Octopamine

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Not to be confused with octopine.
Octopamine
Octopamin.svg
Ball-and-stick model of the octopamine molecule
Systematic (IUPAC) name
(RS)-4-(2-amino-1-hydroxy-ethyl)phenol
Clinical data
Legal status
Routes of
administration
Oral
Pharmacokinetic data
Bioavailability 99.42 %
Metabolism p-hydroxymandelic acid (if p-octopamine) or m-hydroxymandelic acid (if m-octopamine[1][2]
Biological half-life 15 Minutes in insects. 76 and 175 minutes in humans
Excretion Up to 93% of ingested octopamine is eliminated via the urinary route within 24 hour[1]
Identifiers
CAS Registry Number 104-14-3 YesY
ATC code C01CA18
PubChem CID: 4581
IUPHAR/BPS 2149
ChemSpider 4420 YesY
UNII 14O50WS8JD YesY
ChEBI CHEBI:17134 N
ChEMBL CHEMBL53929 YesY
Synonyms Norsympathol, Norsynephrine, para-Octopamine, beta-Hydroxytyramine, para-hydroxy-phenyl-ethanolamine
Chemical data
Formula C8H11NO2
Molecular mass 153.178 g/mol
 N (what is this?)  (verify)

Octopamine (β,4-dihydroxyphenethylamine) is an endogenous biogenic amine that is closely related to norepinephrine, and has effects on the adrenergic and dopaminergic systems. It is also found naturally in numerous plants, including bitter orange.[3][4] Biosynthesis of the D-(–)-enantiomer of octopamine is by β-hydroxylation of tyramine via the enzyme dopamine β-hydroxylase. Under the trade names Epirenor, Norden, and Norfen, octopamine is also used clinically as a sympathomimetic agent.[5][6]

Role in invertebrates[edit]

Octopamine was first discovered by Italian scientist Vittorio Erspamer in 1948[7] in the salivary glands of the octopus and has since been found to act as a neurotransmitter, neurohormone and neuromodulator in invertebrates. Although Erspamer discovered its natural occurrence and named it, octopamine had actually existed for many years as a pharmaceutical product.[8] 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 acts as the insect equivalent of norepinephrine and has been implicated in regulating aggression in invertebrates, with different effects on different species. Studies have shown that reducing the neurotransmitter octopamine and preventing coding of tyramine beta hydroxylase (an enzyme that converts tyramine to octopamine) decreases aggression in Drosophila without influencing other behaviors.[9]

The best-understood role for octopamine is in the locust 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.[citation needed]

In the honey bee and fruit fly, octopamine has a major role in learning and memory. In the firefly, octopamine release leads to light production in the lantern.[citation needed]

Octopamine also plays a role in mollusks, though the role of octopamine has been examined only in the central nervous system of the model organism, the pond snail.[citation needed]

In lobsters, octopamine seems to direct and coordinate neurohormones 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.[10]

Heberlein et al.[11] have conducted studies of alcohol tolerance in fruit flies; they found that a mutation that caused octopamine deficiency also caused lower alcohol tolerance.[12][13][14][15]

The emerald cockroach wasp stings the host for its larvae (a cockroach) in the head ganglion (brain). The venom blocks octopamine receptors[16] 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.[17]

Role in vertebrates[edit]

In vertebrates, octopamine replaces norepinephrine in sympathetic neurons with chronic use of monoamine oxidase inhibitors. It may be responsible for the common side effect of orthostatic hypotension with these agents, though there is also evidence that it is actually mediated by increased levels of N-acetylserotonin.

One study noted that octopamine might be an important amine that influences the therapeutic effects of inhibitors such as monoamine oxidase inhibitors, 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 monoamine oxidase inhibitors. 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.[8]

In mammals, octopamine may mobilize the release of fat from adipocytes (fat cells), which has led to its promotion on the internet 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 blood pressure significantly when combined with other stimulants, as in some weight loss supplements.[18][19]

Owing to lack of research, much is not known about octopamine or its role in humans.

See also[edit]

References[edit]

  1. ^ a b Hengstmann, J. H.; Konen, W; Konen, C; Eichelbaum, M; Dengler, H. J. (1974). "The physiological disposition of p-octopamine in man". Naunyn-Schmiedeberg's Archives of Pharmacology 283 (1): 93–106. PMID 4277715. 
  2. ^ d’Andrea, Giovanni; Nordera, Gianpietro; Pizzolato, Gilberto; Bolner, Andrea; Colavito, Davide; Flaibani, Raffaella; Leon, Alberta (2010). "Trace amine metabolism in Parkinson's disease: Low circulating levels of octopamine in early disease stages". Neuroscience Letters 469 (3): 348–51. doi:10.1016/j.neulet.2009.12.025. PMID 20026245. 
  3. ^ Tang, Fei; Tao, Liang; Luo, Xubiao; Ding, Li; Guo, Manli; Nie, Lihua; Yao, Shouzhuo (2006). "Determination of octopamine, synephrine and tyramine in Citrus herbs by ionic liquid improved 'green' chromatography". Journal of Chromatography A 1125 (2): 182–8. doi:10.1016/j.chroma.2006.05.049. PMID 16781718. 
  4. ^ Jagiełło-Wójtowicz, E (1979). "Mechanism of central action of octopamine". Polish journal of pharmacology and pharmacy 31 (5): 509–16. PMID 121158. 
  5. ^ Swiss Pharmaceutical Society (2000). "Octopamine". Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. p. 756. ISBN 3-88763-075-0. 
  6. ^ Kar, Ashutosh (2003-01-01). Pharmacognosy And Pharmacobiotechnology - Google Books. ISBN 9788122415018. [full citation needed]
  7. ^ Erspamer, V. (2009). "Active Substances in the Posterior Salivary Glands of Octopoda. II. Tyramine and Octopamine (Oxyoctopamine)". Acta Pharmacologica et Toxicologica 4 (3–4): 224–47. doi:10.1111/j.1600-0773.1948.tb03345.x. 
  8. ^ a b Kakimoto, Y; Armstrong, M. D. (1962). "On the identification of octopamine in mammals". The Journal of biological chemistry 237: 422–7. PMID 14453200. 
  9. ^ Zhou, Chuan; Rao, Yong; Rao, Yi (2008). "A subset of octopaminergic neurons are important for Drosophila aggression". Nature Neuroscience 11 (9): 1059–67. doi:10.1038/nn.2164. PMID 19160504. 
  10. ^ Livingstone, M. S.; Harris-Warrick, R. M.; Kravitz, E. A. (1980). "Serotonin and Octopamine Produce Opposite Postures in Lobsters". Science 208 (4439): 76–9. Bibcode:1980Sci...208...76L. doi:10.1126/science.208.4439.76. PMID 17731572. 
  11. ^ Heberlein, U.; Wolf, F. W.; Rothenfluh, A; Guarnieri, D. J. (2004). "Molecular Genetic Analysis of Ethanol Intoxication in Drosophila melanogaster". Integrative and Comparative Biology 44 (4): 269–74. doi:10.1093/icb/44.4.269. PMID 21676709. 
  12. ^ Moore, Monica S; Dezazzo, Jim; Luk, Alvin Y; Tully, Tim; Singh, Carol M; Heberlein, Ulrike (1998). "Ethanol Intoxication in Drosophila: Genetic and Pharmacological Evidence for Regulation by the cAMP Signaling Pathway". Cell 93 (6): 997–1007. doi:10.1016/S0092-8674(00)81205-2. PMID 9635429. 
  13. ^ Tecott, Laurence H; Heberlein, Ulrike (1998). "Y Do We Drink?". Cell 95 (6): 733–5. doi:10.1016/S0092-8674(00)81695-5. PMID 9865690. 
  14. ^ Williams, Ruth (June 22, 2005). "Bar Flies: What our insect relatives can teach us about alcohol tolerance". Naked Scientist. 
  15. ^ Vince, Gaia (22 August 2005). "'Hangover gene' is key to alcohol tolerance". New Scientist. 
  16. ^ Hopkin, Michael (2007). "How to make a zombie cockroach". Nature. doi:10.1038/news.2007.312. 
  17. ^ Gal, Ram; Rosenberg, Lior Ann; Libersat, Frederic (2005). "Parasitoid wasp uses a venom cocktail injected into the brain to manipulate the behavior and metabolism of its cockroach prey". Archives of Insect Biochemistry and Physiology 60 (4): 198–208. doi:10.1002/arch.20092. PMID 16304619. 
  18. ^ Minerd, Jeff (12 September 2005). "Ephedra-Free Supplements Not Necessarily Risk-Free". MedPage Today. Retrieved 12 September 2009. 
  19. ^ Haller, Christine A.; Benowitz, Neal L.; Jacob, Peyton (2005). "Hemodynamic effects of ephedra-free weight-loss supplements in humans". The American Journal of Medicine 118 (9): 998–1003. doi:10.1016/j.amjmed.2005.02.034. PMID 16164886. 

Further reading[edit]

  • P.D. Evans, "Octopamine", in Comprehensive Insect Physiology, 11, 499, Oxford University Press 1985.