Carpaine

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MedKoo CAT#: 412386

CAS#: 3463-92-1

Description: Carpaine is an alkaloid originally isolated from Carica papaya that has antiplasmodial and antithrombocytopenic activities. It is active against T. b. rhodesiense, T. cruzi, and P. falciparum. Carpaine (2 mg/kg) inhibits decreases in platelet counts in a rat model of thrombocytopenia induced by busulfan. It decreases systolic, diastolic, and mean arterial blood pressure in anesthetized rats in a dose-dependent manner.


Chemical Structure

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Carpaine
CAS# 3463-92-1

Theoretical Analysis

MedKoo Cat#: 412386
Name: Carpaine
CAS#: 3463-92-1
Chemical Formula: C28H50N2O4
Exact Mass: 478.3771
Molecular Weight: 478.72
Elemental Analysis: C, 70.25; H, 10.53; N, 5.85; O, 13.37

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: Carpaine; EINECS 222-414-2; (+)-Carpaine; (+) Carpaine;

IUPAC/Chemical Name: (1S,11R,13S,14S,24R,26S)-13,26-dimethyl-2,15-dioxa-12,25-diazatricyclo[22.2.2.211,14]triacontane-3,16-dione

InChi Key: AMSCMASJCYVAIF-QCVMBYIASA-N

InChi Code: InChI=1S/C28H50N2O4/c1-21-25-19-17-23(29-21)13-9-5-3-8-12-16-28(32)34-26-20-18-24(30-22(26)2)14-10-6-4-7-11-15-27(31)33-25/h21-26,29-30H,3-20H2,1-2H3/t21-,22-,23+,24+,25-,26-/m0/s1

SMILES Code: C[C@@H]1N[C@@H]2CCCCCCCC(O[C@H]3CC[C@H](N[C@H]3C)CCCCCCCC(O[C@H]1CC2)=O)=O

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 478.72 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: Soib HH, Ismail HF, Husin F, Abu Bakar MH, Yaakob H, Sarmidi MR. Bioassay- Guided Different Extraction Techniques of Carica papaya (Linn.) Leaves on In Vitro Wound-Healing Activities. Molecules. 2020 Jan 24;25(3):517. doi: 10.3390/molecules25030517. PMID: 31991676; PMCID: PMC7037417.

2: Adedayo BC, Ogunsuyi OB, Akinniyi ST, Oboh G. Effect of Andrographis paniculata and Phyllanthus amarus leaf extracts on selected biochemical indices in Drosophila melanogaster model of neurotoxicity. Drug Chem Toxicol. 2020 Jan 3:1-10. doi: 10.1080/01480545.2019.1708377. Epub ahead of print. PMID: 31899970.

3: Cabral ERM, Moraes D, Levenhagen MA, Matos RAF, Costa-Cruz JM, Rodrigues RM. In vitro ovicidal and larvicidal activity of Carica papaya seed hexane extract against Strongyloides venezuelensis. Rev Inst Med Trop Sao Paulo. 2019 Nov 25;61:e59. doi: 10.1590/S1678-9946201961059. PMID: 31778389; PMCID: PMC6880996.

4: Kumar S, Sahu P, Jena L. An In silico approach to identify potential inhibitors against multiple drug targets of Mycobacterium tuberculosis. Int J Mycobacteriol. 2019 Jul-Sep;8(3):252-261. doi: 10.4103/ijmy.ijmy_109_19. PMID: 31512601.

5: Barroso PT, de Carvalho PP, Rocha TB, Pessoa FL, Azevedo DA, Mendes MF. Evaluation of the composition of Carica papaya L. seed oil extracted with supercritical CO2. Biotechnol Rep (Amst). 2016 Sep 4;11:110-116. doi: 10.1016/j.btre.2016.08.004. PMID: 28352547; PMCID: PMC5042337.

6: Zunjar V, Dash RP, Jivrajani M, Trivedi B, Nivsarkar M. Antithrombocytopenic activity of carpaine and alkaloidal extract of Carica papaya Linn. leaves in busulfan induced thrombocytopenic Wistar rats. J Ethnopharmacol. 2016 Apr 2;181:20-5. doi: 10.1016/j.jep.2016.01.035. Epub 2016 Jan 23. PMID: 26812680.

7: Julianti T, Oufir M, Hamburger M. Quantification of the antiplasmodial alkaloid carpaine in papaya (Carica papaya) leaves. Planta Med. 2014 Aug;80(13):1138-42. doi: 10.1055/s-0034-1382948. Epub 2014 Aug 25. PMID: 25153096.

8: Julianti T, De Mieri M, Zimmermann S, Ebrahimi SN, Kaiser M, Neuburger M, Raith M, Brun R, Hamburger M. HPLC-based activity profiling for antiplasmodial compounds in the traditional Indonesian medicinal plant Carica papaya L. J Ethnopharmacol. 2014 Aug 8;155(1):426-34. doi: 10.1016/j.jep.2014.05.050. Epub 2014 Jun 2. PMID: 24892830.

9: Singh O, Ali M. Phytochemical and antifungal profiles of the seeds of carica papaya L. Indian J Pharm Sci. 2011 Jul;73(4):447-51. doi: 10.4103/0250-474X.95648. PMID: 22707832; PMCID: PMC3374564.

10: Bennett RN, Mellon FA, Rosa EA, Perkins L, Kroon PA. Profiling glucosinolates, flavonoids, alkaloids, and other secondary metabolites in tissues of Azima tetracantha L. (Salvadoraceae). J Agric Food Chem. 2004 Sep 22;52(19):5856-62. doi: 10.1021/jf040091+. PMID: 15366832.

11: Sato T, Aoyagi S, Kibayashi C. Enantioselective total synthesis of (+)-azimine and (+)-carpaine. Org Lett. 2003 Oct 16;5(21):3839-42. doi: 10.1021/ol030088w. PMID: 14535723.

12: Saito T, Hisanaga S. [Regulation of Cdk5 activity in post-mitotic neurons]. Seikagaku. 2001 Apr;73(4):276-8. Japanese. PMID: 11449683.

13: Hornick CA, Sanders LI, Lin YC. Effect of carpaine, a papaya alkaloid, on the circulatory function in the rat. Res Commun Chem Pathol Pharmacol. 1978 Nov;22(2):277-89. PMID: 734216.

14: Govindachari TR, Nagarajan K, Viswanathan N. Carpaine and pseudocarpaine. Tetrahedron Lett. 1965 Jun;(24):1907-16. doi: 10.1016/s0040-4039(01)83886-7. PMID: 5843214.