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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
Structure of OCTOPAMINE

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

HIDE SMILES / InChI

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 ( + / - )

Description

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

Targets

Primary TargetPharmacologyConditionPotency
3.12 µM [EC50]
220.0 µM [Kd]
1.66 µM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Norphen

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
14O50WS8JD
Record Status Validated (UNII)
Record Version