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MedKoo Cat#: 581716 | Name: Pumiliotoxin C

Description:

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

Pumiliotoxins (PTXs), are one of several toxins found in the skin of poison dart frogs. There are three different types of this toxin: A, B and C, of which toxins A and B are more toxic than C. Pumiliotoxins interfere with muscle contraction by affecting calcium channels, causing partial paralysis, difficulty moving, hyperactivity, or death.

Chemical Structure

Pumiliotoxin C
Pumiliotoxin C
CAS#27766-71-8

Theoretical Analysis

MedKoo Cat#: 581716

Name: Pumiliotoxin C

CAS#: 27766-71-8

Chemical Formula: C13H25N

Exact Mass: 195.1987

Molecular Weight: 195.35

Elemental Analysis: C, 79.93; H, 12.90; N, 7.17

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 #
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Synonym
Pumiliotoxin C; 5-Methyl-2-propyldecahydroquinoline; Decahydro-5-methyl-2-propylquinoline.
IUPAC/Chemical Name
(2S,4aS,5R,8aS)-5-methyl-2-propyldecahydroquinoline
InChi Key
PSGDYNNBBROEEW-VOAKCMCISA-N
InChi Code
InChI=1S/C13H25N/c1-3-5-11-8-9-12-10(2)6-4-7-13(12)14-11/h10-14H,3-9H2,1-2H3/t10-,11+,12+,13+/m1/s1
SMILES Code
C1C[C@@H](C)[C@@H]2CC[C@@H](N[C@H]2C1)CCC
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 195.35 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: Qu J, Helmchen G. Applications of Iridium-Catalyzed Asymmetric Allylic Substitution Reactions in Target-Oriented Synthesis. Acc Chem Res. 2017 Oct 17;50(10):2539-2555. doi: 10.1021/acs.accounts.7b00300. Epub 2017 Sep 22. PubMed PMID: 28937739. 2: Tarvin RD, Santos JC, O'Connell LA, Zakon HH, Cannatella DC. Convergent Substitutions in a Sodium Channel Suggest Multiple Origins of Toxin Resistance in Poison Frogs. Mol Biol Evol. 2016 Apr;33(4):1068-81. doi: 10.1093/molbev/msv350. Epub 2016 Jan 18. PubMed PMID: 26782998. 3: Suryavanshi PA, Sridharan V, Maiti S, Menéndez JC. Fully diastereoselective synthesis of polysubstituted, functionalized piperidines and decahydroquinolines based on multicomponent reactions catalyzed by cerium(IV) ammonium nitrate. Chemistry. 2014 Jul 7;20(28):8791-9. doi: 10.1002/chem.201402607. Epub 2014 Jun 6. PubMed PMID: 24909665. 4: Dion I, Vincent-Rocan JF, Zhang L, Cebrowski PH, Lebrun ME, Pfeiffer JY, Bédard AC, Beauchemin AM. Studies on difficult intramolecular hydroaminations in the context of four syntheses of alkaloid natural products. J Org Chem. 2013 Dec 20;78(24):12735-49. doi: 10.1021/jo4023149. Epub 2013 Dec 4. PubMed PMID: 24274926. 5: Gärtner M, Qu J, Helmchen G. Enantioselective syntheses of the alkaloids cis-195A (pumiliotoxin C) and trans-195A based on multiple applications of asymmetric catalysis. J Org Chem. 2012 Jan 20;77(2):1186-90. doi: 10.1021/jo202241b. Epub 2011 Dec 30. PubMed PMID: 22175856. 6: Maiti S, Menéndez JC. Brief, efficient and highly diastereoselective synthesis of (±)-pumiliotoxin C based on the generation of an octahydroquinoline precursor via a four-component reaction. Chem Commun (Camb). 2011 Oct 14;47(38):10554-6. doi: 10.1039/c1cc11246e. Epub 2011 May 6. PubMed PMID: 21547288. 7: Amat M, Fabregat R, Griera R, Florindo P, Molins E, Bosch J. Biomimetic construction of the hydroquinoline ring system. Diastereodivergent enantioselective synthesis of 2,5-disubstituted cis-decahydroquinolines. J Org Chem. 2010 Jun 4;75(11):3797-805. doi: 10.1021/jo1005894. PubMed PMID: 20433146. 8: Fearnley SP, Thongsornkleeb C. Oxazolone cycloadducts as heterocyclic scaffolds for alkaloid construction: synthesis of (+/-)-2-epi-pumiliotoxin C. J Org Chem. 2010 Feb 5;75(3):933-6. doi: 10.1021/jo902172r. PubMed PMID: 20039614; PubMed Central PMCID: PMC2872181. 9: Lauzon S, Tremblay F, Gagnon D, Godbout C, Chabot C, Mercier-Shanks C, Perreault S, DeSève H, Spino C. Sterically biased 3,3-sigmatropic rearrangement of chiral allylic azides: application to the total syntheses of alkaloids. J Org Chem. 2008 Aug 15;73(16):6239-50. doi: 10.1021/jo800817p. Epub 2008 Jul 22. PubMed PMID: 18642871. 10: Holub N, Neidhöfer J, Blechert S. Total synthesis of (+)-trans-195A. Org Lett. 2005 Mar 31;7(7):1227-9. PubMed PMID: 15787473. 11: Mori M. [Development of new synthetic method using organometallic complexes and an application toward natural product synthesis]. Yakugaku Zasshi. 2005 Jan;125(1):51-72. Review. Japanese. PubMed PMID: 15635281. 12: Sklenicka HM, Hsung RP, McLaughlin MJ, Wei LL, Gerasyuto AI, Brennessel WB. Stereoselective formal [3 + 3] cycloaddition approach to cis-1-azadecalins and synthesis of (-)-4a,8a-diepi-pumiliotoxin C. evidence for the first highly stereoselective 6pi-electron electrocyclic ring closures of 1-azatrienes. J Am Chem Soc. 2002 Sep 4;124(35):10435-42. PubMed PMID: 12197745. 13: Akashi M, Sato Y, Mori M. Synthesis of pumiliotoxine C from molecular nitrogen as a nitrogen source. J Org Chem. 2001 Nov 16;66(23):7873-4. PubMed PMID: 11701050. 14: Padwa A, Heidelbaugh TM, Kuethe JT. Using the Pummerer cyclization-deprotonation-cycloaddition cascade of imidosulfoxides for alkaloid synthesis. J Org Chem. 2000 Apr 21;65(8):2368-78. PubMed PMID: 10789448. 15: Daly JW, Nishizawa Y, Padgett WL, Tokuyama T, McCloskey PJ, Waykole L, Schultz AG, Aronstam RS. Decahydroquinoline alkaloids: noncompetitive blockers for nicotinic acetylcholine receptor-channels in pheochromocytoma cells and Torpedo electroplax. Neurochem Res. 1991 Nov;16(11):1207-12. PubMed PMID: 1815136. 16: Daly JW, Nishizawa Y, Edwards MW, Waters JA, Aronstam RS. Nicotinic receptor-elicited sodium flux in rat pheochromocytoma PC12 cells: effects of agonists, antagonists, and noncompetitive blockers. Neurochem Res. 1991 Apr;16(4):489-500. PubMed PMID: 1922660. 17: Warnick JE, Jessup PJ, Overman LE, Eldefrawi ME, Nimit Y, Daly JW, Albuquerque EX. Pumiliotoxin-C and synthetic analogues. A new class of nicotinic antagonists. Mol Pharmacol. 1982 Nov;22(3):565-73. PubMed PMID: 6130469. 18: Daly JW. Alkaloids of neotropical poison frogs (Dendrobatidae). Fortschr Chem Org Naturst. 1982;41:205-340. Review. PubMed PMID: 7049875. 19: Oppolzer W, Fehr C, Warneke J. A new total synthesis of dl-pumiliotoxin-C via an indanone. Helv Chim Acta. 1977 Jan 26;60(1):48-58. PubMed PMID: 838598. 20: Oppolzer W, Flaskamp E. An enantioselective synthesis and the absolute configuration of natural pumiliotoxin-C. Helv Chim Acta. 1977 Jan 26;60(1):204-7. PubMed PMID: 838595.

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PUN88048

PUN88048