Carpaine

Title: Carpaine
CAS Registry Number: 3463-92-1
Molecular Formula: C28H50N2O4
Molecular Weight: 478.71
Percent Composition: C 70.25%, H 10.53%, N 5.85%, O 13.37%
Literature References: Found in Carica papaya L. and in Vasconcellosia hastata Caruel, Caricaceae. Isoln from papaya leaves: Greshoff, Mededeel. uit's Lands. Plant., Buitenzorg. No. 7, 5 (1890); Rapoport, Baldridge, J. Am. Chem. Soc. 73, 343 (1951). Reportedly causes bradycardia, CNS depression: Kakowski, Arch. Int. Pharm. 15, 84 (1905). Structure and stereochemistry: Govindachari et al., Tetrahedron Lett. 1965, 1907. Absolute configuration: Coke, Rice, J. Org. Chem. 30, 3420 (1965). Review of structural studies: Govindachari, J. Indian Chem. Soc. 45, 945 (1968).
Properties: Monoclinic prisms from acetone, mp 119-120°. Sublimes at 120° under 0.05 mm pressure. [a]D12 +24.7° (c = 1.07 in ethanol). Slightly sol in water. Sol in most organic solvents except petr ether.
Melting point: mp 119-120°
Optical Rotation: [a]D12 +24.7° (c = 1.07 in ethanol)
Carpetimycins Carphenazine Carpipramine Carprofen Carpronium Chloride

Carpaine[1]
Carpaine.png
Identifiers
CAS number 3463-92-1 YesY
PubChem 442630
ChemSpider 390994 YesY
Jmol-3D images Image 1
Properties
Molecular formula C28H50N2O4
Molar mass 478.70 g/mol
Melting point 121 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Carpaine is one of the major alkaloid components of papaya leaves which has been studied for its cardiovascular effects.[2] Circulatory effects of carpaine were studied in Wistar male rats weighing 314 +/- 13 g, under pentobarbital (30 mg/kg) anesthesia.[3] Increasing dosages of carpaine from 0.5 mg/kg to 2.0 mg/kg resulted in progressive decrease in systolic, diastolic, and mean arterial blood pressure. Selective autonomic nervous blockade with atropine sulfate (1 mg/kg) or propranolol hydrochloride (8 mg/kg) did not alter the circulatory response to carpaine. Carpaine, 2 mg/kg, reduced cardiac output, stroke volume, stroke work, and cardiac power, but the calculated total peripheral resistance remained unchanged. It is concluded from these results that carpaine affects the myocardium directly. The effects of carpaine may be related to its macrocyclic dilactone structure, a possible cation chelating structure.