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Details

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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
The pharmacology of phenadoxone or dl-6-morpholino-4:4-diphenyl-heptan-3-one hydrochloride.
1950 Mar
[Pharmacology of phenadoxone].
1950 Mar-Apr
The determination of phenadoxone.
1951 Nov
The action of morphine and related substances on contraction and on acetylcholine output of coaxially stimulated guinea-pig ileum.
1957 Mar
Comparative effects of analgesics on pain threshold, respiratory frequency and gastrointestinal propulsion.
1959 Mar
Methadone radioimmunoassay: two simple methods.
1983 Sep
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Dec 16 08:26:02 UTC 2023
Edited
by admin
on Sat Dec 16 08:26:02 UTC 2023
Record UNII
JPI3X77W99
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENADOXONE HYDROCHLORIDE
MI  
Common Name English
HEPTAZONE HYDROCHLORIDE
Common Name English
3-HEPTANONE, 6-(4-MORPHOLINYL)-4,4-DIPHENYL-, HYDROCHLORIDE (1:1)
Systematic Name English
HEPTALGIN
Common Name English
HEPAGIN
Common Name English
SUPRALGIN
Brand Name English
6-TETRAHYDROOXAZINE-4,4-DIPHENYL-3-HEPTANONE HYDROCHLORIDE
Common Name English
PHENADOXONE HYDROCHLORIDE [MI]
Common Name English
HEPTONE
Common Name English
CB-11
Code English
3-HEPTANONE, 6-(4-MORPHOLINYL)-4,4-DIPHENYL-, HYDROCHLORIDE
Systematic Name English
MORPHODONE HYDROCHLORIDE
Common Name English
3-HEPTANONE, 6-MORPHOLINO-4,4-DIPHENYL-, HYDROCHLORIDE
Systematic Name English
HOECHST-10600
Code English
6-(N-MORPHOLINO)-4,4-DIPHENYL-3-HEPTANONE HYDROCHLORIDE
Common Name English
HEPTALIN
Brand Name English
Code System Code Type Description
CAS
545-91-5
Created by admin on Sat Dec 16 08:26:02 UTC 2023 , Edited by admin on Sat Dec 16 08:26:02 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-895-1
Created by admin on Sat Dec 16 08:26:02 UTC 2023 , Edited by admin on Sat Dec 16 08:26:02 UTC 2023
PRIMARY
MERCK INDEX
m1222
Created by admin on Sat Dec 16 08:26:02 UTC 2023 , Edited by admin on Sat Dec 16 08:26:02 UTC 2023
PRIMARY Merck Index
PUBCHEM
11019
Created by admin on Sat Dec 16 08:26:02 UTC 2023 , Edited by admin on Sat Dec 16 08:26:02 UTC 2023
PRIMARY
FDA UNII
JPI3X77W99
Created by admin on Sat Dec 16 08:26:02 UTC 2023 , Edited by admin on Sat Dec 16 08:26:02 UTC 2023
PRIMARY
EPA CompTox
DTXSID00969688
Created by admin on Sat Dec 16 08:26:02 UTC 2023 , Edited by admin on Sat Dec 16 08:26:02 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE