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Technical details about Tox21_202395, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
Also known as: 50-55-5, Serpalan, Serpasil, Apoplon, Serpivite, Hypersil
Molecular Formula
C33H40N2O9
Molecular Weight
608.7  g/mol
InChI Key
QEVHRUUCFGRFIF-MDEJGZGSSA-N
FDA UNII
8B1QWR724A

An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.
Reserpine is a Catecholamine-depleting Sympatholytic. The physiologic effect of reserpine is by means of Decreased Sympathetic Activity.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
2.1.2 InChI
InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1
2.1.3 InChI Key
QEVHRUUCFGRFIF-MDEJGZGSSA-N
2.1.4 Canonical SMILES
COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
2.1.5 Isomeric SMILES
CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
2.2 Other Identifiers
2.2.1 UNII
8B1QWR724A
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Raunervil

2. Raupasil

3. Rausedil

4. Rausedyl

5. Serpasil

6. Serpivite

7. V Serp

8. V-serp

2.3.2 Depositor-Supplied Synonyms

1. 50-55-5

2. Serpalan

3. Serpasil

4. Apoplon

5. Serpivite

6. Hypersil

7. Alserin

8. Sandril

9. Rau-sed

10. Elserpine

11. Hiserpia

12. Raunervil

13. Raupasil

14. Rausedil

15. Rausedyl

16. Rauwasedin

17. Reserpin

18. Serpanray

19. Resine

20. Rivasin

21. Serpate

22. Ascoserpina

23. Austrapine

24. Bioserpine

25. Enipresser

26. Eskaserpine

27. Helfoserpin

28. Hiposerpil

29. Maviserpin

30. Mayserpine

31. Mephaserpin

32. Purserpine

33. Rauserpine

34. Reserpamed

35. Reserpanca

36. Alkarau

37. Apsical

38. Banasil

39. Benazyl

40. Carditivo

41. Carrserp

42. Escaspere

43. Eserpine

44. Eskaserp

45. Hypersine

46. Idsoserp

47. Interpina

48. Lemiserp

49. Loweserp

50. Neoserfin

51. Neoserp

52. Quiescin

53. Raudiford

54. Raudixoid

55. Rauloydin

56. Raumorine

57. Raunorine

58. Raupoid

59. Raurine

60. Rausedan

61. Rauserpol

62. Rausingle

63. Rautrin

64. Rauvlid

65. Rauwilid

66. Rauwipur

67. Rauwoleaf

68. Rawilid

69. Resedrex

70. Reserbal

71. Resercaps

72. Resercen

73. Reserjen

74. Reserlor

75. Reserpal

76. Reserpene

77. Reserpex

78. Reserpil

79. Reserpina

80. Reserpoid

81. Respital

82. Restran

83. Riserpa

84. Roxinoid

85. Kitine

86. Raucap

87. Raugal

88. Raulen

89. Rausan

90. Reserp

91. (-)-reserpine

92. Key-serpine

93. 3p Reserp

94. Crystoserpine

95. Reserpinum

96. Neo-antitensol

97. Rauserpin-alk

98. Deserpine

99. Ryser

100. Reserfia

101. 3,4,5-trimethoxybenzoyl Methyl Reserpate

102. V-serp

103. Carpacil

104. Gilucard

105. Klimanosid

106. Resaltex

107. Resedril

108. Reserpidefe

109. Recipin

110. Serpine

111. Ent 50146

112. Raunova

113. Residin

114. Serpivate

115. Rese-lar

116. Reser-ar

117. Nci-c50157

118. H 520

119. Sedaraupina

120. Temposerpine

121. Eberpine

122. Raudixin

123. Reserpur

124. Residine

125. Resocalm

126. Resperine

127. Rezerpin

128. Sandron

129. Sedaraupin

130. Sedserp

131. Serfolia

132. Serolfia

133. Serpaloid

134. Serpasol

135. Serpazol

136. Serpena

137. Serpentil

138. Serpentina

139. Serpicon

140. Serpiloid

141. Serpogen

142. Serpoid

143. Serpone

144. Sertabs

145. Sertens

146. Sertina

147. Triserpin

148. Unilord

149. Serfin

150. Serpen

151. Roxel

152. Vio-serpine

153. Sk-reserpine

154. Renese R

155. T-serp

156. Nsc-59272

157. Chembl772

158. Nsc-237659

159. Broserpine

160. R-e-s

161. Sederaupin

162. Serpaneurona

163. Tefaserpina

164. Tenserpinie

165. Tepserpine

166. Eberspine

167. Reserpka

168. Resiatric

169. Resperin

170. Rivased

171. Rolserp

172. Roxynoid

173. Serpazil

174. Serpedin

175. Serpentin

176. Serpipur

177. Serpyrit

178. Sertensin

179. Serpil

180. Tempo-reserpina

181. 8b1qwr724a

182. 50-55-5 (free)

183. Mallopress

184. Rcra Waste Number U200

185. Hydropine

186. Hydroserp

187. Rauwita

188. .gamma.-serpine

189. Chebi:28487

190. Hydromox-r

191. Diurese-r

192. Nsc59272

193. Metatensin #2

194. Metatensin #4

195. Ent-50146

196. Component Of Naquival

197. Component Of Regroton

198. Hydropres 25

199. Hydropres 50

200. Hydrosine 25

201. (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic Acid Methyl Ester

202. Methyl (1s,2r,3r,4as,13br,14as)-2,11-dimethoxy-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate

203. Usaf Cb-27

204. Component Of Renese R

205. Component Of Metatensin

206. Ncgc00091250-04

207. Hydroserpalan

208. Diupres 250

209. Diupres 500

210. L-carpserp

211. Component Of Butiserpazide

212. Dsstox_cid_1237

213. Hydroserpine Plus

214. Hydroserpine #1

215. Dsstox_rid_76029

216. Dsstox_gsid_21237

217. Chloroserp-250

218. Chloroserp-500

219. Chloroserpin-250

220. Methyl (1r,15s,17r,18r,19s,20s)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

221. Methyl (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate

222. Yohimban-16-carboxylic Acid,11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, Methyl Ester,(3b,16b,17a,18b,20a)-

223. Serpasil Premix

224. Chloroserpine-500

225. Hydro-reserpine-25

226. Hydro-reserpine-50

227. Hydro-fluserpine #1

228. L -carpserp

229. Caswell No. 722a

230. Serp-afd

231. Reserpina [inn-spanish]

232. 3,5-trimethoxybenzoyl Methyl Reserpate

233. Yohimban-16-carboxylic Acid, 11,17-dimethoxy-18-((3,4,5-trimethoxybenzoyl)oxy)-, Methyl Ester, (3beta,16beta,17alpha,18beta,20alpha)-

234. (1s,2r,3r,4as,13br,14as)-methyl 2,11-dimethoxy-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate

235. Methyl (3beta,16beta,17alpha,18beta,20alpha)-11,17-bis(methyloxy)-18-({[3,4,5-tris(methyloxy)phenyl]carbonyl}oxy)yohimban-16-carboxylate

236. Smr000059122

237. Apoplon (tn)

238. Ccris 550

239. Serpine (pharmaceutical)

240. Hsdb 213

241. Methyl Reserpate 3,5-trimethyloxybenzoic Acid

242. 11,17-dimethoxy-18-((3,4,5-trimethoxybenzoyl)oxy)yohimban-16-carboxylic Acid Methyl Ester

243. Methyl Reserpate 3,5-trimethoxybenzoic Acid Ester

244. Einecs 200-047-9

245. Rcra Waste No. U200

246. Epa Pesticide Chemical Code 123101

247. Nsc 237659

248. Brn 0102014

249. Unii-8b1qwr724a

250. Ai3-50146

251. Wln: T F6 D5 C666 Em On&&tttj Ho1 Sovr Co1 Do1 Eo1& To1 Uvo1

252. Reserpine [usp:inn:ban:jan]

253. Cas-50-55-5

254. Reserpine,(s)

255. Serpalan (tn)

256. 3-.beta., 18-.beta.-hydroxy-11,17-.alpha.-dimethoxy-,methyl Ester, 3,4,5-trimethoxybenzoate (ester)

257. 3.beta., 18.beta.-hydroxy-11,17.alpha.-dimethoxy- Methyl Ester 3,4,5-trimethoxybenzoate (ester)

258. Benz[g]indolo[2, 1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-3-hydroxy-2,11-dimethoxy-, Methyl Ester, 3,4,5-trimethoxybenzoate

259. Methyl (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18-{[(3,4,5-trimethoxyphenyl)carbonyl]oxy}yohimban-16-carboxylate

260. Yohimban-16-carboxylic Acid,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, Methyl Ester, (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-

261. Prestwick_147

262. Methyl Reserpate 3,4,5-trimethoxybenzoic Acid Ester

263. Mfcd00005091

264. Reserpine, 99%

265. Spectrum_000109

266. Reserpic Acid Methyl Ester 3,4,5-trimethoxybenzoate (ester)

267. Reserpine [inn]

268. Reserpine [jan]

269. Reserpine [mi]

270. 79 More Names Available

271. Reserpine [hsdb]

272. Reserpine [iarc]

273. Prestwick0_000875

274. Prestwick1_000875

275. Prestwick2_000875

276. Prestwick3_000875

277. Spectrum3_000894

278. Spectrum4_000989

279. Spectrum5_001415

280. Reserpine [vandf]

281. Reserpinum [hpus]

282. Reserpine [mart.]

283. R 0875

284. Reserpine [usp-rs]

285. Reserpine [who-dd]

286. Reserpine [who-ip]

287. Schembl2589

288. Lopac0_000073

289. Bspbio_000949

290. Kbiogr_001397

291. Kbioss_000549

292. 4-25-00-01319 (beilstein Handbook Reference)

293. Methyl 18beta-hydroxy-11,17alpha-dimethoxy-3beta,20alpha-yohimban-16beta-carboxylate 3,4,5-trimethoxybenzoate (ester)

294. Methyl Dimethoxy-(3,4,5-trimethoxybenzoyl)oxy-[?]carboxylate

295. Mls002154046

296. Mls006011754

297. Divk1c_000012

298. Spectrum1500526

299. Spbio_002870

300. Reserpine (jp17/usp/inn)

301. Amy591

302. Bpbio1_001045

303. Gtpl4823

304. Megxp0_001904

305. Reserpine [orange Book]

306. Dtxsid7021237

307. Reserpine [ep Monograph]

308. Acon1_000086

309. Hms500a14

310. Kbio1_000012

311. Kbio2_000549

312. Kbio2_003117

313. Kbio2_005685

314. Kbio3_001808

315. Reserpine [usp Monograph]

316. Ninds_000012

317. Reserpinum [who-ip Latin]

318. Unipres Component Reserpine

319. Hms1570p11

320. Hms1920p04

321. Hms2092g05

322. Hms2097p11

323. Hms2234e24

324. Hms3260o07

325. Hms3413d20

326. Hms3677d20

327. Hms3714p11

328. Hms3884i21

329. Pharmakon1600-01500526

330. Dralserp Component Reserpine

331. Naquival Component Reserpine

332. Regroton Component Reserpine

333. Hy-n0480

334. Hydropres Component Reserpine

335. Renese-r Component Reserpine

336. Reserpine, Vetec(tm) Reagent Grade

337. Rkl10049

338. Zinc3938746

339. Hydrap-es Component Reserpine

340. Tox21_111107

341. Tox21_202395

342. Tox21_300537

343. Tox21_500073

344. Bbl028800

345. Bdbm50017712

346. Cam-ap-es Component Reserpine

347. H.r.-50 Component Reserpine

348. Metatensin Component Reserpine

349. Nsc237659

350. Nsc757309

351. Salutensin Component Reserpine

352. Ser-a-gen Component Reserpine

353. Ser-ap-es Component Reserpine

354. Stk801975

355. Hydromox R Component Reserpine

356. Reserpine 100 Microg/ml In Methanol

357. Reserpine Component Of Unipres

358. Akos000277559

359. Diutensen-r Component Reserpine

360. Reserpine Component Of Dralserp

361. Reserpine Component Of Naquival

362. Reserpine Component Of Regroton

363. Tox21_111107_1

364. Ccg-204168

365. Cs-1913

366. Db00206

367. Hydro-reserp Component Reserpine

368. Ks-5106

369. Lp00073

370. Nsc-757309

371. Reserpine Component Of Hydropres

372. Reserpine Component Of Renese-r

373. Sdccgsbi-0050061.p005

374. Demi-regroton Component Reserpine

375. Idi1_000012

376. Reserpine Component Of Cam-ap-es

377. Reserpine Component Of Hydrap-es

378. Reserpine Component Of Metatensin

379. Reserpine Component Of Salutensin

380. Reserpine Component Of Ser-a-gen

381. Reserpine Component Of Ser-ap-es

382. Ncgc00091250-01

383. Ncgc00091250-02

384. Ncgc00091250-03

385. Ncgc00091250-05

386. Ncgc00091250-06

387. Ncgc00091250-07

388. Ncgc00091250-08

389. Ncgc00091250-09

390. Ncgc00091250-10

391. Ncgc00091250-12

392. Ncgc00091250-14

393. Ncgc00091250-25

394. Ncgc00254489-01

395. Ncgc00259944-01

396. Ncgc00260758-01

397. Reserpine Component Of H.r.-50

398. Reserpine Component Of Hydromox R

399. 3-beta,20-alpha-yohimban-16-beta-carboxylic Acid, 18-beta-hydroxy-11,17-alpha-dimethoxy-, Methyl Ester, 3,4,5-trimethoxybenzoate (ester)

400. 3beta,20alpha-yohimban-16beta-carboxylic Acid, 18beta-hydroxy-11,17alpha-dimethoxy- Methyl Ester 3,4,5-trimethoxybenzoate (ester)

401. Ac-13142

402. Ac-34405

403. Br164333

404. Methyl (1r,15s,17r,18r,19s,20s)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate

405. Nci60_004446

406. Reserpine Component Of Diutensen-r

407. Reserpine Component Of Hydro-reserp

408. Sbi-0050061.p004

409. Serpasil-esidrix Component Reserpine

410. Reserpine Component Of Demi-regroton

411. Eu-0100073

412. Reserpine, Crystallized, >=99.0% (hplc)

413. Sw196458-3

414. Unm000011053801

415. Reserpine Component Of Serpasil-esidrix

416. Serpasil-apresoline Component Reserpine

417. C06539

418. D00197

419. Ab01562943_01

420. Reserpine Component Of Serpasil-apresoline

421. 005r091

422. A913268

423. Q407841

424. Q-100566

425. Brd-k95921201-001-07-0

426. Hydroserpine Plus (r-h-h) Component Reserpine

427. Methyl Reserpate; 3,4,5-trimethoxybenzoic Acid Ester

428. Reserpine, Certified Reference Material, Tracecert(r)

429. Reserpine Component Of Hydroserpine Plus (r-h-h)

430. Reserpine Solution, 1 Pg/mul In Methanol: Water (1:1)

431. Reserpine, European Pharmacopoeia (ep) Reference Standard

432. Reserpine Standard For Lc-ms, Analytical Standard, For Lc-ms

433. Reserpine, United States Pharmacopeia (usp) Reference Standard

434. Reserpine, Pharmaceutical Secondary Standard; Certified Reference Material

435. Hydralazine Hydrochloride-hydrochlorothiazide-reserpine Component Reserpine

436. Reserpine Component Of Hydralazine Hydrochloride-hydrochlorothiazide-reserpine

437. (1s,2r,3r,4as,13br,14as)-methyl2,11-dimethoxy-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate

438. (3?,16?,17?,18?,20?)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic Acid Methyl Ester

439. (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18- [(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxyl Ic Acid Methyl Ester

440. Methyl (1r,15s,17r,18r,19s,20s)-6,18-dimethoxy-17-[(3,4,5-trimethoxyphenyl)carbonyloxy]-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate

441. Methyl (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-11,17-dimethoxy-18-((3,4,5-trimethoxybenzoyl)oxy)yohimban-16-carboxylate

442. Methyl 18.beta.-hydroxy-11,17.alpha.-dimethoxy-3.beta.,20.alpha.-yohimban-16.beta.-carboxylate 3,4,5-trimethoxybenzoate (ester).

443. Yohimban-16-carboxylic Acid, 11,17-dimethoxy-18-(3,4,5-trimethoxybenzoyl)oxy-, Methyl Ester, (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 608.7 g/mol
Molecular Formula C33H40N2O9
XLogP34
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count10
Rotatable Bond Count10
Exact Mass608.27338086 g/mol
Monoisotopic Mass608.27338086 g/mol
Topological Polar Surface Area118 Ų
Heavy Atom Count44
Formal Charge0
Complexity1000
Isotope Atom Count0
Defined Atom Stereocenter Count6
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 NameReserpine
PubMed HealthReserpine (By mouth)
Drug ClassesAntihypertensive
Drug LabelReserpine, USP is an antihypertensive, available as 0.1 mg and 0.25 mg tablets for oral administration. Its chemical name is methyl 18-hydroxy-11,17 -dimethoxy-3, 20-yohimban-16-carboxylate 3,4,5-trimethoxybenzoate (ester) and its structura...
Active IngredientReserpine
Dosage FormTablet
RouteOral
Strength0.25mg; 0.1mg
Market StatusPrescription
CompanySandoz

2 of 2  
Drug NameReserpine
PubMed HealthReserpine (By mouth)
Drug ClassesAntihypertensive
Drug LabelReserpine, USP is an antihypertensive, available as 0.1 mg and 0.25 mg tablets for oral administration. Its chemical name is methyl 18-hydroxy-11,17 -dimethoxy-3, 20-yohimban-16-carboxylate 3,4,5-trimethoxybenzoate (ester) and its structura...
Active IngredientReserpine
Dosage FormTablet
RouteOral
Strength0.25mg; 0.1mg
Market StatusPrescription
CompanySandoz

4.2 Therapeutic Uses

Adrenergic Uptake Inhibitors; Antihypertensive Agents; Antipsychotic Agents; Sympatholytics

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


RESERPINE ... FOUND TO REDUCE HEART RATE, TREMOR, & STARE IN HYPERTHYROIDISM & RELIEVE PALPITATION, ANXIETY, & TENSION.

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 209


ONLY IMPORTANT APPLICATION OF CARDIOVASCULAR EFFECTS OF RESERPINE IS IN TREATMENT OF HYPERTENSION ... IT IS OCCASIONALLY USED IN MANAGEMENT OF RAYNAUD'S SYNDROME.

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 209


IV ... USEFUL IN ... SEVERE HYPERTENSION & HYPERTENSIVE EMERGENCIES.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 848


For more Therapeutic Uses (Complete) data for RESERPINE (18 total), please visit the HSDB record page.


4.3 Drug Warning

... Should not be given to patients with a history of depression and, if depressive symptoms appear, the drug should be discontinued. Reserpine may incr gastric acid secretion and should be used cautiously in patients with history of peptic ulcers. If symptoms suggest recurrence of the ulcer, the drug should be discontinued.

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 209


WHEN GIVEN PARENTERALLY FOR TREATMENT OF ECLAMPSIA, RESERPINE PASSES THROUGH PLACENTAL CIRCULATION & MAY CAUSE DROWSINESS, NASAL CONGESTION, CYANOSIS, & ANOREXIA IN NEWBORN INFANT. SODIUM & WATER RETENTION MAY OCCUR IF DIURETIC IS NOT GIVEN CONCOMITANTLY.

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 5th ed. Chicago: American Medical Association, 1983., p. 714


BECAUSE OF SERIOUSNESS OF SIDE EFFECTS, RESERPINE IS NO LONGER MUCH USED AS TRANQUILIZER.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 848


... CONTRAINDICATED IN ULCERATIVE COLITIS BECAUSE OF INCR IN BOWEL MOBILITY.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 848


For more Drug Warnings (Complete) data for RESERPINE (23 total), please visit the HSDB record page.


4.4 Drug Indication

For the treatment of hypertension


5 Pharmacology and Biochemistry
5.1 Pharmacology

Reserpine is an adrenergic blocking agent used to treat mild to moderate hypertension via the disruption of norepinephrine vesicular storage. The antihypertensive actions of Reserpine are a result of its ability to deplete catecholamines from peripheral sympathetic nerve endings. These substances are normally involved in controlling heart rate, force of cardiac contraction and peripheral resistance.


5.2 MeSH Pharmacological Classification

Adrenergic Uptake Inhibitors

Drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants (ANTIDEPRESSIVE AGENTS, TRICYCLIC) and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin. (See all compounds classified as Adrenergic Uptake Inhibitors.)


Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)


Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
RESERPINE
5.3.2 FDA UNII
8B1QWR724A
5.3.3 Pharmacological Classes
Physiologic Effects [PE] - Decreased Sympathetic Activity
5.4 ATC Code

C - Cardiovascular system

C02 - Antihypertensives

C02A - Antiadrenergic agents, centrally acting

C02AA - Rauwolfia alkaloids

C02AA02 - Reserpine


5.5 Absorption, Distribution and Excretion

Route of Elimination

Reserpine is extensively metabolized to inactive compounds. It is slowly excreted via the urine and feces.


In man, after oral admin of 0.25 mg (3)H-reserpine, tritium was rapidly absorbed into the blood, reaching a peak within 1-2 hr. Radioactivity was tightly bound to red blood cells and remained constant over a 96 hr period. ... Six percent of the dose was excreted in the urine by 24 hr, mainly as trimethoxybenzoic acid; but radioactivity was still detectable in plasma, urine, and feces 11-12 days after drug admin.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 222 (1976)


PARENTERAL ADMIN OF RESERPINE PRODUCES GREATER CONCN IN NEONATAL RAT BRAIN THAN IN ADULT ANIMALS ... PARALLELED BY GREATER DEPLETION OF NOREPINEPHRINE IN INFANT THAN IN ADULT BRAIN. THIS MAY BE DUE TO LESSER CAPACITY OF RAT NEONATES TO METABOLIZE RESERPINE ... MIGHT ALSO EXPLAIN HIGHER PLASMA & TISSUE LEVELS IN HUMAN ADULTS.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 680


RESERPINE LEAVES BLOOD WITHIN FEW MIN AFTER IV INJECTION & ACCUMULATES IN FATTY TISSUES ... MAX CONCN IN 4-6 HR. LIVER ALSO ACCUMULATES RESERPINE. MOST OF SINGLE DOSE HAS LEFT FAT & LIVER IN 48 HR. BRAIN RETAINS ... RESERPINE & ... METABOLITES ... 5 DAYS AFTER SINGLE DOSE.

Thienes, C., and T.J. Haley. Clinical Toxicology. 5th ed. Philadelphia: Lea and Febiger, 1972., p. 71


... CLAIMED TO BE ADEQUATELY ABSORBED FROM GI TRACT, BUT DIFFERENCE IN EFFICACY OF ORAL & IV DOSES RAISES DOUBTS ABOUT ADEQUACY OF ABSORPTION. ... HAS LONG LATENCY OF ONSET & PROLONGED DURATION OF ACTION.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 848


For more Absorption, Distribution and Excretion (Complete) data for RESERPINE (8 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

YIELDS 3,4,5-TRIMETHOXYBENZOIC ACID IN RAT, CAT, MOUSE;

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. R-1


YIELDS METHYL RESERPATE IN RAT, CAT;

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. R-1


IDENTIFIED METABOLIC PRODUCTS ARE RESERPIC ACID, SYRINGIC ACID, & SYRINGOYL METHYL RESERPATE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 168


In rats, orally administered reserpine is rapidly hydrolysed to methyl reserpate; and in mice, orally or intravenously administered reserpine is metabolized to trimethoxybenzoic acid. In rats, methyl reserpate appears to be formed in the intestinal mucosa. Trimethoxybenzoic acid is rapidly eliminated in the urine of mice.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V24 220 (1980)


5.7 Biological Half-Life

In man, after oral /dose/ of 0.25 mg (3)H-reserpine ... disappearance of radioactivity in plasma was biphasic: first component had half-life of 4.5 hr, and the second, 271 hr.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 222 (1976)


5.8 Mechanism of Action

Reserpine's mechanism of action is through inhibition of the ATP/Mg2+ pump responsible for the sequestering of neurotransmitters into storage vesicles located in the presynaptic neuron. The neurotransmitters that are not sequestered in the storage vesicle are readily metabolized by monoamine oxidase (MAO) causing a reduction in catecholamines.


... DEPLETES OR RELEASES SEROTONIN (5-HYDROXYTRYPTAMINE), DOPAMINE ... NOREPINEPHRINE FROM ... BRAIN & ... BODY ... DEFICIENCY OF DOPAMINE IN BRAIN ... IN STRIATUM, SUBSTANTIA NIGRA ... PALLIDUM. ... HYPOTHERMIC EFFECT ... RELATED TO SEROTONIN DEPLETION OF HYPOTHALAMIC REGION. HYPOTHALMUS CONTAINS ... HIGHEST CONCN OF SEROTONIN. ...

Jones, L.M., et al. Veterinary Pharmacology & Therapeutics. 4th ed. Ames: Iowa State University Press, 1977., p. 395


ANTIHYPERTENSIVE ACTION ... DERIVES FROM ADRENERGIC NEURONAL BLOCKADE CONSEQUENT TO DEPLETION OF CATECHOLAMINE-CONTAINING GRANULES OF POSTGANGLIONIC SYMPATHETIC NEURON. MECHANISM OF CENTRAL EFFECTS IS UNKNOWN. IT DEPLETES BOTH BRAIN SEROTONIN & CATECHOLAMINES.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 848


... REPORTED TO INHIBIT GROWTH OF LEUKEMIA IN L1210 CELLS IN MALE MICE ... AND TO SUPPRESS GROWTH OF SARCOMA 37 IN MICE. ... RESERPINE DID NOT AFFECT GROWTH OF TRANSPLANTED MAMMARY ADENOCARCINOMAS IN C3H MICE. IT BLOCKS RELEASE OF PROLACTIN-INHIBITING FACTOR & THUS RAISES SERUM PROLACTIN LEVELS.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 222


Peripheral-Acting Adrenergic Antagonist /from table/

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 556


For more Mechanism of Action (Complete) data for RESERPINE (8 total), please visit the HSDB record page.


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