Thalicarpine

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

MedKoo CAT#: 206079

CAS#: 5373-42-2

Description: Thalicarpine is a natural aporphine benzylisoquinoline vinca alkaloid with antineoplastic activity. Thalicarpine binds to and inhibits p-glycoprotein, the multidrug resistance efflux pump. Thalicarpine also induces single-strand breaks in DNA and arrests cancer cells at the G2/M and G1 phase of the cell cycle. Check for active clinical trials or closed clinical trials using this agent.


Chemical Structure

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Thalicarpine
CAS# 5373-42-2

Theoretical Analysis

MedKoo Cat#: 206079
Name: Thalicarpine
CAS#: 5373-42-2
Chemical Formula: C41H48N2O8
Exact Mass: 696.34107
Molecular Weight: 696.83
Elemental Analysis: C, 70.67; H, 6.94; N, 4.02; O, 18.37

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Thalicarpine; taliblastine; thaliblastin; thalicarpin.

IUPAC/Chemical Name: (S)-9-(2-(((S)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)-4,5-dimethoxyphenoxy)-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

InChi Key: ZCTJIMXXSXQXRI-KYJUHHDHSA-N

InChi Code: InChI=1S/C41H48N2O8/c1-42-12-10-23-16-32(44-3)34(46-5)20-27(23)29(42)15-26-19-33(45-4)36(48-7)22-31(26)51-37-18-25-14-30-39-24(11-13-43(30)2)17-38(49-8)41(50-9)40(39)28(25)21-35(37)47-6/h16-22,29-30H,10-15H2,1-9H3/t29-,30-/m0/s1

SMILES Code: CN1CCC2=CC(OC)=C(OC)C3=C2[C@]1([H])CC4=CC(OC5=CC(OC)=C(OC)C=C5C[C@@H]6N(C)CCC7=C6C=C(OC)C(OC)=C7)=C(OC)C=C34

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, not in water

Shelf Life: >5 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 696.83 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: Wu WN, McKown LA. The in vitro metabolism of thalicarpine, an aporphine-benzyltetrahydroisoquinoline alkaloid, in the rat. API-MS/MS identification of thalicarpine and metabolites. J Pharm Biomed Anal. 2002 Aug 22;30(1):141-50. PubMed PMID: 12151074.

2: Leimert JT, Corder MP, Elliott TE, Lovett JM. An abbreviated phase II trial of thalicarpine. Cancer Treat Rep. 1980;64(12):1389-90. PubMed PMID: 6451289.

3: Kupchan SM, Dhingra OP, Ramachandran V, Kim CK. Proaporphine--aporphine dimers and a bisaporphine derived from the tumor-inhibitory alkaloid thalicarpine. J Org Chem. 1978 Jan 6;43(1):105-8. PubMed PMID: 145476.

4: Nabih T, Davis PJ, Caputo JF, Rosazza JP. Microbial transformations of natural antitumor agents. 3. Conversion of thalicarpine to (+)-hernandalinol by Streptomyces punipalus. J Med Chem. 1977 Jul;20(7):914-7. PubMed PMID: 141523.

5: Creasey WA. Biochemical effects of d-tetrandrine and thalicarpine. Biochem Pharmacol. 1976 Aug 15;25(16):1887-91. PubMed PMID: 134714.

6: Creaven PJ, Allen LM. Thalicarpine (NSC-68075): plasma decay and urinary excretion in man. Cancer Treat Rep. 1976 Jan;60(1):69-75. PubMed PMID: 137078.

7: Creaven PJ, Cohen MH, Selawry OS, Tejada F, Broder LE. Phase I study of thalicarpine (NAC-68075), a plant alkaloid of noval structure. Cancer Chemother Rep. 1975 Sep-Oct;59(5):1001-6. PubMed PMID: 128411.

8: Creaven PJ, Allen LM, Williams CP. The interaction of the antineoplastic drug thalicarpine with aniline hydroxylase and microsomal cytochrome of rat liver. Xenobiotica. 1974 Apr;4(4):255-61. PubMed PMID: 4152572.

9: Allen LM, Creaven PJ. Binding of a new antitumor agent, thalicarpine, to DNA. J Pharm Sci. 1974 Mar;63(3):474-5. PubMed PMID: 4856551.

10: Allen LM, Creaven PJ. Inhibition of macromolecular biosynthesis in cultured L1210 mouse leukemia cells by thalicarpine (NSC 68075). Cancer Res. 1973 Dec;33(12):3112-6. PubMed PMID: 4796799.



Additional Information