104-14-3 Usage
Description
Octopamine, a biogenic monoamine structurally related to Noradrenaline, is an alkaloid found in annual rye grass. It serves as a neurohormone, neuromodulator, and neurotransmitter in invertebrates and has been suggested as a possible precursor of annuloline.
Uses
Used in Neurotransmission:
Octopamine is used as a neurotransmitter in the nervous systems of invertebrates, playing a crucial role in various physiological processes and behaviors.
Used in Neuromodulation:
As a neuromodulator, Octopamine is involved in modulating the activity of neurons, allowing for the fine-tuning of neural responses and communication.
Used in Hormonal Regulation:
Octopamine acts as a neurohormone, regulating various physiological functions and responses in invertebrates, including stress responses, aggression, and reproductive behaviors.
Used in Research and Drug Development:
Due to its structural similarity to Noradrenaline and its role in invertebrate nervous systems, Octopamine is used in research to study the mechanisms of neurotransmission, neuromodulation, and hormonal regulation. It may also serve as a starting point for the development of new drugs targeting these processes.
Originator
Norfen,Morishita, Japan ,1975
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)
Check Digit Verification of cas no
The CAS Registry Mumber 104-14-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 4 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 104-14:
(5*1)+(4*0)+(3*4)+(2*1)+(1*4)=23
23 % 10 = 3
So 104-14-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2/t8-/m0/s1
104-14-3Relevant articles and documents
Fluorimetric assay for dopamine beta-hydroxylase in rat plasma.
Ohkura,Ohtsubo,Zaitsu,Kohashi
, p. 3385 - 3388 (1980)
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Photoactivatable, biologically-relevant phenols with sensitivity toward 2-photon excitation
McLain, Duncan E.,Rea, Adam. C.,Widegren, Magnus B.,Dore, Timothy M.
, p. 2151 - 2158 (2015/12/04)
Spatio-temporal release of biologically relevant small molecules provides exquisite control over the activation of receptors and signaling pathways. This can be accomplished via a photochemical reaction that releases the desired small molecule in response to irradiation with light. A series of biologically-relevant signaling molecules (serotonin, octopamine, capsaicin, N-vanillyl-nonanoylamide, estradiol, and tyrosine) that contain a phenol moiety were conjugated to the 8-bromo-7-hydroxyquinolinyl (BHQ) or 8-cyano-7-hydroxyquinolinyl (CyHQ) photoremovable protecting groups (PPGs). The CyHQ caged compounds proved sensitive toward 1PE and 2PE processes with quantum efficiencies of 0.2-0.4 upon irradiation at 365 nm and two-photon action cross sections of 0.15-0.31 GM when irradiated at 740 nm. All but one BHQ caged compound, BHQ-estradiol, were found to be sensitive to photolysis through 1PE and 2PE with quantum efficiencies of 0.30-0.40 and two photon cross sections of 0.40-0.60 GM. Instead of releasing estradiol, BHQ-estradiol underwent debromination.
Iron-catalyzed aminohydroxylation of olefins
Williamson, Kevin S.,Yoon, Tehshik P.
supporting information; experimental part, p. 4570 - 4571 (2010/06/12)
We have discovered that N -sulfonyl oxaziridines react with a broad range of olefins in the presence of iron salts to afford 1,3-oxazolidines. This process provides access to 1,2-aminoalcohols with the opposite sense of regioselectivity produced from the copper-catalyzed oxyamination previously reported by our laboratories. Thus, either regioisomeric form of 1,2-aminoalcohols can easily be obtained from the reaction of oxaziridines with olefins, and the sense of regioselectivity can be controlled by the appropriate choice of inexpensive, nontoxic, first-row transition-metal catalyst.
