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)

Safety

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

Toxicity

LD50 oral in rat: 1240mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P322Specific measures (see …on this label).

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

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)