BIFEMELANE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H23NO
Molecular Weight	269.3813
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNCCCCOC1=CC=CC=C1CC2=CC=CC=C2

InChI

InChIKey=QSQQPMHPCBLLGX-UHFFFAOYSA-N

InChI=1S/C18H23NO/c1-19-13-7-8-14-20-18-12-6-5-11-17(18)15-16-9-3-2-4-10-16/h2-6,9-12,19H,7-8,13-15H2,1H3

HIDE SMILES / InChI

Molecular Formula	C18H23NO
Molecular Weight	269.3813
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3335842
Curator's Comment: Description was created based on several sources, including https://drug.mynahcare.com/drugs/genericdetail/bifemelane-Mjg1 | https://www.ncbi.nlm.nih.gov/pubmed/8846747 | https://www.ncbi.nlm.nih.gov/pubmed/8851457 | https://www.ncbi.nlm.nih.gov/pubmed/1794296 | https://www.ncbi.nlm.nih.gov/pubmed/8474231 | https://www.ncbi.nlm.nih.gov/pubmed/1794296 | https://www.ncbi.nlm.nih.gov/pubmed/7490169

Bifemelane is a psychotropic drug, was found to inhibit monoamine oxidase (MAO). It inhibited type A MAO (MAO-A) competitively and type B (MAO-B) noncompetitively and it was a more potent inhibitor of MAO-A than of MAO-B. Bifemelane is an antidepressant and cerebral activator that is used in Japan for the treatment of cerebral infarction patients with depressive symptoms, and in the treatment of senile dementia as well. It also appears to be useful in the treatment of glaucoma.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Monoamine oxidase A 52 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3335842	Inhibitor 8504		4.2 µM [Ki]
Monoamine oxidase B 75 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3335842	Inhibitor 8504		46.0 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7490169	Primary	Approved 8583	BIFEMELANE Approved Use BIFEMELANE is an antidepressant and cerebral activator that is widely used in the treatment of cerebral infarction patients with depressive symptoms , and in the treatment of senile dementia as well. It also appears to be useful in the treatment of glaucoma.
Dementia 27 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8345159 https://www.ncbi.nlm.nih.gov/pubmed/1794296	Primary	Approved 8583	BIFEMELANE Approved Use BIFEMELANE is an antidepressant and cerebral activator that is widely used in the treatment of cerebral infarction patients with depressive symptoms , and in the treatment of senile dementia as well. It also appears to be useful in the treatment of glaucoma.
Cerebral infarction 14 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8474231 https://www.ncbi.nlm.nih.gov/pubmed/8846747	Primary	Approved 8583	BIFEMELANE Approved Use BIFEMELANE is an antidepressant and cerebral activator that is widely used in the treatment of cerebral infarction patients with depressive symptoms , and in the treatment of senile dementia as well. It also appears to be useful in the treatment of glaucoma.
Glaucoma 57 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8851457	Primary	Approved 8583	BIFEMELANE Approved Use BIFEMELANE is an antidepressant and cerebral activator that is widely used in the treatment of cerebral infarction patients with depressive symptoms , and in the treatment of senile dementia as well. It also appears to be useful in the treatment of glaucoma.

C_max

Value	Dose	Analyte	Population
7.57 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/22/4/22_4_737/_article/-char/en	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	BIFEMELANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
18.61 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/22/4/22_4_737/_article/-char/en	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	BIFEMELANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: FED
13.41 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/22/4/22_4_737/_article/-char/en	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	BIFEMELANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3.21 ng/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/22/4/22_4_737/_article/-char/en	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	BIFEMELANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Analyte	Population
46.29 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/22/4/22_4_737/_article/-char/en	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	BIFEMELANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
99.12 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/22/4/22_4_737/_article/-char/en	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	BIFEMELANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: FED
74.26 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/22/4/22_4_737/_article/-char/en	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	BIFEMELANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
20.24 ng × h/mL EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/22/4/22_4_737/_article/-char/en	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	BIFEMELANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
4.73 h EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/22/4/22_4_737/_article/-char/en	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	BIFEMELANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FED
4.69 h EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/22/4/22_4_737/_article/-char/en	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	BIFEMELANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: FED
4.71 h EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/22/4/22_4_737/_article/-char/en	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	BIFEMELANE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3.21 h EXPERIMENT https://www.jstage.jst.go.jp/article/jscpt1970/22/4/22_4_737/_article/-char/en	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	BIFEMELANE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

Doses

Dose	Population	Adverse events
50 mg 3 times / day steady-state, oral Studied dose Dose: 50 mg, 3 times / day Route: oral Route: steady-state Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1794296/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1794296/	Other AEs: urticaria... Other AEs: urticaria (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/1794296/
50 mg 3 times / day steady-state, oral Studied dose Dose: 50 mg, 3 times / day Route: oral Route: steady-state Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7490169/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7490169/	Sources: https://pubmed.ncbi.nlm.nih.gov/7490169/
50 mg 3 times / day steady-state, oral Studied dose Dose: 50 mg, 3 times / day Route: oral Route: steady-state Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7923314/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7923314/	Sources: https://pubmed.ncbi.nlm.nih.gov/7923314/
50 mg 3 times / day steady-state, oral Studied dose Dose: 50 mg, 3 times / day Route: oral Route: steady-state Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8846747/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8846747/	Sources: https://pubmed.ncbi.nlm.nih.gov/8846747/
50 mg 3 times / day steady-state, oral Studied dose Dose: 50 mg, 3 times / day Route: oral Route: steady-state Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8851457/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8851457/	Sources: https://pubmed.ncbi.nlm.nih.gov/8851457/

AEs

AE	Significance	Dose	Population
urticaria	1 pt	50 mg 3 times / day steady-state, oral Studied dose Dose: 50 mg, 3 times / day Route: oral Route: steady-state Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1794296/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1794296/

PubMed

Title	Date	PubMed
Effects of bifemelane on the calcium level and ATP release of the human origin astrocyte clonal cell.	2006-09	16974067
A novel effect of bifemelane, a nootropic drug, on intracellular Ca2+ levels in rat cerebral astrocytes.	2006-02	16474207
The clinical effect of bifemelane hydrochloride on dementia in aged patients.	1991	1794296
4-(O-benzylphenoxy)-N-methylbutylamine (bifemelane) and other 4-(O-benzylphenoxy)-N-methylalkylamines as new inhibitors of type A and B monoamine oxidase.	1988-01	3335842
Synthesis and antidepressant activity of substituted (omega-aminoalkoxy)benzene derivatives.	1981-02	7205881
Pharmacological evaluation of 2-(4-methylaminobutoxy)diphenylmethane hydrochloride (MCI-2016), a new psychotropic drug with antidepressant activity.	1981	7197535

Patents

Sample Use Guides

In Vivo Use Guide

150 mg daily in divided doses.

Route of Administration: Oral

In Vitro Use Guide

Bifemelane 10 nM to 1 uM significantly augmented the long-term potentiation in the CA3 region of guinea pig hippocampal slices

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:55:59 GMT 2025` Edited by `admin` on `Wed Apr 02 09:55:59 GMT 2025`
Record UNII	Z4501GN13G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

bifemelane [INN]

Preferred Name

English

BIFEMELANE

Official Name

English

N-METHYL-4-((.ALPHA.-PHENYL-O-TOLYL)OXY)BUTYLAMINE

Common Name

English

4-(2-BENZYLPHENOXY)-N-METHYLBUTAN-1-AMINE

Systematic Name

English

BIFEMELANE [MART.]

Common Name

English

Bifemelane [WHO-DD]

Common Name

English

2-(4-METHYLAMINOBUTOXY)DIPHENYLMETHANE

Common Name

English

4-(O-BENZYLPHENOXY)-N-METHYLBUTYLAMINE

Common Name

English

N-METHYL-4-(2-(PHENYLMETHYL)PHENOXY)-1-BUTANAMINE

Systematic Name

English

4-(2-BENZYLPHENOXY)-N-METHYLBUTYLAMINE

Systematic Name

English

1-BUTANAMINE, N-METHYL-4-(2-(PHENYLMETHYL)PHENOXY)-

Systematic Name

English

BIFEMELANE [MI]

Common Name

English

2-BENZYL-1-(4-(METHYLAMINO)BUTOXY)BENZENE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

N06AX08