MedKoo Cat#: 412386 | Name: Carpaine

Description:

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

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

Carpaine
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

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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
More Info
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
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 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
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.