Octopamine Chemical Properties
- Melting point:
- 157-158 °C
- Boiling point:
- 276.1°C (rough estimate)
- 1.1577 (rough estimate)
- refractive index
- 1.5010 (estimate)
- pKa 8.88 (Uncertain);9.53 (Uncertain)
- CAS DataBase Reference
- 104-14-3(CAS DataBase Reference)
Octopamine Usage And Synthesis
An alkaloid found in annual rye grass, this base has been suggested as a possible precursor of annuloline (q.v.).
Norfen,Morishita, Japan ,1975
Octopamine is a biogenic monoamine structurally related to Noradrenaline (N661038), it acts as a neurohormone, neuromodulator and a neurotransmitter in invertebrates.
A solution of 33 grams of anhydrous aluminum chloride in 60 grams of nitrobenzene, to which a mixture of 14 grams of phenol and 9.3 grams of hydrochloride of amino-acetonitrile was added, had dry hydrochloric acid gas introduced into it for 3 hours, while stirring and cooling to keep the temperature between 20° and 30°C. The reaction mixture was then poured, with cooling, into 70 cc of water and the deposit obtained was sucked off, washed with acetone and dissolved in 300 cc of water. The solution thus prepared was decolorized with carbon, 50 grams of 30% sodium citrate solution was added to it, and then it was made slightly alkaline with ammonia. Thereupon hydroxy-4'-phenyl-1-amino-2-ethanone crystallized out in the form of leaflets. The yield was 7.7 grams.
The hydrochloride of this base, obtained by evaporation to dryness of a solution of the base in dilute hydrochloric acid and subsequent treatment of the residue with ethyl alcohol and acetone, had a chlorine content of 18.84%, (calculated, 18.90%).
This hydrochloride, on being dissolved in water and hydrogenated with hydrogen and a nickel catalyst, gave a good yield of hydrochloride of hydroxy4'-phenyl-1-amino-2-ethanol melting, after crystallization from a mixture of ethyl alcohol and butanone-2, at from 177° to 179°C with decomposition
Hardwick, Axelrod, Plant Physiol., 44, 1745 (1969)
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