Oxysophocarpine
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MedKoo CAT#: 573972

CAS#: 26904-64-3

Description: Oxysophocarpine is an alkaloid from S. flavescens that has neuroprotective, anticancer, anti-inflammatory, and analgesic properties. It increases cell survival and decreases lactate dehydrogenase (LDH) leakage and loss of mitochondrial membrane potential in rat primary hippocampal neurons in a model of oxygen-glucose deprivation and reperfusion injury when used at concentrations of 1, 2, and 5 μM. Oxysophocarpine inhibits proliferation and reduces migration and invasion of SCC-9 and SCC-15 oral squamous cell carcinoma (OSCC) cells in vitro. It reduces tumor growth in an SCC-9 mouse xenograft model and inhibits xylene-induced ear swelling and carrageenan-induced paw edema. It also reduces carrageenan-induced decreases in the paw withdrawal threshold and prevents carrageenan-induced increases in paw tissue levels of TNF-α, IL-1β, IL-6, and prostaglandin E2 (PGE2) in mice when administered at a dose of 80 mg/kg.


Chemical Structure

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Oxysophocarpine
CAS# 26904-64-3

Theoretical Analysis

MedKoo Cat#: 573972
Name: Oxysophocarpine
CAS#: 26904-64-3
Chemical Formula: C15H22N2O2
Exact Mass: 262.1681
Molecular Weight: 262.35
Elemental Analysis: C, 68.67; H, 8.45; N, 10.68; O, 12.20

Price and Availability

Size Price Availability Quantity
10.0mg USD 310.0 2 Weeks
50.0mg USD 810.0 2 Weeks
100.0mg USD 1425.0 2 Weeks
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Synonym: (+)-Oxysophocarpine; Oxysophocarpine, Sophocarpine N-oxide

IUPAC/Chemical Name: (4R,7aS,13aR,13bR,13cS)-2,3,6,7,7a,8,13,13a,13b,13c-decahydro-1H,5H,10H-dipyrido[2,1-f:3',2',1'-ij][1,6]naphthyridin-10-one, 4-oxide

InChi Key: QMGGMESMCJCABO-RDVIFRKPSA-N

InChi Code: InChI=1S/C15H22N2O2/c18-14-7-1-6-13-12-5-3-9-17(19)8-2-4-11(15(12)17)10-16(13)14/h1,7,11-13,15H,2-6,8-10H2/t11-,12+,13+,15?,17+/m0/s1

SMILES Code: O=C1C=CC[C@]2([H])[C@@]3([H])CCC[N@@+]4([O-])C3[C@](CCC4)([H])CN21

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

Preparing Stock Solutions

The following data is based on the product molecular weight 262.35 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

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1. Zhu, Q.-L., Li, Y.-X., Zhou, R., et al. Neuroprotective effects of oxysophocarpine on neonatal rat primary cultured hippocampal neurons injured by oxygen-glucose deprivation and reperfusion. Pharm. Biol. 52(8), 1052-1059 (2014).

2. Liu, R., Peng, J., Wang, H., et al. Oxysophocarpine retards the growth and metastasis of oral squamous cell carcinoma by targeting the Nrf2/HO-1 axis. Cell Physiol. Biochem. 49(5), 1717-1733 (2018).

3. Yang, Y., Li, Y.-X., Wang, H.-L., et al. Oxysophocarpine ameliorates carrageenan-induced inflammatory pain via inhibiting expressions of prostaglandin E2 and cytokines in mice. Planta Med. 81(10), 791-797 (2015).