Pachycarpine
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Hodoodo CAT#: H584979

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.

Chemical Structure

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Pachycarpine
CAS# 492-08-0
Instruction

Theoretical Analysis

Hodoodo Cat#: H584979
Name: Pachycarpine
CAS#: 492-08-0
Chemical Formula: C15H26N2
Exact Mass: 234.21
Molecular Weight: 234.387
Elemental Analysis: C, 76.87; H, 11.18; N, 11.95

Price and Availability

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500mg USD 230 2 Weeks
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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:

Biological target:
In vitro activity:
In vivo activity:

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:
In vitro protocol:
In vivo protocol:

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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.

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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.

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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.

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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.