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MedKoo Cat#: 530273 | Name: Hippadine

Description:

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

Hippadine is isolated from Crinum bulbs and has reproductive effect.

Chemical Structure

Hippadine
Hippadine
CAS#52886-06-3

Theoretical Analysis

MedKoo Cat#: 530273

Name: Hippadine

CAS#: 52886-06-3

Chemical Formula: C16H9NO3

Exact Mass: 263.0582

Molecular Weight: 263.25

Elemental Analysis: C, 73.00; H, 3.45; N, 5.32; O, 18.23

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Hippadine
IUPAC/Chemical Name
7H-(1,3)Dioxolo(4,5-j)pyrrolo(3,2,1-de)phenanthridin-7-one
InChi Key
DONUVZIVKLIMJU-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H9NO3/c18-16-12-7-14-13(19-8-20-14)6-11(12)10-3-1-2-9-4-5-17(16)15(9)10/h1-7H,8H2
SMILES Code
O=C1N2C3=C(C=C2)C=CC=C3C4=C1C=C5C(OCO5)=C4
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 263.25 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: Masi M, Cala A, Tabanca N, Cimmino A, Green IR, Bloomquist JR, van Otterlo WA, Macias FA, Evidente A. Alkaloids with Activity against the Zika Virus Vector Aedes aegypti (L.)-Crinsarnine and Sarniensinol, Two New Crinine and Mesembrine Type Alkaloids Isolated from the South African Plant Nerine sarniensis. Molecules. 2016 Oct 27;21(11). pii: E1432. PubMed PMID: 27801807. 2: Presley CC, Krai P, Dalal S, Su Q, Cassera M, Goetz M, Kingston DGI. New potently bioactive alkaloids from Crinum erubescens. Bioorg Med Chem. 2016 Nov 1;24(21):5418-5422. doi: 10.1016/j.bmc.2016.08.058. Epub 2016 Aug 30. PubMed PMID: 27624525; PubMed Central PMCID: PMC5065785. 3: Mugabo P, Philander A, Raji I, Dietrich D, Green I. Effects of hippadine on the blood pressure and heart rate in male spontaneously hypertensive Wistar rats. J Ethnopharmacol. 2014 Dec 2;158 Pt A:123-31. doi: 10.1016/j.jep.2014.10.011. Epub 2014 Oct 18. PubMed PMID: 25456427. 4: Tsukano C, Muto N, Enkhtaivan I, Takemoto Y. Synthesis of pyrrolophenanthridine alkaloids based on C(sp³)-H and C(sp²)-H functionalization reactions. Chem Asian J. 2014 Sep;9(9):2628-34. doi: 10.1002/asia.201402490. Epub 2014 Jul 14. PubMed PMID: 25044314. 5: Kumar A, Akula HK, Lakshman MK. Simple Synthesis of Amides and Weinreb Amides via Use of PPh(3) or Polymer-Supported PPh(3) and Iodine. European J Org Chem. 2010 May;2010(14). doi: 10.1002/ejoc.200901420. PubMed PMID: 24223494; PubMed Central PMCID: PMC3818920. 6: Nkanwen ER, Gatsing D, Ngamga D, Fodouop SP, Tane P. Antibacterial agents from the leaves of Crinum purpurascens herb (Amaryllidaceae). Afr Health Sci. 2009 Dec;9(4):264-9. PubMed PMID: 21503179; PubMed Central PMCID: PMC3074400. 7: Mentzel UV, Tanner D, Tønder JE. Comparative study of the Kumada, Negishi, Stille, and Suzuki-Miyaura reactions in the synthesis of the indole alkaloids hippadine and pratosine. J Org Chem. 2006 Jul 21;71(15):5807-10. PubMed PMID: 16839172. 8: Kissling J, Ioset JR, Marston A, Hostettmann K. Bio-guided isolation of cholinesterase inhibitors from the bulbs of Crinum x powellii. Phytother Res. 2005 Nov;19(11):984-7. PubMed PMID: 16317657. 9: Ganton MD, Kerr MA. A domino amidation route to indolines and indoles: rapid syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine. Org Lett. 2005 Oct 13;7(21):4777-9. PubMed PMID: 16209533. 10: Hiroya K, Itoh S, Sakamoto T. Development of an efficient procedure for indole ring synthesis from 2-ethynylaniline derivatives catalyzed by CuII salts and its application to natural product synthesis. J Org Chem. 2004 Feb 20;69(4):1126-36. PubMed PMID: 14961661. 11: Hartung CG, Fecher A, Chapell B, Snieckus V. Directed ortho metalation approach to C-7-substituted indoles. Suzuki-Miyaura cross coupling and the synthesis of pyrrolophenanthridone alkaloids. Org Lett. 2003 May 29;5(11):1899-902. PubMed PMID: 12762681. 12: Padwa A, Brodney MA, Liu B, Satake K, Wu T. A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines. J Org Chem. 1999 May 14;64(10):3595-3607. PubMed PMID: 11674487. 13: Boger DL, Wolkenberg SE. Total synthesis of Amaryllidaceae alkaloids utilizing sequential intramolecular heterocyclic azadiene Diels-Alder reactions of an unsymmetrical 1,2,4,5-tetrazine. J Org Chem. 2000 Dec 29;65(26):9120-4. PubMed PMID: 11149859. 14: Koorbanally N, Mulholland DA, Crouch N. Alkaloids and triterpenoids from Ammocharis coranica (Amaryllidaceae). Phytochemistry. 2000 May;54(1):93-7. PubMed PMID: 10846753. 15: Chattopadhyay S, Chattopadhyay U, Mathur PP, Saini KS, Ghosal S. Effects of hippadine, an Amaryllidaceae alkaloid, on testicular function in rats. Planta Med. 1983 Dec;49(4):252-4. PubMed PMID: 6669644.