Sarpagine

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

MedKoo CAT#: 461173

CAS#: 482-68-8

Description: Sarpagine is an alkaloid that acts as an antihypertonic.


Chemical Structure

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Sarpagine
CAS# 482-68-8

Theoretical Analysis

MedKoo Cat#: 461173
Name: Sarpagine
CAS#: 482-68-8
Chemical Formula: C19H22N2O2
Exact Mass: 310.1681
Molecular Weight: 310.39
Elemental Analysis: C, 73.52; H, 7.14; N, 9.03; O, 10.31

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Sarpagine; Raupin;

IUPAC/Chemical Name: (E)-9-ethylidene-11-(hydroxymethyl)-5,6,8,9,10,11,11a,12-octahydro-6,10-methanoindolo[3,2-b]quinolizin-2-ol

InChi Key: VTVQHYQGTTVKDE-SGAXSIHGSA-N

InChi Code: InChI=1S/C19H22N2O2/c1-2-10-8-21-17-7-14-13-5-11(23)3-4-16(13)20-19(14)18(21)6-12(10)15(17)9-22/h2-5,12,15,17-18,20,22-23H,6-9H2,1H3/b10-2-

SMILES Code: OCC1C2/C(CN3C(C2)C(NC4=C5C=C(O)C=C4)=C5CC13)=C\C

Appearance: Solid 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: >3 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: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 310.39 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

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1: Namjoshi OA, Cook JM. Sarpagine and Related Alkaloids. Alkaloids Chem Biol. 2016;76:63-169. doi: 10.1016/bs.alkal.2015.08.002. Epub 2015 Oct 9. Review. PubMed PMID: 26827883; PubMed Central PMCID: PMC4864735.

2: Lim SH, Low YY, Sinniah SK, Yong KT, Sim KS, Kam TS. Macroline, akuammiline, sarpagine, and ajmaline alkaloids from Alstonia macrophylla. Phytochemistry. 2014 Feb;98:204-15. doi: 10.1016/j.phytochem.2013.11.014. Epub 2013 Dec 13. PubMed PMID: 24342109.

3: Tan SJ, Lim JL, Low YY, Sim KS, Lim SH, Kam TS. Oxidized derivatives of macroline, sarpagine, and pleiocarpamine alkaloids from Alstonia angustifolia. J Nat Prod. 2014 Sep 26;77(9):2068-80. doi: 10.1021/np500439u. Epub 2014 Sep 11. PubMed PMID: 25211145.

4: Krüger S, Gaich T. Enantioselective, protecting-group-free total synthesis of sarpagine alkaloids--a generalized approach. Angew Chem Int Ed Engl. 2015 Jan 2;54(1):315-7. doi: 10.1002/anie.201407280. Epub 2014 Oct 24. PubMed PMID: 25346454.

5: Tan SJ, Lim KH, Subramaniam G, Kam TS. Macroline-sarpagine and macroline-pleiocarpamine bisindole alkaloids from Alstonia angustifolia. Phytochemistry. 2013 Jan;85:194-202. doi: 10.1016/j.phytochem.2012.08.016. Epub 2012 Sep 17. PubMed PMID: 22995929.

6: Edwankar RV, Edwankar CR, Deschamps JR, Cook JM. General strategy for synthesis of C-19 methyl-substituted sarpagine/macroline/ajmaline indole alkaloids including total synthesis of 19(S),20(R)-dihydroperaksine, 19(S),20(R)-dihydroperaksine-17-al, and peraksine. J Org Chem. 2014 Nov 7;79(21):10030-48. doi: 10.1021/jo5016163. Epub 2014 Oct 15. PubMed PMID: 25247616; PubMed Central PMCID: PMC4227583.

7: Kitajima M, Watanabe K, Maeda H, Kogure N, Takayama H. Asymmetric Total Synthesis of Sarpagine-Related Indole Alkaloids Hydroxygardnerine, Hydroxygardnutine, Gardnerine, (E)-16-epi-Normacusine B, and Koumine. Org Lett. 2016 Apr 15;18(8):1912-5. doi: 10.1021/acs.orglett.6b00661. Epub 2016 Apr 1. PubMed PMID: 27035053.

8: Edwankar CR, Edwankar RV, Namjoshi OA, Liao X, Cook JM. Stereospecific approach to the synthesis of ring-A oxygenated sarpagine indole alkaloids. Total synthesis of the dimeric indole alkaloid P-(+)-dispegatrine and six other monomeric indole alkaloids. J Org Chem. 2013 Jul 5;78(13):6471-87. doi: 10.1021/jo400469t. Epub 2013 Jun 18. PubMed PMID: 23721107; PubMed Central PMCID: PMC3722876.

9: Lim SH, Tan SJ, Low YY, Kam TS. Lumutinines A-D, linearly fused macroline-macroline and macroline-sarpagine bisindoles from Alstonia macrophylla. J Nat Prod. 2011 Dec 27;74(12):2556-62. doi: 10.1021/np200730j. Epub 2011 Dec 7. PubMed PMID: 22148233.

10: Rahman MT, Tiruveedhula VV, Cook JM. Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review. Molecules. 2016 Nov 14;21(11). pii: E1525. Review. PubMed PMID: 27854259; PubMed Central PMCID: PMC5214337.

11: Edwankar CR, Edwankar RV, Deschamps JR, Cook JM. Nature-inspired stereospecific total synthesis of P-(+)-dispegatrine and four other monomeric sarpagine indole alkaloids. Angew Chem Int Ed Engl. 2012 Nov 19;51(47):11762-5. doi: 10.1002/anie.201206015. Epub 2012 Oct 16. PubMed PMID: 23073985; PubMed Central PMCID: PMC3970238.

12: Edwankar RV, Edwankar CR, Deschamps J, Cook JM. Regiospecific, enantiospecific total synthesis of C-19 methyl substituted sarpagine alkaloids dihydroperaksine-17-al and dihydroperaksine. Org Lett. 2011 Oct 7;13(19):5216-9. doi: 10.1021/ol202101p. Epub 2011 Aug 30. PubMed PMID: 21877687; PubMed Central PMCID: PMC3184356.

13: Gan CY, Low YY, Robinson WT, Komiyama K, Kam TS. Aspidospermatan-aspidospermatan and eburnane-sarpagine bisindole alkaloids from Leuconotis. Phytochemistry. 2010 Aug;71(11-12):1365-70. doi: 10.1016/j.phytochem.2010.05.015. Epub 2010 Jun 11. PubMed PMID: 20542302.

14: Pan L, Terrazas C, Muñoz Acuña U, Ninh TN, Chai H, Carcache de Blanco EJ, Soejarto DD, Satoskar AR, Kinghorn AD. Bioactive indole alkaloids isolated from Alstonia angustifolia.. Phytochem Lett. 2014 Dec;10:54-59. PubMed PMID: 25584095; PubMed Central PMCID: PMC4287998.

15: Yu J, Wang T, Liu X, Deschamps J, Flippen-Anderson J, Liao X, Cook JM. General approach for the synthesis of sarpagine indole alkaloids. Enantiospecific total synthesis of (+)-vellosimine, (+)-normacusine B, (-)-alkaloid Q3, (-)-panarine, (+)-Na-methylvellosimine, and (+)-Na-methyl-16-epipericyclivine. J Org Chem. 2003 Oct 3;68(20):7565-81. PubMed PMID: 14510528.

16: Schmidt D, Stöckigt J. Enzymatic formation of the sarpagan-bridge: a key step in the biosynthesis of sarpagine- and ajmaline-type alkaloids. Planta Med. 1995 Jun;61(3):254-8. PubMed PMID: 17238077.

17: Zaima K, Koga I, Iwasawa N, Hosoya T, Hirasawa Y, Kaneda T, Ismail IS, Lajis NH, Morita H. Vasorelaxant activity of indole alkaloids from Tabernaemontana dichotoma. J Nat Med. 2013 Jan;67(1):9-16. doi: 10.1007/s11418-012-0638-y. Epub 2012 Feb 21. PubMed PMID: 22350216.

18: Zhou H, Liao X, Yin W, Ma J, Cook JM. General approach for the synthesis of 12-methoxy-substituted sarpagine indole alkaloids including (-)-12-methoxy-N(b)-methylvoachalotine, (+)-12-methoxy-N(a)-methylvellosimine, (+)-12-methoxyaffinisine, and (-)-fuchsiaefoline. J Org Chem. 2006 Jan 6;71(1):251-9. PubMed PMID: 16388644.

19: Sheludko Y, Gerasimenko I, Kolshorn H, Stöckigt J. New alkaloids of the sarpagine group from Rauvolfia serpentina hairy root culture. J Nat Prod. 2002 Jul;65(7):1006-10. PubMed PMID: 12141861.

20: Pfitzner A, Stöckigt J. Characterization of polyneuridine aldehyde esterase, a key enzyme in the biosynthesis of sarpagine/ajmaline type alkaloids. Planta Med. 1983 Aug;48(8):221-7. PubMed PMID: 17404987.