnoda sinuata, is calcium dependent. | 2001 Dec |
|
Octopamine influences division of labor in honey bee colonies. | 2001 Feb |
|
Dopamine-synthesizing neurons include the putative H-cell homologue in the moth Manduca sexta. | 2001 Feb 19 |
|
[Some regularities in the genetic control of the stress reaction in Drosophila]. | 2001 Jan |
|
Phenolamine-dependent adenylyl cyclase activation in Drosophila Schneider 2 cells. | 2001 Mar 15 |
|
Involvement of reactive oxygen species in the induction of (S)-N-p-coumaroyloctopamine accumulation by beta-1,3-glucooligosaccharide elicitors in potato tuber tissues. | 2001 Mar-Apr |
|
Mixtures of octopamine and serotonin have nonadditive effects on the CNS of the medicinal leech. | 2001 May |
|
Substituent-dependent, positive and negative modulation of Bombyx mori adenylate cyclase by synthetic octopamine/tyramine analogues. | 2001 May |
|
Modulating the modulators: parasites, neuromodulators and host behavioral change. | 2002 |
|
In vivo alpha(1)-adrenergic lipolytic activity in subcutaneous adipose tissue of obese subjects. | 2002 Apr |
|
Three-dimensional common-feature hypotheses for octopamine agonist 2-(arylimino)imidazolidines. | 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 |
|
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 |
|
Behavioural pharmacology of octopamine, tyramine and dopamine in honey bees. | 2002 Nov 15 |
|
Stress response in Drosophila melanogaster strain inactive with decreased tyramine and octopamine contents. | 2002 Oct |
|
Characterization of a tyramine receptor from Caenorhabditis elegans. | 2002 Sep |
|
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 |
|
Octopaminergic modulation of synaptic transmission between an identified sensory afferent and flight motoneuron in the locust. | 2003 Jul 14 |
|
Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase. | 2003 Jun |
|
Modulation of early olfactory processing by an octopaminergic reinforcement pathway in the honeybee. | 2003 Jun 15 |
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
LOINC |
2672-4
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
||
|
WHO-VATC |
QC01CA18
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
||
|
DSLD |
2862 (Number of products:99)
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
||
|
WHO-ATC |
C01CA18
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
||
|
NCI_THESAURUS |
C29709
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
58025
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
CHEMBL53929
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
14O50WS8JD
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
DB13251
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
100000083847
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
OCTOPAMINE
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
4581
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
D009655
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
44715
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
17134
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
104-14-3
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
14O50WS8JD
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
3653
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
203-179-5
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
m8118
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | Merck Index | ||
|
C75043
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
3396
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
DTXSID7043873
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
757399
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
SUB09415MIG
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | |||
|
1311141
Created by
admin on Sat Dec 16 17:47:58 GMT 2023 , Edited by admin on Sat Dec 16 17:47:58 GMT 2023
|
PRIMARY | RxNorm |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)