59-92-7
L-DOPA
CAS: 59-92-7
Molecular Formula: C9H11NO4
59-92-7 - Names and Identifiers
| Name | L-DOPA |
| Synonyms | L-DOPA Levodopa H-Tyr(3-OH)-OH L-3-Hydroxytyrosine 3-HYDROXY-L-TYROSINE 3-Hydroxy-L-tyrosine 3,4-L-DIHYDROXYPHENYLALANINE 3,4-DIHYDROXY-L-PHENYLALANINE 3,4-Dihydroxyphenyl-L-alanine L-3-(3,4-Dihydroxyphenyl)alanine 3,4-Dihydroxyphenylalanine(form2) 3-(3,4-DIHYDROXYPHENYL)-L-ALANINE L-DOPA 3,4-L-Dihydroxyphenylalanine BETA-(3,4-DIHYDROXYPHENYL)-L-ALANINE 2-amino-3-(3,4-dihydroxyphenyl)propanoicacid |
| CAS | 59-92-7 |
| EINECS | 200-445-2 |
| InChI | InChI=1/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1 |
| InChIKey | WTDRDQBEARUVNC-LURJTMIESA-N |
59-92-7 - Physico-chemical Properties
| Molecular Formula | C9H11NO4 |
| Molar Mass | 197.19 |
| Density | 1.3075 (rough estimate) |
| Melting Point | 276-278 °C (lit.) |
| Boling Point | 334.28°C (rough estimate) |
| Specific Rotation(α) | -11.7 º (c=5.3, 1N HCl) |
| Flash Point | 225°C |
| Water Solubility | Slightly soluble in water, dilute hydrochloric acid and formic acid. Insoluble in ethanol. |
| Solubility | Easily soluble in dilute hydrochloric acid and formic acid, soluble in water, insoluble in ethanol, benzene, chloroform and ethyl acetate |
| Vapor Presure | 7.97E-09mmHg at 25°C |
| Appearance | White to milky white crystalline powder |
| Color | White to creamy |
| Merck | 14,5464 |
| BRN | 2215169 |
| pKa | 2.32(at 25℃) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents. Light and air sensitive. |
| Sensitive | Sensitive to light and air |
| Refractive Index | -12 ° (C=5, 1mol/L H |
| MDL | MFCD00002598 |
| Physical and Chemical Properties | melting point 295°C specific optical rotation -11.7 ° (c = 5.3, 1N HCl) |
| Use | An effective drug for the treatment of paralysis of shock, mainly used for Parkinson's syndrome, etc |
59-92-7 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | AY5600000 |
| FLUKA BRAND F CODES | 10-23 |
| TSCA | Yes |
| HS Code | 29225090 |
| Toxicity | LD50 in mice (mg/kg): 3650 ±327 orally, 1140 ±66 i.p., 450 ±42 i.v., >400 s.c.; in male, female rats (mg/kg): >3000, >3000 orally; 624, 663 i.p.; >1500, >1500 s.c. (Clark) |
59-92-7 - Reference
| Reference Show more | 1. Yu Xiaoming, Xu Xuefeng, Cai Changyou et al. Browning and related enzyme activities of three Tricholoma megaterianum strains during storage [J]. Science and Technology of Food Industry 2018 039(021):275-279. 2. Cui Li, song, Shuangshuang, Liu Feng, Liu Wei, Wang Xiao, Geng, Yan Ling, Liu Jianhua. Effects of different drying methods on Browning related enzymes and active components of Chrysanthemum morifolium [J]. Food Science and Technology 2015 40(02):39-44. 3. Xu Fangzheng, Jiang Xunping, Liu Guiqiong et al. Analysis of melanin source in muscle tissue of wugu goat [J]. Chinese Journal of Animal Husbandry, 2015, 51(011):10-13. 4. Cui, Li, song, Bi-Bi, Bi-Bi, Dooley, equality. Study on Browning and changes of active components of Chaenomeles speciosa during low-temperature blast drying [J]. Food and machinery 2015 031(006):70-74 123. 5. Xu Mengjie, Liu zuwang, Li Qianxin et al. Effects of different extracts from Rosa roxburghii Tratt on proliferation and tyrosinase activity of B16 cells [J]. Journal of Zhejiang University of Chinese Medicine, 2018, 42(11):883-889. 6. Geng, your son. Analysis of levodopa content in various organs of broad bean in field [J]. Northern horticulture, 2012, 000(002):26-27. 7. Liu Lin, Yang Zhigang. Inhibitory and antioxidant effects of extracts from leaves of Ilex on tyrosinase [J]. Natural product research and development, 2018,30(01):114-119. 8. Liu Dongru, Ren yamee, Bo Jifang, et al. Inhibitory effects of phlorizin and polyphenols from young apple fruits on tyrosinase activity [J]. Modern food science and technology, 2019, v.35;No.240(08):113-119. 9. Lu Yudong, Yuan Lin, Fan Min, et al. Effect of polyphenols from Camellia oleifera shell on tyrosinase activity [J]. Guangzhou chemistry, 2018, v.43;No.176(04):47-50 70. 10. Geng, your son, Liu, Yu, Yang, Xi, Juan. Analysis of L-DOPA content in Vicia faba L. During growth [J]. Agricultural machinery, 2012(09):120-122. 11. Zhong Xinxin, Cao Limin, Lin Hong, Shi Peiyu, Sui Jianxin. Preparation of tyrosinase-specific yolk antibody Fab' fragment and its inhibitory activity [J]. Food Science, 2018,39(02):119-123. 12. Yang Fang, Wang Yihan, Yuan Xinrui, et al. Inhibition of tyrosinase by tremella polyalditol precipitation fraction [J]. Food industry, 2020, v.41;No.282(03):6-9. 13. Yang Na, Zhao, Yuqing, Zhang Shuai, et al. Optimization of extraction of whitening components from Rhizoma typhonii by response surface methodology [J]. Journal of Harbin University of Commerce (Natural Science) 2019 v.35;No.159(04):12-15 19. 14. Pu Yuehua, Tong Yinhong. Study on whitening mechanism of hydrolyzed Pearl [J]. Spices and fragrances, 2015(03):43-46. 15. Lu Cheng, Xiang Xie, Liu Zhongyuan, et al. Whitening and anti-aging effects of saponins extracted from sea cucumber [J]. Fine Chemicals,, 35(002):267-271,290. 16. Li Junqiang, Li Xingchen, Liu Xiaojing. Biotransformation and tyrosinase inhibitory activity of total saponins from Glycyrrhiza uralensis [J]. China Pharmaceutical Affairs, 2018, 032(002):234-241. 17. Yu Lijuan, Wu Lihua, Wang Jinxiang, etc. Antioxidant Capacity Analysis and effect on tyrosinase activity of Phyllanthus emblica L. Extracts [J]. Southwest Agricultural Journal 2020(7). 18. Chen Rongda, Shi yuirui, Liu Guiming, Tao Yanzhou, fan Yangyang, Li Li. Study on tyrosinase inhibitory activity of anthocyanins extracted from Zijuan tea [J]. Journal of Changchun Normal University, 2020,39(12):90-93. 19. Su, Jia, et al. "Antioxidant and anti-tyrosinase activities of bee silicone and identification of active components." Journal of Pharmaceutical Research 60.2 (2021): 297-307.https:// doi.org/10.1080/00218839.2020.1722356 20. [IF = 7.514] Na-na Liu et al."Purification and partial characterization of polyphenol oxidase from the flower buds of Lonicera japonica Thunb.."Food Chem. 2013 May;138:478 21. [IF=4.237] Ji Liu et al."Experimental study on the antioxidant activity of Malus hupehensis (Pamp.) Rehd extracts in vitro and in vivo."J Cell Biochem. 2019 Jul;120(7):11878-11889 22. [IF=2.72] Xiao-Feng Feng et al."Purification and Characterization of Polyphenol Oxidase from the Bud of Lonicera confusa."J Food Biochem. 2014 Dec;38(6):533-541 23. [IF=13.273] Jia An et al."Multichannel ratiometric fluorescence sensor arrays for rapid visual monitoring of epinephrine, norepinephrine, and levodopa."Chem Eng J. 2021 Dec;425:130595 24. [IF=7.312] Yunhai Fu et al."RNase-free RNA removal and DNA purification by functionalized magnetic particles."Sep Purif Technol. 2021 Jul;267:118616 25. [IF=6.321] Xudong Tang et al."Anti-Melanogenic Mechanism of Tetrahydrocurcumin and Enhancing Its Topical Delivery Efficacy Using a Lecithin-Based Nanoemulsion."Pharmaceutics. 2021 Aug;13(8):1185 26. [IF=4.952] Jingyang Yao et al."Free soluble-bound and insoluble-bound phenolics and their bioactivity in raspberry pomace."Lwt Food Sci Technol. 2021 Jan;135:109995 27. [IF=4.641] Fei Qu et al."Aggregation-induced emission of lead halide perovskites modulated by dispersed/aggregated gold nanoparticles for application in the detection of dopamine."Mater Res Bull. 2021 Oct;142:111405 28. [IF=4.24] Qun Yu et al."Antityrosinase and antioxidant activity of asparagus and its inhibition on B16F10 melanoma cells before and after hydrothermal treatment."Food Biosci. 2021 Jun;41:101026 29. [IF=3.361] Ruixue Yu et al."Targeted neurotransmitter metabolomics profiling of oleanolic acid in the treatment of spontaneously hypertensive rats."Rsc Adv. 2019 Jul;9(40):23276-23288 30. [IF=2.584] Jia Su et al."Antioxidant and anti-tyrosinase activities of bee pollen and identification of active components."J Apicult Res. 2021;60(2):297-307 31. [IF=2.196] Yang Lv et al."Central inhibition prevents the in vivo acute toxicity of harmine in mice."Journal Of Toxicological Sciences. 2021 Jun 01 |
59-92-7 - Nature
Open Data Verified Data
- This product is white or white crystalline powder, odorless, tasteless. Melting point 276~278 °c (decomposition). Slightly soluble in water, insoluble in ethanol, chloroform or ether, soluble in dilute acid. Color can darken under the influence of air or light.
- levodopa is an intermediate in the formation of catecholamines from tyrosine, a precursor of dopamine. About 95% of L-dopa absorbed into blood is decarboxylated by DOPA decarboxylase in peripheral tissues to form catecholamines, which are not easy to pass through the blood-brain barrier and cause many adverse reactions. Only 1% of L-dopa enters the cerebral circulation, and reaches the central nervous system, which is converted into catecholamines to exert a therapeutic effect. It does not have a significant pharmacological effect, but indirectly through the catecholamine.
Last Update：2024-01-02 23:10:35
59-92-7 - Preparation Method
Open Data Verified Data
- extraction method.
- Artificial synthesis.
Last Update：2022-01-01 11:10:38
59-92-7 - Standard
Authoritative Data Verified Data
This product is (-)-3-(3, 4-dihydroxyphenyl)-L-alanine. The content of C9H11NO4 shall not be less than 98.%
calculated as dried product.Last Update：2024-01-02 23:10:35
59-92-7 - Trait
Authoritative Data Verified Data
- This product is white or white crystalline powder; Odorless.
- This product is slightly soluble in water, insoluble in ethanol, chloroform or ether; Soluble in dilute acid.
specific rotation
take about 0.2g of this product, weigh it accurately, put it in a 25ml brown measuring flask, add 5g of urotropine, add hydrochloric acid solution (9-100) to dissolve and dilute to the scale, shake well, after being kept in the dark for 3 hours and measured according to the law (General rule 0621), the specific rotation was 159 ° to -168 °.
absorption coefficient
take this product, precision weighing, and hydrochloric acid solution (9-1000) dissolved and quantitatively diluted into about 30ug solution per lml, the absorbance was measured at a wavelength of 0401 NM according to ultraviolet-visible spectrophotometry (General Rule 136), and the absorption coefficient was 146.
Last Update：2022-01-01 11:35:52
59-92-7 - Introduction
Pharmacological effects: anti-tremor paralysis drugs. It enters the brain tissue through the blood-brain barrier, and is decarboxylated by dopa decarboxylase and converted into dopamine, which plays a role. It is used for primary tremor paralysis and non-drug-induced tremor paralysis syndrome. It has good effect on moderate and mild, severe or poor elderly.
Last Update：2022-10-16 17:26:43
59-92-7 - Use
Open Data Verified Data
- antiparkinsonian drugs.
- usage and dosage oral usual dosage, start day 0. 25~0.5g, every 3~4 days increased by 0.125~0.5G, maintain the amount of 3~6g a day, divided into 4~6 times to take. It can be used for the treatment of hepatic coma, peptic ulcer, congestive heart failure, restless legs syndrome, other neuromuscular disorders, neuralgia, alopecia, etc.
Last Update：2022-01-01 11:10:38
59-92-7 - Differential diagnosis
Authoritative Data Verified Data
- take about 5mg of this product, add 5ml of hydrochloric acid solution (9-1000) to dissolve, and add 2 drops of iron gas test solution to show green. Take 2.5ml of the solution, add excess dilute ammonia solution, that is, purple; The remaining solution with excess sodium hydroxide solution, that is, red.
- take about 5mg of this product, add 5ml of water to dissolve, add lml of 1% ninhydrin solution, and heat in water bath.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 87).
Last Update：2022-01-01 11:35:52
59-92-7 - Safety
Open Data Verified Data
- Nausea, Vomit, loss of appetite, orthostatic hypotension, atrial and ventricular premature beats, and Sleep Initiation and Maintenance Disorders. Occasionally elevated blood pressure, hallucination and visual hallucination. Exacerbation of peptic ulcer and cause bleeding. A large number of tongue, lips, face, jaw and neck occur involuntary movement, occasionally found in the limbs. Severe cardiovascular disease, organic encephalopathy, endocrine disorders and psychiatric disorders disabled. The formulations were (1) Levodopa Tablets;(2) LevodopaCapsules.
- under shading, sealed and preserved.
Last Update：2022-01-01 11:10:39
59-92-7 - Exam
Authoritative Data Verified Data
clarity and color of acidic solution
take 0.4g of this product and add 10ml of hydrochloric acid solution (9-l00) to dissolve. The solution should be clear and colorless; If it is colored, it should be used with yellow-green or yellow -2 standard colorimetric solution (General rule 0901 first method). Comparison, not deeper.
chloride
take 0.30g of this product and check it according to law (General rule 0801). Compared with the control solution made of 6.0ml of standard sodium chloride solution, it should not be more concentrated (0.02%).
other amino acids
take this product, add hydrochloric acid solution (9-1000) to dissolve and make 10mg solution (1) and 0.10mg solution (2) per 1 mL respectively, and containing lOmg and tyrosine O. 10mg solution (3). According to the thin layer chromatography (General 0502) test, absorb 10 u1 of each of the above three solutions, respectively point on the same microcrystalline cellulose thin layer plate (microcrystalline cellulose 0.15g/10 cm2), with n-butanol-glacial acetic acid-water (2:1:1) as the developing solvent, the solvent was dispersed in air, spray with 10% ferric chloride solution and 5% potassium ferricyanide solution of equal volume mixed solution (ready to use new system), immediately check. Solution (1) should not be deeper than the main spot of solution (2) if it shows impurity spots; And solution (3) should show the respective spots of levodopa and tyrosine.
loss on drying
take this product, dry to constant weight at 105°C, weight loss shall not exceed 1.0% (General rule 0831).
ignition residue
take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.1%.
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 10 parts per million of heavy metal when examined by law (General Principles 0821, Law II).
Last Update：2022-01-01 11:35:53
59-92-7 - Content determination
Authoritative Data Verified Data
take this product about 0.lg, precision weighing, add anhydrous formic acid 2ml to dissolve, add glacial acetic acid 20ml, shake, add crystal violet indicator 2 drops, with perchloric acid titration solution (0.1 mol/L) titration to the solution is green, and the result of the titration is corrected with a blank test. Each 1 ml of perchloric acid titration solution (0.1 mol/L) corresponds to 19.72mg of C9H11N04.
Last Update：2022-01-01 11:35:54
59-92-7 - Category
Authoritative Data Verified Data
Anti-Parkinson's disease drugs.
Last Update：2022-01-01 11:35:54
59-92-7 - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 11:35:54
59-92-7 - Levodopa Tablets
Authoritative Data Verified Data
This product contains levodopa (C9H11N04) should be 95.0% to 105.0% of the label.
trait
This product is white or white-like tablets or film-coated tablets, white or white-like after removing the coating.
identification
- The fine powder of this product was taken, and the same reaction was shown according to the test of (1) and (2) under the item of levodopa.
- take an appropriate amount of fine powder of this product (about 750mg of levodopa), add 25ml of 3mol/L hydrochloric acid solution, shake to dissolve levodopa, filter, A human ammonia solution was added dropwise to the filtrate to adjust the pH value to 4.0, and the mixture was stirred, and allowed to stand in the dark for several hours to precipitate levodopa. After filtration, the precipitate was washed with water, and the precipitate was dried at 105-c. The infrared absorption pattern of the precipitate should be consistent with that of the control (Spectrum set 87).
examination
- dissolution dissolution of this product, according to the dissolution and release determination method (General rule 0931 The first method), hydrochloric acid solution (9-100) as the dissolution medium, the speed is rpm, operate according to law, after 30 minutes, take 10ml of solution, filter, take 5ml of filtrate with precision, put 10ml(50mg specification) or 25ml(125mg specification) or 50ml(250mg specification) in the measuring flask, dilute to the scale with hydrochloric acid solution (9-1000), shake well, according to the method under the content determination item, from the "ultraviolet-visible spectrophotometry, the dissolution amount of each tablet was calculated. The limit is 80% of the labeled amount and shall be in accordance with the provisions.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
Take 10 tablets of this product, precision weighing, fine grinding, precision weighing an appropriate amount (about 30mg equivalent to levodopa), put it in a 100ml measuring flask, and add an appropriate amount of hydrochloric acid solution (9-1000), shake to dissolve levodopa, dilute to the scale with hydrochloric acid solution (9-1000), shake well, filter, take 10ml of the filtrate and place it in another 100ml measuring flask, dilute to the scale with hydrochloric acid solution (9-1000), shake well, measure absorbance at the wavelength of 280nm by UV-visible spectrophotometry (General rule 0401), it is obtained by calculating the absorption coefficient of C9H11N04 as 141.
category
Same as levodopa.
specification
(l)50mg (2)125mg (3)250mg
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:35:55
59-92-7 - LevodopaCapsules
Authoritative Data Verified Data
This product contains levodopa (C9H11N04) should be 90.0% to 110.0% of the label.
trait
The content of this product is white or white particles or powder.
identification
- taking an appropriate amount of the contents of this product, the same reaction was shown according to the tests of (1) and (2) under the item of levodopa.
- take an appropriate amount of the content of this product (about 750mg of levodopa), add 3mol/L hydrochloric acid solution 25ml, shake to dissolve levodopa, filter, to the filtrate, a human ammonia solution was added dropwise to adjust the pH value to 4.0, stirred, and left in the dark for several hours to precipitate levodopa. After filtration, the precipitate was washed with water, and the precipitate was dried at 105°C. The infrared absorption pattern of the precipitate should be consistent with that of the control (Spectrum set 87).
examination
- dissolution dissolution of this product, according to the dissolution and release determination method (General rule 0931 The first method), hydrochloric acid solution (9-100) as the dissolution medium, the speed is rpm, operate according to law, after 30 minutes, take 10ml of solution, filter, take 5ml of filtrate accurately, put it in 50ml measuring flask, dilute to the scale with hydrochloric acid solution (9-1000), shake well, according to the method under the content determination item, from the "ultraviolet-visible spectrophotometry", according to the law, the dissolution of each particle is calculated. The limit is 80% of the labeled amount and shall be in accordance with the provisions.
- other requirements shall be in accordance with the relevant provisions under the paragraph of glue (General rule 0103).
Content determination
take the contents under the difference of loading amount, mix evenly, accurately weigh an appropriate amount (about 30mg equivalent to levodopa), and follow the method under item Levodopa Tablets, from "in 100ml measuring flask", it is measured and calculated according to law.
category
Same as levodopa.
specification
0.25g
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:35:56
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