octopamine

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octopamine hydrochloride

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/09/07 18:32:47」(JST)

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Not to be confused with octopine.

Octopamine

Systematic (IUPAC) name
(RS)-4-(2-amino-1-hydroxy-ethyl)phenol
Clinical data
Pregnancy cat.	?
Legal status	℞ Prescription only
Routes	Oral
Pharmacokinetic data
Half-life	15 Minutes in insects. Theorized to be longer in vertebrates.
Identifiers
CAS number	104-14-3 Y
ATC code	C01CA18
PubChem	CID 4581
IUPHAR ligand	2149
ChemSpider	4420 Y
UNII	14O50WS8JD Y
ChEBI	CHEBI:17134 N
ChEMBL	CHEMBL53929 Y
Synonyms	Norsympathol, Norsynephrine, para-Octopamine, beta-Hydroxytyramine, para-hydroxy-phenyl-ethanolamine
Chemical data
Formula	C8H11NO2
Mol. mass	153.178 g/mol
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 Y Key:QHGUCRYDKWKLMG-UHFFFAOYSA-N Y
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. 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 a 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

• Trace amines
• Phenethylamine
• Tyramine

References

Further reading

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

UpToDate Contents

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• 1. 成人における急性中毒性代謝性脳症 acute toxic metabolic encephalopathy in adults
• 2. 肝性脳症：病因 hepatic encephalopathy pathogenesis

English Journal

• Further Insights Into the Pharmacology of the Human Trace Amine-Associated Receptors: Discovery of Novel Ligands for TAAR1 by a Virtual Screening Approach.

• Cichero E1, Espinoza S, Franchini S, Guariento S, Brasili L, Gainetdinov RR, Fossa P.
• Chemical biology & drug design.Chem Biol Drug Des.2014 Dec;84(6):712-720. doi: 10.1111/cbdd.12367. Epub 2014 Jun 30.
• Trace Amine-Associated Receptor 1 (TAAR1) is a G protein-coupled receptor that is expressed in brain and periphery and responds to a class of compounds called trace amines, such as β-phenylethylamine (β-PEA), tyramine, tryptamine, octopamine. The receptor is known to have a very rich pharmacology
• PMID 24894156

• Division of labour in honey bees: age- and task-related changes in the expression of octopamine receptor genes.

• Reim T1, Scheiner R.
• Insect molecular biology.Insect Mol Biol.2014 Dec;23(6):833-41. doi: 10.1111/imb.12130. Epub 2014 Sep 4.
• The honey bee (Apis mellifera L.) has developed into an important ethological model organism for social behaviour and behavioural plasticity. Bees perform a complex age-dependent division of labour with the most pronounced behavioural differences occurring between in-hive bees and foragers. Wherea
• PMID 25187440

• Transiently Increasing cAMP Levels Selectively in Hippocampal Excitatory Neurons during Sleep Deprivation Prevents Memory Deficits Caused by Sleep Loss.

• Havekes R1, Bruinenberg VM2, Tudor JC3, Ferri SL3, Baumann A4, Meerlo P5, Abel T1.
• The Journal of neuroscience : the official journal of the Society for Neuroscience.J Neurosci.2014 Nov 19;34(47):15715-21. doi: 10.1523/JNEUROSCI.2403-14.2014.
• The hippocampus is particularly sensitive to sleep loss. Although previous work has indicated that sleep deprivation impairs hippocampal cAMP signaling, it remains to be determined whether the cognitive deficits associated with sleep deprivation are caused by attenuated cAMP signaling in the hippoca
• PMID 25411499

Japanese Journal

• Expression of β-adrenergic-like Octopamine Receptors during Drosophila Development

• Ohhara Yuya,Kayashima Yasunari,Hayashi Yoshiki
• Zoological science 29(2), 83-89, 2012-02
• NAID 40019149489

• A Secreted Placental Alkaline Phosphatase-Based Reporter Assay System for Screening of Compounds Acting at an Octopamine Receptor Stably Expressed in a Mammalian Cell Line

• OHTA Hiroto,OSHIUMI Hiroshi,HAYASHI Naotaka,IMAI Tetsuya,OZOE Yoshihisa,MORIMURA Shigeru,KIDA Kenji
• Bioscience, biotechnology, and biochemistry 76(1), 209-211, 2012-01-23
• … Octopamine receptors are attractive insecticide targets. … To screen compounds acting at octopamine receptors simply and rapidly, we constructed a chemiluminescent reporter gene assay system that detects secreted placental alkaline phosphatase transcriptionally regulated by the cAMP response element for a silkworm octopamine receptor. … This system proved useful in high-throughput screening to develop octopamine receptor-specific insecticides. …
• NAID 10030399213

• Changes in the Content of Brain Biogenic Amine Associated with Early Colony Establishment in the Queen of the Ant, Formica japonica

• Aonuma Hitoshi,Watanabe Takayuki
• PLoS One 7(8), 43377, 2012
• … The levels of serotonin (5HT), octopamine (OA) and dopamine (DA) decreased significantly in the brain of the queen after starting a colony. …
• NAID 120004857014

Related Links

• Octopamine - Wikipedia, the free encyclopedia

InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2 Yes Y Key:QHGUCRYDKWKLMG-UHFFFAOYSA-N Yes Y. N (what is this?) (verify). Octopamine (β,4-dihydroxyphenethylamine) is an endogenous biogenic amine that is ...

• Octopamine in invertebrates.

Prog Neurobiol. 1999 Dec;59(5):533-61. Octopamine in invertebrates. Roeder T. Universität Hamburg, Zoologisches Institut, Neurophysiologie, Germany. roeder @zoologie.uni-hamburg.de. Octopamine (OA), a biogenic monoamine ...

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