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Chemistry

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Also known as: 555-30-6, Alphamethyldopa, Alpha medopa, Methyl dopa, Methyldopa anhydrous, Aldomet
Molecular Formula
C10H13NO4
Molecular Weight
211.21  g/mol
InChI Key
CJCSPKMFHVPWAR-JTQLQIEISA-N
FDA UNII
M4R0H12F6M

Methyldopa
An alpha-2 adrenergic agonist that has both central and peripheral nervous system effects. Its primary clinical use is as an antihypertensive agent.
Methyldopa anhydrous is a Central alpha-2 Adrenergic Agonist. The mechanism of action of methyldopa anhydrous is as an Adrenergic alpha2-Agonist.
1 2D Structure

Methyldopa

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
2.1.2 InChI
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
2.1.3 InChI Key
CJCSPKMFHVPWAR-JTQLQIEISA-N
2.1.4 Canonical SMILES
CC(CC1=CC(=C(C=C1)O)O)(C(=O)O)N
2.1.5 Isomeric SMILES
C[C@](CC1=CC(=C(C=C1)O)O)(C(=O)O)N
2.2 Other Identifiers
2.2.1 UNII
M4R0H12F6M
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Aldomet

2. Alpha Methyl L Dopa

3. Alpha Methyldopa

4. Alpha-methyl-l-dopa

5. Alpha-methyldopa

6. Alphamethyldopa

7. Apo Methyldopa

8. Apo-methyldopa

9. Dopamet

10. Dopegit

11. Dopegyt

12. Dopergit

13. Hydopa

14. Meldopa

15. Methyldopate

16. Nu Medopa

17. Nu-medopa

18. Sembrina

2.3.2 Depositor-Supplied Synonyms

1. 555-30-6

2. Alphamethyldopa

3. Alpha Medopa

4. Methyl Dopa

5. Methyldopa Anhydrous

6. Aldomet

7. Baypresol

8. L-alpha-methyldopa

9. Dopamet

10. Alpha-methyl Dopa

11. Hyperpax

12. Presolisin

13. Sedometil

14. Medomet

15. Alpha-methyldopa

16. Dopegyt

17. Methyl-l-dopa

18. L-(-)-alpha-methyldopa

19. L-methyl Dopa

20. Methyldopum

21. Metildopa

22. Medopren

23. Presinol

24. (s)-(-)-alpha-methyldopa

25. 3-(3,4-dihydroxyphenyl)-2-methyl-l-alanine

26. L-(alpha-md)

27. 3-hydroxy-alpha-methyl-l-tyrosine

28. L-alpha-methyl Dopa

29. Sembrina

30. Alpha-methyl-l-dopa

31. Dopamethyperpax

32. Aldometil

33. Grospisk

34. Methoplain

35. Becanta

36. Dopatec

37. Hypolag

38. Medopa

39. Medopal

40. Alpha-methyldopa (van)

41. Aldoril

42. Alpha-methyldihydroxyphenylalanine

43. L-3-(3,4-dihydroxyphenyl)-2-methylalanine

44. (s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic Acid

45. Alpha-methyl-l-3,4-dihydroxyphenylalanine

46. L-alpha-methyl-3,4-dihydroxyphenylalanine

47. L-methyldopa

48. (-)-methyldopa

49. Anhydrous Methyldopa

50. Methyldopa [inn]

51. (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic Acid

52. Aldoril D30

53. Aldoril D50

54. Methyldopa (l,-)

55. Bayer 1440 L

56. Levo-3-(3,4-dihydroxyphenyl)-2-methylalanine

57. Amd

58. C10h13no4

59. Methyldopa (levorotatory)

60. L-(-)-3-(3,4-dihydroxyphenyl)-2-methylalanine

61. Alpha-methyl-beta-(3,4-dihydroxyphenyl)-l-alanine

62. L(-)-beta-(3,4-dihydroxyphenyl)-alpha-methylalanine

63. L-(-)-alpha-methyl-beta-(3,4-dihydroxyphenyl)alanine

64. Methyldopa (inn)

65. L-2-amino-2-methyl-3-(3,4-dihydroxyphenyl)propionic Acid

66. Methyldopa, Anhydrous

67. Mk-351;methyldopa

68. Chebi:61058

69. Aldomet (tn)

70. Dopegit

71. (-)-.alpha.-methyldopa

72. Methyldopa Sesquihydrate

73. 41372-08-1

74. Lederdopa

75. Bayer-1440l

76. Mls000028644

77. M4r0h12f6m

78. Mk-351

79. Apo-methyldopa

80. Nu-medopa

81. Nsc-169916

82. Nsc-760080

83. J9.247i

84. L-.alpha.-methyldopa

85. Methyldopa Hydrate

86. Novomedopa

87. Smr000059170

88. .alpha.-methyl-l-dopa

89. L-tyrosine, 3-hydroxy-.alpha.-methyl-

90. Methyldopum [inn-latin]

91. Metildopa [inn-spanish]

92. (s)-(-)-.alpha.-methyldopa

93. Methyldopa (anhydrous)

94. 3-hydroxy-.alpha.-methyl-l-tyrosine

95. L-tyrosine, 3-hydroxy-alpha-methyl-

96. 27289-76-5

97. Ccris 4671

98. Hsdb 218

99. Sr-01000597712

100. Einecs 209-089-2

101. Nsc 169916

102. Unii-m4r0h12f6m

103. Medoba

104. L-a-methyldopa

105. A-methyl Dopa

106. Nsc169916

107. Tyrosine, 3-hydroxy-.alpha.-methyl-

108. A-methyl-l-dopa

109. 3,4-dihydroxy-2-methylphenylalanine #

110. Cas-555-30-6

111. Prestwick_732

112. (-)-a-methyldopa

113. A-methyldopa (van)

114. .alpha.-methyl-l-3,4-dihydroxyphenylalanine

115. Methyldopa (aldomet)

116. 88620-56-8

117. Alanine, 3-(3,4-dihydroxyphenyl)-2-methyl-, L-(-)-

118. Methyldopa 250 Tab

119. (-)-alpha-methyldopa

120. L-(-)--methyldopa

121. L(-)-a-methylalanine

122. L-(-)-a-methyldopa

123. Spectrum_000937

124. Tocris-0584

125. Mk-351; Methyldopa

126. Methyldopa [mi]

127. Nu-medopa Tab 125mg

128. Nu-medopa Tab 250mg

129. Nu-medopa Tab 500mg

130. L-(-)-?-methyldopa

131. (-)-3-(3,4-dihydroxyphenyl)-2-methyl-l-alanine Sesqui-hydrate

132. Novo-medopa Tab 125mg

133. Novo-medopa Tab 250mg

134. Novo-medopa Tab 500mg

135. Prestwick0_000326

136. Prestwick1_000326

137. Prestwick2_000326

138. Prestwick3_000326

139. Spectrum2_001068

140. Spectrum3_000501

141. Spectrum4_000054

142. Spectrum5_001295

143. Methyldopa [hsdb]

144. (s)-(-)-a-methyldopa

145. L(-)-alpha-methylalanine

146. Dsstox_cid_3295

147. Chembl459

148. Epitope Id:146097

149. L-(-)- Alpha-methyldopa

150. Apo Methyldopa Tab 125mg

151. Apo Methyldopa Tab 250mg

152. Apo Methyldopa Tab 500mg

153. Dsstox_rid_76962

154. Methyldopa [who-dd]

155. Dsstox_gsid_23295

156. L-(-)- Alpha -methyldopa

157. L-(a-md)

158. Lopac0_000853

159. Schembl34003

160. Bspbio_000331

161. Bspbio_002021

162. Kbiogr_000547

163. Kbioss_001417

164. Cid_38853

165. Mls006011978

166. Bidd:gt0620

167. Divk1c_000142

168. Methyldopa 125 Tab 125mg

169. Methyldopa 500 Tab 500mg

170. Spectrum1500403

171. Spbio_001056

172. Spbio_002252

173. Bpbio1_000365

174. Gtpl5217

175. Dtxsid5023295

176. Bdbm48449

177. Hms500h04

178. Kbio1_000142

179. Kbio2_001417

180. Kbio2_003985

181. Kbio2_006553

182. Kbio3_001521

183. Zinc20255

184. 3-(3,4-dihydroxyphenyl)-2-methyl-l-alanine Sesquihydrate

185. 5-amino-2-fluorophenylboronicacid

186. Ninds_000142

187. Hms1569a13

188. Hms1920n09

189. Hms2090b11

190. Hms2091f04

191. Hms2096a13

192. Hms2235n11

193. Hms3262l07

194. Hms3372j14

195. Hms3411g18

196. Hms3675g18

197. Hms3713a13

198. Hms3887i15

199. Mk-35

200. Pharmakon1600-01500403

201. L-(-)-a-methyl-a-methyl-aldomin

202. Hy-b0225

203. Tox21_202610

204. Tox21_500853

205. Anhydrous Methyldopa [mart.]

206. Ccg-40120

207. Dl-443

208. Mfcd00004186

209. Nsc760080

210. S1642

211. A-methyl-l-3,4-dihydroxyphenylalanine

212. Akos015960582

213. Ac-8431

214. Db00968

215. Ks-1424

216. Lp00853

217. Sdccgsbi-0050829.p002

218. Idi1_000142

219. Ncgc00024667-01

220. Ncgc00024667-02

221. Ncgc00024667-03

222. Ncgc00024667-05

223. Ncgc00024667-06

224. Ncgc00024667-07

225. Ncgc00024667-08

226. Ncgc00024667-09

227. Ncgc00024667-10

228. Ncgc00024667-11

229. Ncgc00024667-13

230. Ncgc00024667-21

231. Ncgc00260158-01

232. Ncgc00261538-01

233. Ac-11671

234. As-13052

235. L-(-)-alpha-methyl-alpha-methyl-aldomin

236. Carbidopa Impurity A [ep Impurity]

237. L-a-methyl-(3, 4-dihydroxyphenyl)alanine

238. D1817

239. Eu-0100853

240. 3-(3,4-dihydroxyphenyl)-?-methyl-l-alanine

241. L-alpha-methyl-(3, 4-dihydroxyphenyl)alanine

242. C07194

243. D08205

244. D82313

245. Ab00052043_09

246. Ab01275508-01

247. Ab01275508_02

248. 3-(3,4-dihydroxyphenyl)-alpha-methyl-l-a Lanine

249. L-tyrosine, 3-hydroxy-alpha-methyl-, Homopolymer

250. Q412621

251. L-(-)-3-(3,4-dihydroxyphenyl)-2-methyl-alanine

252. Q-201392

253. Sr-01000597712-1

254. Sr-01000597712-3

255. W-105555

256. 3,4-dihydroxy-2-methylphenylalanine (acd/name 4.0)

257. (-)-.alpha.-methyl-3,4-dihydroxyphenylalanine

258. L-.alpha.-methyl-3-(3,4)-dihydroxyphenylalanine

259. Z1565440340

260. (s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoicacid

261. Methyldopa, European Pharmacopoeia (ep) Reference Standard

262. (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methyl-propanoic Acid

263. (2s)-2-azaniumyl-3-(3,4-dihydroxyphenyl)-2-methylpropanoate

264. Methyldopa, United States Pharmacopeia (usp) Reference Standard

265. 3-(3,4-dihydroxyphenyl)-2-methyl-l-alanine (h-l-ametyr(3-oh)-oh)

266. Methyldopa For System Suitability, European Pharmacopoeia (ep) Reference Standard

267. L-(-)-afae'a Centa' Nota Inverted Exclamation Markafasa'a

268. Afae'adaggeratrade Mark?-methyldopa

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 211.21 g/mol
Molecular Formula C10H13NO4
XLogP3-1.9
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass211.08445790 g/mol
Monoisotopic Mass211.08445790 g/mol
Topological Polar Surface Area104 Ų
Heavy Atom Count15
Formal Charge0
Complexity246
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameMethyldopa
PubMed HealthMethyldopa (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent
Drug LabelMethyldopa is an antihypertensive and is the L-isomer of alpha-methyldopa. It is levo-3-(3,4-dihydroxyphenyl)-2-methylalanine sesquihydrate. Methyldopa is supplied as tablets for oral administration, containing 125 mg, 250 mg and 500 mg of methyldopa...
Active IngredientMethyldopa
Dosage FormTablet
RouteOral
Strength250mg; 500mg
Market StatusPrescription
CompanyAccord Hlthcare; Watson Labs; Ivax Sub Teva Pharms; Mylan

2 of 2  
Drug NameMethyldopa
PubMed HealthMethyldopa (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent
Drug LabelMethyldopa is an antihypertensive and is the L-isomer of alpha-methyldopa. It is levo-3-(3,4-dihydroxyphenyl)-2-methylalanine sesquihydrate. Methyldopa is supplied as tablets for oral administration, containing 125 mg, 250 mg and 500 mg of methyldopa...
Active IngredientMethyldopa
Dosage FormTablet
RouteOral
Strength250mg; 500mg
Market StatusPrescription
CompanyAccord Hlthcare; Watson Labs; Ivax Sub Teva Pharms; Mylan

4.2 Therapeutic Uses

Adrenergic alpha-Agonists; Antihypertensive Agents; Sympatholytics

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Methyldopa is indicated in the treatment of moderate to severe hypertension, including that complicated by renal disease. /Included in US product labeling/

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 2000


Methyldopa is an effective antihypertensive agent when given in conjunction with a diuretic.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 788


THE USUAL INITIAL DOSE OF METHYLDOPA IS 250 MG TWICE DAILY, AND THERE APPEARS TO BE LITTLE ADDNL EFFECT WITH DOSES OVER 2 G.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 788


For more Therapeutic Uses (Complete) data for METHYLDOPA (6 total), please visit the HSDB record page.


4.3 Drug Warning

Methyldopa should be used with caution in patients with a history of previous liver disease or dysfunction and is not recommended for use in patients with pheochromocytoma. Methyldopa is contraindicated in patients with active hepatic disease, such as acute hepatitis and active cirrhosis, and in patients in whom previous methyldopa therapy was associated with liver abnormalities or direct Coombs' positive hemolytic anemia. Methyldopa is contraindicated in patients receiving monoamine oxidase (MAO) inhibitors.

McEvoy, G.K. (ed.). American Hospital Formulary Service-Drug Information 19 98. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1998 (Plus Supplements)., p. 1512


Patients who are receiving methyldopa and who undergo dialysis may occasionally become hypertensive after the dialysis, since the drug is dialyzable.

McEvoy, G.K. (ed.). American Hospital Formulary Service-Drug Information 19 98. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1998 (Plus Supplements)., p. 1512


Positive direct antiglobulin (Coombs') test results have been reported in about 10-20% of patients receiving methyldopa, usually after 6-12 months of therapy. This phenomenon is dose related, with the lowest incidence in patients receiving 1 g or less of methyldopa daily. In most patients, a postive Coombs' test associated with mehtyldopa therapy is not clinically important. Reversal of the positive Coombs' test occurs within weeks to months after discontinuance of the drug and usually becomes negative within 6 months. Hemolytic anemia has only rarely occurred, although 2 deaths have been reported in patients with methyldopa-induced hemolytic anemia. If anemia or a positive Coombs' test occurs, appropriate laboratory studies should be performed to determine if hemolysis is present; if there is evidence of hemolytic anemia, the drug should be discontinued. Discontinuance of the drug alone or initiation of corticosteroid therapy has produced remission of methyldopa-induced hemolytic anemia.

McEvoy, G.K. (ed.). American Hospital Formulary Service-Drug Information 19 98. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1998 (Plus Supplements)., p. 1511


Nasal congestion occurs commonly in patients receiving methyldopa. Decreased libido and impotence frequently occur in males during therapy with the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service-Drug Information 19 98. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1998 (Plus Supplements)., p. 1511


For more Drug Warnings (Complete) data for METHYLDOPA (16 total), please visit the HSDB record page.


4.4 Drug Indication

Methyldopa is indicated for the management of hypertension as monotherapy or in combination with hydrochlorothiazide. Methyldopa injection is used to manage hypertensive crises.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Antihypertensive effects of methyldopa are mostly mediated by its pharmacologically active metabolite, alpha-methylnorepinephrine, which works as an agonist at central inhibitory alpha-adrenergic receptors. Stimulation of alpha-adrenergic receptors leads to decreased peripheral sympathetic tone and reduced arterial pressure. Methyldopa causes a net reduction in the tissue concentration of serotonin, dopamine, norepinephrine, and epinephrine. Overall, meth