Octopamine

Octopamine
Clinical data
Trade names	Epirenor, Norden, Norfen
Other names	OCT, 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	C01CA18 (WHO) ;
Physiological data
Source tissues	Invertebrate nervous systems; trace amine in vertebrates
Target tissues	System-wide in invertebrates
Receptors	TAAR1 (mammals); OctαR, OctβR, TyrR (invertebrates), Oct-TyrR
Agonists	Formamidines (amitraz (AMZ) and chlordimeform (CDM))
Antagonists	Epinastine
Precursor	Tyramine
Biosynthesis	Tyramine β-hydroxylase; dopamine β-hydroxylase
Metabolism	p-Hydroxymandelic acid; N-acetyltransferases; phenylethanolamine N-methyltransferase
Legal status
Legal status	US: Prohibited from use in food or supplements.; Rx / Uncontrolled / Banned by World Anti-Doping Agency;
Pharmacokinetic data
Bioavailability	99.42%
Metabolism	p-Hydroxymandelic acid; N-acetyltransferases; phenylethanolamine N-methyltransferase
Elimination half-life	15 minutes in insects. Between 76 and 175 minutes in humans
Excretion	Up to 93% of ingested octopamine is eliminated via the urinary route within 24 hours
Identifiers
	IUPAC name (RS)-4-(2-amino-1-hydroxy-ethyl)phenol;
CAS Number	104-14-3 ;
PubChem CID	4581;
IUPHAR/BPS	2149;
ChemSpider	4420 ;
UNII	14O50WS8JD;
KEGG	C04227;
ChEBI	CHEBI:17134 ;
ChEMBL	ChEMBL53929 ;
CompTox Dashboard (EPA)	DTXSID7043873 ;
ECHA InfoCard	100.002.890
Chemical and physical data
Formula	C8H11NO2
Molar mass	153.181 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 ; Key:QHGUCRYDKWKLMG-UHFFFAOYSA-N ;
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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.^[4]^[5]

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

^ ^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.
^ 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.
^ "FDA's New Dietary Supplement Ingredient Directory | Foley & Lardner LLP". www.foley.com. 5 June 2023. Retrieved 10 June 2023.
^ 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.
^ Jagiełło-Wójtowicz E (1979). "Mechanism of central action of octopamine". Polish Journal of Pharmacology and Pharmacy. 31 (5): 509–516. PMID 121158.

[pmid4277715-1] 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.

[TangTaoLuo2006-4] 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.

[pmid121158-5] Jagiełło-Wójtowicz E (1979). "Mechanism of central action of octopamine". Polish Journal of Pharmacology and Pharmacy. 31 (5): 509–516. PMID 121158.

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