ChemicalBook > CAS DataBase List > Octopamine

Octopamine

CAS No.104-14-3
Chemical Name:Octopamine
CBNumber:CB8482020
Molecular Formula:C8H11NO2
Formula Weight:153.18
MOL File:104-14-3.mol

Octopamine Property

Melting point 157-158 °C
Boiling point 276.1°C (rough estimate)
Density 1.1577 (rough estimate)
refractive index 1.5010 (estimate)
solubility Water (Easy)
pka pKa 8.88 (Uncertain);9.53 (Uncertain)
optical activity D -56.025 (0.1 mol dm-3 HCl)
CAS DataBase Reference 104-14-3(CAS DataBase Reference)
EWG's Food Scores 1-3
FDA UNII 14O50WS8JD
ATC code C01CA18

Safety

RIDADR :3249
HazardClass :6.1(b)
PackingGroup :III
Toxicity :LD50 oral in rat: 1240mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302-H312
Precautionary statements P264-P270-P301+P312-P330-P501-P280-P302+P352-P312-P322-P363-P501

Octopamine Chemical Properties,Usage,Production

Description An alkaloid found in annual rye grass, this base has been suggested as a possible precursor of annuloline (q.v.).
Originator Norfen,Morishita, Japan ,1975
Uses Octopamine is a biogenic monoamine structurally related to Noradrenaline (N661038), it acts as a neurohormone, neuromodulator and a neurotransmitter in invertebrates.
Definition ChEBI: Octopamine is a member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates. It has a role as a neurotransmitter. It is a member of phenylethanolamines and a member of tyramines. It is a conjugate base of an octopaminium.
Manufacturing Process 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
Therapeutic Function Hypertensive
References Hardwick, Axelrod, Plant Physiol., 44, 1745 (1969)