Octopamine production

To follow the biosynthetic route ofp-octopamine, we exposed isolated groups of DUM neurons to deuterated [ H6] p-tyramine for 24 h (4). This procedure yielded significant quantities of pHj] and pHg] p-octopamine (approx 0.04 0.01 ng/cell body), Nondeuterated endogenous p-octopamme was also present (Fig. 3 Table 2). Controls showed no detectable amounts of deuterated p-octopamine (4). The mixture of deuterated (pHsJ and [ Hg] p-octopamine) products is consistent with the [ Hs] p-tyramine containing approx 20% of pHs] p-tyramine and/or the possibility that the hydroxylation of the nng or side chain of the precursor may involve the loss of a hydrogen atom or a deuterium atom. We cannot readily distinguish between these two possibilities. There is only slight evidence for the formation of deuterated dopamine from pHe] p-tyramine this would be seen as a peak at approx 14.75 min. 

The role of the nervous system in pheromone biosynthesis in moths is not clearly understood. Christensen and co-workers [208-211] proposed that the neurotransmitter octopamine may be involved as an intermediate messenger during the stimulation of sex pheromone production in H. virescens. These workers suggested that octopamine was involved in the regulation of pheromone production and that PBAN s role lies in the stimulation of octopamine release at nerve endings. However, contradicting results concerning octopa-mine-stimulated pheromone production were reported in the same species as well as other moth species [163,172,212-214]. 

Rafaeli A., Gileadi C. and Hirashima A. (1999) Identification of novel synthetic octopamine receptor agonists which inhibit moth sex pheromone production. Pestic. Biochem. Physiol. 65, 194-204. 

Dopamine /3-hydroxylase is a monoxygenase that catalyzes the hydroxylation of dopamine to form norepinephrine. This enzyme is localized in the chromaffin granules of the adrenal medulla and in the storage vesicles of central and peripheral catecholaminergic neurons. Since these compounds are unstable, this activity is often assayed by following the formation of octopamine from tyramine. For example, in the assay developed by Feilchenfeld et al. (1982), the reactant tyramine was separated from the product octopamine by reversed-phase, ion-paired HPLC (/uBondapak C18 using a mobile phase of 17% (v/v)... 

Figure 9.11 Time course of production of octopamine with varying DBH concentrations 0.01 and 0.02 mg/mL for line A (A) and line B (O), respectively. Lines represent the least-squares fits of the initial data (From Feilchenfeld et al., 1982.)...

Substrates (p-octopamine, dopamine, or 5-hydroxytryptamine) were separated from their N-acetylated products on an Ultrasphere I.P. C18 column (4.6 mm x 250 mm, 5 pm). The mobile phase was comprised of 75 mAf monobasic sodium phosphate, 1 pAf EDTA, 0.35 mAf 1-octanesulfonate (sodium salt), 11% methanol, and 4% acetonitrile. Coulometric detection was used. Detection of p-octopamine and its N-acetylated product was achieved at a potential of +0.75 V, while dopamine, 5-hydroxytryptamine and their products were detected at +0.50 V. 

Figure 7.26 Hydrolysis of amitraz showing its hydrolysis product resembling the structure of octopamine.

These results indicate that the N-demethylation products of chlordimeform have inhibitory effects on both the reuptake of OA into the cockroach nerve cord and on its subsequent N-acetylation to the putatively inactive NAOA. In both cases the tendency of these results would be to increase the activity of endogenous octopamine. Whether these effects occur with a potency that would make them... 

Table IV. Rate of Removal of -Octopamine and Production of N-Acetyl -Octopamine by Incubated Malpighian Tubules of Periplaneta americana...

Octopamine, a < -4 ml nomet by l)-4-hydroxy benz-enemethauol -taminomethyt1-p-hydroxybenzyt alcohol 1-(p-hydroxyphenyl)-2-aminoethanol norsympatol nor-synephrine p- hyd roxypheny let hanolam i ne WV 569. Cs -H N02 mo] wt 153.18. C 62.72%, H 7.24%, N 9.14%, O 20.89%. A biogenic amine that is the phenol analog of noradrenaline (norepinephrine, q.v,). It is a neurosecretory product found in several vertebrates and invertebrates. Formed by f)-hydroxylation of tyramine by the enzyme dopamine 0 -hydroxylase Pisano et a ., Btochlm. Biophys. 

A. galli, B. pahangi, N. brasiliensis, A. suum and C. elegans (173,174). 0-methylated products of octopamine, DA, epinephrine and NA were described in T. colubri-formis, suggesting that at least some nematodes have catechol 0-methyl transferase activity (167). 

Fig. 3. GC-MS selected ion-monitoring trace of pHj] and [ Hg] p-octopamine (as their DTFMB-TMS derivatives) from 50 DUM cells incubated with pHg] p-tyramme (A) Detection of endogenous p-octopamine (mass-to-charge ration 537) (B,C) Deu-terated pHg] p-octopamine (mass-to-charge ratio 542) and pHgjp-octopamine (mass-to-charge ration 543), respectively. These deuterated products must have been synthesized by the DUM cells from [ Hg] p-tyramine, because they are not present m the controls. Int. Std. Internal stan d (PH3] m-octopamine) added at the time of derivatization to allow quantification of amines recovered. The y-axis of the figine represents instrument response in arbitrary units. M/Z Mass-to-charge ratio for the particular 10ns being monitored, which in each case corresponds to the molecular weights of the derivatives of the species present.

Maries, R. 2011. Synephrine, octopamine and caffeine Health Risk Assessment (HSR) Report. Flealth Canada. Natural Health Products Directorate. 

Finally, Griengl s group has developed the synthesis of aromatic 1,2-amino alcohols on the basis of a bienzymatic DYKAT process. The reaction occurred between a benzaldehyde derivative and glycine in the presence of L-threonine aldolase from Pseudomonas putida and L-tyrosine decarboxylase from either Enterococcus faecalis or two genes from Enterococcus faecium. The best results were obtained for the production of (5)-octopamine (99%, ee = 81%), and (5)-noradrenaline (76%, ee = 79%), as shown in Scheme 3.64. 

Balfanz, S., T. Striinker, S. Frings, and A. Baumann, 2005. A family of octopamine [corrected] receptors that sped cally induce cyclic AMP production or Ca + release in Drosophila melanogaster. J. Neumchem.. 93 440-451. 

Dopamine was produced by incubating liver microsomes of rabbits with p- and m-tyramine, noradrenaline, and normetanephrine by incubation with w-octopamine, and adrenaline by incubation with p- and w-methyloctop-amine/" The injection of labelled tyramine as well as of labelled octopamine in the intact animal (rat) caused the appearance of labelled noradrenaline and normetanephrine in the urine/ As tyramine is also hydroxylated to octopamine, it is possible that the production of noradrenaline from tyramine not only takes place via its conversion to dopamine, but also via its conversion to octopamine. The possibility that octopamine is produced by the hydroxylation of tyrosine to hydroxyphenylserine with ensuing decarboxylation is under discussion. The production of noradrenaline from 3,4-dihydroxyphenylserine, 192-201) amino-acid so far not discovered in the mammal could be demonstrated both in organ extracts and in intact animals. Finally, a transamination of 3-hydroxy- or 3,4-dihydroxyphenylpyruvate to the corresponding amino-acids (m-tyrosin, dopa), and their decarboxylation to m-tyramine and dopamine was observed in intact animals (cats). For the time being it is impossible to determine the importance of the means of formation of catecholamines which have been referred to here. Of the above-mentioned precursor substances, p- and m-tyramine,( octopamine, ... 

Tyramine is oxidized to octopamine by dopamine-jS hydroxylase causing hydroxylation of the carbon atom of its side chain. Octopamine is converted to / -hydroxymandelic acid either directly or after being methylated to AT-methyloctopamine. The introduction of an OH group in the meta or para position in the nucleus of / - and m-tyramine respectively leads in vitro to the production of dopamine it is not known if... 

Neuroblastoma 96 Neurocirculatory disturbance 124 Noradrenaline (norepinephrine, arterenol) excretion 10, 11 human brain 57 ff kidney function 72, 74, 80 localization 4, 10 metabolism 15, 16 microcirculation 80, 81, 86 occurrence 30 If Parkinson s disease 62 pharmacology 65 production 3,7 respiratory metabolism 87, 90 turnover 24, 25 Noradrenochrome 21 Normetanephrine (= 3-O-methylnoradrena-line) 11, 15, 34, 66 Norsynephrine see /7-Octopamine... 

In the transformation of biogenic amines to other biologically active products, a number of different oxygenases, methyltrans-ferases and other enzymes take part (Figure 10.17). Oxidation of tyramine yields 4-(2-amino-l-hydroxyethyl)phenol, known as octopamine, first demonstrated in Octopus species, which acts as a neurohormone and neuromodulator in invertebrates. Methylation... 

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