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Home > Encyclopedia > 2-(Dimethylamino)ethyl (2E)-[(1R,4aS,4bR,7S,8aR,10aS)-dodecahydro-7-hydroxy-1,4b,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene]acetate

2-(Dimethylamino)ethyl (2E)-[(1R,4aS,4bR,7S,8aR,10aS)-dodecahydro-7-hydroxy-1,4b,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene]acetate

2-(Dimethylamino)ethyl (2E)-[(1R,4aS,4bR,7S,8aR,10aS)-dodecahydro-7-hydroxy-1,4b,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene]acetate structure

2-(Dimethylamino)ethyl (2E)-[(1R,4aS,4bR,7S,8aR,10aS)-dodecahydro-7-hydroxy-1,4b,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene]acetate 

structure
  • CAS No:

    468-76-8

  • Formula:

    C24H39NO4

  • Chemical Name:

    2-(Dimethylamino)ethyl (2E)-[(1R,4aS,4bR,7S,8aR,10aS)-dodecahydro-7-hydroxy-1,4b,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene]acetate

  • Synonyms:

    Acetic acid,[(1R,4aS,4bR,7S,8aR,10aS)-dodecahydro-7-hydroxy-1,4b,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene]-,2-(dimethylamino)ethyl ester,(2E)-;Cassaine;Acetic acid,(dodecahydro-7-hydroxy-1,4b,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene)-,2-(dimethylamino)ethyl ester,[1R-(1α,2E,4aα,4bβ,7β,8aα,10aβ)]-;Podocarpane-Δ13,α-acetic acid,3β-hydroxy-14α-methyl-7-oxo-,2-(dimethylamino)ethyl ester,(E)-;2-(Dimethylamino)ethyl (2E)-[(1R,4aS,4bR,7S,8aR,10aS)-dodecahydro-7-hydroxy-1,4b,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene]acetate;(+)-Cassaine

Description

Cassaine is a tricyclic diterpenoid isolated from several plant species of the genus Erythrophleum. It has a role as a plant metabolite, a cardiotonic drug, a local anaesthetic, an antihypertensive agent, a poison and an EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor. It is a tricyclic diterpenoid, a tertiary amino compound, an enoate ester and an organic hydroxy compound. It derives from a hydride of a podocarpane.

2-(Dimethylamino)ethyl (2E)-[(1R,4aS,4bR,7S,8aR,10aS)-dodecahydro-7-hydroxy-1,4b,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene]acetate Basic Attributes

405.579

405.57

PQK203C49T

GLOSSY FLAKES FROM ETHER

Characteristics

66.8

3.1

1.093±0.06 g/cm3(Predicted)

142.5 °C

405 °C

SOL IN METHANE, ETHANOL, ACETONE, ACETIC ACID, CHLOROFORM, ETHER, BENZENE

SPECIFIC OPTICAL ROTATION: -110.5 DEG @ 23 °C/D (ALC); -101 °C @ 23 °C/D (0.1 N HCL)

Safety Information

A review with approx 25 references of interaction of ouabain and cassaine with (Na-K)-dependent adenosine triphosphatase and its relation to their inotropic actions.[Tobin T, Akera T; Interaction of ouabain and cassaine with (sodium-potassium ion)-dependent ATPase and its relationship to their inotropic actions; Drug Action Mol Level (Rep Symp): 213-33 (1977)]

Toxicity

THE BARK OF THE AFRICAN ERYTHROPHLEUM GUINEENSE ('SASSY BARK') IS WELL KNOWN AS AN ORDEAL POISON & AN INGREDIENT OF ARROW POISONS. IT CONTAINS CASSAINE & OTHER ALKALOIDS, & HAS BEEN USED FOR MALICIOUS POISONING OF ANIMALS.

Drug Information

THE ERYTHROPHLEUM ALKALOID CASSAINE-HCL AND ITS METHIODINE AND ETHIODIDE EXHIBITED A POSITIVE INOTROPIC EFFECT ON STIMULATED LEFT ATRIA OF RABBITS.|Cassaine, an alkaloid of Erythrophleum guineense (Leguminosae) bark, is one of the few natural compounds that has a digitalis-like action on the heart muscle.|THE STRUCTURE-CARDIOTONIC AND TOXIC ACTIVITY RELATIONSHIP OF 20 ERYTHROPHLEUM ALKALOIDS WAS STUDIED IN ISOLATED RABBIT AND GUINEA PIGS PAPILLARY MUSCLE. THE PRESENCE OF A 3-OH GROUP INCREASED CARDIOTONIC ACTIVITY WHICH WAS FURTHER ENHANCED BY ESTERIFICATION.

THE ALKALOIDS ERYTHROPHLEINE & CASSAINE (NERVOCIDINE) ARE KNOWN TO HAVE ANESTHETIC ACTION, BUT WHEN APPLIED TO THE EYE ARE EXCESSIVELY IRRITATING & INJURIOUS TO THE CORNEA, CONJUNCTIVA, & IRIS. THESE ALKALOIDS APPLIED TO ...HUMAN EYES BY SUBCONJUNCTIVAL INJECTION ALSO LOWERED THE INTRAOCULAR PRESSURE FOR SEVERAL DAYS, PRESUMABLY BY POISONING THE AQ SECRETORY MECHANISM, BUT CHEMOSIS & CORNEAL EDEMA WERE TOO MUCH FOR ANTIGLAUCOMA THERAPEUTIC USE. ONLY SLIGHT MIOSIS WAS INDUCED.

cassaine

2-(Dimethylamino)ethyl (2E)-[(1R,4aS,4bR,7S,8aR,10aS)-dodecahydro-7-hydroxy-1,4b,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene]acetate Use and Manufacturing

EXTRACTED FROM THE BARK OF ERYTHROPHLEUM GUINEENSE G DON, LEGUMINOSAE: DALMA, HELV CHIM ACTA 22, 1497 (1939).

Computed Properties

Molecular Weight:405.6
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:405.28790873
Monoisotopic Mass:405.28790873
Topological Polar Surface Area:66.8
Heavy Atom Count:29
Complexity:682
Defined Atom Stereocenter Count:6
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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