U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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

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

PubMed

TitleDatePubMed
Amine modulation of the transient potassium current in identified cells of the lobster stomatogastric ganglion.
2001 Dec
Amphetamine, 3,4-methylenedioxymethamphetamine, lysergic acid diethylamide, and metabolites of the catecholamine neurotransmitters are agonists of a rat trace amine receptor.
2001 Dec
Hormonal stimulation of proline synthesis in the fat body of the fruit beetle, Pachnoda sinuata, is calcium dependent.
2001 Dec
Inositol trisphosphate mediates the action of hypertrehalosemic hormone on fat body of the American cockroach, Periplaneta americana.
2001 Dec
Dopamine-synthesizing neurons include the putative H-cell homologue in the moth Manduca sexta.
2001 Feb 19
Quantitative trait loci for the monoamine-related traits heart rate and headless behavior in Drosophila melanogaster.
2001 Jan
An in vitro method for recording the electrical activity of the isolated heart of the adult Drosophila melanogaster.
2001 Jul-Aug
Serotonergic and octopaminergic systems in the squat lobster Munida quadrispina (Anomura, Galatheidae).
2001 Oct 29
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
Biogenic amines evoke heartbeat reversal in larvae of the sweet potato hornworm, Agrius convolvuli.
2002 Nov
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
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
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
Patents

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
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
OCTOPAMINE
INCI   INN   MART.   MI   WHO-DD  
INN   INCI  
Official Name English
OCTOPAMINE [MART.]
Common Name English
ND-50
Code English
ND 50
Code English
Octopamine [WHO-DD]
Common Name English
octopamine [INN]
Common Name English
OCTOPAMINE [INCI]
Common Name English
NSC-757399
Code English
OCTOPAMINE [MI]
Common Name English
RACTOPAMINE HYDROCHLORIDE SUSPENSION IMPURITY, OCTOPAMINE- [USP IMPURITY]
Common Name English
.ALPHA.-(AMINOMETHYL)-P-HYDROXYBENZYL ALCOHOL
Common Name English
4-(2-AMINO-1-HYDROXYETHYL)PHENOL
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
CHEBI
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
ChEMBL
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
DAILYMED
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
DRUG BANK
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
SMS_ID
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
WIKIPEDIA
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
PUBCHEM
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
MESH
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
CHEBI
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
CHEBI
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
CAS
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
FDA UNII
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
INN
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
ECHA (EC/EINECS)
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
MERCK INDEX
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
NCI_THESAURUS
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
DRUG CENTRAL
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
EPA CompTox
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
NSC
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
EVMPD
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
RXCUI
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