Noscapine HCl | CAS#912-60-7

MedKoo Cat#: 329459 | Name: Noscapine HCl

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Description:

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

Noscapine is an opioid alkaloid derived from the opium poppy (Papaver somniferum). It is a non-addictive antitussive (cough suppressant) used to treat persistent, non-productive cough. Noscapine's antitussive effects appear to be primarily mediated by its σ–receptor agonist activity. Evidence for this mechanism is suggested by experimental evidence in rats. Pretreatment with rimcazole, a σ-specific antagonist, causes a dose-dependent reduction in antitussive activity of noscapine. Noscapine, and its synthetic derivatives called noscapinoids, are known to interact with microtubules and inhibit cancer cell proliferation. Noscapine HCl was discontinued.

Chemical Structure

Noscapine HCl

CAS#912-60-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 329459

Name: Noscapine HCl

CAS#: 912-60-7 (HCl)

Chemical Formula: C22H24ClNO7

Exact Mass: 0.0000

Molecular Weight: 449.88

Elemental Analysis: C, 58.74; H, 5.38; Cl, 7.88; N, 3.11; O, 24.89

Price and Availability

Size	Price	Availability
1g	USD 350.00	2 Weeks
2g	USD 550.00	2 Weeks
5g	USD 950.00	2 Weeks

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Related CAS #

128-62-1 (free base) 25333-79-3 (camphorsulfonate) 912-60-7 (HCl) 106611-48-7 (embonate)

Synonym

Noscapine Hydrochloride; Narcotine, Nectodon, Nospen, Anarcotine and (archaic) Opiane.

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 hydrochloride

InChi Key

MFLVZFXCSKVCSH-URBRKQAFSA-N

InChi Code

InChI=1S/C22H23NO7.ClH/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;1H/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.[H]Cl

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

Related CAS# 128-62-1 (Noscapine free base) 912-60-7 (Noscapine hydrochloride)

Product Data

Product Data

Instruction

View handling instruction

Biological target:

An alkaloid with anticancer and antitussive activities.

In vitro activity:

Noscapine suppressed both inducible and constitutive NF-kappaB activation in tumor cells through inhibition of IkappaB kinase, leading to inhibition of phosphorylation and degradation of IkappaBalpha. Noscapine also suppressed phosphorylation and nuclear translocation of p65, leading to inhibition of NF-kappaB reporter activity induced by various components of the NF-kappaB activation pathway. Reference: Cancer Res. 2010 Apr 15;70(8):3259-68. https://pubmed.ncbi.nlm.nih.gov/20354190/

In vivo activity:

In a syngeneic murine model of established s.c. melanoma, noscapine treatment resulted in an 85% inhibition of tumor volume on day 17 when delivered by gavage compared with untreated animals (P <or= 0.01), without evidence of toxicity to the spleen, liver, duodenum, bone marrow, or peripheral blood. This inhibition was greater than that seen in vivo by paclitaxel (Taxol) alone and similar to the inhibition of tumor volume observed when noscapine was combined with paclitaxel. Importantly, noscapine also demonstrated the ability to significantly inhibit melanoma progression by 83% on day 18 when delivered in drinking water (P <or= 0.01) and conferred a significant survival advantage (P <or= 0.01). Reference: Cancer Res. 2002 Jul 15;62(14):4109-14. https://pubmed.ncbi.nlm.nih.gov/12124349/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	66.68
	DMSO	30.0	66.68
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.11
	Ethanol	1.0	2.22

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 449.88 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:

1. Akhter S, Irfan HM, Alamgeer, Ullah A, Jahan S, Roman M, Latif MB, Mustafa Z, Almutairi FM, Althobaiti YS. Noscapine hydrochloride (benzyl-isoquinoline alkaloid) effectively prevents protein denaturation through reduction of IL-6, NF-kB, COX-2, Prostaglandin-E2 in rheumatic rats. Saudi Pharm J. 2022 Dec;30(12):1791-1801. doi: 10.1016/j.jsps.2022.10.008. Epub 2022 Oct 19. PMID: 36601515; PMCID: PMC9805980. 2. Sung B, Ahn KS, Aggarwal BB. Noscapine, a benzylisoquinoline alkaloid, sensitizes leukemic cells to chemotherapeutic agents and cytokines by modulating the NF-kappaB signaling pathway. Cancer Res. 2010 Apr 15;70(8):3259-68. doi: 10.1158/0008-5472.CAN-09-4230. Epub 2010 Mar 30. PMID: 20354190; PMCID: PMC2855771. 3. Landen JW, Lang R, McMahon SJ, Rusan NM, Yvon AM, Adams AW, Sorcinelli MD, Campbell R, Bonaccorsi P, Ansel JC, Archer DR, Wadsworth P, Armstrong CA, Joshi HC. Noscapine alters microtubule dynamics in living cells and inhibits the progression of melanoma. Cancer Res. 2002 Jul 15;62(14):4109-14. PMID: 12124349. 4. Mahmoudian M, Mojaverian N. Efffect of noscapine, the antitussive opioid alkaloid, on bradykinin-induced smooth muscle contraction in the isolated ileum of the guinea-pig. Acta Physiol Hung. 2001;88(3-4):231-7. doi: 10.1556/APhysiol.88.2001.3-4.5. PMID: 12162581.

In vitro protocol:

In vivo protocol:

1. Landen JW, Lang R, McMahon SJ, Rusan NM, Yvon AM, Adams AW, Sorcinelli MD, Campbell R, Bonaccorsi P, Ansel JC, Archer DR, Wadsworth P, Armstrong CA, Joshi HC. Noscapine alters microtubule dynamics in living cells and inhibits the progression of melanoma. Cancer Res. 2002 Jul 15;62(14):4109-14. PMID: 12124349. 2. Mahmoudian M, Mojaverian N. Efffect of noscapine, the antitussive opioid alkaloid, on bradykinin-induced smooth muscle contraction in the isolated ileum of the guinea-pig. Acta Physiol Hung. 2001;88(3-4):231-7. doi: 10.1556/APhysiol.88.2001.3-4.5. PMID: 12162581.

1: Gali-Muhtasib H, Hmadi R, Kareh M, Tohme R, Darwiche N. Cell death mechanisms of plant-derived anticancer drugs: beyond apoptosis. Apoptosis. 2015 Dec;20(12):1531-62. doi: 10.1007/s10495-015-1169-2. Review. PubMed PMID: 26362468. 2: Rida PC, LiVecche D, Ogden A, Zhou J, Aneja R. The Noscapine Chronicle: A Pharmaco-Historic Biography of the Opiate Alkaloid Family and its Clinical Applications. Med Res Rev. 2015 Sep;35(5):1072-96. doi: 10.1002/med.21357. Review. PubMed PMID: 26179481; PubMed Central PMCID: PMC4778555. 3: Chen X, Dang TT, Facchini PJ. Noscapine comes of age. Phytochemistry. 2015 Mar;111:7-13. doi: 10.1016/j.phytochem.2014.09.008. Review. PubMed PMID: 25583437. 4: Lopus M, Naik PK. Taking aim at a dynamic target: Noscapinoids as microtubule-targeted cancer therapeutics. Pharmacol Rep. 2015 Feb;67(1):56-62. doi: 10.1016/j.pharep.2014.09.003. Review. PubMed PMID: 25560576. 5: King NB, Fraser V, Boikos C, Richardson R, Harper S. Determinants of increased opioid-related mortality in the United States and Canada, 1990-2013: a systematic review. Am J Public Health. 2014 Aug;104(8):e32-42. doi: 10.2105/AJPH.2014.301966. Review. PubMed PMID: 24922138; PubMed Central PMCID: PMC4103240. 6: Fang ZZ, Gonzalez FJ. LC-MS-based metabolomics: an update. Arch Toxicol. 2014 Aug;88(8):1491-502. doi: 10.1007/s00204-014-1234-6. Review. PubMed PMID: 24710571. 7: Beaudoin GA, Facchini PJ. Benzylisoquinoline alkaloid biosynthesis in opium poppy. Planta. 2014 Jul;240(1):19-32. doi: 10.1007/s00425-014-2056-8. Review. PubMed PMID: 24671624. 8: Alberti C. Taxane- and epothilone-based chemotherapy: from molecule cargo cytoskeletal logistics to management of castration-resistant prostate carcinoma. Eur Rev Med Pharmacol Sci. 2013 Jun;17(12):1658-64. Review. PubMed PMID: 23832735. 9: Jain V, Jain B, Tiwari P, Saini J, Jain UK, Pandey RS, Kumar M, Katare OP, Chandra R, Madan J. Nanosolvated microtubule-modulating chemotherapeutics: a case-to-case study. Anticancer Drugs. 2013 Apr;24(4):327-36. doi: 10.1097/CAD.0b013e32835ec414. Review. PubMed PMID: 23411683. 10: Hagel JM, Facchini PJ. Benzylisoquinoline alkaloid metabolism: a century of discovery and a brave new world. Plant Cell Physiol. 2013 May;54(5):647-72. doi: 10.1093/pcp/pct020. Review. PubMed PMID: 23385146. 11: Singh H, Singh P, Kumari K, Chandra A, Dass SK, Chandra R. A review on noscapine, and its impact on heme metabolism. Curr Drug Metab. 2013 Mar;14(3):351-60. Review. PubMed PMID: 22935070. 12: Verlee L, Verheij TJ, Hopstaken RM, Prins JM, Salomé PL, Bindels PJ. [Summary of NHG practice guideline 'Acute cough']. Ned Tijdschr Geneeskd. 2012;156(0):A4188. Review. Dutch. PubMed PMID: 22917039. 13: Gajewski MM, Alisaraie L, Tuszynski JA. Peloruside, laulimalide, and noscapine interactions with beta-tubulin. Pharm Res. 2012 Nov;29(11):2985-93. doi: 10.1007/s11095-012-0809-2. Review. PubMed PMID: 22733149. 14: Chandra R, Madan J, Singh P, Chandra A, Kumar P, Tomar V, Dass SK. Implications of nanoscale based drug delivery systems in delivery and targeting tubulin binding agent, noscapine in cancer cells. Curr Drug Metab. 2012 Dec;13(10):1476-83. Review. PubMed PMID: 22571485. 15: Bughani U, Li S, Joshi HC. Recent patents reveal microtubules as persistent promising target for novel drug development for cancers. Recent Pat Antiinfect Drug Discov. 2009 Nov;4(3):164-82. Review. PubMed PMID: 19673697. 16: Småbrekke L, Melbye H. [Pharmacological treatment of acute cough]. Tidsskr Nor Laegeforen. 2009 May 14;129(10):998-9. doi: 10.4045/tidsskr.08.0438. Review. Norwegian. PubMed PMID: 19448753. 17: Mahmoudian M, Rahimi-Moghaddam P. The anti-cancer activity of noscapine: a review. Recent Pat Anticancer Drug Discov. 2009 Jan;4(1):92-7. Review. PubMed PMID: 19149691. 18: Kingston DG. Tubulin-interactive natural products as anticancer agents. J Nat Prod. 2009 Mar 27;72(3):507-15. doi: 10.1021/np800568j. Review. Erratum in: J Nat Prod. 2011 May 27;74(5):1352. PubMed PMID: 19125622; PubMed Central PMCID: PMC2765517. 19: Ohlsson S, Holm L, Myrberg O, Sundström A, Yue QY. Noscapine may increase the effect of warfarin. Br J Clin Pharmacol. 2008 Feb;65(2):277-8. Review. PubMed PMID: 17875192; PubMed Central PMCID: PMC2291222. 20: Zhou J, Giannakakou P. Targeting microtubules for cancer chemotherapy. Curr Med Chem Anticancer Agents. 2005 Jan;5(1):65-71. Review. PubMed PMID: 15720262.