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 |
MOL RATIO
1 MOL RATIO (average) |
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
Originator
Approval Year
PubMed
Patents
Sample Use Guides
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