DIMEMORFAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H25N
Molecular Weight	255.3978
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC4=CC=C(C)C=C34

InChI

InChIKey=KBEZZLAAKIIPFK-NJAFHUGGSA-N

InChI=1S/C18H25N/c1-13-6-7-14-12-17-15-5-3-4-8-18(15,16(14)11-13)9-10-19(17)2/h6-7,11,15,17H,3-5,8-10,12H2,1-2H3/t15-,17+,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H25N
Molecular Weight	255.3978
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/9152562

Dimemorfan is a nonnarcotic antitussive drug. The antitussive action of dimemorfan appears to be directly on the cough center in the medulla.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9152562	Curative		Approved 8583	ASTOMIN Approved Use Unknown

C_max

Value	Dose	Analyte	Population
0.94 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25262813/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.19 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25262813/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5.3 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25262813/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.03 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.71 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.19 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.95 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
6.52 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	20 mg 3 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT

AUC

Value	Dose	Analyte	Population
12.14 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25262813/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
28.46 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25262813/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
57.26 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25262813/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
21.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
46.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
117 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
49.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
124 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	20 mg 3 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT

T_1/2

Value	Dose	Analyte	Population
10.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25262813/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
11 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25262813/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25262813/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
11.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
11.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
10.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28243685/	20 mg 3 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DIMEMORFAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT

Doses

Dose	Population	Adverse events
90 mg single, oral Highest studied dose Dose: 90 mg Route: oral Route: single Dose: 90 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9152562/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9152562/	Sources: https://pubmed.ncbi.nlm.nih.gov/9152562/
20 mg 3 times / day multiple, oral Recommended\|Highest studied dose Dose: 20 mg, 3 times / day Route: oral Route: multiple Dose: 20 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28243685/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28243685/	Other AEs: Drowsiness, Felt giddy... Other AEs: Drowsiness (grade 1, 50%) Felt giddy (grade 1, 8%) Sources: https://pubmed.ncbi.nlm.nih.gov/28243685/

AEs

AE	Significance	Dose	Population
Drowsiness	grade 1, 50%	20 mg 3 times / day multiple, oral Recommended\|Highest studied dose Dose: 20 mg, 3 times / day Route: oral Route: multiple Dose: 20 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28243685/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28243685/
Felt giddy	grade 1, 8%	20 mg 3 times / day multiple, oral Recommended\|Highest studied dose Dose: 20 mg, 3 times / day Route: oral Route: multiple Dose: 20 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/28243685/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/28243685/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2B6 776 CYP2C19 1119

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19593786/ \| https://pubmed.ncbi.nlm.nih.gov/25159483/	major [Km 20 uM]	yes (pharmacogenomic study) Comment: The C max values were significantly higher in subjects with CYP2D610 TT (8.06 ± 4.43 ng/mL) than CYP2D610 CC (3.41 ± 2.79 ng/mL), CYP2D6*10 CT (3.11 ± 2.47 ng/mL), so was AUC0-inf. Sources: https://pubmed.ncbi.nlm.nih.gov/19593786/ \| https://pubmed.ncbi.nlm.nih.gov/25159483/
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19593786/	yes
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19593786/	yes
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19593786/	yes
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19593786/	yes

PubMed

Title	Date	PubMed
The oxidative metabolism of dimemorfan by human cytochrome P450 enzymes.	2010-02	19593786
Pharmacology and therapeutic potential of sigma(1) receptor ligands.	2008-12	19587856
Concise synthesis of dimemorfan (DF) starting from 3-hydroxymorphinan (3-HM).	2008-07	18591815
Anti-inflammatory effects of dimemorfan on inflammatory cells and LPS-induced endotoxin shock in mice.	2008-07	18500357
Dimemorfan protects rats against ischemic stroke through activation of sigma-1 receptor-mediated mechanisms by decreasing glutamate accumulation.	2008-01	18173806
[Otorhinolaringologyc approach of the chronic cough. Clinical case].	2007	17405461
Dimemorfan N-demethylation by mouse liver microsomal cytochrome P450 enzymes.	2005-07-01	15936348
The dextromethorphan analog dimemorfan attenuates kainate-induced seizures via sigma1 receptor activation: comparison with the effects of dextromethorphan.	2005-04	15723099
Dimemorfan enhances acetylcholine release from rat hippocampal slices.	2004-05-15	15081388
Dimemorfan prevents seizures induced by the L-type calcium channel activator BAY k-8644 in mice.	2004-05-05	15084442
Anti-amnesic effect of dimemorfan in mice.	2003-03	12642396
Binding of dimemorfan to sigma-1 receptor and its anticonvulsant and locomotor effects in mice, compared with dextromethorphan and dextrorphan.	1999-03-13	10064839
The nonnarcotic antitussive drug dimemorfan: a review.	1997-03-01	9152562
Effect of the centrally acting antitussives on ascites tumor cells.	1983-04	6887645

Patents

Sample Use Guides

In Vivo Use Guide

20 mg three times daily.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:18:56 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:56 GMT 2025`
Record UNII	623OAC38YU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIMEMORFAN [MI]

Preferred Name

English

DIMEMORFAN

Official Name

English

dimemorfan [INN]

Common Name

English

Dimemorfan [WHO-DD]

Common Name

English

(+)-3,17-DIMETHYLMORPHINAN

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66917