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MedKoo Cat#: 531034 | Name: Reserpine
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Description:

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

Reserpine is an alkaloid vesicular monoamine transporter 2 (VMAT2) inhibitor, that inhibits the uptake of norepinephrine into storage vesicles, resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. Reserpine has been used as an antihypertensive and an antipsychotic.

Chemical Structure

Reserpine
Reserpine
CAS#50-55-5 (free)

Theoretical Analysis

MedKoo Cat#: 531034

Name: Reserpine

CAS#: 50-55-5 (free)

Chemical Formula: C33H40N2O9

Exact Mass: 608.2734

Molecular Weight: 608.69

Elemental Analysis: C, 65.12; H, 6.62; N, 4.60; O, 23.66

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 550.00
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Related CAS #
50-55-5 (free) 1263-94-1 (phosphate) 16994-56-2 (HCl)
Synonym
Reserpine, Reserpine phosphate, Raudixin, Serpalan, Serpasil
IUPAC/Chemical Name
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
InChi Key
QEVHRUUCFGRFIF-MDEJGZGSSA-N
InChi Code
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
SMILES Code
CO[C@H]1[C@H](OC(C2=CC(OC)=C(OC)C(OC)=C2)=O)C[C@@H]3CN4CCC5=C([C@H]4C[C@@H]3[C@@H]1C(OC)=O)NC6=CC(OC)=CC=C56
Appearance
White to light yellow crystalline 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
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:
Reserpine irreversibly inhibits both human isoforms of vesicular monoamine transporter, VMAT1 and VMAT2 (Kis = 34 and 12 nM, respectively). As this leads to metabolism of monoamines, reserpine is used to experimentally deplete monoamines in animals. Reserpine inhibits the multidrug resistance protein P-glycoprotein (IC50 = 0.5 µM).
In vitro activity:
Reserpine inhibits DNA synthesis by arresting prostate cancer cells at the G2 phase and showed all standard sequential features of apoptosis including, destabilization of mitochondrial membrane potential, reduced production of reactive oxygen species and DNA ladder formation. Reserpine could be a novel therapeutic agent for the treatment of androgen-independent prostate cancer. Reference: Anticancer Agents Med Chem. 2018;18(9):1313-1322. https://pubmed.ncbi.nlm.nih.gov/29424320/
In vivo activity:
In cyclophosphamide-treated C57Bl/6 mice, reserpine reduced the level of short-term hematopoietic stem cells and increased the count of progenitor hematopoietic cells in the bone marrow in parallel with recruitment of the progenitors into the peripheral blood. Reference: Bull Exp Biol Med. 2016 Feb;160(4):439-43. https://pubmed.ncbi.nlm.nih.gov/26902356/
Solvent mg/mL mM
Solubility
DMF 20.0 32.86
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 608.69 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. Ramamoorthy MD, Kumar A, Ayyavu M, Dhiraviam KN. Reserpine Induces Apoptosis and Cell Cycle Arrest in Hormone Independent Prostate Cancer Cells through Mitochondrial Membrane Potential Failure. Anticancer Agents Med Chem. 2018;18(9):1313-1322. doi: 10.2174/1871520618666180209152215. PMID: 29424320. 2. Bhat UG, Winter MA, Pearce HL, Beck WT. A structure-function relationship among reserpine and yohimbine analogues in their ability to increase expression of mdr1 and P-glycoprotein in a human colon carcinoma cell line. Mol Pharmacol. 1995 Oct;48(4):682-9. PMID: 7476894. 3. Skurikhin EG, Ermakova NN, Pershina OV, Krupin VA, Pakhomova AV, Dygai AM. Response of Hematopoietic Stem and Progenitor Cells to Reserpine in C57Bl/6 Mice. Bull Exp Biol Med. 2016 Feb;160(4):439-43. doi: 10.1007/s10517-016-3191-y. Epub 2016 Feb 23. PMID: 26902356. 4. Stanwood GD, Lucki I, McGonigle P. Differential regulation of dopamine D2 and D3 receptors by chronic drug treatments. J Pharmacol Exp Ther. 2000 Dec;295(3):1232-40. PMID: 11082460.
In vitro protocol:
1. Ramamoorthy MD, Kumar A, Ayyavu M, Dhiraviam KN. Reserpine Induces Apoptosis and Cell Cycle Arrest in Hormone Independent Prostate Cancer Cells through Mitochondrial Membrane Potential Failure. Anticancer Agents Med Chem. 2018;18(9):1313-1322. doi: 10.2174/1871520618666180209152215. PMID: 29424320. 2. Bhat UG, Winter MA, Pearce HL, Beck WT. A structure-function relationship among reserpine and yohimbine analogues in their ability to increase expression of mdr1 and P-glycoprotein in a human colon carcinoma cell line. Mol Pharmacol. 1995 Oct;48(4):682-9. PMID: 7476894.
In vivo protocol:
1. Skurikhin EG, Ermakova NN, Pershina OV, Krupin VA, Pakhomova AV, Dygai AM. Response of Hematopoietic Stem and Progenitor Cells to Reserpine in C57Bl/6 Mice. Bull Exp Biol Med. 2016 Feb;160(4):439-43. doi: 10.1007/s10517-016-3191-y. Epub 2016 Feb 23. PMID: 26902356. 2. Stanwood GD, Lucki I, McGonigle P. Differential regulation of dopamine D2 and D3 receptors by chronic drug treatments. J Pharmacol Exp Ther. 2000 Dec;295(3):1232-40. PMID: 11082460.
1: Nur S, Adams CE. Chlorpromazine versus reserpine for schizophrenia. Cochrane Database Syst Rev. 2016 Apr 28;4:CD012122. doi: 10.1002/14651858.CD012122.pub2. Review. PubMed PMID: 27124109. 2: Maldonado M, Maeyama K. The metabolism of histamine in rat hypothalamus and cortex after reserpine treatment. Neurochem Int. 2015 Jun-Jul;85-86:31-9. doi: 10.1016/j.neuint.2015.04.005. Epub 2015 Apr 29. PubMed PMID: 25936509. 3: Antkiewicz-Michaluk L, Wąsik A, Możdżeń E, Romańska I, Michaluk J. Withdrawal from repeated administration of a low dose of reserpine induced opposing adaptive changes in the noradrenaline and serotonin system function: a behavioral and neurochemical ex vivo and in vivo studies in the rat. Prog Neuropsychopharmacol Biol Psychiatry. 2015 Mar 3;57:146-54. doi: 10.1016/j.pnpbp.2014.10.009. Epub 2014 Nov 8. PubMed PMID: 25445479. 4: Shamon SD, Perez MI. Blood pressure-lowering efficacy of reserpine for primary hypertension. Cochrane Database Syst Rev. 2016 Dec 21;12:CD007655. doi: 10.1002/14651858.CD007655.pub3. Review. PubMed PMID: 27997978. 5: Rajapaksa NS, McGowan MA, Rienzo M, Jacobsen EN. Enantioselective total synthesis of (+)-reserpine. Org Lett. 2013 Feb 1;15(3):706-9. doi: 10.1021/ol400046n. Epub 2013 Jan 18. PubMed PMID: 23331099; PubMed Central PMCID: PMC3578295. 6: Begum S, Naqvi SQ, Ahmed A, Tauseef S, Siddiqui BS. Antimycobacterial and antioxidant activities of reserpine and its derivatives. Nat Prod Res. 2012;26(22):2084-8. doi: 10.1080/14786419.2011.625502. Epub 2012 Jan 25. PubMed PMID: 22273392. 7: National Toxicology Program. Reserpine. Rep Carcinog. 2011;12:370-1. PubMed PMID: 21863092. 8: Sharaf El-Din MM, Nassar MW, Attia KA, Demellawy MA, Kaddah MM. Validated liquid chromatography-tandem mass spectrometry method for simultaneous determination of clopamide, reserpine and dihydroergotoxine: Application to pharmacokinetics in human plasma. J Pharm Biomed Anal. 2016 Jun 5;125:236-44. doi: 10.1016/j.jpba.2016.03.051. Epub 2016 Mar 25. PubMed PMID: 27037980. 9: Verheij MM, Cools AR. Reserpine differentially affects cocaine-induced behavior in low and high responders to novelty. Pharmacol Biochem Behav. 2011 Mar;98(1):43-53. doi: 10.1016/j.pbb.2010.11.021. Epub 2010 Dec 9. PubMed PMID: 21145910. 10: Baumeister AA, Hawkins MF, Uzelac SM. The myth of reserpine-induced depression: role in the historical development of the monoamine hypothesis. J Hist Neurosci. 2003 Jun;12(2):207-20. PubMed PMID: 12953623. 11: Fernandes VS, Santos JR, Leão AH, Medeiros AM, Melo TG, Izídio GS, Cabral A, Ribeiro RA, Abílio VC, Ribeiro AM, Silva RH. Repeated treatment with a low dose of reserpine as a progressive model of Parkinson's disease. Behav Brain Res. 2012 May 16;231(1):154-63. doi: 10.1016/j.bbr.2012.03.008. Epub 2012 Mar 16. PubMed PMID: 22446059. 12: Ma XJ, Lu GC, Song SW, Liu W, Wen ZP, Zheng X, Lü QZ, Su DF. The features of reserpine-induced gastric mucosal lesions. Acta Pharmacol Sin. 2010 Aug;31(8):938-43. doi: 10.1038/aps.2010.74. PubMed PMID: 20686519; PubMed Central PMCID: PMC4007818. 13: Barcan GA, Patel A, Houk KN, Kwon O. A torquoselective 6π electrocyclization approach to reserpine alkaloids. Org Lett. 2012 Nov 2;14(21):5388-91. doi: 10.1021/ol302265z. Epub 2012 Oct 5. PubMed PMID: 23039026; PubMed Central PMCID: PMC3488149. 14: Grondin G, Leblond FA, Morisset J, LeBel D. Light and electron microscopy of the exocrine pancreas in the chronically reserpinized rat. Pediatr Res. 1989 May;25(5):482-9. PubMed PMID: 2717265. 15: Shugalev NP, Stavrovskaia AV, Iamshchikova NG, Ol'shanskiĭ AS, Miroshnichenko EV. [Reproduction of passive avoidance reactions after neurotensin microinjection into nucleus accumbens of rat brain against the background of reserpine action]. Zh Vyssh Nerv Deiat Im I P Pavlova. 2012 May-Jun;62(3):357-63. Russian. PubMed PMID: 22891581. 16: Nammi S, Boini KM, Koppula S, Sreemantula S. Reserpine-induced central effects: pharmacological evidence for the lack of central effects of reserpine methiodide. Can J Physiol Pharmacol. 2005 Jun;83(6):509-15. PubMed PMID: 16049551. 17: Ohmi K, Nakamura S. Analysis of the interaction of reserpine with actin by the photoaffinity labelling method. Eur J Pharmacol. 1991 Aug 14;207(4):305-10. PubMed PMID: 1783001. 18: Stitzel RE. The biological fate of reserpine. Pharmacol Rev. 1976 Sep;28(3):179-208. Review. PubMed PMID: 16280. 19: Parti R, Ozkan ED, Harnadek GJ, Njus D. Inhibition of norepinephrine transport and reserpine binding by reserpine derivatives. J Neurochem. 1987 Mar;48(3):949-53. PubMed PMID: 3806108. 20: Jerie P. [Milestones of cardiovascular therapy. IV. Reserpine]. Cas Lek Cesk. 2007;146(7):573-7. Review. Czech. PubMed PMID: 17722843.

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