Stylopine | CAS#4312-32-7 | Anti-inflammatory alkaloid

MedKoo Cat#: 562622 | Name: Stylopine

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Description:

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

Tetrahydrocoptisine is an alkaloid that has been found in C. impatiens and has anti-inflammatory and antioxidant activities. It inhibits LPS-induced NF-κB activation and production of nitric oxide (NO), TNF-α, and IL-6 in isolated mouse peritoneal macrophages when used at concentrations ranging from 0.001 to 1 µg/ml. Tetrahydrocoptisine (10 and 30 mg/kg) inhibits xylene-induced ear edema in mice, and it decreases serum levels of TNF-α in a mouse model of LPS-induced septic shock. It reduces the severity of ethanol-induced gastric ulcers in mice when administered at doses of 10 or 20 mg/kg.

Chemical Structure

Stylopine

CAS#4312-32-7 (racemic)

Theoretical Analysis

MedKoo Cat#: 562622

Name: Stylopine

CAS#: 4312-32-7 (racemic)

Chemical Formula: C19H17NO4

Exact Mass: 323.1100

Molecular Weight: 323.34

Elemental Analysis: C, 70.58; H, 5.30; N, 4.33; O, 19.79

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 #

84-39-9 (S-isomer) 4312-32-7 (racemic) 7461-02-1 (racemic)

Synonym

Stylopine; (±)-Stylopine; Tetrahydrocoptisine; (R,S±)-Stylopine; (R,S±) Stylopine; NSC 110382; NSC-110382; NSC110382; NSC 404529; NSC-404529; NSC404529;

IUPAC/Chemical Name

6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4',5':7,8]isoquinolino[3,2-a][1,3]dioxolo[4,5-g]isoquinoline

InChi Key

UXYJCYXWJGAKQY-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2

SMILES Code

C12=CC(OCO3)=C3C=C1C(CC(C=CC4=C5OCO4)=C5C6)N6CC2

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

>2 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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	DMF	1.0	3.09
	Chloroform	5.0	15.46

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 323.34 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

1: BANDELIN FJ, MALESH W. Alkaloids of Chelidonium majus, L., leaves and stems. I. dl-Tetrahydrocoptisine. J Am Pharm Assoc Am Pharm Assoc. 1956 Oct;45(10):702-4. doi: 10.1002/jps.3030451014. PMID: 13366815. 2: Lavenir R, Paris RR. Sur les alcaloïdes de la chélidoine (Chelidonium majus L.). Répartition dans divers organes, isolement de la stylopine à partir des fruits [On the alkaloids of the great celandine (Chelidonium majus L.). Distribution in different organs, isolation of stylopine from the fruit]. Ann Pharm Fr. 1965 May;23(5):307-12. French. PMID: 5891472. 3: Preininger V, Thakur RS, Santavý F. Isolation and chemistry of alkaloids from plants of the family Papaveraceae LXVII: Corydalis cava (L.) Sch. et K. (C. tuberosa DC). J Pharm Sci. 1976 Feb;65(2):294-6. doi: 10.1002/jps.2600650230. PMID: 1255467. 4: El-Masry S, El-Ghazooly MG, Omar AA, Khafagy SM, Phillipson JD. Alkaloids from Egyptian Papaver rhoeas. Planta Med. 1981 Jan;41(1):61-4. doi: 10.1055/s-2007-971675. PMID: 17401817. 5: Kiryakov HG, Iskrenova E, Kuzmanov B, Evstatieva L. Alkaloids from Corydalis marschalliana. Planta Med. 1981 Mar;41(3):298-302. doi: 10.1055/s-2007-971718. PMID: 17401850. 6: Kiryakov HG, Iskrenova E, Kuzmanov B, Evstatieva L. Alkaloids from Corydalis bulbosa. Planta Med. 1981 Sep;43(1):51-5. doi: 10.1055/s-2007-971472. PMID: 17402008. 7: Kiryakov HG, Iskrenova E, Daskalova E, Kuzmanov B, Evstatieva L. Alkaloids of Corydalis slivenensis. Planta Med. 1982 Mar;44(3):168-70. doi: 10.1055/s-2007-971432. PMID: 17402105. 8: Popova ME, Simánek V, Dolejs L, Smysl B, Preininger V. Alkaloids from Fumaria parviflora and F. kralikii. Planta Med. 1982 Jun;45(2):120-2. doi: 10.1055/s-2007-971259. PMID: 17396798. 9: Bhakuni DS, Chaturvedi R. The alkaloids of Corydalis meifolia. J Nat Prod. 1983 May-Jun;46(3):320-4. doi: 10.1021/np50027a004. PMID: 6619883. 10: Bhakuni DS, Chaturvedi R. The alkaloids of Corydalis meifolia. J Nat Prod. 1983 Jul-Aug;46(4):466-70. doi: 10.1021/np50028a006. PMID: 6631434. 11: Válka I, Walterová D, Popova ME, Preininger V, Simánek V. Separation and Quantification of Some Alkaloids from Fumaria parviflora by Capillary Isotachophoresis1. Planta Med. 1985 Aug;51(4):319-22. doi: 10.1055/s-2007-969501. PMID: 17340523. 12: Han BY, Liu GQ. [Effect of tetrahydroisoquinoline alkaloids on alpha adrenoceptors in rat brain]. Yao Xue Xue Bao. 1988 Nov;23(11):806-11. Chinese. PMID: 2855775. 13: Hou YF, Liu GQ. [The effects of tetrandrine, berbamine and some other tetrahydroisoquinolines on [3H] QNB binding to M-cholinergic receptors in rat brain]. Yao Xue Xue Bao. 1988 Nov;23(11):801-5. Chinese. PMID: 3257033. 14: Zhou JY, Tong XJ, Lian WY, Fang QC. Chemical Study on the Alkaloids of Corydalis hsuchowensis. Planta Med. 1991 Apr;57(2):156-8. doi: 10.1055/s-2006-960054. PMID: 17226140. 15: Kubo M, Matsuda H, Tokuoka K, Ma S, Shiomoto H. Anti-inflammatory activities of methanolic extract and alkaloidal components from Corydalis tuber. Biol Pharm Bull. 1994 Feb;17(2):262-5. doi: 10.1248/bpb.17.262. PMID: 7515744. 16: Häberlein H, Tschiersch KP, Boonen G, Hiller KO. Chelidonium majus L.: components with in vitro affinity for the GABAA receptor. Positive cooperation of alkaloids. Planta Med. 1996 Jun;62(3):227-31. doi: 10.1055/s-2006-957865. PMID: 8693034. 17: Satou T, Koga M, Matsuhashi R, Koike K, Tada I, Nikaido T. Assay of nematocidal activity of isoquinoline alkaloids using third-stage larvae of Strongyloides ratti and S. venezuelensis. Vet Parasitol. 2002 Mar 1;104(2):131-8. doi: 10.1016/s0304-4017(01)00619-7. PMID: 11809332. 18: Suau R, Cabezudo B, Rico R, Nájera F, López-Romero JM. Direct determination of alkaloid contents in Fumaria species by GC-MS. Phytochem Anal. 2002 Nov- Dec;13(6):363-7. doi: 10.1002/pca.669. PMID: 12494757. 19: Ikezawa N, Tanaka M, Nagayoshi M, Shinkyo R, Sakaki T, Inouye K, Sato F. Molecular cloning and characterization of CYP719, a methylenedioxy bridge- forming enzyme that belongs to a novel P450 family, from cultured Coptis japonica cells. J Biol Chem. 2003 Oct 3;278(40):38557-65. doi: 10.1074/jbc.M302470200. Epub 2003 May 5. PMID: 12732624. 20: Jang SI, Kim BH, Lee WY, An SJ, Choi HG, Jeon BH, Chung HT, Rho JR, Kim YJ, Chai KY. Stylopine from Chelidonium majus inhibits LPS-induced inflammatory mediators in RAW 264.7 cells. Arch Pharm Res. 2004 Sep;27(9):923-9. doi: 10.1007/BF02975845. PMID: 15473662.