METHOPHOLINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H24ClNO2
Molecular Weight	345.863
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC2=C(C=C1OC)C(CCC3=CC=C(Cl)C=C3)N(C)CC2

InChI

InChIKey=YBCPYHQFUMNOJG-UHFFFAOYSA-N

InChI=1S/C20H24ClNO2/c1-22-11-10-15-12-19(23-2)20(24-3)13-17(15)18(22)9-6-14-4-7-16(21)8-5-14/h4-5,7-8,12-13,18H,6,9-11H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C20H24ClNO2
Molecular Weight	345.863
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.thieme-connect.com/products/ejournals/pdf/10.1055/s-0032-1317331.pdf | https://www.federalregister.gov/documents/2014/07/02/2014-15371/additions-and-modifications-to-the-list-of-drug-products-that-have-been-withdrawn-or-removed-from

METHOPHOLINE, an isoquinoline derivative, is an opioid analgesic drug. Its (R)-enatiomer is approximately six times more potent than codeine, and (S)-enantiomer is inactive. METHOPHOLINE was withdrawn from the market for reasons of safety.

Approval Year

PubMed

Title	Date	PubMed
Clinical studies of Versidyne, a non-narcotic analgesic.	1961 Dec	14495926
An evaluation of the efficacy of methopholine for the relief of postoperative pain.	1962 Sep	14475666
Versidyne. Its use in vascular headache.	1963 Jan	13975764
METHOPHOLINE, A NEW ANALGESIC AGENT.	1963 Nov	14082642
METABOLIC STUDIES OF VERSIDYNE, A NEW ANALGESIC, IN THE RABBIT AND IN MAN.	1964 May	14181280
Plasma levels and renal excretion of unchanged methopholine in man.	1967 Nov 15	6057015

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:01:44 GMT 2023` Edited by `admin` on `Fri Dec 15 15:01:44 GMT 2023`
Record UNII	72L4ZT2W1P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHOPHOLINE

Official Name

English

ARC-I-K-1

Code

English

ARC I-K-1

Code

English

RO 4-1778/1

Code

English

NIH 7672

Code

English

1-(P-CHLOROPHENETHYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYLISOQUINOLINE

Common Name

English

ISOQUINOLINE, 1-(2-(4-CHLOROPHENYL)ETHYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYL-

Systematic Name

English

metofoline [INN]

Common Name

English

ISOQUINOLINE, 1-(P-CHLOROPHENETHYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYL-

Systematic Name

English

METOPHOLINE

Common Name

English

NSC-169889

Code

English

NIH-7672

Code

English

METOFOLINE [MI]

Common Name

English

RO-4-1778/1

Code

English

METOFOLINE

Official Name

English

METHOPHOLINE [USAN]

Common Name

English

VERSIDYNE

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413