Deltaline | CAS#6836-11-9 | Alkaloid & toxin

MedKoo Cat#: 465411 | Name: Deltaline

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Description:

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

Deltaline is an alkaloid and a toxin that has been found in D. barbeyi. It reduces sciatic nerve stimulation-induced compound muscle action potentials (CMAPs) in isolated lizard extensor digitorum longus muscle (IC50 = 156 µM). Deltaline (85 mg/kg) increases the number of falls from a beam and decreases the time spent mobile in an open field test, markers of neuromuscular impairment, in mice. It also induces lethality in mice (LD50 = 113 mg/kg).

Chemical Structure

Deltaline

CAS#6836-11-9

Theoretical Analysis

MedKoo Cat#: 465411

Name: Deltaline

CAS#: 6836-11-9

Chemical Formula: C27H41NO8

Exact Mass: 507.2832

Molecular Weight: 507.62

Elemental Analysis: C, 63.89; H, 8.14; N, 2.76; O, 25.21

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 600.00	2 Weeks

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Related CAS #

No Data

Synonym

Deltaline; Delphelatine; Eldeline

IUPAC/Chemical Name

(3aR,5S,6R,7aS,8S,9S,12R,15S,16R)-14-ethyl-8-hydroxy-5,7,9-trimethoxy-12-methyldodecahydro-9H-8a,12,14b-(epiethane[1,1,2]triyl)-6,8-methano[1,3]dioxolo[4',5':1,8a]naphtho[2,3-b]azocin-15-yl acetate

InChi Key

DTTPWCNKTMQMTE-KDBXVETRSA-N

InChi Code

InChI=1S/C27H41NO8/c1-7-28-12-23(3)9-8-17(32-5)26-20(23)21(36-14(2)29)27(22(26)28)25(34-13-35-27)11-16(31-4)15-10-24(26,30)19(25)18(15)33-6/h15-22,30H,7-13H2,1-6H3/t15-,16+,17+,18?,19+,20-,21+,22?,23+,24+,25-,26?,27?/m1/s1

SMILES Code

CO[C@H]1CC[C@](C2)(C)[C@]([C@@H]3OC(C)=O)([H])C14[C@@](O)([C@@]([H])([C@@]5(C3(C4N2CC)OCO5)C[C@@H]6OC)C7(OC)[H])C[C@@]76[H]

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

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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	59.10
	DMF:PBS (pH 7.2) (1:7)	0.1	0.24
	DMSO	20.0	39.40
	Ethanol	10.0	19.70

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 507.62 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.

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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Sex-dependent differences for larkspur (Delphinium barbeyi) toxicosis in yearling Angus cattle1. J Anim Sci. 2019 Mar 1;97(3):1424-1432. doi: 10.1093/jas/skz002. PMID: 30772914; PMCID: PMC6396263. 5: Huo D, Sun L, Zhang L, Ru X, Liu S, Yang H. Metabolome responses of the sea cucumber Apostichopus japonicus to multiple environmental stresses: Heat and hypoxia. Mar Pollut Bull. 2019 Jan;138:407-420. doi: 10.1016/j.marpolbul.2018.11.063. Epub 2018 Dec 5. PMID: 30660290. 6: Welch KD, Gardner DR, Stonecipher CA, Green BT, Pfister JA. Serum toxicokinetics after intravenous and oral dosing of larkspur toxins in goats. Toxicon. 2017 Jul;133:91-94. doi: 10.1016/j.toxicon.2017.05.008. Epub 2017 May 4. PMID: 28479311. 7: Welch KD, Stonecipher CA, Green BT, Gardner DR, Cook D, Pfister JA. Administering multiple doses of a non N-(methylsuccinimido) anthranoyllycoctonine (MSAL)-containing tall larkspur (Delphinium occidentale) to cattle. Toxicon. 2017 Mar 15;128:46-49. doi: 10.1016/j.toxicon.2017.01.020. Epub 2017 Jan 30. PMID: 28153491. 8: Welch KD, Gardner DR, Green BT, Stonecipher CA, Cook D, Pfister JA. Comparison of the serum toxicokinetics of larkspur toxins in cattle, sheep and goats. Toxicon. 2016 Sep 1;119:270-3. doi: 10.1016/j.toxicon.2016.06.020. Epub 2016 Jun 30. PMID: 27374834. 9: Chen QF, Wang FP, Liu XY. Generating skeletal diversity from the C19 -diterpenoid alkaloid deltaline: a ring-distortion approach. Chemistry. 2015 Jun 8;21(24):8946-50. doi: 10.1002/chem.201500839. Epub 2015 May 7. PMID: 25950550. 10: Wang L, Chen QF, Wang FP. Conversional synthesis of heteratisine. Nat Prod Commun. 2012 Dec;7(12):1583-6. PMID: 23413557. 11: Welch KD, Pfister JA, Lima FG, Green BT, Gardner DR. Effect of α₇ nicotinic acetylcholine receptor agonists and antagonists on motor function in mice. Toxicol Appl Pharmacol. 2013 Feb 1;266(3):366-74. doi: 10.1016/j.taap.2012.11.024. Epub 2012 Dec 4. PMID: 23219611. 12: Wang L, Chen QH, Wang FP. Unusual reactions of a 7,17-seco-type C19-diterpenoid alkaloid derived from deltaline. Nat Prod Commun. 2012 Jun;7(6):721-4. PMID: 22816291. 13: Song L, Chen QH, She XK, Chen XG, Wang FP. Conversional synthesis and cytotoxic evaluation of novel taxoid analogs. J Asian Nat Prod Res. 2011 Sep;13(9):787-98. doi: 10.1080/10286020.2011.591787. PMID: 21830882. 14: Wang XQ, Song Q, Guo XQ, Yan J. Deltaline from Delphinium delavayi Franch. Acta Crystallogr Sect E Struct Rep Online. 2011 Jan 22;67(Pt 2):o439. doi: 10.1107/S1600536811001681. PMID: 21523103; PMCID: PMC3051497. 15: Scholte E, Den Hartog W, Dik M, Schoelitsz B, Brooks M, Schaffner F, Foussadier R, Braks M, Beeuwkes J. Introduction and control of three invasive mosquito species in the Netherlands, July-October 2010. Euro Surveill. 2010 Nov 11;15(45):19710. PMID: 21087591. 16: Green BT, Welch KD, Gardner DR, Stegelmeier BL, Pfister JA, Cook D, Davis TZ. 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