MedKoo Cat#: 128967 | Name: Reserpine HCl
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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 HCl
Reserpine HCl
CAS#16994-56-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 128967

Name: Reserpine HCl

CAS#: 16994-56-2 (HCl)

Chemical Formula: C33H41ClN2O9

Exact Mass: 0.0000

Molecular Weight: 645.15

Elemental Analysis: C, 61.44; H, 6.41; Cl, 5.49; N, 4.34; O, 22.32

Price and Availability

Size Price Availability Quantity
5mg USD 550.00 2 Weeks
25mg USD 950.00 2 Weeks
100mg USD 1,650.00 2 Weeks
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Related CAS #
50-55-5 (free) 1263-94-1 (phosphate) 16994-56-2 (HCl)
Synonym
Reserpine HCl; 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 hydrochloride
InChi Key
ZYWIWGUMKCZKOO-BQTSRIDJSA-N
InChi Code
InChI=1S/C33H40N2O9.ClH/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;1H/t18-,22+,24-,27-,28+,31+;/m1./s1
SMILES Code
O=C([C@H]([C@@H](OC)[C@H](OC(C1=CC(OC)=C(OC)C(OC)=C1)=O)C[C@]2([H])CN3CC4)[C@@]2([H])C[C@]3([H])C5=C4C(C=CC(OC)=C6)=C6N5)OC.Cl
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 645.15 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
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.