(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethanaminium
DL-Octopamine hydrochloride
CAS: 770-05-8
Molecular Formula: C8H12ClNO2
(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethanaminium - Names and Identifiers
(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethanaminium - Physico-chemical Properties
| Molecular Formula | C8H12ClNO2 |
| Molar Mass | 189.64 |
| Density | 1.39[at 20℃] |
| Melting Point | ~170°C (dec.)(lit.) |
| Boling Point | 290℃[at 101 325 Pa] |
| Flash Point | 172°C |
| Water Solubility | soluble |
| Solubility | H2O: soluble |
| Vapor Presure | 0.002Pa at 20℃ |
| Appearance | solid |
| Color | white or off-white |
| Merck | 13,6791 |
| BRN | 3915414 |
| Storage Condition | 2-8°C |
| Stability | Stable. |
| MDL | MFCD00012881 |
| Use | α-adrenoceptor agonists; neurotransmitters in invertebrates. |
| In vitro study | Octopamine is present in relatively high concentrations in neuronal as well as non-neuronal tissues of most invertebrates studied and regulates almost every physiological process. Octopamine acts as a neurohormonal, including desensitization of sensory inputs, effects on learning and memory, or regulation of emotions in the animal's central nervous system. Octopamine is the only non-peptide transmitter that stimulates nervous tissue. Its physiological function is limited to invertebrates. All octopamine receptors belong to the G-protein coupled receptor family. |
| In vivo study | Octopamine (10 mg/mL) is necessary for the acquisition of sucrose memory in Drosophila. Octopamine treatment increased responsiveness to larval pheromones and decreased response to social impairments. Octopamine functions as an important source of variation in the sensitivity threshold and as a regulator of pheromone communication in insect populations. Octopamine (10 μm) injected into the calyx or antennal lobe of the fungoides (MB), but not into the transverse forebrain lobe, produced a durable, pair-specific enhancement of the kiss flexion-extension reflex. The injection of Octopamine (10 μm) into the calyx of MB resulted in an additional pair-specific effect, as it did not elicit post-training cognitive acquisition, but rather consolidated it. Octopamine treatment significantly increased octopamine levels in the brain and significantly increased the number of new foragers in a dose-dependent manner. Otopamine treatment is only effective on bees that are old enough to forage, such as those older than 4 days. Octopamine affects the division of labor in bee colonies. |
(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethanaminium - Risk and Safety
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | 3249 |
| WGK Germany | 3 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
(2R)-2-hydroxy-2-(4-hydroxyphenyl)ethanaminium - Reference Information
| LogP | -2.6 at 20.1℃ |
| Overview | the chemical name: 1-(4-hydroxyphenyl)-2-aminoethanol hydrochloride, alias, synephrine, norhydroxyfurin. The molecular formula is C8H11NO2 · HCl and the molecular weight is 189.64. Its use is similar to that of synephrine hydrochloride. The dried young fruit derived from the Rutaceae plant Citrus aurantium L. Is an adrenergic alpha-receptor agonist, and has the effect of constricting blood vessels and increasing blood pressure. |
| Application | reported in the Nordic pharmacopoeia and the German Pharmacopoeia, it is a natural stimulant without any side effects and positive reactions, clinical for the treatment of bronchial asthma and surgery and anesthesia hypotension, collapse and Shock, postural hypotension, and is widely used in medicine, food, beverage and other health industries. Foreign studies have found that synephrine not only has a boost, anti-Shock effect, but also has the following effects: improve metabolism, increase calorie consumption, improve energy levels, oxidation of fat, weight loss. Therefore, the commonly used as the effective component of weight loss drugs, and has the advantages of high purity, stable nature, easy preservation, etc., so that it has a wider range of application value. |
| preparation | a) acylation reaction to the reaction kettle, KG of dichloromethane, 38.5kg of phenol and 35kg of aminoethylenitrile hydrochloride were added sequentially. The temperature was lowered to 5±5 ° C., and 10±10 of anhydrous aluminum trichloride was slowly added in portions, and the temperature was controlled at ° C. After completion of feeding, hydrogen chloride gas was passed through until absorption was not achieved. 20±5 ℃ to keep the reaction for 18 hours, add 220kg of drinking water to another reactor, and drop the temperature of ice-passing brine to 5±5 ℃. Pump the heat-insulating reaction materials into the reactor, and slowly pump them in, the temperature was controlled at 40±10 ° C., the feeding was completed, and the temperature was raised to 55±5 ° C. For half an hour. At the end of the reaction, the temperature was cooled to 30±5 ° C. By cooling water, centrifuged and spin dried to obtain a crude product of Intermediate 1-(4-hydroxyphenyl)-2-aminoethanone hydrochloride, which was recrystallized with an appropriate amount of methanol. The yield was 80%. B) reduction reaction the intermediate obtained in the above preparation was dissolved in 100kg of drinking water, and was drawn into a hydrogenation kettle. The Palladium carbon was diluted with methanol and drawn into the kettle, and the remaining methanol (100kg in total) was further drawn. The mixture was replaced with nitrogen for 3 times, and then replaced with hydrogen for 2 times, stirred, and hydrogenated at room temperature to 1.5±0.1Mpa for 24h through hydrogen reaction. After completion of the reaction, the reaction is placed in an open bucket, and first filtered into a pressure filter kettle, then 1kg of activated carbon is added, the pressure filter is placed in an open bucket, and then is drawn into a water bath concentration kettle, Distillation to dryness. Then 0.5 times the weight of ethanol is pumped, water bath distillation with water to dryness, then 0.8 times the weight of ethanol is pumped, and the temperature is raised at atmospheric pressure until ethanol is distilled out, still, and 0.8 times of ethyl acetate is pumped, the mixture was stirred and cooled to 25±5 ° C., centrifuged, and the centrifuged material was put into the reaction vessel and 1.5 times of acetone was pumped. The temperature was raised to 40±5 ° C., and the mixture was stirred and centrifuged while hot for 30 minutes to obtain the amikacin hydrochloride, which was dried in the drying room. The yield was 95%. |
| biological activity | ( ,-)-Octopamine HCl, an essential monoamine, structurally related to norepinephrine, it acts as a neurohormone, neuromodulator, and neurotransmitter in invertebrates. |
| Use | α-adrenoceptor agonists; Neurotransmitters in invertebrates. |
Last Update：2024-04-09 21:04:16
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