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			{{Short description|Group of stereoisomers}}
	{{Drugbox
			{{cs1 config|name-list-style=vanc|display-authors=6}}
	| verifiedrevid = 408984003
			{{for|para-octopamine's isomer|m-octopamine}}
	| drug_name = Octopamine
			{{Use dmy dates|date=April 2020}}
	| IUPAC_name = (''RS'')-4-(2-amino-1-hydroxy-ethyl)phenol
			{{infobox drug
	| image = Octopamin.svg
			| Verifiedfields = changed
	| imagename = 1 : 1 mixture (racemate)
			| verifiedrevid = 408985899
	| width = 200
			| drug_name = Octopamine
	| CASNo_Ref = {{cascite|correct|CAS}}
			| image = Octopamin.svg
			| width =
			| image2 = (S)-Octopamine molecule ball.png
			| width2 =
			| alt2 = Ball-and-stick model of the octopamine molecule
			<!-- Clinical data -->
			| tradename = Epirenor, Norden, Norfen
			| pregnancy_category =
			| legal_US = Prohibited from use in food or supplements.<ref>{{Cite web |title=FDA's New Dietary Supplement Ingredient Directory {{!}} Foley & Lardner LLP |url=https://www.foley.com/en/insights/publications/2023/06/fda-new-dietary-supplement-ingredient-directory |access-date=2023-06-10 |website=www.foley.com |date=5 June 2023 |language=en}}</ref>
			| legal_status = Rx / Uncontrolled / Banned by ]
			| routes_of_administration = ]
			<!-- Pharmacokinetic data -->
			| bioavailability = 99.42%
			| metabolism = ''p''-Hydroxymandelic acid;<ref name="pmid4277715">{{cite journal | vauthors = Hengstmann JH, Konen W, Konen C, Eichelbaum M, Dengler HJ | title = The physiological disposition of p-octopamine in man | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 283 | issue = 1 | pages = 93–106 | year = 1974 | pmid = 4277715 | doi = 10.1007/bf00500148 | s2cid = 35523412 }}</ref><ref>{{cite journal | vauthors = D'Andrea G, Nordera G, Pizzolato G, Bolner A, Colavito D, Flaibani R, Leon A | title = Trace amine metabolism in Parkinson's disease: low circulating levels of octopamine in early disease stages | journal = Neuroscience Letters | volume = 469 | issue = 3 | pages = 348–351 | date = January 2010 | pmid = 20026245 | doi = 10.1016/j.neulet.2009.12.025 | s2cid = 12797090 }}</ref> ]s; ]
			| 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<ref name="pmid4277715" />
			<!-- Identifiers -->
			| CAS_number_Ref = {{cascite|correct|??}}
			| CAS_number = 104-14-3
			| ATC_prefix = C01
			| ATC_suffix = CA18
			| PubChem = 4581
			| IUPHAR_ligand = 2149
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID = 4420
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 14O50WS8JD		| UNII = 14O50WS8JD
			| KEGG = C04227
	| InChI = 1/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2
			| ChEBI_Ref = {{ebicite|changed|EBI}}
	| InChIKey = QHGUCRYDKWKLMG-UHFFFAOYAX
			| ChEBI = 17134
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 53929		| ChEMBL = 53929
			| synonyms = OCT, Norsympathol, Norsynephrine, ''para''-Octopamine, beta-Hydroxytyramine, 4,β-dihydroxyphenethylamine, para-hydroxy-phenyl-ethanolamine, α-(Aminomethyl)-4 hydroxybenzenemethanol, 1-(p-Hydroxyphenyl)-2-aminoethanol
			<!--Chemical data-->
			| IUPAC_name = (''RS'')-4-(2-amino-1-hydroxy-ethyl)phenol
			| C=8 | H=11 | N=1 | O=2
			| SMILES = OC(c1ccc(O)cc1)CN
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2		| StdInChI = 1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = QHGUCRYDKWKLMG-UHFFFAOYSA-N		| StdInChIKey = QHGUCRYDKWKLMG-UHFFFAOYSA-N
	| CAS_number = 104-14-3
			<!-- Physiological data -->
	| ATC_prefix = C01
			| source_tissues = Invertebrate nervous systems; ] in vertebrates
	| ATC_suffix = CA18
			| target_tissues = System-wide in invertebrates
	| PubChem = 4581
			| receptors = ] (mammals)<br />OctαR, OctβR, TyrR (invertebrates), Oct-TyrR
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| agonists = Formamidines (amitraz (AMZ) and chlordimeform (CDM))
	| ChemSpiderID = 4420
			| antagonists = ]
	| C = 8 | H = 11 | N = 1 | O = 2
			| precursor = ]
	| molecular_weight = 153.178 g/mol
			| biosynthesis = ]; ]
	| smiles = OC(c1ccc(O)cc1)CN
	| synonyms = Norsympathol, Norsynephrine, para-Octopamine, beta-Hydroxytyramine
	| bioavailability =
	| metabolism =
	| elimination_half-life = 15 Minutes in insects. Theorized to be longer in vertebrates.
	| excretion =
	| pregnancy_category =
	| legal_status = Rx-only
	| routes_of_administration = Oral
	}}		}}
			'''Octopamine''' ('''OA'''), also known as '''''para''-octopamine''' and '''norsynephrine''' among synonyms, is an ] closely related to ], and ] by a homologous pathway. Octopamine is often considered the major "fight-or-flight" ] of ]s. Its name is derived from the fact that it was first identified in the ]s of the ].
	'''Octopamine''', also known as '''β,4-dihydroxyphenethylamine''', is an ] ] that is closely related to ], and has effects on the ] and ] systems.<ref name="pmid121158">{{cite journal |author=Jagiełło-Wójtowicz E |title=Mechanism of central action of octopamine |journal=Pol J Pharmacol Pharm |volume=31 |issue=5 |pages=509–16 |year=1979 |pmid=121158 |doi= |url=}}</ref> ] of the <small>D</small>-(—)-] of octopamine is by β-] of ] via the ] ]. Under the trade names '''Epirenor''', '''Norden''', and '''Norfen''', octopamine is also used ] as a ] ].<ref name="isbn3-88763-075-0">{{cite book | author = Swiss Pharmaceutical Society | title = Index Nominum 2000: International Drug Directory (Book with CD-ROM) | publisher = Medpharm Scientific Publishers | location = Boca Raton | year = 2000 | pages = | isbn = 3-88763-075-0 | oclc = | doi = | url = http://books.google.com/?id=5GpcTQD_L2oC&lpg=PA1499&dq=octopamine%20index&pg=PA756#v=onepage&q}}</ref><ref name="urlPharmacognosy And Pharmacobiotechnology - Google Books">{{cite web | url = http://books.google.com/books?id=PlMi4XvHCYoC&lpg=PA810&dq=Epirenor%20octopamine&pg=PA810#v=onepage&q&f=false | title = Pharmacognosy And Pharmacobiotechnology - Google Books | format = | work = | accessdate = }}</ref>
			In many types of invertebrates, octopamine is an important ] and ]. In ]s—]s, ]s, and several types of ]s—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 ]), and no biological function has been solidly established for it. It is also found ] in numerous plants, including ].<ref name="TangTaoLuo2006">{{cite journal | vauthors = Tang F, Tao L, Luo X, Ding L, Guo M, Nie L, Yao S | title = Determination of octopamine, synephrine and tyramine in Citrus herbs by ionic liquid improved 'green' chromatography | journal = Journal of Chromatography A | volume = 1125 | issue = 2 | pages = 182–188 | date = September 2006 | pmid = 16781718 | doi = 10.1016/j.chroma.2006.05.049 }}</ref><ref name="pmid121158">{{cite journal | vauthors = Jagiełło-Wójtowicz E | title = Mechanism of central action of octopamine | journal = Polish Journal of Pharmacology and Pharmacy | volume = 31 | issue = 5 | pages = 509–516 | year = 1979 | pmid = 121158 }}</ref>
	==Role in invertebrates==
	Octopamine was first discovered by Italian scientist ] in 1948<ref>{{cite journal | doi = 10.1111/j.1600-0773.1948.tb03345.x | author = Erspamer, V., Active substances in the posterior salivary glands of Octopoda. 2. Tyramine and octopamine (oxyoctopamine) | title = Active Substances in the Posterior Salivary Glands of Octopoda. II. Tyramine and Octopamine (Oxyoctopamine). | journal = Acta Pharmacologica et Toxicologica | volume = 4 | issue = 3-4 | pages = 224–247 | year = 1948}}</ref> in the salivary glands of the ] and has since been found to act as ], ] and ] in ]s. It is widely used in energy-demanding behaviors by all insects, crustaceans (crabs, lobsters, crayfish), and spiders. Such behaviors include flying, egg-laying, and jumping.
			Octopamine has been sold under trade names such as '''Epirenor''', '''Norden''', and '''Norfen''' for use as a ], available by prescription.
	The best-understood role for octopamine is in the ] jump. Here it modulates muscle activity, making the leg muscles contract more effectively. This is at least in part due to an increase in the rate of contraction and of relaxation.
			==Functions==
	In the ] and ], octopamine has a major role in learning and memory. In the ], octopamine release leads to light production in the lantern.
			===Cellular effects===
			Octopamine exerts its effects by binding to and activating receptors located on the surface of cells. These receptors have mainly been studied in insects, where they can be divided into distinct types:
			# OctαR (]-like), are structurally and functionally similar to noradrenergic alpha-1 receptors in mammals. There are multiple subtypes of the OctαR receptor. For example, the kissing bug ('']'') has Octα<sub>1</sub>-R, Octα<sub>2</sub>R.<ref>{{cite journal | vauthors = Hana S, Lange AB | title = Cloning and Functional Characterization of Octβ2-Receptor and Tyr1-Receptor in the Chagas Disease Vector, ''Rhodnius prolixus'' | journal = Frontiers in Physiology | volume = 8 | pages = 744 | date = 2017-09-26 | pmid = 29018364 | pmc = 5623054 | doi = 10.3389/fphys.2017.00744 | doi-access = free }}</ref>
	Octopamine also plays a role in ]s, though the role of octopamine has been examined only in the ] of the model organism, the pond ].
			# OctβR (]-like), are structurally and functionally similar to noradrenergic beta receptors in mammals. There are multiple subtypes of the OctβR receptor. For example, the fruit fly ('']'') has DmOctβ1R, DmOctβ2R, and DmOctβ3R.<ref>{{cite journal | vauthors = Maqueira B, Chatwin H, Evans PD | title = Identification and characterization of a novel family of Drosophila beta-adrenergic-like octopamine G-protein coupled receptors | journal = Journal of Neurochemistry | volume = 94 | issue = 2 | pages = 547–560 | date = July 2005 | pmid = 15998303 | doi = 10.1111/j.1471-4159.2005.03251.x | s2cid = 83666118 }}</ref>
			# OAMB. The diversity of this receptor is relatively unknown. The fruit fly (Drosophila melanogaster) has two distinct isoforms which are functionally distinct: Oamb<sup>K3</sup> and Oamb<sup>AS</sup>.<ref>{{cite journal | vauthors = Lee HG, Rohila S, Han KA | title = The octopamine receptor OAMB mediates ovulation via Ca2+/calmodulin-dependent protein kinase II in the Drosophila oviduct epithelium | journal = PLOS ONE | volume = 4 | issue = 3 | pages = e4716 | date = 2009-03-05 | pmid = 19262750 | pmc = 2650798 | doi = 10.1371/journal.pone.0004716 | doi-access = free | bibcode = 2009PLoSO...4.4716L }}</ref>
			# TyrR (mixed octopamine/tyramine receptors), which are structurally and functionally similar to noradrenergic alpha-2 receptors in mammals.<ref name="Pfluger3">{{cite journal|vauthors=Pflüger HJ, Stevensonb PA|year=2005|title=Evolutionary aspects of octopaminergic systems with emphasis on arthropods|url=https://www.researchgate.net/publication/235927256|journal=Arthropod Structure & Development|volume=34|issue=3|pages=379–396|doi=10.1016/j.asd.2005.04.004}}</ref> Receptors in the TyrR class, however, are generally more strongly activated by ] than by octopamine.<ref name="Pfluger3" />
			Phylogenetic studies claim that in ancient ] such as ] there is a co-existence of ], ] and octopamine receptor signaling. However, due to partial overlapping in their signalling functionality tyramine and octopamine receptors have been lost in vertebrates.<ref>{{cite journal | vauthors = Bauknecht P, Jékely G | title = Ancient coexistence of norepinephrine, tyramine, and octopamine signaling in bilaterians | journal = BMC Biology | volume = 15 | issue = 1 | pages = 6 | date = January 2017 | pmid = 28137258 | pmc = 5282848 | doi = 10.1186/s12915-016-0341-7 | doi-access = free }}</ref>
	Heberlein et al. <ref>{{cite journal | last1 = Heberlein | first1 = U. | title = Molecular Genetic Analysis of Ethanol Intoxication in Drosophila melanogaster | journal = Integrative and Comparative Biology | volume = 44 | pages = 269 | year = 2004 | doi = 10.1093/icb/44.4.269}}</ref> have conducted studies of alcohol tolerance in fruit flies; they found that a mutation that caused octopamine deficiency also caused lower alcohol tolerance.<ref>{{cite journal | doi = 10.1016/S0092-8674(00)81205-2 | author = Moore, M. S., Dezazzo, J., Luk, A. Y., Tully, T., Singh, C. M., and Heberlein, U. | year = 1998 | title = Ethanol intoxication in Drosophila: Genetic and pharmacological evidence for regulation by the cAMP pathway | journal = Cell | volume = 93 | issue = 6 | pages = 997–1007 | pmid = 9635429}}</ref><ref>{{cite journal | doi = 10.1016/S0092-8674(00)81695-5 | author = Tecott, L. H. and Heberlein, U. | year = 1998 | title = Y do we drink? | journal = Cell | volume = 95 | issue = 6 | pages = 733–735 | pmid = 9865690}}</ref><ref>, Ruth Williams, Naked Scientist</ref><ref>, Gaia Vince, NewScientist.com news service, 22 August 2005</ref>
			In vertebrates no octopamine-specific receptors have been identified. Octopamine binds weakly to receptors for ] and ], but it is not clear whether this has any functional significance. It binds more strongly to ]s (TAARs), especially ].<ref name="Pfluger3" />
	The ] stings the host for its larvae (a cockroach) in the head ganglion (brain). The venom blocks octopamine receptors<ref>, ''Nature News'', 29 September 2007</ref> and the cockroach fails to show normal escape responses, grooming itself excessively. It becomes docile and the wasp leads it to the wasp's den by pulling its antenna like a leash. <ref>{{cite journal|last=Gal|first=Ram|coauthors=Rosenberg, Lior Ann; Libersat, Frederic|date=22 November 2005|title=Parasitoid wasp uses a venom cocktail injected into the brain to manipulate the behavior and metabolism of its cockroach prey|journal=Archives of Insect Biochemistry and Physiology|volume=60|issue=4|pages=198–208|url=http://www3.interscience.wiley.com/journal/112152224/abstract|doi=10.1002/arch.20092|pmid=16304619}}</ref>
			===Invertebrates===
	==Role in vertebrates==
			Octopamine was first discovered by Italian scientist ] in 1948<ref>{{cite journal| vauthors = Erspamer V |year=2009|title=Active Substances in the Posterior Salivary Glands of Octopoda. II. Tyramine and Octopamine (Oxyoctopamine)|journal=Acta Pharmacologica et Toxicologica|volume=4|issue=3–4|pages=224–47|doi=10.1111/j.1600-0773.1948.tb03345.x}}</ref> in the salivary glands of the ] and has since been found to act as a ], ] and ] in ]s. Although Erspamer discovered its natural occurrence and named it, octopamine had actually existed for many years as a pharmaceutical product.<ref name="jbc3">{{cite journal | vauthors = Kakimoto Y, Armstrong MD | title = On the identification of octopamine in mammals | journal = The Journal of Biological Chemistry | volume = 237 | issue = 2 | pages = 422–427 | date = February 1962 | pmid = 14453200 | doi = 10.1016/S0021-9258(18)93937-2 | doi-access = free }}</ref> It is widely used in energy-demanding behaviors by all insects, crustaceans (crabs, lobsters, crayfish), and spiders. Such behaviors include modulating muscle tension,<ref name="Action of octopamine and tyramine o">{{cite journal | vauthors = Ormerod KG, Hadden JK, Deady LD, Mercier AJ, Krans JL | title = Action of octopamine and tyramine on muscles of Drosophila melanogaster larvae | journal = Journal of Neurophysiology | volume = 110 | issue = 8 | pages = 1984–1996 | date = October 2013 | pmid = 23904495 | doi = 10.1152/jn.00431.2013 | hdl-access = free | hdl = 10464/6361 }}</ref> flying,<ref name=":0">{{Cite journal| vauthors = Orchard I, Ramirez JM, Lange AB |date=January 1993|title=A Multifunctional Role for Octopamine in Locust Flight|journal=Annual Review of Entomology|language=en|volume=38|issue=1|pages=227–249|doi=10.1146/annurev.en.38.010193.001303|issn=0066-4170}}</ref> ovulation and egg-laying,<ref name=":6">{{cite journal | vauthors = Lee HG, Seong CS, Kim YC, Davis RL, Han KA | title = Octopamine receptor OAMB is required for ovulation in Drosophila melanogaster | journal = Developmental Biology | volume = 264 | issue = 1 | pages = 179–190 | date = December 2003 | pmid = 14623240 | doi = 10.1016/j.ydbio.2003.07.018 | doi-access = free }}</ref><ref name=":3">{{cite journal | vauthors = Li Y, Fink C, El-Kholy S, Roeder T | title = The octopamine receptor octß2R is essential for ovulation and fertilization in the fruit fly Drosophila melanogaster | journal = Archives of Insect Biochemistry and Physiology | volume = 88 | issue = 3 | pages = 168–178 | date = March 2015 | pmid = 25353988 | doi = 10.1002/arch.21211 }}</ref><ref name=":4">{{cite journal | vauthors = Lim J, Sabandal PR, Fernandez A, Sabandal JM, Lee HG, Evans P, Han KA | title = The octopamine receptor Octβ2R regulates ovulation in Drosophila melanogaster | journal = PLOS ONE | volume = 9 | issue = 8 | pages = e104441 | date = 2014-08-06 | pmid = 25099506 | pmc = 4123956 | doi = 10.1371/journal.pone.0104441 | bibcode = 2014PLoSO...9j4441L | doi-access = free | veditors = Broughton S }}</ref><ref name=":5">{{cite journal | vauthors = Lee HG, Rohila S, Han KA | title = The octopamine receptor OAMB mediates ovulation via Ca2+/calmodulin-dependent protein kinase II in the Drosophila oviduct epithelium | journal = PLOS ONE | volume = 4 | issue = 3 | pages = e4716 | date = 2009-03-05 | pmid = 19262750 | pmc = 2650798 | doi = 10.1371/journal.pone.0004716 | bibcode = 2009PLoSO...4.4716L | doi-access = free | veditors = Louis M }}</ref><ref name=":7">{{cite journal | vauthors = Monastirioti M | title = Distinct octopamine cell population residing in the CNS abdominal ganglion controls ovulation in Drosophila melanogaster | journal = Developmental Biology | volume = 264 | issue = 1 | pages = 38–49 | date = December 2003 | pmid = 14623230 | doi = 10.1016/j.ydbio.2003.07.019 | doi-access = free }}</ref><ref name=":8">{{cite journal | vauthors = Deady LD, Sun J | title = A Follicle Rupture Assay Reveals an Essential Role for Follicular Adrenergic Signaling in Drosophila Ovulation | journal = PLOS Genetics | volume = 11 | issue = 10 | pages = e1005604 | date = October 2015 | pmid = 26473732 | pmc = 4608792 | doi = 10.1371/journal.pgen.1005604 | veditors = Wolfner MF | doi-access = free }}</ref> and jumping.<ref>{{cite journal | vauthors = Pollack AJ, Ritzmann RE, Westin J | title = Activation of DUM cell interneurons by ventral giant interneurons in the cockroach, Periplaneta americana | journal = Journal of Neurobiology | volume = 19 | issue = 6 | pages = 489–497 | date = September 1988 | pmid = 3171574 | doi = 10.1002/neu.480190602 }}</ref><ref>{{Cite journal| vauthors = Orchard I |date=1982-04-01|title=Octopamine in insects: neurotransmitter, neurohormone, and neuromodulator|journal=Canadian Journal of Zoology|volume=60|issue=4|pages=659–669|doi=10.1139/z82-095|issn=0008-4301}}</ref>
	In ]s, octopamine replaces ] in ] ]s with chronic use of ]s. It may be responsible for the common ] of ] with these agents, though there is also evidence that it is actually mediated by increased levels of ].
			==== In non-insect invertebrates ====
	In ]s, octopamine may mobilize the release of ] from ] (fat cells), which has led to its promotion on the ] as a slimming aid. However, the released fat is likely to be promptly taken up into other cells, and there is no evidence that octopamine facilitates weight loss. Octopamine may also increase ] significantly when combined with other ]s, as in some ]s.
			In lobsters, octopamine seems to direct and coordinate ]s to some extent in the central nervous system, and it was observed that injecting octopamine into a lobster and crayfish resulted in limb and abdomen extension.<ref>{{cite journal | vauthors = Livingstone MS, Harris-Warrick RM, Kravitz EA | title = Serotonin and octopamine produce opposite postures in lobsters | journal = Science | volume = 208 | issue = 4439 | pages = 76–79 | date = April 1980 | pmid = 17731572 | doi = 10.1126/science.208.4439.76 | bibcode = 1980Sci...208...76L | s2cid = 32141532 }}</ref>
	<ref>{{cite web|url=http://www.medpagetoday.com/Cardiology/Hypertension/tb1/1713?pfc=101&spc=235|title=Ephedra-Free Supplements Not Necessarily Risk-Free |last=Minerd, Jeff|date=12 September 2005|work=MedPage Today|accessdate = 2009-09-12}}</ref>
	<ref>{{cite journal | last1 = Haller | first1 = C | last2 = Benowitz | first2 = N | last3 = Jacobiii | first3 = P | title = Hemodynamic effects of ephedra-free weight-loss supplements in humans | journal = The American Journal of Medicine | volume = 118 | pages = 998 | year = 2005 | doi = 10.1016/j.amjmed.2005.02.034}}</ref>
			In the ], octopamine is found in high concentrations in adults, decreasing egg-laying and pharyngeal pumping behaviors with an antagonistic effect to ].<ref>{{cite journal | vauthors = Horvitz HR, Chalfie M, Trent C, Sulston JE, Evans PD | title = Serotonin and octopamine in the nematode Caenorhabditis elegans | journal = Science | volume = 216 | issue = 4549 | pages = 1012–1014 | date = May 1982 | pmid = 6805073 | doi = 10.1126/science.6805073 | bibcode = 1982Sci...216.1012H }}</ref>
	Owing to lack of research, much is not known about octopamine or its role in humans.
			Octopaminergic nerves in the ] may be present in the heart, with high concentrations in the nervous system.<ref>{{Cite journal | vauthors = Dougan DF, Duffield PH, Wade DN, Duffield AM |date= January 1981 |title=Occurrence and synthesis of octopamine in the heart and ganglia of the mollusc Tapes watlingi |journal=Comparative Biochemistry and Physiology Part C: Comparative Pharmacology |language=en |volume=70 |issue=2 |pages=277–280 |doi=10.1016/0306-4492(81)90064-2 |issn=0306-4492}}</ref>
	==See also==
	* ]
	* ]
			==== In non-''Drosophila'' insects ====
	==References==
			In insects, octopamine is released by a select number of neurons, but acts broadly throughout the central brain, on all sense organs, and on several non-neuronal tissues.<ref name=":1">{{Citation| vauthors = Atwood HL, Klose MK |title= Neuromuscular Transmission Modulation at Invertebrate Neuromuscular Junctions|date=2009-01-01|url=http://www.sciencedirect.com/science/article/pii/B9780080450469012626|encyclopedia=Encyclopedia of Neuroscience|pages=671–690| veditors = Squire LR |place=Oxford|publisher=Academic Press|doi= 10.1016/B978-008045046-9.01262-6|language=en|isbn=978-0-08-045046-9|access-date=2020-07-10}}</ref><ref>{{cite journal | vauthors = Roeder T | title = Octopamine in invertebrates | journal = Progress in Neurobiology | volume = 59 | issue = 5 | pages = 533–561 | date = December 1999 | pmid = 10515667 | doi = 10.1016/s0301-0082(99)00016-7 | s2cid = 25654298 }}</ref> In the thoracic ganglia, octopamine is primarily released by DUM (dorsal unpaired median) and VUM (ventral unpaired median) neurons, which release octopamine onto neural, muscular, and peripheral targets.<ref>{{cite journal | vauthors = Eckert M, Rapus J, Nürnberger A, Penzlin H | title = A new specific antibody reveals octopamine-like immunoreactivity in cockroach ventral nerve cord | language = fr | journal = The Journal of Comparative Neurology | volume = 322 | issue = 1 | pages = 1–15 | date = August 1992 | pmid = 1430305 | doi = 10.1002/cne.903220102 | s2cid = 41099770 }}</ref><ref>{{Cite journal| vauthors = Sinakevitch IG, Geffard M, Pelhate M, Lapied B |date=April 1994|title=Octopamine-like immunoreactivity in the dorsal unpaired median (DUM) neurons innervating the accessory gland of the male cockroach Periplaneta americana|journal=Cell and Tissue Research|volume=276|issue=1|pages=15–21|doi=10.1007/bf00354779|s2cid=23485136|issn=0302-766X}}</ref> These neurons are important for mediating energy-demanding motor behaviors, such as escape-induced jumping and flight. For example, the locust DUMeti neuron releases octopamine onto the extensor tibia muscle to increase muscle tension and increase relaxation rate. These actions promote efficient leg muscle contraction for jumping.<ref name=":1" /> During flight, DUM neurons are also active and release octopamine throughout the body to synchronize energy metabolism, respiration, muscle activity and flight interneuron activity.<ref name=":0" /> Octopamine in ] is four times more concentrated in the axon than in the soma, and decreases the locust's ].<ref>{{cite journal | vauthors = Evans PD, O'Shea M | title = The identification of an octopaminergic neurone and the modulation of a myogenic rhythm in the locust | journal = The Journal of Experimental Biology | volume = 73 | pages = 235–260 | date = April 1978 | pmid = 25941 | doi = 10.1242/jeb.73.1.235 }}</ref>
	{{Reflist|2}}
			In the ], octopamine has a major role in learning and memory. In the ], octopamine release leads to light production in the lantern.<ref>{{cite journal | vauthors = Greenfield MD | title = Missing link in firefly bioluminescence revealed: NO regulation of photocyte respiration | journal = BioEssays | volume = 23 | issue = 11 | pages = 992–995 | date = November 2001 | pmid = 11746215 | doi = 10.1002/bies.1144 }}</ref><ref>{{cite journal | vauthors = Trimmer BA, Aprille JR, Dudzinski DM, Lagace CJ, Lewis SM, Michel T, Qazi S, Zayas RM | title = Nitric oxide and the control of firefly flashing | journal = Science | volume = 292 | issue = 5526 | pages = 2486–2488 | date = June 2001 | pmid = 11431567 | doi = 10.1126/science.1059833 | s2cid = 1095642 }}</ref>
	==Further reading==
	* P.D. Evans, "Octopamine", in ''Comprehensive Insect Physiology'', 11, 499, Oxford University Press 1985.
			In larvae of the ], octopamine is immunologically beneficial, increasing survival rates in high-density populations.<ref>{{cite journal | vauthors = Kong H, Yuan L, Dong C, Zheng M, Jing W, Tian Z, Hou Q, Cheng Y, Zhang L, Jiang X, Luo L | title = Immunological regulation by a β-adrenergic-like octopamine receptor gene in crowded larvae of the oriental Armyworm, Mythmina separata | journal = Developmental and Comparative Immunology | volume = 113 | pages = 103802 | date = December 2020 | pmid = 32712170 | doi = 10.1016/j.dci.2020.103802 | s2cid = 220797641 }}</ref>
			The ] stings the host for its larvae (a cockroach) in the head ganglion (brain). The venom blocks octopamine receptors<ref>{{cite journal | vauthors = Hopkin M |year=2007 |title=How to make a zombie cockroach |journal=Nature |doi=10.1038/news.2007.312}}</ref> and the cockroach fails to show normal escape responses, grooming itself excessively. It becomes docile and the wasp leads it to the wasp's den by pulling its antenna like a leash.<ref>{{cite journal | vauthors = Gal R, Rosenberg LA, Libersat F | title = Parasitoid wasp uses a venom cocktail injected into the brain to manipulate the behavior and metabolism of its cockroach prey | journal = Archives of Insect Biochemistry and Physiology | volume = 60 | issue = 4 | pages = 198–208 | date = December 2005 | pmid = 16304619 | doi = 10.1002/arch.20092 }}</ref>
			==== In ''Drosophila'' ====
			Octopamine affects almost every process of the fruit fly and is widely present in both the adult and larval fly. A non-exhaustive list of some of the areas in which Octopamine modulates:
			* Learning and memory<ref>{{cite journal | vauthors = Sabandal JM, Sabandal PR, Kim YC, Han KA | title = Concerted Actions of Octopamine and Dopamine Receptors Drive Olfactory Learning | journal = The Journal of Neuroscience | volume = 40 | issue = 21 | pages = 4240–4250 | date = May 2020 | pmid = 32277043 | pmc = 7244198 | doi = 10.1523/JNEUROSCI.1756-19.2020 }}</ref><ref>{{cite journal | vauthors = Burke CJ, Huetteroth W, Owald D, Perisse E, Krashes MJ, Das G, Gohl D, Silies M, Certel S, Waddell S | title = Layered reward signalling through octopamine and dopamine in Drosophila | journal = Nature | volume = 492 | issue = 7429 | pages = 433–437 | date = December 2012 | pmid = 23103875 | pmc = 3528794 | doi = 10.1038/nature11614 | bibcode = 2012Natur.492..433B }}</ref><ref>{{cite journal | vauthors = Schwaerzel M, Monastirioti M, Scholz H, Friggi-Grelin F, Birman S, Heisenberg M | title = Dopamine and octopamine differentiate between aversive and appetitive olfactory memories in Drosophila | journal = The Journal of Neuroscience | volume = 23 | issue = 33 | pages = 10495–10502 | date = November 2003 | pmid = 14627633 | pmc = 6740930 | doi = 10.1523/JNEUROSCI.23-33-10495.2003 }}</ref>
			* Ovulation and Egg-Laying<ref name=":6"/><ref name=":3" /><ref name=":4" /><ref name=":5" /><ref name=":7" /><ref name=":8" />
			* Locomotion<ref>{{cite journal | vauthors = Schützler N, Girwert C, Hügli I, Mohana G, Roignant JY, Ryglewski S, Duch C | title = Tyramine action on motoneuron excitability and adaptable tyramine/octopamine ratios adjust ''Drosophila'' locomotion to nutritional state | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 116 | issue = 9 | pages = 3805–3810 | date = February 2019 | pmid = 30808766 | pmc = 6397572 | doi = 10.1073/pnas.1813554116 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Selcho M, Pauls D, El Jundi B, Stocker RF, Thum AS | title = The role of octopamine and tyramine in Drosophila larval locomotion | journal = The Journal of Comparative Neurology | volume = 520 | issue = 16 | pages = 3764–3785 | date = November 2012 | pmid = 22627970 | doi = 10.1002/cne.23152 | s2cid = 17014658 | url = http://nbn-resolving.de/urn:nbn:de:bsz:352-217701 }}</ref><ref>{{cite journal | vauthors = Saraswati S, Fox LE, Soll DR, Wu CF | title = Tyramine and octopamine have opposite effects on the locomotion of Drosophila larvae | journal = Journal of Neurobiology | volume = 58 | issue = 4 | pages = 425–441 | date = March 2004 | pmid = 14978721 | doi = 10.1002/neu.10298 }}</ref>
			* Muscle Physiology<ref name="Action of octopamine and tyramine o"/><ref>{{cite journal | vauthors = Ormerod KG, Jung J, Mercier AJ | title = Modulation of neuromuscular synapses and contraction in Drosophila 3rd instar larvae | journal = Journal of Neurogenetics | volume = 32 | issue = 3 | pages = 183–194 | date = September 2018 | pmid = 30303434 | doi = 10.1080/01677063.2018.1502761 | s2cid = 52948972 | doi-access = free }}</ref>
			* Aggression<ref>{{cite journal | vauthors = Andrews JC, Fernández MP, Yu Q, Leary GP, Leung AK, Kavanaugh MP, Kravitz EA, Certel SJ | title = Octopamine neuromodulation regulates Gr32a-linked aggression and courtship pathways in Drosophila males | journal = PLOS Genetics | volume = 10 | issue = 5 | pages = e1004356 | date = May 2014 | pmid = 24852170 | pmc = 4031044 | doi = 10.1371/journal.pgen.1004356 | veditors = Clandinin T | doi-access = free }}</ref><ref>{{cite journal | vauthors = Luo J, Lushchak OV, Goergen P, Williams MJ, Nässel DR | title = Drosophila insulin-producing cells are differentially modulated by serotonin and octopamine receptors and affect social behavior | journal = PLOS ONE | volume = 9 | issue = 6 | pages = e99732 | date = 2014-06-12 | pmid = 24923784 | pmc = 4055686 | doi = 10.1371/journal.pone.0099732 | bibcode = 2014PLoSO...999732L | doi-access = free | veditors = Broughton S }}</ref><ref>{{cite journal | vauthors = Williams MJ, Goergen P, Rajendran J, Klockars A, Kasagiannis A, Fredriksson R, Schiöth HB | title = Regulation of aggression by obesity-linked genes TfAP-2 and Twz through octopamine signaling in Drosophila | journal = Genetics | volume = 196 | issue = 1 | pages = 349–362 | date = January 2014 | pmid = 24142897 | pmc = 3872196 | doi = 10.1534/genetics.113.158402 }}</ref>
			* Alcohol and drug tolerance<ref>{{cite journal | vauthors = Heberlein U, Wolf FW, Rothenfluh A, Guarnieri DJ | title = Molecular Genetic Analysis of Ethanol Intoxication in Drosophila melanogaster | journal = Integrative and Comparative Biology | volume = 44 | issue = 4 | pages = 269–274 | date = August 2004 | pmid = 21676709 | doi = 10.1093/icb/44.4.269 | s2cid = 14762870 | citeseerx = 10.1.1.536.262 }}</ref><ref>{{cite journal | vauthors = Tecott LH, Heberlein U | title = Y do we drink? | journal = Cell | volume = 95 | issue = 6 | pages = 733–735 | date = December 1998 | pmid = 9865690 | doi = 10.1016/S0092-8674(00)81695-5 | doi-access = free }}</ref><ref>{{cite web|url=http://www.thenakedscientists.com/HTML/articles/article/ruthwilliamscolumn1.htm/|title=Bar Flies: What our insect relatives can teach us about alcohol tolerance| vauthors = Williams R |date=June 22, 2005|work=Naked Scientist}}</ref><ref>{{cite web|url=https://www.newscientist.com/article.ns?id=dn7830|title='Hangover gene' is key to alcohol tolerance| vauthors = Vince G |date=22 August 2005|work=New Scientist}}</ref>
			* Feeding<ref>{{cite journal | vauthors = Selcho M, Pauls D | title = Linking physiological processes and feeding behaviors by octopamine | journal = Current Opinion in Insect Science | volume = 36 | pages = 125–130 | date = December 2019 | pmid = 31606580 | doi = 10.1016/j.cois.2019.09.002 | s2cid = 203470883 }}</ref><ref>{{cite journal | vauthors = Sayin S, De Backer JF, Siju KP, Wosniack ME, Lewis LP, Frisch LM, Gansen B, Schlegel P, Edmondson-Stait A, Sharifi N, Fisher CB, Calle-Schuler SA, Lauritzen JS, Bock DD, Costa M, Jefferis GS, Gjorgjieva J, Grunwald Kadow IC | title = A Neural Circuit Arbitrates between Persistence and Withdrawal in Hungry Drosophila | journal = Neuron | volume = 104 | issue = 3 | pages = 544–558.e6 | date = November 2019 | pmid = 31471123 | pmc = 6839618 | doi = 10.1016/j.neuron.2019.07.028 }}</ref>
			* Microbiome and gut physiology<ref>{{cite journal | vauthors = Jia Y, Jin S, Hu K, Geng L, Han C, Kang R, Pang Y, Ling E, Tan EK, Pan Y, Liu W | title = Gut microbiome modulates Drosophila aggression through octopamine signaling | journal = Nature Communications | volume = 12 | issue = 1 | pages = 2698 | date = May 2021 | pmid = 33976215 | pmc = 8113466 | doi = 10.1038/s41467-021-23041-y | bibcode = 2021NatCo..12.2698J }}</ref><ref>{{cite journal | vauthors = Schretter CE, Vielmetter J, Bartos I, Marka Z, Marka S, Argade S, Mazmanian SK | title = A gut microbial factor modulates locomotor behaviour in Drosophila | journal = Nature | volume = 563 | issue = 7731 | pages = 402–406 | date = November 2018 | pmid = 30356215 | pmc = 6237646 | doi = 10.1038/s41586-018-0634-9 | bibcode = 2018Natur.563..402S }}</ref>
			* Sleep<ref>{{cite journal | vauthors = Nall A, Sehgal A | title = Monoamines and sleep in Drosophila | journal = Behavioral Neuroscience | volume = 128 | issue = 3 | pages = 264–272 | date = June 2014 | pmid = 24886188 | doi = 10.1037/a0036209 }}</ref><ref>{{cite journal | vauthors = Erion R, DiAngelo JR, Crocker A, Sehgal A | title = Interaction between sleep and metabolism in Drosophila with altered octopamine signaling | journal = The Journal of Biological Chemistry | volume = 287 | issue = 39 | pages = 32406–32414 | date = September 2012 | pmid = 22829591 | pmc = 3463357 | doi = 10.1074/jbc.M112.360875 | doi-access = free }}</ref>
			* Modulating effects of exercise<ref>{{cite journal | vauthors = Sujkowski A, Gretzinger A, Soave N, Todi SV, Wessells R | title = Alpha- and beta-adrenergic octopamine receptors in muscle and heart are required for Drosophila exercise adaptations | journal = PLOS Genetics | volume = 16 | issue = 6 | pages = e1008778 | date = June 2020 | pmid = 32579604 | pmc = 7351206 | doi = 10.1371/journal.pgen.1008778 | veditors = Bai H | doi-access = free }}</ref><ref>{{cite journal | vauthors = Cobb T, Sujkowski A, Morton C, Ramesh D, Wessells R | title = Variation in mobility and exercise adaptations between Drosophila species | journal = Journal of Comparative Physiology A| volume = 206 | issue = 4 | pages = 611–621 | date = July 2020 | pmid = 32335730 | pmc = 7314734 | doi = 10.1007/s00359-020-01421-x }}</ref>
			* Metabolism<ref>{{cite journal | vauthors = Ahmed MA, Vogel CF | title = Hazardous effects of octopamine receptor agonists on altering metabolism-related genes and behavior of Drosophila melanogaster | journal = Chemosphere | volume = 253 | pages = 126629 | date = August 2020 | pmid = 32283422 | pmc = 9888421 | doi = 10.1016/j.chemosphere.2020.126629 | s2cid = 215757990 | bibcode = 2020Chmsp.25326629A }}</ref><ref>{{cite journal | vauthors = Li Y, Hoffmann J, Li Y, Stephano F, Bruchhaus I, Fink C, Roeder T | title = Octopamine controls starvation resistance, life span and metabolic traits in Drosophila | journal = Scientific Reports | volume = 6 | issue = 1 | pages = 35359 | date = October 2016 | pmid = 27759117 | pmc = 5069482 | doi = 10.1038/srep35359 | bibcode = 2016NatSR...635359L }}</ref>
			=== Vertebrates ===
			In ]s, octopamine replaces ] in ] ]s with chronic use of ]s. It may be responsible for the common ] of ] with these agents, though there is also evidence that it is actually mediated by increased levels of ].
			One study noted that octopamine might be an important amine that influences the therapeutic effects of inhibitors such as ]s, especially because a large increase in octopamine levels was observed when animals were treated with this inhibitor. Octopamine was positively identified in the urine samples of mammals such as humans, rats, and rabbits treated with ]s. Very small amounts of octopamine were also found in certain animal tissues. It was observed that within a rabbit's body, the heart and kidney held the highest concentrations of octopamine. Octopamine was found to be 93% eluted by urine within 24 hours of being produced in the body as a byproduct of Iproniazid in rabbits.<ref name="jbc3" />
			==Pharmacology==
			Octopamine has been sold under trade names such as '''Epirenor''', '''Norden''', and '''Norfen''' for use in medicine as a ], available by prescription. However, very little information exists concerning its clinical usefulness or safety.<ref name="Stohs2015">{{cite journal | vauthors = Stohs SJ | title = Physiological functions and pharmacological and toxicological effects of p-octopamine | journal = Drug and Chemical Toxicology | volume = 38 | issue = 1 | pages = 106–112 | date = January 2015 | pmid = 24654910 | doi = 10.3109/01480545.2014.900069 | s2cid = 21901553 }}</ref> It has been studied as an ] and has been shown to increase ] when administered ], ], and ] at sufficiently high doses, whereas ] was ineffective.<ref name="Stohs2015" />
			Octopamine is an ] of ] ]s like ] and ]s like ].<ref name="Stohs2015" /> However, octopamine has 400- to 2,000-fold lower ] for the mammalian ] and ]s than norepinephrine.<ref name="Stohs2015" /> In any case, it can produce significant sympathomimetic effects, like pressor responses, at sufficiently high doses.<ref name="Stohs2015" />
			In ]s, octopamine may mobilize the release of ] from ] (fat cells), which has led to its promotion on the ] as a slimming aid. However, the released fat is likely to be promptly taken up into other cells, and there is no evidence that octopamine facilitates weight loss. Octopamine may also increase ] significantly when combined with other ]s, as in some ].<ref>{{cite journal | vauthors = Haller CA, Benowitz NL, Jacob P | title = Hemodynamic effects of ephedra-free weight-loss supplements in humans | journal = The American Journal of Medicine | volume = 118 | issue = 9 | pages = 998–1003 | date = September 2005 | pmid = 16164886 | doi = 10.1016/j.amjmed.2005.02.034 }}</ref>
			The ] lists octopamine as a banned substance for in competition use, as a "specified stimulant"<ref>{{cite web|url=https://www.wada-ama.org/en/content/what-is-prohibited/prohibited-in-competition/stimulants|title=Prohibited In Competition – Stimulants|publisher=WADA|access-date=6 May 2019|archive-date=6 May 2019|archive-url=https://web.archive.org/web/20190506173946/https://www.wada-ama.org/en/content/what-is-prohibited/prohibited-in-competition/stimulants|url-status=dead}}</ref> on the 2019 Prohibited List.
			== Insecticides ==
			The octopamine receptor is a target of insecticides, as its blockage leads to decreased ] (cAMP) levels. Essential oils can have such a neuro-insecticidal effect,<ref>{{cite journal | vauthors = Enan E | title = Insecticidal activity of essential oils: octopaminergic sites of action | journal = Comparative Biochemistry and Physiology. Toxicology & Pharmacology | volume = 130 | issue = 3 | pages = 325–337 | date = November 2001 | pmid = 11701389 | doi = 10.1016/S1532-0456(01)00255-1 }}</ref> and this octopamine-receptor mechanism is naturally utilized by plants with active insecticidal phytochemicals.<ref>{{Cite journal| vauthors = Rattan RS |date=2010-09-01|title=Mechanism of action of insecticidal secondary metabolites of plant origin |journal=Crop Protection|language=en|volume=29|issue=9|pages=913–920|doi=10.1016/j.cropro.2010.05.008|issn=0261-2194}}</ref>
			==Biochemical mechanisms==
			=== Mammals ===
			{{Further|Trace amine-associated receptor 1}}
			Octopamine is one of four primary ]s of human ] together with ], ] and ].<ref name="TAAR1 IUPHAR">{{cite web | title=Trace amine receptor: TA<sub>1</sub> receptor | work= IUPHAR/BPS Guide to PHARMACOLOGY | publisher=International Union of Basic and Clinical Pharmacology |vauthors=Maguire JJ, Davenport AP | date=20 February 2018 |url=http://www.guidetopharmacology.org/GRAC/ObjectDisplayForward?objectId=364 | access-date= 16 July 2018}}</ref><ref>{{cite journal | vauthors = Heffernan ML, Herman LW, Brown S, Jones PG, Shao L, Hewitt MC, Campbell JE, Dedic N, Hopkins SC, Koblan KS, Xie L | title = Ulotaront: A TAAR1 Agonist for the Treatment of Schizophrenia | journal = ACS Medicinal Chemistry Letters | volume = 13 | issue = 1 | pages = 92–98 | date = January 2022 | pmid = 35047111 | pmc = 8762745 | doi = 10.1021/acsmedchemlett.1c00527 | publication-date = December 6, 2021 }}</ref>
			=== Invertebrates ===
			Octopamine binds to its respective G-protein coupled receptors (GPCRs) to initiate a cell signal transduction pathway. At least three groups of octopamine GPCR have been defined. OctαR (OCTOPAMINE1 receptors) are more closely related to α-adrenergic receptors, while OctβR (OCTOPAMINE2 receptors) are more closely related to β-adrenergic receptors. The Octopamine/Tyramine receptors (including Oct-TyrR) can bind both ligands, and display agonist-specific coupling. Oct-TyrR is listed in both OCTOPAMINE and TYRAMINE RECEPTORS gene groups.<ref>{{cite web | url = http://flybase.org/reports/FBgg0000133.html | title = Gene Group : OCTOPAMINE RECEPTORS | work = FlyBase | date = 16 October 2018 }}</ref>
			== Biosynthesis ==
			]
			=== In insects ===
			Octopamine acts as the ] equivalent of ] and has been implicated in regulating ] in ]s, with different effects on different species. Studies have shown that reducing the neurotransmitter octopamine and preventing coding of ] (an ] that converts ] to octopamine) decreases aggression in '']'' without influencing other behaviors.<ref>{{cite journal | vauthors = Zhou C, Rao Y, Rao Y | title = A subset of octopaminergic neurons are important for Drosophila aggression | journal = Nature Neuroscience | volume = 11 | issue = 9 | pages = 1059–1067 | date = September 2008 | pmid = 19160504 | doi = 10.1038/nn.2164 | s2cid = 1134848 }}</ref>
			==Chemistry==
			Octopamine, or ''para''-octopamine, also known as 4,β-dihydroxyphenethylamine, is a ] ]. It is related to ]s including ] (β-hydroxyphenethylamine), ] (''para''-tyramine; 4-hydroxyphenethylamine), and ] (''meta''-octopamine; 3,β-dihydroxyphenethylamine), among others.
			== References ==
			{{Reflist}}
	{{Adrenergic and dopaminergic agents}}
	{{Adrenergics}}
	{{Phenethylamines}}
	{{Neurotransmitters}}		{{Neurotransmitters}}
			{{Cardiac stimulants}}
	{{Use dmy dates|date=September 2010}}
			{{Adrenergic receptor modulators}}
			{{Monoamine releasing agents}}
			{{TAAR ligands}}
			{{Phenethylamines}}
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