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Encyclopedia > Octopamine
Octopamine
Systematic (IUPAC) name
4-(2-amino-1-hydroxy-ethyl)phenol
Identifiers
CAS number 104-14-3
ATC code C01CA18
PubChem 4581
Chemical data
Formula C8H11NO2 
Mol. mass 153.178
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

? Image File history File links Octopamine_structure. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status
Routes  ?

Octopamine is a biogenic amine which is closely related to noradrenaline, and has a similar action to dopamine. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... A biogenic amine is a biogenic substance with an amine group. ... Norepinephrine, known as noradrenaline outside the USA, is a catecholamine and a phenethylamine with chemical formula C8H11NO3. ... For other uses, see Dopamine (disambiguation). ...


Role in invertebrates

Octopamine was first discovered by Italian scientist Vittorio Erspamer in 1948[1] in the salivary glands of the octopus and has since been found to act as neurotransmitter, neurohormone and neuromodulator in invertebrates. It is widely used in energetically demanding behaviours by all insects, crustaceans (crabs, lobsters, crayfish) and spiders. Such behaviours include flying, egg-laying and jumping. For other uses, see Octopus (disambiguation). ... Chemical structure of D-aspartic acid, a common amino acid neurotransmitter. ... A neurohormone is any hormone produced by neurosecretory cells, usually in the brain. ... A neuromodulator is a substance other than a neurotransmitter, released by a neuron at a synapse and conveying information to adjacent or distant neurons, either enhancing or damping their activities. ... Invertebrate is an English word that describes any animal without a spinal column. ...


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. Desert locust Nymph of Locust Schistocera americana with distinct wing-rudiments Locust nymph from the Philippines Egyptian grasshopper Anacridium aegyptum Locust from the 1915 Locust Plague For other uses, see Locust (disambiguation). ...


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. The honeybee is a colonial insect that is often maintained, fed, and transported by farmers. ... Fruit fly may refer to: Tephritidae, the family of large fruit flies. ...


Octopamine also plays a role in mollusks, though the role of octopamine has only been examined in the CNS of the model organism, the pond snail. Classes Caudofoveata Aplacophora Polyplacophora Monoplacophora Bivalvia Scaphopoda Gastropoda Cephalopoda † Rostroconchia The mollusks or molluscs are the large and diverse phylum Mollusca, which includes a variety of familiar creatures well-known for their decorative shells or as seafood. ... For other uses, see Snail (disambiguation). ...


Heberlein et al (2004) have conducted studies of fruit fly intoxication at the University of California, San Francisco and linked octopamine to alcohol tolerance in fruit flies.[1][2][3][4] UCSF in 1908, with the streetcar that used to run on Parnassus Avenue The University of California, San Francisco (UCSF) is one of the worlds leading centers of health sciences research, patient care, and education. ...


Role in vertebrates

In vertebrates, octopamine also replaces norepinephrine in sympathetic neurons with chronic use of Monoamine Oxidase Inhibitors. It is responsible for the common side-effect profile of orthostatic hypotension with these agents. MAOI redirects here. ... Orthostatic hypotension (also known as postural hypotension, orthostatic intolerance and, colloquially, as head rush or a dizzy spell) is a sudden fall in blood pressure, typically greater than 20/10 mm Hg, that occurs when a person assumes a standing position, usually after a prolonged period of rest. ...


In mammals, octopamine may mobilise the release of fat from adipocytes (fat cells), and this 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. Furthermore, the safety of ephedra-free weight-loss supplements in humans is uncertain, as they have significant cardiovacular actions. [5] In some countries it is gaining increased commercial interest as an ingredient in benzylpiperazine free 'party pills' [2] due to the fact that in countries such as New Zealand where it is currently legal, BZP faces a probable ban before the end of 2007. Adipose tissue is an anatomical term for loose connective tissue composed of energy in the form of fat, although it also cushions and insulates the body. ... Benzylpiperazine (street names include A2, frenzy and nemesis [1] However, there are some references to BZP in the literature that predate interest in piperazines as anthelmintics. ... A selection of products containing BZP. Party Pills, also known as Herbal Highs, Pep Pills and Dance Pills, is a colloquialism for a type of recreational drug whose main ingredient is Benzylpiperazine (BZP). ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ...


References

  1. ^ Moore, M. S., Dezazzo, J., Luk, A. Y., Tully, T., Singh, C. M., and Heberlein, U. (1998) Ethanol intoxication in Drosophila: Genetic and pharmacological evidence for regulation by the cAMP pathway. Cell 93, 997-1007
  2. ^ Tecott, L. H. and Heberlein, U. (1998) Y do we drink? Cell 95: 733-735
  3. ^ Bar Flies: What our insect relatives can teach us about alcohol tolerance., Ruth Williams, Naked Scientist
  4. ^ ‘Hangover gene’ is key to alcohol tolerance, Gaia Vince, NewScientist.com news service, 22 August 2005
  5. ^ Haller, CA, et al (2005) Am J Med : 118:998-1003 http://dx.doi.org/10.1016/j.amjmed.2005.02.034
  1. ^ Erspamer, V., Active substances in the posterior salivary glands of Octopoda. 2. Tyramine and octopamine (oxyoctopamine) Acta Pharmacologica et Toxicologica 4 (3-4): 224-247 1948.
  2. P.D. Evans, "Octopamine", in Comprehensive Insect Physiology, 11, 499, Oxford University Press 1985.
  3. Molecular Genetic Analysis of Ethanol Intoxication in Drosophila melanogaster, Ulrike Heberlein, Fred W. Wolf, Adrian Rothenfluh and Douglas J. Guarnieri, Integrative and Comparative Biology 2004 44(4):269-274; doi:10.1093/icb/44.4.269

  Results from FactBites:
 
JIS: Tschinkel 2.12.2002 (5112 words)
Octopaminergic agonists for the cockroach neuronal octopamine receptor
Octopamine was first discovered in the salivary glands of the octopus by Erspamer and Boretti (1951).
Octopamine, theophylline (1,3-dimethylxanthine), tyramine 41 and EGTA were purchased from Nacalai Tesque, www.nacalai.co.jp/en/; GTP and DL-synephrine 8 was from Sigma Chemical Co., www.sigmaaldrich.com; ATP disodium salt was from Kohjin Co., www.kohjin.co.jp/english; LAH was from Chemetall GmbH, www.chemetall.com.
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