Carpaine

Carpaine^[1]

Names
IUPAC names (1S,11R,13S,14S,24R,26S)-13,26-Dimethyl-2,15-dioxa- 12,25-diazatricyclo[22.2.2.211,14]triacontane-3,16-dione
Other names (+)-Carpaine
Identifiers
CAS Number	3463-92-1
3D model (Jmol)	Interactive image
ChEBI	CHEBI:3433
ChemSpider	390994
ECHA InfoCard	100.020.378
PubChem	442630
InChI 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 Key: AMSCMASJCYVAIF-QCVMBYIASA-N InChI=1/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 Key: AMSCMASJCYVAIF-QCVMBYIABP
SMILES O=C3O[C@H]1CC[C@H](N[C@H]1C)CCCCCCCC(=O)O[C@@H]2[C@@H](N[C@@H](CC2)CCCCCCC3)C
Properties
Chemical formula	C28H50N2O4
Molar mass	478.70 g/mol
Melting point	121 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

References

1. Merck Index, 11th Edition, 1866.
2. Burdick, Everette M. "Carpaine. An alkaloid of Carica papaya. Chemistry and pharmacology." Economic Botany (1971), 25(4), 363-365.
3. Hornick, C. A.; Sanders, L. I.; Lin, Y. C. "Effect of carpaine, a papaya alkaloid, on the circulatory function in the rat." Research Communications in Chemical Pathology and Pharmacology (1978), 22(2), 277-289.