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Details

Stereochemistry UNKNOWN
Molecular Formula C23H29NO2.ClH
Molecular Weight 387.943
Optical Activity ( - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENADOXONE HYDROCHLORIDE, (-)-

SMILES

Cl.CCC(=O)C(CC(C)N1CCOCC1)(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=QGUPBYVADAJUNT-UHFFFAOYSA-N
InChI=1S/C23H29NO2.ClH/c1-3-22(25)23(20-10-6-4-7-11-20,21-12-8-5-9-13-21)18-19(2)24-14-16-26-17-15-24;/h4-13,19H,3,14-18H2,1-2H3;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C23H29NO2
Molecular Weight 351.4819
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Phenadoxone hydrochloride is one of some forty amino-ketones and amino-esters related to amidone. The compound is a very potent analgesic for the rat; by the subcutaneous route it is more active than either morphine or amidone. In spite of this its acute toxicity to mice is lower than that of amidone and its therapeutic index is therefore correspondingly higher, giving a wider margin of safety. Side effects in dogs, such as narcosis, sedation, and general depression, were much less with phenadoxone than with amidone or morphine. Nausea and vomiting did not occur after phenadoxone in non-tolerant dogs. Clinical results show that for relieving certain types of pain in human subjects it is a potent analgesic that compares favorably with morphine and amidone. At therapeutic dose levels undesirable pharmacological effects, such as cardiac depression and vasomotor disturbance, are absent, and it is only at extremely high dose levels that untoward effects occur. However, the drug has a strong respiratory depressant action when given in high doses; it should be used with special caution if injected intravenously.

Originator

Approval Year

PubMed

Patents

Substance Class Chemical
Record UNII
SX58ZM5M5J
Record Status Validated (UNII)
Record Version