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MedKoo Cat#: 525617 | Name: Methyldopa
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Methyldopa is a centrally acting antihypertensive agent. It is metabolized to alpha-methylnorepinephrine in the brain, and this compound activates central alpha-2 adrenergic receptors. Being a selective agonist for α2 adrenergic receptors, psychoactive drug is used as a sympatholytic or antihypertensive.

Chemical Structure

Methyldopa
Methyldopa
CAS#555-30-6

Theoretical Analysis

MedKoo Cat#: 525617

Name: Methyldopa

CAS#: 555-30-6

Chemical Formula: C10H13NO4

Exact Mass: 211.0845

Molecular Weight: 211.22

Elemental Analysis: C, 56.87; H, 6.20; N, 6.63; O, 30.30

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 weeks
25g USD 550.00 2 weeks
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Related CAS #
41372-08-1(Sesquihydrate) 555-30-6
Synonym
Dopamet; Dopegit; Dopegyt; Dopergit; Hydopa; Meldopa; Nu-Medopa; Nu Medopa; NuMedopa; Methyldopa
IUPAC/Chemical Name
(S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
InChi Key
CJCSPKMFHVPWAR-JTQLQIEISA-N
InChi Code
InChI=1S/C10H13NO4/c1-10(11,9(14)15)5-6-2-3-7(12)8(13)4-6/h2-4,12-13H,5,11H2,1H3,(H,14,15)/t10-/m0/s1
SMILES Code
O=C(O)[C@@](C)(N)CC1=CC=C(O)C(O)=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Methyldopa (L-(-)-α-Methyldopa), a potent antihyoertensive agent, is an alpha-adrenergic agonist (selective for α2-adrenergic receptors).
In vitro activity:
After endothelial cellular networks appeared, trophoblast derived HTR-8/SVneo cells were co-cultured in the presence of clinically relevant doses of methyldopa, labetalol, hydralazine or clonidine for 24 hours. Methyldopa, labetalol, hydralazine and clonidine reversed the inhibitory effect of TNF-α on eNOS mRNA expression. Reference: Clin Exp Pharmacol Physiol. 2017 Mar;44(3):421-427. https://pubmed.ncbi.nlm.nih.gov/27998008/
In vivo activity:
Blood pressure (BP), hypothalamic tissue concentrations and the in vivo overflow of endogenous and alpha-methylated catecholamines were measured in urethane anaesthetised rats after alpha-methylDOPA (mDOPA) administration (200 mg/kg i.p.). Four hours after mDOPA, BP fell to its lowest value, 60% of control, and slowly returned towards control levels by 24 h. Reference: Eur J Pharmacol. 1989 May 30;164(3):531-8. https://pubmed.ncbi.nlm.nih.gov/2767124/
Solvent mg/mL mM comments
Solubility
5% TFA 6.0 28.50
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 211.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Xu B, Bobek G, Makris A, Hennessy A. Antihypertensive methyldopa, labetalol, hydralazine, and clonidine reversed tumour necrosis factor-α inhibited endothelial nitric oxide synthase expression in endothelial-trophoblast cellular networks. Clin Exp Pharmacol Physiol. 2017 Mar;44(3):421-427. doi: 10.1111/1440-1681.12712. PMID: 27998008. 2. Kirtland HH 3rd, Mohler DN, Horwitz DA. Methyldopa inhibition of suppressor-lymphocyte function: a proposed cause of autoimmune hemolytic anemia. N Engl J Med. 1980 Apr 10;302(15):825-32. doi: 10.1056/NEJM198004103021502. PMID: 6244489. 3. Kapoor V, Chalmers J. Correlation between fall in blood pressure and in vivo amine release after alpha-methylDOPA. Eur J Pharmacol. 1989 May 30;164(3):531-8. doi: 10.1016/0014-2999(89)90261-6. PMID: 2767124. 4. Fox GR, Virgo BB. The effects of phenobarbital, atropine, L-alpha-methyldopa, and DL-propranolol on dieldrin-induced hyperglycemia in the adult rat. Toxicol Appl Pharmacol. 1985 May;78(3):342-50. doi: 10.1016/0041-008x(85)90239-x. PMID: 4049384.
In vitro protocol:
1. Xu B, Bobek G, Makris A, Hennessy A. Antihypertensive methyldopa, labetalol, hydralazine, and clonidine reversed tumour necrosis factor-α inhibited endothelial nitric oxide synthase expression in endothelial-trophoblast cellular networks. Clin Exp Pharmacol Physiol. 2017 Mar;44(3):421-427. doi: 10.1111/1440-1681.12712. PMID: 27998008. 2. Kirtland HH 3rd, Mohler DN, Horwitz DA. Methyldopa inhibition of suppressor-lymphocyte function: a proposed cause of autoimmune hemolytic anemia. N Engl J Med. 1980 Apr 10;302(15):825-32. doi: 10.1056/NEJM198004103021502. PMID: 6244489.
In vivo protocol:
1. Kapoor V, Chalmers J. Correlation between fall in blood pressure and in vivo amine release after alpha-methylDOPA. Eur J Pharmacol. 1989 May 30;164(3):531-8. doi: 10.1016/0014-2999(89)90261-6. PMID: 2767124. 2. Fox GR, Virgo BB. The effects of phenobarbital, atropine, L-alpha-methyldopa, and DL-propranolol on dieldrin-induced hyperglycemia in the adult rat. Toxicol Appl Pharmacol. 1985 May;78(3):342-50. doi: 10.1016/0041-008x(85)90239-x. PMID: 4049384.
1: Chien YH, Chen PW, Lee NC, Hsieh WS, Chiu PC, Hwu WL, Tsai FJ, Lin SP, Chu SY, Jong YJ, Chao MC. 3-O-methyldopa levels in newborns: Result of newborn screening for aromatic l-amino-acid decarboxylase deficiency. Mol Genet Metab. 2016 May 16. pii: S1096-7192(16)30086-5. doi: 10.1016/j.ymgme.2016.05.011. [Epub ahead of print] PubMed PMID: 27216367. 2: Shahabadi N, Maghsudi M, Kashanian S. A fluorescent sensor based on methyldopa drug modified γ-Fe2O3 nanoparticles for ultrasensitive detection of calf thymus DNA. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Mar 15;157:104-9. doi: 10.1016/j.saa.2015.12.023. Epub 2015 Dec 22. PubMed PMID: 26742013. 3: Koizumi T, Furuya K, Baba M, Sadaoka K, Sekiya C, Hattori A, Goto R, Aoyagi T, Yamashita K, Shimamura T. [Case Report; A case of subacute fulminant hepatitis induced by methyldopa]. Nihon Naika Gakkai Zasshi. 2015 Mar 10;104(3):586-9. Japanese. PubMed PMID: 26571747. 4: Reznikov AG, Nosenko ND, Tarasenko LV, Limareva AA. [CHANGES IN THE BRAIN TESTOSTERONE METABOLISM AND SEXUAL BEHAVIOR IN MALE RATS PRENATALLY EXPOSED TO METHYLDOPA AND STRESS]. Fiziol Zh. 2015;61(4):41-7. Ukrainian. PubMed PMID: 26552304. 5: Shahabadi N, Maghsudi M, Shiri F. Application of a fluorescent biosensor based-on magneto-γ-Fe2 O3 -methyldopa nanoparticles for adsorption of human serum albumin. Luminescence. 2016 Jun;31(4):937-44. doi: 10.1002/bio.3053. Epub 2015 Nov 5. PubMed PMID: 26542088. 6: Seyit M, Erdur B, Kortunay S, Yuksel A, Yilmaz A, Ozen M, Uyanik A, Tomruk O, Ergin A. A Comparison of Dexmedetomidine, Moxonidine and Alpha-Methyldopa Effects on Acute, Lethal Cocaine Toxicity. Iran Red Crescent Med J. 2015 Jun 1;17(6):e18780. doi: 10.5812/ircmj.17(5)2015.18780. eCollection 2015 Jun. PubMed PMID: 26290748; PubMed Central PMCID: PMC4537789. 7: Magee LA; CHIPS Study Group, von Dadelszen P, Singer J, Lee T, Rey E, Ross S, Asztalos E, Murphy KE, Menzies J, Sanchez J, Gafni A, Gruslin A, Helewa M, Hutton E, Koren G, Lee SK, Logan AG, Ganzevoort JW, Welch R, Thornton JG, Moutquin JM. Do labetalol and methyldopa have different effects on pregnancy outcome? Analysis of data from the Control of Hypertension In Pregnancy Study (CHIPS) trial. BJOG. 2016 Jun;123(7):1143-51. doi: 10.1111/1471-0528.13569. Epub 2015 Aug 11. PubMed PMID: 26265372. 8: Magee LA; CHIPS Study Group, von Dadelszen P, Singer J, Lee T, Rey E, Ross S, Asztalos E, Murphy KE, Menzies J, Sanchez J, Gafni A, Gruslin A, Helewa M, Hutton E, Koren G, Lee SK, Logan AG, Ganzevoort JW, Welch R, Thornton JG, Moutquin JM. Control of Hypertension In Pregnancy Study randomised controlled trial-are the results dependent on the choice of labetalol or methyldopa? BJOG. 2016 Jun;123(7):1135-41. doi: 10.1111/1471-0528.13568. Epub 2015 Aug 11. PubMed PMID: 26259808. 9: Shahabadi N, Maghsudi M, Nemati L. Design of green magneto-fluorescent γ-Fe2O3-methyldopa conjugate nanocrystal as a targeted probe for monitoring of esterase activity. J Photochem Photobiol B. 2015 Aug;149:215-23. doi: 10.1016/j.jphotobiol.2015.05.021. Epub 2015 Jun 10. PubMed PMID: 26093233. 10: Peitzsch M, Adaway JE, Eisenhofer G. Interference from 3-O-methyldopa with ultra-high performance LC-MS/MS measurements of plasma metanephrines: chromatographic separation remains important. Clin Chem. 2015 Jul;61(7):993-6. doi: 10.1373/clinchem.2015.239962. Epub 2015 Apr 30. PubMed PMID: 25931454. 11: Emara S, Masujima T, Zarad W, Kamal M, Fouad M, El-Bagary R. An Eco-Friendly Direct Injection HPLC Method for Methyldopa Determination in Serum by Mixed-Mode Chromatography Using a Single Protein-Coated Column. J Chromatogr Sci. 2015 Sep;53(8):1353-60. doi: 10.1093/chromsci/bmv024. Epub 2015 Apr 1. PubMed PMID: 25834172. 12: Pedersen BW, Ringholm L, Damm P, Tabor A, Søgaard K, Hellmuth E, Mathiesen ER. Stable fetal hemodynamics measured by Doppler flow after initiation of anti-hypertensive treatment with methyldopa in pregnant women with diabetes. J Matern Fetal Neonatal Med. 2016;29(4):550-3. doi: 10.3109/14767058.2015.1010198. Epub 2015 Feb 6. PubMed PMID: 25655528. 13: Ribeiro RP, Gasparetto JC, de Oliveira Vilhena R, Guimarães de Francisco TM, Martins CA, Cardoso MA, Pontarolo R, de Carvalho KA. Simultaneous determination of levodopa, carbidopa, entacapone, tolcapone, 3-O-methyldopa and dopamine in human plasma by an HPLC-MS/MS method. Bioanalysis. 2015;7(2):207-20. doi: 10.4155/bio.14.230. Erratum in: Bioanalysis. 2015;7(7):924. de Francisco, Thais Martins Guimarães [corrected to Guimarães de Francisco, Thais Martins]. PubMed PMID: 25587837. 14: Cizmeci MN, Kanburoglu MK, Akelma AZ, Malli DD, Akin K, Tatli MM. Neonatal inflammatory submandibular sialadenitis associated with prenatal methyldopa exposure. J Pediatr Pharmacol Ther. 2014 Apr;19(2):132-4. doi: 10.5863/1551-6776-19.2.132. PubMed PMID: 25024674; PubMed Central PMCID: PMC4093666. 15: Su JA, Tang W, Rivero N, Bar-Cohen Y. Prenatal exposure to methyldopa leading to hypertensive crisis and cardiac failure in a neonate. Pediatrics. 2014 May;133(5):e1392-5. doi: 10.1542/peds.2013-1438. PubMed PMID: 24777213. 16: Chan TY, Joynt GM. Prolonged profound hypotension complicating severe methyldopa overdose. Int J Clin Pharmacol Ther. 2014 Jul;52(7):628-30. doi: 10.5414/CP202031. PubMed PMID: 24755131. 17: Kashkooli S, Baraty B, Kalantar J. α-Methyldopa-induced hepatitis during the postpartum period. BMJ Case Rep. 2014 Feb 27;2014. pii: bcr2014203712. doi: 10.1136/bcr-2014-203712. PubMed PMID: 24577181; PubMed Central PMCID: PMC3939412. 18: Xu B, Charlton F, Makris A, Hennessy A. Antihypertensive drugs methyldopa, labetalol, hydralazine, and clonidine improve trophoblast interaction with endothelial cellular networks in vitro. J Hypertens. 2014 May;32(5):1075-83; discussion 1083. doi: 10.1097/HJH.0000000000000134. PubMed PMID: 24572430. 19: Chen PW, Lee NC, Chien YH, Wu JY, Wang PC, Hwu WL. Diagnosis of aromatic L-amino acid decarboxylase deficiency by measuring 3-O-methyldopa concentrations in dried blood spots. Clin Chim Acta. 2014 Apr 20;431:19-22. doi: 10.1016/j.cca.2014.01.034. Epub 2014 Feb 7. PubMed PMID: 24513538. 20: Kamibayashi D, Nishijima K, Uchinami I, Takahashi J, Tsuyoshi H, Sato K, Orisaka M, Yoshida Y. Necessity of antihypertensive therapy with alpha-methyldopa for pregnant women with hypertensive disorders after 36 weeks of gestation. Med Glas (Zenica). 2014 Feb;11(1):246-7. PubMed PMID: 24496374.