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Octopamine

Clinical data
Other names	Norsympathol, Norsynephrine, para-Octopamine, beta-Hydroxytyramine
Routes of administration	Oral
ATC code	C01CA18 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life	15 Minutes in insects. Theorized to be longer in vertebrates.
Identifiers
IUPAC name (RS)-4-(2-amino-1-hydroxy-ethyl)phenol
CAS Number	104-14-3
PubChem CID	4581
ChemSpider	4420
UNII	14O50WS8JD
ChEMBL	ChEMBL53929
CompTox Dashboard (EPA)	DTXSID7043873
ECHA InfoCard	100.002.890
Chemical and physical data
Formula	C8H11NO2
Molar mass	153.178 g/mol g·mol
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
(verify)

Octopamine, also known as β,4-dihydroxyphenethylamine, is an endogenous biogenic amine that is closely related to norepinephrine, and has effects on the adrenergic and dopaminergic systems. 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.

Role in invertebrates

Octopamine was first discovered by Italian scientist Vittorio Erspamer in 1948 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 energy-demanding behaviors by all insects, crustaceans (crabs, lobsters, crayfish), and spiders. Such behaviors include flying, egg-laying, and jumping.

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.

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.

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.

Heberlein et al. have conducted studies of alcohol tolerance in fruit flies; they found that a mutation that caused octopamine deficiency also caused lower alcohol tolerance.

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

Role in vertebrates

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.

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.

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

See also

• Phenethylamine
• Tyramine

References

1. Jagiełło-Wójtowicz E (1979). "Mechanism of central action of octopamine". Pol J Pharmacol Pharm. 31 (5): 509–16. PMID 121158.
2. Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.
3. "Pharmacognosy And Pharmacobiotechnology - Google Books".
4. Erspamer, V., Active substances in the posterior salivary glands of Octopoda. 2. Tyramine and octopamine (oxyoctopamine) (1948). "Active Substances in the Posterior Salivary Glands of Octopoda. II. Tyramine and Octopamine (Oxyoctopamine)". Acta Pharmacologica et Toxicologica. 4 (3–4): 224–247. doi:10.1111/j.1600-0773.1948.tb03345.x.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
5. Heberlein, U. (2004). "Molecular Genetic Analysis of Ethanol Intoxication in Drosophila melanogaster". Integrative and Comparative Biology. 44: 269. doi:10.1093/icb/44.4.269.
6. 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 (6): 997–1007. doi:10.1016/S0092-8674(00)81205-2. PMID 9635429.{{cite journal}}: CS1 maint: multiple names: authors list (link)
7. Tecott, L. H. and Heberlein, U. (1998). "Y do we drink?". Cell. 95 (6): 733–735. doi:10.1016/S0092-8674(00)81695-5. PMID 9865690.{{cite journal}}: CS1 maint: multiple names: authors list (link)
8. Bar Flies: What our insect relatives can teach us about alcohol tolerance., Ruth Williams, Naked Scientist
9. ‘Hangover gene’ is key to alcohol tolerance, Gaia Vince, NewScientist.com news service, 22 August 2005
10. How to make a zombie cockroach, Nature News, 29 September 2007
11. Gal, Ram (22 November 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. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
12. Minerd, Jeff (12 September 2005). "Ephedra-Free Supplements Not Necessarily Risk-Free". MedPage Today. Retrieved 12 September 2009.
13. Haller, C; Benowitz, N; Jacobiii, P (2005). "Hemodynamic effects of ephedra-free weight-loss supplements in humans". The American Journal of Medicine. 118: 998. doi:10.1016/j.amjmed.2005.02.034.

Further reading

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

• Use dmy dates from September 2010
• Phenethylamines
• Alpha-adrenergic agonists
• Phenols