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Showing toxin card for Reserpine (T3D2713)

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Version 1.0
Creation Date 2009-07-21 20:26:17
Update Date 2010-05-18 20:59:24
Accession Number T3D2713
Name Reserpine
Compound Type
  • Adrenergic Uptake Inhibitor
  • Antihypertensive Agent
  • Antipsychotic Agent
  • Drug
  • Peripheral Adrenergic Inhibitor
Description 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. [PubChem]
Synonyms
  1. "l"-carpserp
  2. «gamma»-serpine
  3. (-)-reserpine
  4. .gamma.-serpine
  5. 3,4,5-Trimethoxybenzoyl methyl reserpate
  6. 3P Reserp
  7. 79 more names available
  8. :reserpine
  9. Abesta
  10. Abicol
  11. Adelfan
  12. Adelphane
  13. Adelphin
  14. Adelphin-esidrex-k
  15. Alkarau
  16. Alkaserp
  17. Alserin
  18. Anquil
  19. Apoplon
  20. Apoplon (TN)
  21. Apsical
  22. Arcum r-s
  23. Ascoserp
  24. Ascoserpina
  25. Austrapine
  26. Banasil
  27. Banisil
  28. Benazyl
  29. Bendigon
  30. Bioserpine
  31. Brinderdin
  32. Briserine
  33. Broserpine
  34. Butiserpazide-25
  35. Butiserpazide-50
  36. Butiserpine
  37. Cam-ap-es
  38. Cardioserpin
  39. Carditivo
  40. Carpacil
  41. Carrserp
  42. Caswell No. 722A
  43. Chloroserp-250
  44. Chloroserp-500
  45. Chloroserpin-250
  46. Chloroserpine-500
  47. Chlorothiazide and reserpine
  48. Chlorothiazide w/ reserpine
  49. Chlorothiazide-reserpine
  50. Crystoserpine
  51. DIUPRES-250
  52. DIUPRES-500
  53. Darebon
  54. Demi-regroton
  55. Deserpine
  56. Diupres
  57. Diupres 250
  58. Diupres 500
  59. Diurese-r
  60. Diutensen-r
  61. Dralserp
  62. Drenusil-r
  63. Dypertane compound
  64. Eberpine
  65. Eberspine
  66. Ebserpine
  67. Elfanex
  68. Elserpine
  69. Enipresser
  70. Esc aspere
  71. Escaspere
  72. Eserpine
  73. Eskaserp
  74. Eskaserpine
  75. Gamaserpin
  76. Gammaserpine
  77. Gilucard
  78. HYDRO-SERP "25"
  79. HYDRO-SERP "50"
  80. Helfoserpin
  81. Hexaplin
  82. Hiposerpil
  83. Hiserpia
  84. Hydralazine HCL, hydrochlorothiazide and reserpine
  85. Hydralazine HCL-hydrochlorothiazide-reserpine
  86. Hydralazine, hydrochlorothiazide w/ reserpine
  87. Hydrap-es
  88. Hydro-Fluserpine #1
  89. Hydro-Reserpine-25
  90. Hydro-Reserpine-50
  91. Hydro-reserp
  92. Hydrochlorothiazide w/ reserpine
  93. Hydrochlorothiazide w/ reserpine and hydralazine
  94. Hydroflumethiazide and reserpine
  95. Hydromox r
  96. Hydromox-r
  97. Hydropine
  98. Hydropres
  99. Hydropres 25
  100. Hydropres 50
  101. Hydropres ka
  102. Hydroserp
  103. Hydroserpalan
  104. Hydroserpine #1
  105. Hydroserpine plus
  106. Hydroserpine plus (r-h-h)
  107. Hydrosine 25
  108. Hygroton-reserpine
  109. Hypercal b
  110. Hypersil
  111. Hypersine
  112. Hypertane forte
  113. Hypertensan
  114. Idoserp
  115. Idsoserp
  116. Interpina
  117. Key-serpine
  118. Kitine
  119. Klimanosid
  120. L -carpserp
  121. L"-carpserp
  122. Lemiserp
  123. Loweser p
  124. Loweserp
  125. Mallopress
  126. Marnitension simple
  127. Maviserpin
  128. Mayserpine
  129. Mephaserpin
  130. Metatensin
  131. Metatensin #2
  132. Metatensin #4
  133. Methyl reserpate 3,4,5-trimethoxybenzoate
  134. Methyl reserpate 3,4,5-trimethoxybenzoate (ester)
  135. Methyl reserpate 3,4,5-trimethoxybenzoic Acid ester
  136. Methyl reserpate 3,4,5-trimethyloxybenzoic Acid
  137. Methylreserpate 3,4,5-Trimethoxybenzoic Acid ester
  138. Methylreserpate 3,4,5-trimethoxybenzoic Acid
  139. Mio-pressin
  140. Mixture name
  141. Modenol
  142. Naquival
  143. Nembu-serpin
  144. Nembuserpin
  145. Neo-antitensol
  146. Neo-antitersol
  147. Neo-serp
  148. Neose rfin
  149. Neoserfin
  150. Neoserp
  151. Neoslowten
  152. Orthoserpina
  153. Perskleran
  154. Pressimedin
  155. Prestwick_147
  156. Purserpine
  157. Quemicetina
  158. Quiescin
  159. R-e-s
  160. R0875_SIGMA
  161. RCRA waste no. U200
  162. RESERPINE AND HYDROCHLOROTHIAZIDE-50
  163. Rau sedyl
  164. Rau-sed
  165. Raucap
  166. Raudiford
  167. Raudixin
  168. Raudixoid
  169. Raugal
  170. Raulen
  171. Rauloycin
  172. Rauloydin
  173. Raumorine
  174. Raunervil
  175. Raunorine
  176. Raunormin 'orzan'
  177. Raunova
  178. Raupasil
  179. Raupoid
  180. Raurine
  181. Rausan
  182. Rausedan
  183. Rausedil
  184. Rausedyl
  185. Rauserpen-alk
  186. Rauserpin
  187. Rauserpin-alk
  188. Rauserpine
  189. Rauserpol
  190. Rausingle
  191. Rautrin
  192. Rauvilid
  193. Rauvlid
  194. Rauwasedin
  195. Rauwilid
  196. Rauwiloid
  197. Rauwiloid+
  198. Rauwipur
  199. Rauwita
  200. Rauwoleaf
  201. Rauwopur'BYK'
  202. Rawilid
  203. Rcra waste number U200
  204. Recipin
  205. Regroton
  206. Renese r
  207. Renese-r
  208. Resaltex
  209. Rese rpamed
  210. Rese-lar
  211. Resedin
  212. Resedrex
  213. Resedril
  214. Reser-ar
  215. Reserbal
  216. Resercaps
  217. Resercen
  218. Resercrine
  219. Reserfia
  220. Reserjen
  221. Reserlor
  222. Reserp
  223. Reserp 'wander'
  224. Reserpal
  225. Reserpamed
  226. Reserpanca
  227. Reserpene
  228. Reserpex
  229. Reserpic Acid methyl ester 3,4,5-trimethoxybenzoate
  230. Reserpic Acid methyl ester 3,4,5-trimethoxybenzoate (ester)
  231. Reserpidefe
  232. Reserpil
  233. Reserpin
  234. Reserpina
  235. Reserpina [inn-spanish]
  236. Reserpine (JP15/USP/INN)
  237. Reserpine BP
  238. Reserpine [usan:inn:ban:jan]
  239. Reserpine and hydrochlorothiazide
  240. Reserpine and hydroflumethiazide
  241. Reserpine, hydralazine HCL and hydrochlorothiazide
  242. Reserpine, hydrochlorothiazide, and hydralazine HCL
  243. Reserpinum
  244. Reserpka
  245. Reserpoid
  246. Reserpur
  247. Resersana
  248. Reserutin
  249. Resiatric
  250. Residin
  251. Residine
  252. Resine
  253. Resocalm
  254. Resomine
  255. Resperin
  256. Resperine
  257. Respital
  258. Restran
  259. Rezerpin
  260. Riserpa
  261. Rivased
  262. Rivasin
  263. Rolserp
  264. Roxel
  265. Roxinoid
  266. Roxynoid
  267. Ryser
  268. SERP
  269. SERPASIL-ESIDRIX #1
  270. SERPASIL-ESIDRIX #2
  271. SK-reserpine
  272. Salupres
  273. Salutensin
  274. Salutensin-demi
  275. Sandril
  276. Sandron
  277. Sarpagan
  278. Sarpagen
  279. Se rpate
  280. Seda-recipin
  281. Seda-salurepin
  282. Sedaraupin
  283. Sedaraupina
  284. Sederaupin
  285. Sedserp
  286. Seominal
  287. Ser-a-gen
  288. Ser-ap-es
  289. Serfin
  290. Serfolia
  291. Serolfia
  292. Serp-afd
  293. Serpalan
  294. Serpalan (TN)
  295. Serpaloid
  296. Serpaneurona
  297. Serpanray
  298. Serpasil
  299. Serpasil apresoline
  300. Serpasil premix
  301. Serpasil-apresoline
  302. Serpasil-esidrex
  303. Serpasil-esidrex k
  304. Serpasil-esidrex no. 1
  305. Serpasil-esidrex no. 2
  306. Serpasol
  307. Serpate
  308. Serpatone
  309. Serpax
  310. Serpazil
  311. Serpazol
  312. Serpedin
  313. Serpen
  314. Serpena
  315. Serpentil
  316. Serpentin
  317. Serpentina
  318. Serpentine 'pharbil'
  319. Serpicon
  320. Serpil
  321. Serpiloid
  322. Serpilum
  323. Serpine
  324. Serpine (pharmaceutical)
  325. Serpipur
  326. Serpivate
  327. Serpivite
  328. Serplex k
  329. Serpogen
  330. Serpoid
  331. Serpone
  332. Serpresan
  333. Serpyrit
  334. Sertabs
  335. Sertens
  336. Sertensin
  337. Sertina
  338. Sinesalin composition
  339. Solfo serpine
  340. Supergan
  341. T-serp
  342. Tefaserpina
  343. Tempo-reserpina
  344. Temposerpine
  345. Tendoscen-compr.
  346. Tensanyl
  347. Tenserlix
  348. Tenserpine 'assia'
  349. Tenserpinie
  350. Tensional
  351. Tensionorme
  352. Tepserpine
  353. Terbolan
  354. Transerpin
  355. Trichlormethiazide w/ reserpine
  356. Trimethoxybenzoyl methyl reserpate
  357. Triserpin
  358. Tylandril
  359. UNII-8B1QWR724A
  360. USAF cb-27
  361. Unilord
  362. Unipres
  363. Unitensen
  364. V-serp
  365. VIXO
  366. Veriloid
  367. Vi xo
  368. Vio-serpine
  369. a,18a)-
  370. methyl o-(3,4,5-trimethoxybenzo yl)reserpate
  371. methyl o-(3,4,5-trimethoxybenzoyl)reserpate
Chemical IUPAC Name methyl 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(9),5,7-tetraene-19-carboxylate
Chemical Formula C33H40N2O9
Chemical Structure Structure
CAS Registry Number 50-55-5
InChI Identifier 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
InChI Key InChIKey=QEVHRUUCFGRFIF-UHFFFAOYSA-N
PubChem Compound ID 5770 Link Image
KEGG ID C06539 Link Image
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID 28487 Link Image
BioCyc ID Not Available
SuperToxic ID Not Available
CTD ID Not Available
Stitch ID Reserpine Link Image
DrugBank ID DB00206 Link Image
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Reserpine Link Image
Monoisotopic Mass 608.273381
MOL File Show
PDB File Show
SDF File Show
SMILES COC1C(CC2CN3CCC4=C(NC5=C4C=CC(OC)=C5)C3CC2C1C(=O)OC)OC(=O)C1=CC(OC)=C(OC)C(OC)=C1
Appearance Not Available
Melting Point 264.5 oC
Solubility 73 mg/L
Predicted LogP 3.5315
Route of Exposure Oral
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.
Metabolism Not Available
Toxicity Values LD50: 420 mg/kg (Oral, Rat) (S405) LD50: 44 mg/kg (Intraperitoneal(parenteral), Rat) (S405) LD50: 15 mg/kg (Intravenous(parenteral), Rat) (S405) LD50: 200 mg/kg (Oral, Mouse) (S405) LD50: 52 mg/kg (Subcutaneous(parenteral), Mouse) (S405) LD50: 7 mg/kg (Intraperitoneal(parenteral), Rabbit) (S405)
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Not Available
Minimum Risk Level Not Available
Health Effects Not Available
Symptoms Not Available
Treatment Not Available
General References
  • T317 - : Effects of treatment on morbidity in hypertension. Results in patients with diastolic blood pressures averaging 115 through 129 mm Hg. JAMA. 1967 Dec 11;202(11):1028-34. [PubMed Link Image]
  • T320 - Moser M: "Cost containment" in the management of hypertension. Ann Intern Med. 1987 Jul;107(1):107-9. [PubMed Link Image]
  • T318 - : Prevention of stroke by antihypertensive drug treatment in older persons with isolated systolic hypertension. Final results of the Systolic Hypertension in the Elderly Program (SHEP). SHEP Cooperative Research Group. JAMA. 1991 Jun 26;265(24):3255-64. [PubMed Link Image]
  • T316 - : Five-year findings of the hypertension detection and follow-up program. I. Reduction in mortality of persons with high blood pressure, including mild hypertension. Hypertension Detection and Follow-up Program Cooperative Group. JAMA. 1979 Dec 7;242(23):2562-71. [PubMed Link Image]
  • T319 - Chobanian AV, Bakris GL, Black HR, Cushman WC, Green LA, Izzo JL Jr, Jones DW, Materson BJ, Oparil S, Wright JT Jr, Roccella EJ: The Seventh Report of the Joint National Committee on Prevention, Detection, Evaluation, and Treatment of High Blood Pressure: the JNC 7 report. JAMA. 2003 May 21;289(19):2560-72. Epub 2003 May 14. [PubMed Link Image]
  • T315 - Drugs.com
Targets
  1. Synaptic vesicular amine transporter
Target 1 [top]
Target 1 ID 1162
Target 1 Name Synaptic vesicular amine transporter
Target 1 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.
Target 1 Description Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis
Target 1 Synonyms
  1. Vesicular amine transporter 2; VAT2; Monoamine transporter; Solute carrier family 18 member 2
Target 1 Gene Name SLC18A2
Target 1 Protein Sequence >Synaptic vesicular amine transporter 
MALSELALVRWLQESRRSRKLILFIVFLALLLDNMLLTVVVPIIPSYLYSIKHEKNATEI
QTARPVHTASISDSFQSIFSYYDNSTMVTGNATRDLTLHQTATQHMVTNASAVPSDCPSE
DKDLLNENVQVGLLFASKATVQLITNPFIGLLTNRIGYPIPIFAGFCIMFVSTIMFAFSS
SYAFLLIARSLQGIGSSCSSVAGMGMLASVYTDDEERGNVMGIALGGLAMGVLVGPPFGS
VLYEFVGKTAPFLVLAALVLLDGAIQLFVLQPSRVQPESQKGTPLTTLLKDPYILIAAGS
ICFANMGIAMLEPALPIWMMETMCSRKWQLGVAFLPASISYLIGTNIFGILAHKMGRWLC
ALLGMIIVGVSILCIPFAKNIYGLIAPNFGVGFAIGMVDSSMMPIMGYLVDLRHVSVYGS
VYAIADVAFCMGYAIGPSAGGAIAKAIGFPWLMTIIGIIDILFAPLCFFLRSPPAKEEKM
AILMDHNCPIKTKMYTQNNIQSYPIGEDEESESD
Target 1 Number of Residues 514
Target 1 Molecular Weight 55712.1
Target 1 Theoretical pI 5.91
Target 1 GO Classification
Function
transporter activity
Process
physiological process
cellular physiological process
transport
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Carbohydrate transport and metabolism
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 21-41
  • 130-150
  • 160-180
  • 190-210
  • 220-242
  • 249-271
  • 292-311
  • 329-352
  • 358-378
  • 390-410
  • 415-435
  • 441-462
Target 1 Essentiality Non Essential
Target 1 Domain Function PF07690:MFS_1
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB ID Q05940 Link Image
Target 1 Cellular Location Cytoplasmic vesicle membrane
Target 1 Gene Sequence >1545 bp 
ATGGCCCTGAGCGAGCTGGCGCTGGTCCGCTGGCTGCAGGAGAGCCGCCGCTCGCGGAAG
CTCATCCTGTTCATCGTGTTCCTGGCGCTGCTGCTGGACAACATGCTGCTCACTGTCGTG
GTCCCCATCATCCCAAGTTATCTGTACAGCATTAAGCATGAGAAGAATGCTACAGAAATC
CAGACGGCCAGGCCAGTGCACACTGCCTCCATCTCAGACAGCTTCCAGAGCATCTTCTCC
TATTATGATAACTCGACTATGGTCACCGGGAATGCTACCAGAGACCTGACACTTCATCAG
ACCGCCACACAGCACATGGTGACCAACGCGTCCGCTGTTCCTTCCGACTGTCCCAGTGAA
GACAAAGACCTCCTGAATGAAAACGTGCAAGTTGGTCTGTTGTTTGCCTCGAAAGCCACC
GTCCAGCTCATCACCAACCCTTTCATAGGACTACTGACCAACAGAATTGGCTATCCAATT
CCCATATTTGCGGGATTCTGCATCATGTTTGTCTCAACAATTATGTTTGCCTTCTCCAGC
AGCTATGCCTTCCTGCTGATTGCCAGGTCGCTGCAGGGCATCGGCTCGTCCTGCTCCTCT
GTGGCTGGGATGGGCATGCTTGCCAGTGTCTACACAGATGATGAAGAGAGAGGCAACGTC
ATGGGAATCGCCTTGGGAGGCCTGGCCATGGGGGTCTTAGTGGGCCCCCCCTTCGGGAGT
GTGCTCTATGAGTTTGTGGGGAAGACGGCTCCGTTCCTGGTGCTGGCCGCCCTGGTACTC
TTGGATGGAGCTATTCAGCTCTTTGTGCTCCAGCCGTCCCGGGTGCAGCCAGAGAGTCAG
AAGGGGACACCCCTAACCACGCTGCTGAAGGACCCGTACATCCTCATTGCTGCAGGCTCC
ATCTCCTTTGCAAACATGGGCATCGCCATGCTGGAGCCAGCCCTGCCCATCTGGATGATG
GAGACCATGTGTTCCCGCAAGTGGCAGCTGGGCGTTGCCTTCTTGCCAGCTAGTATCTCT
TATCTCATTGGAACCAATATTTTTGGGATACTTGCACACACAATGGGGAGGTGGCTTTGT
GCTCTTCTGGGAATGATAATTGTTGGAGTCAGCATTTTATGTATTCCATTTCCAAAAAAC
ATTTATGGACTCATAGCTCCGAACTTTGGAGTTGGTTTTGCAAATGGAATGGTGGATTCG
TCAATGATGCCTATCATGGGCTACCTCGTAGACCTGCGGCACGTGTCCGTCTATGGGAGT
GTGTACGCCATTGCGGATGTGGCATTTTGTATGGGGTATGCTATAGGTCCTTCTGCTGGT
GGTGCTATTGCAAAGGCAATTGGATTTCCATGGCTCATGACAATTATTGGGATAATTGAT
ATTCTTTTTGCCCCTCTCTGCTTTTTTCTTCGAAGTCCACCTGCCAAAGAAGAAAAAATG
GCTATTCTCATGGATCACAACTGCCCTATTAAAACAAAAATGTACACTCAGAATAATATC
CAGTCATATCCGATAGGTGAAGATGAAGAATCTGAAAGTGACTGA
Target 1 GenBank Gene ID Not Available
Target 1 GeneCard ID SLC18A2 Link Image
Target 1 GenAtlas ID SLC18A2 Link Image
Target 1 HGNC ID HGNC:10935 Link Image
Target 1 Chromosome Location Chromosome:10
Target 1 Locus 10q25
Target 1 SNPs SNPJam Report Link Image
Target 1 Toxin References
  • S912 - Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  • T322 - Naudon L, Leroux-Nicollet I, Raisman-Vozari R, Botton D, Costentin J: Time-course of modifications elicited by reserpine on the density and mRNA synthesis of the vesicular monoamine transporter, and on the density of the membrane dopamine uptake complex. Synapse. 1995 Sep;21(1):29-36. [PubMed Link Image]
  • S911 - Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  • T321 - Sievert MK, Hajipour AR, Ruoho AE: Specific derivatization of the vesicle monoamine transporter with novel carrier-free radioiodinated reserpine and tetrabenazine photoaffinity labels. Anal Biochem. 2007 Aug 1;367(1):68-78. Epub 2007 May 3. [PubMed Link Image]
  • T323 - Erickson JD, Eiden LE, Hoffman BJ: Expression cloning of a reserpine-sensitive vesicular monoamine transporter. Proc Natl Acad Sci U S A. 1992 Nov 15;89(22):10993-7. [PubMed Link Image]
Target 1 General References 8095030; 8245983; 7905859; 8373557; 11443533; 15164054; 15489334; 12009896; 18088087

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government.