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Octopamine information


Octopamine
Ball-and-stick model of the octopamine molecule
Clinical data
Other namesOCT, Norsympathol, Norsynephrine, para-Octopamine, beta-Hydroxytyramine, para-hydroxy-phenyl-ethanolamine, α-(Aminomethyl)-4 hydroxybenzenemethanol, 1-(p-Hydroxyphenyl)-2-aminoethanol
Routes of
administration
Oral
ATC code
  • C01CA18 (WHO)
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 (3-amino-9, 13b-dihydro-1H-dibenz(c,f)imidazo(1,5a)azepine hydrochloride)
Precursortyramine
Biosynthesistyramine β-hydroxylase; dopamine β-hydroxylase
Metabolismp-hydroxymandelic acid;[1][2] N-acetyltransferases; phenylethanolamine N-methyltransferase
Legal status
Legal status
  • US: Prohibited from use in food or supplements.[3]
  • Rx / Uncontrolled / Banned by World Anti-Doping Agency
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
IUPAC name
  • (RS)-4-(2-amino-1-hydroxy-ethyl)phenol
CAS Number
  • 104-14-3 checkY
PubChem CID
  • 4581
IUPHAR/BPS
  • 2149
ChemSpider
  • 4420 checkY
UNII
  • 14O50WS8JD
KEGG
  • C04227
ChEBI
  • CHEBI:17134 ☒N
ChEMBL
  • ChEMBL53929 checkY
CompTox Dashboard (EPA)
  • DTXSID7043873 Edit this at Wikidata
ECHA InfoCard100.002.890 Edit this at Wikidata
Chemical and physical data
FormulaC8H11NO2
Molar mass153.181 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • OC(c1ccc(O)cc1)CN
InChI
  • 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 (molecular formula C8H11NO2; also known as OA, and also norsynephrine, para-octopamine and others) 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, 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.

and 28 Related for: Octopamine information

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Octopamine

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Octopamine (molecular formula C8H11NO2; also known as OA, and also norsynephrine, para-octopamine and others) is an organic chemical closely related to...

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Amitraz

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is traced back on alpha-adrenergic agonist activity, interaction with octopamine receptors of the central nervous system and inhibition of monoamine oxidases...

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Norfenefrine

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Norfenefrine (INN; also known as meta-octopamine, 3-octopamine, and 3,β-dihydroxyphenethylamine) is an adrenergic agent used as a sympathomimetic drug...

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Synephrine

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occur in animals, involving octopamine: tyramine → octopamine → synephrine, where the conversion of tyramine to octopamine is mediated by dopamine-β-hydroxylase...

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Octopamine dehydratase

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The enzyme octopamine dehydratase (EC 4.2.1.87) catalyzes the chemical reaction 1-(4-hydroxyphenyl)-2-aminoethanol ⇌ {\displaystyle \rightleftharpoons...

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Tyramine

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circulating neurotransmitters and neuromodulators (including tyramine, octopamine, and synephrine) in the hypothalamus, amygdala, and dopaminergic system...

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Medetomidine

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encounters a surface containing medetomidine the molecule interacts with the octopamine receptor in the larva. This causes the settling larva to increase its...

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C8H11NO2

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4-Deoxypyridoxine Dopamine, a neurotransmitter Isobutyl cyanoacrylate Norfenefrine Octopamine Vanillylamine This set index page lists chemical structure articles associated...

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Norepinephrine

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etc.) it is replaced by octopamine, a closely related chemical with a closely related synthesis pathway. In insects, octopamine has alerting and activating...

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Monoamine neurotransmitter

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Phenylethanolamine m-Tyramine p-Tyramine 3-Methoxytyramine N-Methyltyramine m-Octopamine p-Octopamine Synephrine Tryptamine Specific transporter proteins called monoamine...

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Chlorpromazine

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silk moth (Bombyx mori) octopamine receptor α, intermediate for Bm tyramine receptors 1 & 2, weak for Drosophila octopamine receptor β, high for Drosophila...

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Mushroom bodies

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inhibited by serotonin, GABA, and the combination of both. On the other hand octopamine does not seem to affect the MB's sleep function. We know that mushroom...

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TAAR1

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N-methylphenethylamine, p-tyramine, m-tyramine, N-methyltyramine, p-octopamine, m-octopamine, and synephrine. These share structural similarities with the three...

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Emerald cockroach wasp

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responses. The venom is reported to block receptors for the neurotransmitter octopamine. Once the host is incapacitated, the wasp proceeds to chew off half of...

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Party pills

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many others) include caffeine, theobromine, other stimulant alkaloids, octopamine, blue lotus extract (Nymphaea caerulea), natural sources of the LSD precursor...

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Serotonin

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The released serotonin activates the muscles used for feeding, while octopamine suppresses them. Serotonin diffuses to serotonin-sensitive neurons, which...

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Ampulex dementor

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toxin into the victim's neural nodes. This toxin blocks the cockroach's octopamine receptors, leaving the cockroach alive, but docile and with impaired motility...

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Rilmenidine

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Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine Oxymetazoline Phenylephrine Phenylpropanolamine Synephrine Tetryzoline...

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Edward Kravitz

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Later, Kravitz's work with neuroamines demonstrated that serotonin and octopamine act as synaptic modulators. Kravitz continued to explore the function...

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Bitter orange

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suppressant. Bitter orange contains the tyramine metabolites N-methyltyramine, octopamine, and synephrine, substances similar to epinephrine, which act on the α1...

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Cocaine

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Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex...

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MDMA

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Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex...

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Phentermine

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at human TAAR1 of several other compounds, including the trace amines octopamine and tryptamine, the amphetamine derivatives l-amphetamine, d-methamphetamine...

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Aromatic amino acid

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(adrenaline), and the thyroid hormone thyroxine. It is also precursor to octopamine and melanin in numerous organisms. Phenylalanine is the precursor to tyrosine...

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Martin Heisenberg

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Scholz, F. Friggi-Grelin, S. Birman, and M. Heisenberg: Dopamine and octopamine differentiate between aversive and appetitive olfactory memories in Drosophila...

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Methamphetamine

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Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex...

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LSD

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Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine Oxymetazoline Phenylephrine Phenylpropanolamine Synephrine Tetryzoline...

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Adderall

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Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex...

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