Structure via PubChem · Public domain (PubChem)
octopamine
Sign in to saveAlso known as alpha-(aminomethyl)-p-hydroxybenzyl alcohol, 1-(p-hydroxyphenyl)-2-aminoethanol, beta-hydroxytyramine, norsynephrine, alpha-(aminomethyl)-4-hydroxybenzenemethanol
Octopamine (OA), also known as '''para-octopamine and norsynephrine''' among synonyms, is an organic chemical closely related to norepinephrine, and synthesized biologically by a homologous pathway. Octopamine is often considered the major "fight-or-flight" neurohormone of invertebrates. Its name is derived from the fact that it was first identified in the salivary glands of the octopus.
Key facts
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 408985899
- Drug.drug_name
- Octopamine
- Drug.image
- Octopamin.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 220px
- Drug.image2
- Octopamine---3D BALL AND STICK.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200px
- Drug.alt2
- Ball-and-stick model of the octopamine molecule
- Drug.tradename
- Epirenor, Norden, Norfen
- Drug.legal_US
- Prohibited from use in food or supplements.
- Drug.legal_status
- Rx / Uncontrolled / Banned by World Anti-Doping Agency
- Drug.routes_of_administration
- Oral
- Drug.bioavailability
- 99.42%
- Drug.metabolism
- p-Hydroxymandelic acid; N-acetyltransferases; phenylethanolamine N-methyltransferase
- Drug.elimination_half life
- 15 minutes in insects. Between 76 and 175 minutes in humans
- Drug.excretion
- Up to 93% of ingested octopamine is eliminated via the urinary route within 24 hours
via Wikipedia infobox
Chemical data
- Formula
- C8H11NO2
- Molecular weight
- 153.18 g/mol
- IUPAC name
- 4-(2-amino-1-hydroxyethyl)phenol
- SMILES
- C1=CC(=CC=C1C(CN)O)O
- InChIKey
- QHGUCRYDKWKLMG-UHFFFAOYSA-N
- XLogP
- -1.1
- Polar surface area
- 66.5 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
2,663 papers- Octopamine in the mushroom body circuitry for learning and memory.Learning & memory (Cold Spring Harbor, N.Y.) · 2024
- Octopamine.Nature · 1977
- Octopamine in invertebrates.Progress in neurobiology · 1999
- Octopamine drives honeybee thermogenesis.eLife · 2022
- Octopamine-mediated neuromodulation of insect senses.Neurochemical research · 2007
via PubMed
~11 min read
Encyclopedic overview
16 sectionsContents
- Functions
- Cellular effects
- Invertebrates
- In non-insect invertebrates
- In non-''Drosophila'' insects
- In ''Drosophila''
- Vertebrates
- Pharmacology
- Insecticides
- Biochemical mechanisms
- Mammals
- Invertebrates
- Biosynthesis
- In insects
- Chemistry
- References
Octopamine (OA), also known as '''para-octopamine and norsynephrine among synonyms, is an organic chemical closely related to norepinephrine, and synthesized biologically by a homologous pathway. Octopamine is often considered the major "fight-or-flight" neurohormone of invertebrates. Its name is derived from the fact that it was first identified in the salivary glands of the octopus.
In many types of invertebrates, octopamine is an important neurotransmitter and hormone. In protostomes—arthropods, molluscs, and several types of worms—it substitutes for norepinephrine and performs functions apparently similar to those of norepinephrine in mammals, functions that have been described as mobilizing the body and nervous system for action. In mammals, octopamine is found only in trace amounts (i.e., it is a trace amine), and no biological function has been solidly established for it. It is also found naturally in numerous plants, including bitter orange.
Excerpted from Wikipedia’s “octopamine” article, available under the CC BY-SA 4.0 licence.