Pachycarpine
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MedKoo CAT#: 584979

CAS#: 492-08-0

Description: 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.


Price and Availability

Size
Price

500mg
USD 230
Size
Price

Size
Price

Pachycarpine, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 584979
Name: Pachycarpine
CAS#: 492-08-0
Chemical Formula: C15H26N2
Exact Mass: 234.2096
Molecular Weight: 234.387
Elemental Analysis: C, 76.87; H, 11.18; N, 11.95


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


Technical Data

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).

Harmonized System Code:
2934.99.90.01


References

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.