Sphygmogenin
L(-)-Epinephrine
CAS: 51-43-4
Molecular Formula: C9H13NO3
Sphygmogenin - Names and Identifiers
| Name | L(-)-Epinephrine |
| Synonyms | Simplene Soladren Sindrenina Adrenaline Epinephrine Scurenaline Renostyptin Styptirenal L-Adrenalin Stryptirenal Sphygmogenin L-Adrenaline L-Epinephrine L(-)-Epinephrine L-Adrenaline base Epinephrine, L(-)- 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol l-3,4-Dihydroxy-alpha-(methylaminomethyl)benzyl alcohol (2S)-2-(3,4-dihydroxyphenyl)-2-hydroxy-N-methylethanaminium (2R)-2-(3,4-dihydroxyphenyl)-2-hydroxy-N-methylethanaminium |
| CAS | 51-43-4 |
| EINECS | 200-098-7 |
| InChI | InChI=1/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/p+1/t9-/m1/s1 |
Sphygmogenin - Physico-chemical Properties
| Molecular Formula | C9H13NO3 |
| Molar Mass | 183.2 |
| Density | 1.1967 (rough estimate) |
| Melting Point | 215°C (dec.)(lit.) |
| Boling Point | 316.88°C (rough estimate) |
| Specific Rotation(α) | -51.5 º (c=4, 1M HCl, dry sub) |
| Flash Point | 207.9°C |
| Solubility | Practically insoluble in water, in ethanol (96 per cent) and in methylene chloride. It dissolves in hydrochloric acid. |
| Vapor Presure | 1.45E-07mmHg at 25°C |
| Appearance | Fine Crystalline Powder |
| Color | White to light beige |
| Merck | 14,3619 |
| BRN | 2368277 |
| pKa | 8.66(at 25℃) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents. Light sensitive. |
| Sensitive | Air & Light Sensitive |
| Refractive Index | -51.5 ° (C=4, 1mol/L |
| Physical and Chemical Properties | White crystalline powder. Melting Point 213 ℃ (decomposition), soluble in mineral acid and hydroxide alkali solution, slightly soluble in water, insoluble in alcohol, ether, acetone, chloroform. No odor, bitter taste. The air was exposed and the light color was darkened. |
Sphygmogenin - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R52/53 - Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36/37/38 - Irritating to eyes, respiratory system and skin. R33 - Danger of cumulative effects |
| Safety Description | S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S23 - Do not breathe vapour. |
| UN IDs | UN 2811 6.1/PG 2 |
| WGK Germany | 3 |
| RTECS | DO2625000 |
| FLUKA BRAND F CODES | 8-10-23 |
| TSCA | Yes |
| HS Code | 29373100 |
| Hazard Class | 6.1 |
| Packing Group | II |
| Toxicity | LD50 i.p. in mice: 4 mg/kg (Lands) |
Sphygmogenin - Reference Information
| Decomposition | > 212°C |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | epinephrine, also known as pararenin and pararenine, is extracted from the adrenal medulla of livestock (cattle, sheep) or synthesized by artificial methods. it is white or white-like crystalline powder and has an agonistic effect on α and β receptors. Adrenaline is a hormone secreted by chromaffin cells in the adrenal medulla. Mainly involved in sympathetic nervous system regulation. When its secretion increases, it causes increased heart activity-increased heart rate, increased cardiac output, and increased blood pressure; liver glycogen decomposition becomes glucose to increase blood sugar, and fat decomposition accelerates metabolism; bronchial smooth muscle relaxation, etc. The activity of the sympathetic nervous system is significantly enhanced during rapid changes in the environment, strenuous exercise, tension, fear, cold, and massive blood loss. At the same time, the secretion of the adrenal medulla also increases, and the content of adrenaline in the body increases. When adrenaline acts on adrenergic receptors (α, β adrenergic receptors), it causes a series of changes in body activities and metabolism. Among the hormones secreted by the adrenal medulla when sympathetic nerves are excited, the 80% is epinephrine and the 20% is norepinephrine. |
| character | is white or white-like crystalline powder, odorless and bitter. Very slightly soluble in water, insoluble in organic solvents such as ethanol and chloroform, and easily soluble in mineral acid or sodium hydroxide solution. Unstable in neutral or alkaline aqueous solutions, saturated aqueous solutions show weak alkaline reactions. Commonly used, its hydrochloride is easily soluble in water, and the pH of 0.1% aqueous solution is 2.5~5.0. This product and its salt are easy to decompose, deteriorate and oxidize into pink to brown red when exposed to oxides, alkalis, light and heat. |
| Producing organ | Adrenaline is produced and secreted by the adrenal gland. The adrenal gland is a very important endocrine organ in the human body. Because it is located above the kidneys on both sides, it is named adrenal gland. The adrenal glands are located on the upper side of the kidney and are wrapped together by the renal fascia and adipose tissue. The left adrenal gland is half-moon, and the right adrenal gland is triangular. The adrenal gland weighs about 30g on both sides. From the side, the glands are divided into adrenal cortex and adrenal medulla, the surrounding part is the cortex, and the inside is the medulla. The two are different in occurrence, structure and function. In fact, they are two kinds of endocrine glands. Fig. 1 shows adrenal gland |
| effect | 1. effect on the heart adrenergic can excite the β1 receptor of the heart, strengthen myocardial contractility, accelerate conduction, accelerate heart rate and increase cardiac output; It can also expand coronary blood vessels and improve myocardial blood supply. Improved myocardial metabolism can increase myocardial oxygen consumption and improve myocardial excitability. If the dose is too large or the intravenous injection speed is too fast, it can cause arrhythmia and even ventricular fibrillation. 2. Effect on blood vessels. Adrenaline has two effects on blood vessels: contraction and relaxation, mainly because of the different types of receptors in blood vessels in various parts of the body. This product has a strong contraction effect on the skin, mucous membranes and visceral blood vessels (such as kidneys) dominated by α receptors, and has a relaxation effect on the coronary blood vessels and skeletal muscle blood vessels dominated by β2 receptors. 3. While raising blood pressure and exciting the heart, small doses can increase systolic blood pressure, and diastolic blood pressure remains unchanged or decreases; large doses can increase both systolic and diastolic blood pressure. 4. The effect on smooth muscle excites the bronchial smooth muscle β2 receptor, which can quickly and powerfully relax the bronchial smooth muscle, especially when the bronchial smooth muscle spasm is more obvious; it has a weak relaxation effect on the gastrointestinal tract and bladder smooth muscle, but it has a contraction effect on its sphincter. In addition, epinephrine can also stimulate alpha receptors, constrict bronchial mucosal blood vessels, reduce bronchial mucosal edema, reduce the secretion of bronchial glands. Inhibition of gastrointestinal smooth muscle peristalsis, contraction of pylorus and ileal sphincter, but when sphincter spasm, it has a relaxation effect, can also reduce the secretion of digestive glands. Contraction of the iris radiation muscle, so that the pupil dilation, for animals with a transient membrane can cause the transient membrane contraction. The effect on uterine smooth muscle is relatively complex, mainly related to factors such as animal species, different stages of the sexual cycle and pregnancy. In addition, epinephrine can also excite the respiratory center and raise blood sugar. |
| main use | 1. as an emergency medicine for restoring cardiac function: it is often used for weak heartbeat or sudden arrest caused by anaphylactic shock, drowning, infectious diseases, drug poisoning, surgical accidents and heart block. When the heartbeat completely stops, it can be injected into the heart, and with effective artificial respiration, heart massage and other measures. 2. Used for allergic diseases: Subcutaneous or intramuscular injection can treat allergic diseases, such as anaphylactic shock, urticaria, bronchial asthma, hoof lobitis, etc., and it is also effective for allergic reactions caused by immune serum and vaccines. 3. Compatible application with local anesthetics: add 0.5~1ml of 0.1% epinephrine solution to every 100ml of local anesthetics to constrict local blood vessels, delay the absorption of local anesthetics, prolong the anesthesia time and reduce the toxic reaction of anesthetics. 4. External use as a local hemostatic drug: local use of 1:5000~1: 100,000 solution can make local vasoconstriction and stop bleeding in nasal mucosa, uterus, gums or surgical site. |
| Biosynthesis | Adrenaline is synthesized in the adrenal medulla in the enzymatic pathway, which converts tyrosine into a series of intermediates and finally forms adrenaline. Tyrosine is first oxidized to levodopa, and then decarboxylated to obtain dopamine. Oxidation produces norepinephrine. The final step in epinephrine biosynthesis is the methylation of the primary amine of norepinephrine. |
| drug interaction | 1.α-receptor blockers and various vasodilators can resist the pressurization of this product. 2. Combined with general anesthesia drugs, it is easy to produce arrhythmia and even ventricular fibrillation. 3. In combination with digitalis and tricyclic antidepressants, it can cause arrhythmia. 4. When combined with ergot preparations, such as ergotamine, it can cause severe hypertension and tissue ischemia. 5. In combination with reserpine and guanethidine, it can cause hypertension and tachycardia. 6. Combined with β-blockers, the β-receptor effects of the two cancel each other, and abnormal blood pressure, bradycardia and bronchoconstriction may occur. 7. When combined with other sympathomimetic amines, cardiovascular effects are aggravated and side effects are prone to occur. 8. When combined with nitrates, the boosting effect of this product is offset, and the anti-angina effect of nitrates is weakened. 9. The combination with monoamine oxidase inhibitor can enhance the boosting effect of this product. 10. In combination with chlorpromazine, can cause severe hypotension. 11. When combined with hypoglycemic drugs, it can weaken the effect of oral hypoglycemic drugs and insulin. |
| Research on epinephrine in cardiopulmonary resuscitation | epinephrine-a naturally occurring catecholamine in the human body, which has both alpha and beta adrenergic activities, and has the effect of increasing peripheral vascular resistance, increasing coronary artery and cerebrovascular perfusion pressure, and promoting circulation recovery. It has been used as the first choice for rescuing cardiac arrest during cardiopulmonary resuscitation for decades. However, due to moral and ethical limitations and the lack of large-scale clinical randomized controlled trials, the effectiveness of epinephrine has not yet been determined. In recent years, the possible cardiac and brain damage and poor long-term prognosis of epinephrine used in cardiac arrest have been controversial. 1. Pharmacological action and mechanism of epinephrine. As an alpha and beta receptor agonist, epinephrine mainly contracts small arteries and precapillary sphincter, followed by veins and large arteries. Due to the different responses of vascular receptors to adrenaline in different parts, blood flow redistribution can be formed. Adrenaline can relax coronary arteries and improve myocardial blood supply without increasing aortic blood pressure; it can accelerate heart rate and conduction by stimulating β1 receptors in myocardium, sinoatrial node and conduction system, and enhance myocardial contractility. Increase cardiac output. Small doses and therapeutic amounts of epinephrine can increase myocardial contractility, increase heart rate and cardiac output, constrict skin and mucosal blood vessels, and increase systolic and diastolic blood pressure; in large doses, adrenaline can not only strongly excite the heart, but also The excitement of vascular smooth muscle α1 receptors is dominant, which significantly increases peripheral resistance and reduces cardiac output. For cerebral arterioles, the therapeutic dose of epinephrine does not have a significant contractile effect, but due to increased blood pressure, cerebral blood flow increases. Under normal circumstances, the self-regulation of cerebral blood flow will limit this increase. Therefore, the pharmacological effects of epinephrine on cardiovascular and cerebrovascular diseases are summarized as follows: (1) increase peripheral vascular resistance;(2) increase arterial systolic and diastolic blood pressure;(3) enhance myocardial electrical activity and improve the automatic rhythm of the heart;(4) Enhance myocardial contractility;(5) Increase myocardial oxygen consumption;(6) Increase coronary and cerebral blood flow. In the process of cardiopulmonary resuscitation, the application of epinephrine is mainly to contract the peripheral blood vessels, so that the blood flow occurs beneficial redistribution, from the periphery to the central circulation, thereby increasing the coronary artery and cerebrovascular perfusion pressure. 2. New perspectives on epinephrine and recovery of spontaneous circulation after cardiac arrest (ROSC) and long-term survival. In recent years, the evaluation of epinephrine effectiveness has focused more on the long-term prognosis after resuscitation, including discharge rate, long-term survival rate, and long-term survival quality. Adrenaline can increase the probability of ROSC after cardiac arrest. A new view on the long-term prognosis is that epinephrine may increase myocardial dysfunction, interfere with cerebral microcirculation, and be detrimental to the long-term survival rate and quality of survival of patients with cardiac arrest. 3. Dosage of epinephrine in cardiopulmonary resuscitation The pharmacological effects of epinephrine are dose-dependent, so the dosage of epinephrine in cardiopulmonary resuscitation is controversial. The traditional view is that the standard dose is used, that is, the dose recommended by the American Heart Association is 0. 5~1.0 mg (equivalent to 0. 02 mg /kg), repeated every 3~5min. The traditional view supports the use of standard dose epinephrine (SDE). It is considered that high dose epinephrine (HDE) can increase myocardial oxygen consumption, increase self-discipline, and significantly increase peripheral vascular resistance, which may aggravate myocardial ischemia, Reduce cardiac output, produce heavier myocardial toxicity and affect brain microcirculation, these will lead to cardiac insufficiency and brain damage after ROSC, reduce the long-term survival rate of patients after resuscitation and affect the quality of survival. 4. The problem of the combination of epinephrine and other vasopressor drugs in cardiopulmonary resuscitation due to the release of a large amount of endogenous catecholamines caused by stress and the application of large doses of exogenous epinephrine in cardiopulmonary resuscitation, resulting in myocardial α1 and β1 receptor Overexpression, which will significantly increase myocardial oxygen consumption, aggravate myocardial ischemia and produce myocardial toxic side effects. Therefore, some experts have proposed the use of vasopressin instead of epinephrine. A large number of animal experiments have confirmed that vasopressin alone or in combination with epinephrine is superior to epinephrine alone in improving hemodynamics and ROSC rate. A recent large animal experiment confirmed that the combined application of epinephrine, vasopressin, and nitroglycerin can improve brain function. In summary, epinephrine is still the first-line drug during cardiopulmonary resuscitation during cardiac arrest. Adrenaline can promote ROSC, but the effect of epinephrine on the long-term function and survival rate after cardiac arrest resuscitation, whether HDE will cause more serious myocardial damage and brain function damage, and whether epinephrine combined with other vasopressor drugs can improve survival rate, there is still a lack of large-scale multi-center randomized controlled clinical studies. In addition, in most of the existing studies, ventricular fibrillation or ventricular tachycardia are used as the inclusion criteria for experimental subjects. It is not clear whether the use of epinephrine will achieve consistent results for cardiac arrest caused by asphyxia. Therefore, the effectiveness and advantages of epinephrine in cardiopulmonary resuscitation need to be confirmed by more in-depth experimental studies and more clinical evidence-based studies. |
| Research on adrenaline in prostate cancer | Adrenergic receptors are superfamily members of guanylate binding protein (G protein)-coupled receptors. Studies have found that adrenergic receptors play an important role in the growth and metastasis of prostate cancer cells. The expression of adrenergic receptors is significantly increased in prostate cancer cells and tissues. Activating receptor activity can stimulate the growth and migration of prostate cancer cells, and blocking the activity of these receptors can inhibit the growth of prostate cancer cells and induce cancer cells Apoptosis and prevent prostate cancer from invading neighboring lymph nodes. Clinical studies have found that taking receptor antagonists can not only significantly reduce the incidence of prostate cancer, but also significantly reduce the cancer mortality of patients after castration treatment. |
| adverse reactions | palpitations, irritability, anxiety, fear, tremor, sweating and pale skin are common. the above symptoms can disappear after drug withdrawal. Excessive dose, subcutaneous injection into blood vessels or intravenous injection too fast can cause blood pressure to rise sharply, and even cause the risk of cerebral hemorrhage. It can also cause arrhythmia, and even develop into ventricular fibrillation, which can be fatal in severe cases. Local medication may have edema, congestion, inflammation. When using this product to drop eyes:(1) Excessive liquid medicine can flow out through the nasolacrimal duct, causing nasal vasoconstriction and nasal dryness. The product of oxidation can be deposited in the nasolacrimal duct to cause obstruction, so that the lacrimal point is blocked, thereby causing overflowing tears. (2) Occasionally, conjunctival local allergies and hyperemia, increased palpebral conjunctival follicles and corneal epithelial damage caused by corneal opacity, edema, iridescence, fog vision, burning sensation, lacrimation and other symptoms. (3) Long-term application of this product can also cause conjunctiva, eyelid margin, nasolacrimal duct, corneal pigmentation, macular edema, vasospasm, small hemorrhage, and even the formation of macular punctate cystic deformation. (4) occasionally can cause eyelashes or eyebrow hair shedding, conjunctival or subretinal hemorrhage, dark spot periorbital edema, etc. (5) It can also cause the increase of blood sugar and serum lactic acid level. |
| contraindications, cautious use | hypertension, coronary artery disease, cardiogenic asthma, diabetes, hyperthyroidism, childbirth, arrhythmia, angle-closure glaucoma patients are prohibited. The following conditions should be used with caution:(1) Organic brain damage;(2) Cardiovascular disease, including angina pectoris, arrhythmia, heart enlargement, cerebrovascular sclerosis, coronary artery disease, various organic heart diseases;(3) Diabetes;(4) Glaucoma;(5) Hypertension;(6) Hyperthyroidism;(7) Parkinson's disease (8) Phenothiazine-induced circulatory collapse or hypotension:(9) The symptoms of mental and neurological disorders worsen;(10) Cardiogenic, traumatic or hemorrhagic shock patients and the elderly. |
| sex and taste return to the meridian | sex is hot, spicy and bitter. Return to heart, kidney, lung meridian. |
| efficacy | return yang to save the reverse, invigorate the heart yang, relieve asthma and stop bleeding. |
| Uses | Non-steroidal hormone drugs are also used as intermediates for hemostatic drugs Anluoxue. Mainly used for the rescue of anaphylactic shock, bronchial asthma and cardiac arrest. |
| Production method | 3, 4-dihydroxy-α-methamidoacetophenone (I. e. renal proketone) is prepared into hydrochloride, which is catalyzed by palladium. Hydrogen reaction. The hydrogenation temperature is 30-35α, the pressure is 0.05-0.1MPa, and the obtained racemaline is separated with tartaric acid and neutralized with ammonium hydroxide to obtain L-adrenaline. |
| category | toxic substances |
| toxicity classification | highly toxic |
| acute toxicity | oral-rat LD50 30 mg/kg; Oral-mouse LD50: 50 mg/kg |
| flammability hazard characteristics | flammability; fire scene decomposition toxic nitrogen oxide smoke |
| storage and transportation characteristics | warehouse is low temperature, ventilated and dry; Store separately from food raw materials |
| fire extinguishing agent | water, carbon dioxide, dry powder, sand |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:09
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