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MedKoo Cat#: 584979 | Name: Pachycarpine
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Description:

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

Pachycarpine may decrease hyperexcitability through the activation of the M2 and M4 subtypes of mAChRs, which is a probable mechanism of action that together with its systemic effects may favor its anticonvulsant effects against seizures and SE.

Chemical Structure

Pachycarpine
Pachycarpine
CAS#492-08-0

Theoretical Analysis

MedKoo Cat#: 584979

Name: Pachycarpine

CAS#: 492-08-0

Chemical Formula: C15H26N2

Exact Mass: 234.2096

Molecular Weight: 234.39

Elemental Analysis: C, 76.87; H, 11.18; N, 11.95

Price and Availability

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500mg USD 425.00
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Related CAS #
No Data
Synonym
Pachycarpine; (+)-Sparteine; d-Sparteine
IUPAC/Chemical Name
(7R-(7alpha,7aalpha,14alpha,14abeta))-Dodecahydro-7,14-methano-2H,6H-dipyrido (1,2-a:1',2'-e)(1,5)diazocine
InChi Key
SLRCCWJSBJZJBV-TUVASFSCSA-N
InChi Code
InChI=1S/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14-,15+/m1/s1
SMILES Code
[H][C@]1(C2)[C@@](CCCC3)([H])N3C[C@]2([H])[C@](CCCC4)([H])N4C1
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
(+)-Sparteine competitively blocks nicotinic ACh receptor in the neurons.
In vitro activity:
The effects of (+)-sparteine, a ganglionic blocking agent, on acetylcholine (ACh)-induced membrane currents and on fast excitatory postsynaptic currents (EPSCs) were studied in the neurons of rat isolated superior cervical ganglion, with the whole-cell patch-clamp recording method and the two-electrode voltage-clamp method, respectively. (+)-Sparteine (2 microM) reduced the ACh-induced current caused by activation of nicotinic ACh receptors (AChRs) in a voltage-independent manner at membrane potentials of -50 mV to +30 mV, whereas its blocking effect increased at more negative membrane potentials. The dose-response relationship for ACh was modified by 2 microM (+)-sparteine at -50 mV and at -90 mV in a fashion typical for competitive rather than noncompetitive antagonists. Reference: Mol Pharmacol. 1991 Aug;40(2):180-5. https://pubmed.ncbi.nlm.nih.gov/1715014/
In vivo activity:
In the nervous system, sparteine has been shown to display anti-cholinergic and depressive activity, although how sparteine exerts its toxic effects in the brain remains unclear. This study has addressed this issue by administering subcutaneous injections of sparteine (25 mg/kg of body weight) to rats on postnatal days 1 and 3, and then examining the expression of the muscarinic acetylcholine receptor (mAChR) subunits m1-m4 in the brains of the neonatal rats 14-60 days later. Administration of sparteine to neonatal rats caused neuronal damage in the cerebral motor cortex accompanied by transient changes in the expression of m1-m4 mAChR subunits as revealed by both RT-PCR and Western blotting. Reference: Int J Dev Neurosci. 2006 Oct;24(6):401-10. https://pubmed.ncbi.nlm.nih.gov/16843632/
Solvent mg/mL mM
Solubility
DMF 11.0 46.93
DMSO 33.0 140.79
Ethanol 20.0 85.33
PBS (pH 7.2) 2.0 8.53
Water 2.9 12.20
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 234.39 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
Formulation protocol:
1. Boido V, Ercoli M, Tonelli M, Novelli F, Tasso B, Sparatore F, Cichero E, Fossa P, Dorigo P, Froldi G. New arylsparteine derivatives as positive inotropic drugs. J Enzyme Inhib Med Chem. 2017 Dec;32(1):588-599. doi: 10.1080/14756366.2017.1279156. PMID: 28133984; PMCID: PMC6009970. 2. Voitenko S, Purnyn S, Omeltchenko I, Dyadyusha GG, Zhorov B, Brovtsina N, Skok V. Effect of (+)-sparteine on nicotinic acetylcholine receptors in the neurons of rat superior cervical ganglion. Mol Pharmacol. 1991 Aug;40(2):180-5. PMID: 1715014. 3. Flores-Soto ME, Bañuelos-Pineda J, Orozco-Suárez S, Schliebs R, Beas-Zárate C. Neuronal damage and changes in the expression of muscarinic acetylcholine receptor subtypes in the neonatal rat cerebral cortical upon exposure to sparteine, a quinolizidine alkaloid. Int J Dev Neurosci. 2006 Oct;24(6):401-10. doi: 10.1016/j.ijdevneu.2006.05.004. Epub 2006 Jul 14. PMID: 16843632.
In vitro protocol:
1. Boido V, Ercoli M, Tonelli M, Novelli F, Tasso B, Sparatore F, Cichero E, Fossa P, Dorigo P, Froldi G. New arylsparteine derivatives as positive inotropic drugs. J Enzyme Inhib Med Chem. 2017 Dec;32(1):588-599. doi: 10.1080/14756366.2017.1279156. PMID: 28133984; PMCID: PMC6009970. 2. Voitenko S, Purnyn S, Omeltchenko I, Dyadyusha GG, Zhorov B, Brovtsina N, Skok V. Effect of (+)-sparteine on nicotinic acetylcholine receptors in the neurons of rat superior cervical ganglion. Mol Pharmacol. 1991 Aug;40(2):180-5. PMID: 1715014.
In vivo protocol:
1. Flores-Soto ME, Bañuelos-Pineda J, Orozco-Suárez S, Schliebs R, Beas-Zárate C. Neuronal damage and changes in the expression of muscarinic acetylcholine receptor subtypes in the neonatal rat cerebral cortical upon exposure to sparteine, a quinolizidine alkaloid. Int J Dev Neurosci. 2006 Oct;24(6):401-10. doi: 10.1016/j.ijdevneu.2006.05.004. Epub 2006 Jul 14. PMID: 16843632.
1: Piotrovskiĭ VK, Belolipetskaia VG, Rumiantsev DO, Metelitsa VI. [The polymorphism of pachycarpine oxidation]. Eksp Klin Farmakol. 1992 Jul-Aug;55(4):56-8. Russian. PubMed PMID: 1458193. 2: Gawali VS, Simeonov S, Drescher M, Knott T, Scheel O, Kudolo J, Kählig H, Hochenegg U, Roller A, Todt H, Maulide N. C2-Modified Sparteine Derivatives Are a New Class of Potentially Long-Acting Sodium Channel Blockers. ChemMedChem. 2017 Nov 22;12(22):1819-1822. doi: 10.1002/cmdc.201700568. Epub 2017 Nov 6. PubMed PMID: 29045055. 3: Parmaki S, Vyrides I, Vasquez MI, Hartman V, Zacharia I, Hadjiadamou I, Barbeitos CBM, Ferreira FC, Afonso CAM, Drouza C, Koutinas M. Bioconversion of alkaloids to high-value chemicals: Comparative analysis of newly isolated lupanine degrading strains. Chemosphere. 2018 Feb;193:50-59. doi: 10.1016/j.chemosphere.2017.10.165. Epub 2017 Oct 30. PubMed PMID: 29126065. 4: Boido V, Ercoli M, Tonelli M, Novelli F, Tasso B, Sparatore F, Cichero E, Fossa P, Dorigo P, Froldi G. New arylsparteine derivatives as positive inotropic drugs. J Enzyme Inhib Med Chem. 2017 Dec;32(1):588-599. doi: 10.1080/14756366.2017.1279156. PubMed PMID: 28133984; PubMed Central PMCID: PMC6009970. 5: ANISIMOVA MI. [Acceleration of labor with pachycarpine]. Akush Ginekol (Mosk). 1953 Jul-Aug;4:35-7. Undetermined Language. PubMed PMID: 13091990. 6: Villalpando-Vargas F, Medina-Ceja L. Sparteine as an anticonvulsant drug: Evidence and possible mechanism of action. Seizure. 2016 Jul;39:49-55. doi: 10.1016/j.seizure.2016.05.010. Epub 2016 May 24. Review. PubMed PMID: 27262285. 7: Ebner T, Eichelbaum M, Fischer P, Meese CO. [Stereospecific hydroxylation of (+)-sparteine (pachycarpine) in the rat]. Arch Pharm (Weinheim). 1989 Jul;322(7):399-403. German. PubMed PMID: 2783013. 8: MASHKOVSKII MD. [Pachycarpine]. Med Prom SSSR. 1952 Sep-Oct;6(5):37-8. Undetermined Language. PubMed PMID: 13012774. 9: Basilico N, Parapini S, Sparatore A, Romeo S, Misiano P, Vivas L, Yardley V, Croft SL, Habluetzel A, Lucantoni L, Renia L, Russell B, Suwanarusk R, Nosten F, Dondio G, Bigogno C, Jabes D, Taramelli D. In Vivo and In Vitro Activities and ADME-Tox Profile of a Quinolizidine-Modified 4-Aminoquinoline: A Potent Anti-P. falciparum and Anti-P. vivax Blood-Stage Antimalarial. Molecules. 2017 Dec 1;22(12). pii: E2102. doi: 10.3390/molecules22122102. PubMed PMID: 29194347; PubMed Central PMCID: PMC6149971. 10: SHASS EIu. [Pachycarpine]. Feldsher Akush. 1954 Jan;1:52-4. Undetermined Language. PubMed PMID: 13142061. 11: Davies SG, Fletcher AM, Foster EM, Houlsby IT, Roberts PM, Schofield TM, Thomson JE. An efficient asymmetric synthesis of (-)-lupinine. Chem Commun (Camb). 2014 Aug 7;50(61):8309-11. doi: 10.1039/c4cc02135e. PubMed PMID: 24938152. 12: Meraz Medina T, Bañuelos Pineda J, Gómez Rodiles CC, Vallejo SJ, Zamora RS, García López PM. Identification of brain areas sensitive to the toxic effects of sparteine. Exp Toxicol Pathol. 2017 Jan;69(1):27-31. doi: 10.1016/j.etp.2016.10.005. Epub 2016 Nov 5. PubMed PMID: 27825754. 13: RABINOVICH IuIa, SHAPIRO IuV. [CLINICAL PICTURE AND TREATMENT OF PACHYCARPINE POISONING]. Sov Med. 1964 Nov;27:126-30. Russian. PubMed PMID: 14311410. 14: Detheridge AP, Griffith GW, Hopper DJ. Genome Sequence Analysis of Two Pseudomonas putida Strains to Identify a 17-Hydroxylase Putatively Involved in Sparteine Degradation. Curr Microbiol. 2018 Dec;75(12):1649-1654. doi: 10.1007/s00284-018-1573-2. Epub 2018 Sep 28. PubMed PMID: 30267141; PubMed Central PMCID: PMC6208669. 15: Kolodiazhnyi OI. Recent advances in asymmetric synthesis of Р-stereogenic phosphorus compounds. Top Curr Chem. 2015;360:161-236. doi: 10.1007/128_2014_564. Review. PubMed PMID: 25326833. 16: Cochrane EJ, Leonori D, Hassall LA, Coldham I. Synthesis and kinetic resolution of N-Boc-2-arylpiperidines. Chem Commun (Camb). 2014 Sep 7;50(69):9910-3. doi: 10.1039/c4cc04576a. PubMed PMID: 25030082. 17: Ebner T, Meese CO, Eichelbaum M. Regioselectivity and stereoselectivity of the metabolism of the chiral quinolizidine alkaloids sparteine and pachycarpine in the rat. Xenobiotica. 1991 Jul;21(7):847-57. PubMed PMID: 1776260. 18: Green BT, Lee ST, Welch KD, Cook D. Anagyrine desensitization of peripheral nicotinic acetylcholine receptors. A potential biomarker of quinolizidine alkaloid teratogenesis in cattle. Res Vet Sci. 2017 Dec;115:195-200. doi: 10.1016/j.rvsc.2017.04.019. Epub 2017 May 2. PubMed PMID: 28494312. 19: Arnold SE, Peralta Idrovo ME, Lomas Arias LJ, Belmain SR, Stevenson PC. Herbivore defence compounds occur in pollen and reduce bumblebee colony fitness. J Chem Ecol. 2014 Aug;40(8):878-81. doi: 10.1007/s10886-014-0467-4. Epub 2014 Jun 21. PubMed PMID: 24952086. 20: Wiedemann M, Gurrola-Díaz CM, Vargas-Guerrero B, Wink M, García-López PM, Düfer M. Lupanine Improves Glucose Homeostasis by Influencing KATP Channels and Insulin Gene Expression. Molecules. 2015 Oct 20;20(10):19085-100. doi: 10.3390/molecules201019085. PubMed PMID: 26492234; PubMed Central PMCID: PMC6332548.