Octopamine

Octopamine
Ball-and-stick model of the octopamine molecule
Clinical data
Trade namesEpirenor, Norden, Norfen
Other namesOCT, Norsympathol, Norsynephrine, para-Octopamine, beta-Hydroxytyramine, 4,β-dihydroxyphenethylamine, para-hydroxy-phenyl-ethanolamine, α-(Aminomethyl)-4 hydroxybenzenemethanol, 1-(p-Hydroxyphenyl)-2-aminoethanol
Routes of
administration
Oral
ATC code
Physiological data
Source tissuesInvertebrate nervous systems; trace amine in vertebrates
Target tissuesSystem-wide in invertebrates
ReceptorsTAAR1 (mammals)
OctαR, OctβR, TyrR (invertebrates), Oct-TyrR
AgonistsFormamidines (amitraz (AMZ) and chlordimeform (CDM))
AntagonistsEpinastine
PrecursorTyramine
BiosynthesisTyramine β-hydroxylase; dopamine β-hydroxylase
Metabolismp-Hydroxymandelic acid;[1][2] N-acetyltransferases; phenylethanolamine N-methyltransferase
Legal status
Legal status
Pharmacokinetic data
Bioavailability99.42%
Metabolismp-Hydroxymandelic acid;[1][2] N-acetyltransferases; phenylethanolamine N-methyltransferase
Elimination half-life15 minutes in insects. Between 76 and 175 minutes in humans
ExcretionUp to 93% of ingested octopamine is eliminated via the urinary route within 24 hours[1]
Identifiers
  • (RS)-4-(2-amino-1-hydroxy-ethyl)phenol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.002.890 Edit this at Wikidata
Chemical and physical data
FormulaC8H11NO2
Molar mass153.181 g·mol−1
3D model (JSmol)
  • OC(c1ccc(O)cc1)CN
  • InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2 checkY
  • Key:QHGUCRYDKWKLMG-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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 protostomesarthropods, 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.[4][5]

Octopamine has been sold under trade names such as Epirenor, Norden, and Norfen for use as a sympathomimetic drug, available by prescription.

  1. ^ a b Hengstmann JH, Konen W, Konen C, Eichelbaum M, Dengler HJ (1974). "The physiological disposition of p-octopamine in man". Naunyn-Schmiedeberg's Archives of Pharmacology. 283 (1): 93–106. doi:10.1007/bf00500148. PMID 4277715. S2CID 35523412.
  2. ^ D'Andrea G, Nordera G, Pizzolato G, Bolner A, Colavito D, Flaibani R, et al. (January 2010). "Trace amine metabolism in Parkinson's disease: low circulating levels of octopamine in early disease stages". Neuroscience Letters. 469 (3): 348–351. doi:10.1016/j.neulet.2009.12.025. PMID 20026245. S2CID 12797090.
  3. ^ "FDA's New Dietary Supplement Ingredient Directory | Foley & Lardner LLP". www.foley.com. 5 June 2023. Retrieved 10 June 2023.
  4. ^ Tang F, Tao L, Luo X, Ding L, Guo M, Nie L, et al. (September 2006). "Determination of octopamine, synephrine and tyramine in Citrus herbs by ionic liquid improved 'green' chromatography". Journal of Chromatography A. 1125 (2): 182–188. doi:10.1016/j.chroma.2006.05.049. PMID 16781718.
  5. ^ Jagiełło-Wójtowicz E (1979). "Mechanism of central action of octopamine". Polish Journal of Pharmacology and Pharmacy. 31 (5): 509–516. PMID 121158.