U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C23H29NO2
Molecular Weight 351.4819
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENADOXONE

SMILES

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

InChI

InChIKey=LOXCOAXRHYDLOW-UHFFFAOYSA-N
InChI=1S/C23H29NO2/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

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 ( + / - )

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
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 16:30:05 UTC 2023
Edited
by admin
on Fri Dec 15 16:30:05 UTC 2023
Record UNII
375W3TA42N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENADOXONE
INN   MI  
INN  
Official Name English
PHENODOXONE
Common Name English
PHENADOXONE [MI]
Common Name English
IDS-NP-005
Code English
HEPTAZONE
Common Name English
3-HEPTANONE, 6-MORPHOLINO-4,4-DIPHENYL-
Systematic Name English
6-MORPHOLIN-4-YL-4,4-DIPHENYLHEPTAN-3-ONE
Systematic Name English
MORPHODONE
Common Name English
phenadoxone [INN]
Common Name English
CB-11 FREE BASE
Code English
Classification Tree Code System Code
NCI_THESAURUS C1506
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
DEA NO. 9637
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
Code System Code Type Description
SMS_ID
100000082227
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
PRIMARY
EVMPD
SUB09747MIG
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
PRIMARY
DRUG CENTRAL
3435
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
PRIMARY
ChEMBL
CHEMBL2104551
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
PRIMARY
FDA UNII
375W3TA42N
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
PRIMARY
PUBCHEM
10089
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
PRIMARY
CAS
467-84-5
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
PRIMARY
WIKIPEDIA
PHENADOXONE
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
PRIMARY Phenadoxone (Heptalgin, Morphidone, Heptazone) is an opioid analgesic of the open chain class (methadone and relatives) invented in by Hoechst in 1947.
MERCK INDEX
m1222
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
PRIMARY Merck Index
CAS
7576-91-2
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
SUPERSEDED
ECHA (EC/EINECS)
207-400-6
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
PRIMARY
INN
4168
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
PRIMARY
EPA CompTox
DTXSID70861963
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
PRIMARY
NCI_THESAURUS
C66364
Created by admin on Fri Dec 15 16:30:05 UTC 2023 , Edited by admin on Fri Dec 15 16:30:05 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Related Record Type Details
ACTIVE MOIETY