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=C(OC)C=C2C(CCC3=CC=C(Cl)C=C3)N(C)CCC2=C1

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withdrawn-or-removed-from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 METHOPHOLINE was withdrawn from the market for reasons of safety.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
Plasma levels and renal excretion of unchanged methopholine in man.	1967-11-15	6057015
METABOLIC STUDIES OF VERSIDYNE, A NEW ANALGESIC, IN THE RABBIT AND IN MAN.	1964-05	14181280
METHOPHOLINE, A NEW ANALGESIC AGENT.	1963-11	14082642
Versidyne. Its use in vascular headache.	1963-01	13975764
An evaluation of the efficacy of methopholine for the relief of postoperative pain.	1962-09	14475666
Clinical studies of Versidyne, a non-narcotic analgesic.	1961-12	14495926

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:49 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:49 GMT 2025`
Record UNII	72L4ZT2W1P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHOPHOLINE

Official Name

English

METOFOLINE

Preferred 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

METHOPHOLINE [USAN]

Common Name

English

VERSIDYNE

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413