Noscapine

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

MedKoo CAT#: 596824

CAS#: 128-62-1

Description: Noscapine is a naturally occurring opium alkaloid that is a centrally acting antitussive agent. Noscapine is discontinued.

Chemical Structure

Noscapine

CAS# 128-62-1

Instruction

Theoretical Analysis

MedKoo Cat#: 596824
Name: Noscapine
CAS#: 128-62-1
Chemical Formula: C22H23NO7
Exact Mass: 413.15
Molecular Weight: 413.420
Elemental Analysis: C, 63.92; H, 5.61; N, 3.39; O, 27.09

Price and Availability

Size	Price	Availability	Quantity
5g	USD 240
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Noscapine; HSDB 3372; Narcotin; NSC 5366; NSC-5366; NSC5366; Oripavine

IUPAC/Chemical Name: (S)-6,7-dimethoxy-3-((R)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one

InChi Key: AKNNEGZIBPJZJG-MSOLQXFVSA-N

InChi Code: InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1

SMILES Code: O=C1O[C@H]([C@@H]2N(C)CCC3=CC4=C(OCO4)C(OC)=C23)C5=C1C(OC)=C(OC)C=C5

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

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 413.42 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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Park MR, Chen X, Lang DE, Ng KKS, Facchini PJ. Heterodimeric O-methyltransferases involved in the biosynthesis of noscapine in opium poppy. Plant J. 2018 May 3. doi: 10.1111/tpj.13947. [Epub ahead of print] PubMed PMID: 29723437.

2: Li Y, Li S, Thodey K, Trenchard I, Cravens A, Smolke CD. Complete biosynthesis of noscapine and halogenated alkaloids in yeast. Proc Natl Acad Sci U S A. 2018 Apr 24;115(17):E3922-E3931. doi: 10.1073/pnas.1721469115. Epub 2018 Apr 2. PubMed PMID: 29610307; PubMed Central PMCID: PMC5924921.

3: Abedini D, Monfared SR, Abbasi A. The effects of promoter variations of the N-Methylcanadine 1-Hydroxylase (CYP82Y1) gene on the noscapine production in opium poppy. Sci Rep. 2018 Mar 21;8(1):4973. doi: 10.1038/s41598-018-23351-0. PubMed PMID: 29563567; PubMed Central PMCID: PMC5862900.

4: Rabzia A, Khazaei M, Rashidi Z, Khazaei MR. Synergistic Anticancer Effect of Paclitaxel and Noscapine on Human Prostate Cancer Cell Lines. Iran J Pharm Res. 2017 Fall;16(4):1432-1442. PubMed PMID: 29552052; PubMed Central PMCID: PMC5843305.

5: Jablonická V, Ziegler J, Vatehová Z, Lišková D, Heilmann I, Obložinský M, Heilmann M. Inhibition of phospholipases influences the metabolism of wound-induced benzylisoquinoline alkaloids in Papaver somniferum L. J Plant Physiol. 2018 Apr;223:1-8. doi: 10.1016/j.jplph.2018.01.007. Epub 2018 Jan 31. PubMed PMID: 29433083.

6: Soichot M, Julliand S, Filatriau J, Hurbain A, Bourgogne E, Mihoubi A, Gourlain H, Delhotal-Landes B. Diagnosis of Heroin Overdose in an 8-Year-Old Boy: Reliable Contribution of Toxicological Investigations. J Anal Toxicol. 2017 Dec 28. doi: 10.1093/jat/bkx111. [Epub ahead of print] PubMed PMID: 29301012.

7: Azarian M, Amani A, Faramarzi MA, Divsalar A, Eidi A. Design and optimization of noscapine nanosuspensions and study of its cytotoxic effect. J Biomol Struct Dyn. 2018 Jan 5:1-9. doi: 10.1080/07391102.2017.1420490. [Epub ahead of print] PubMed PMID: 29283030.

8: Doddapaneni R, Patel K, Chowdhury N, Singh M. Reversal of drug-resistance by noscapine chemo-sensitization in docetaxel resistant triple negative breast cancer. Sci Rep. 2017 Nov 20;7(1):15824. doi: 10.1038/s41598-017-15531-1. PubMed PMID: 29158480; PubMed Central PMCID: PMC5696458.

9: Hu L, Cui R, Liu H, Wang F. Emodin and rhein decrease levels of hypoxia-inducible factor-1α in human pancreatic cancer cells and attenuate cancer cachexia in athymic mice carrying these cells. Oncotarget. 2017 Sep 27;8(50):88008-88020. doi: 10.18632/oncotarget.21330. eCollection 2017 Oct 20. PubMed PMID: 29152137; PubMed Central PMCID: PMC5675689.

10: Carlin MG, Dean JR, Bookham JL, Perry JJB. Investigation of the acid/base behaviour of the opium alkaloid thebaine in LC-ESI-MS mobile phase by NMR spectroscopy. R Soc Open Sci. 2017 Oct 4;4(10):170715. doi: 10.1098/rsos.170715. eCollection 2017 Oct. PubMed PMID: 29134077; PubMed Central PMCID: PMC5666260.

11: López P, Pereboom-de Fauw DPKH, Mulder PPJ, Spanjer M, de Stoppelaar J, Mol HGJ, de Nijs M. Straightforward analytical method to determine opium alkaloids in poppy seeds and bakery products. Food Chem. 2018 Mar 1;242:443-450. doi: 10.1016/j.foodchem.2017.08.045. Epub 2017 Aug 18. PubMed PMID: 29037712.

12: Srivastava A, Agrawal L, Raj R, Jaidi M, Raj SK, Gupta S, Dixit R, Singh PC, Tripathi T, Sidhu OP, Singh BN, Shukla S, Chauhan PS, Kumar S. Ageratum enation virus Infection Induces Programmed Cell Death and Alters Metabolite Biosynthesis in Papaver somniferum. Front Plant Sci. 2017 Jul 6;8:1172. doi: 10.3389/fpls.2017.01172. eCollection 2017. PubMed PMID: 28729873; PubMed Central PMCID: PMC5498505.

13: Taheri M, Bagheri M, Moazeni-Pourasil RS, Ghassempour A. Response surface methodology based on central composite design accompanied by multivariate curve resolution to model gradient hydrophilic interaction liquid chromatography: Prediction of separation for five major opium alkaloids. J Sep Sci. 2017 Sep;40(18):3602-3611. doi: 10.1002/jssc.201700416. Epub 2017 Aug 28. PubMed PMID: 28714264.

14: Bagheri M, Taheri M, Farhadpour M, Rezadoost H, Ghassempour A, Aboul-Enein HY. Evaluation of hydrophilic interaction liquid chromatography stationary phases for analysis of opium alkaloids. J Chromatogr A. 2017 Aug 18;1511:77-84. doi: 10.1016/j.chroma.2017.06.072. Epub 2017 Jun 30. PubMed PMID: 28689582.

15: Maas A, Madea B, Hess C. Confirmation of recent heroin abuse: Accepting the challenge. Drug Test Anal. 2018 Jan;10(1):54-71. doi: 10.1002/dta.2244. Epub 2017 Sep 5. Review. PubMed PMID: 28681463.

16: Tian X, Liu M, Zhu Q, Tan J, Liu W, Wang Y, Chen W, Zou Y, Cai Y, Han Z, Huang X. Down-regulation of liver-intestine cadherin enhances noscapine-induced apoptosis in human colon cancer cells. Expert Rev Anticancer Ther. 2017 Sep;17(9):857-863. doi: 10.1080/14737140.2017.1344097. Epub 2017 Jun 27. PubMed PMID: 28622054.

17: Han Z, Huang X, Liu M, Tan J, Zhu Q, Wang Y, Cai Y, Chen A, Tian X. [Knock-down of cadherin 17 inhibits proliferation and promote apoptosis in noscapine-resistant human SW480 colon cancer cells]. Xi Bao Yu Fen Zi Mian Yi Xue Za Zhi. 2017 May;33(5):606-610. Chinese. PubMed PMID: 28502297.

18: Soni N, Jyoti K, Jain UK, Katyal A, Chandra R, Madan J. Noscapinoids bearing silver nanocrystals augmented drug delivery, cytotoxicity, apoptosis and cellular uptake in B16F1, mouse melanoma skin cancer cells. Biomed Pharmacother. 2017 Jun;90:906-913. doi: 10.1016/j.biopha.2017.04.042. Epub 2017 Apr 22. PubMed PMID: 28441716.

19: Jagerdeo E, Wriston A. Rapid analysis of forensic-related samples using two ambient ionization techniques coupled to high-resolution mass spectrometers. Rapid Commun Mass Spectrom. 2017 May 15;31(9):782-790. doi: 10.1002/rcm.7844. PubMed PMID: 28263006.

20: Dekeyser S, van Tomme M, Boone B, van Geel N, Lapeere H. Occupational allergic contact dermatitis caused by thebaine and oripavine. Contact Dermatitis. 2017 Feb;76(2):120-122. doi: 10.1111/cod.12654. PubMed PMID: 28095631.

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