BIFEMELANE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H23NO.ClH
Molecular Weight	305.842
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CNCCCCOC1=CC=CC=C1CC2=CC=CC=C2

InChI

InChIKey=MEAHDXWXNNDSAK-UHFFFAOYSA-N

InChI=1S/C18H23NO.ClH/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;1H

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

Molecular Formula	ClH
Molecular Weight	36.461
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 49 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3335842	Inhibitor 8297		4.2 µM [Ki]
Monoamine oxidase B 72 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3335842	Inhibitor 8297		46.0 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7490169	Primary	Approved 8429	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 8429	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 8429	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 8429	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.

PubMed

Title	Date	PubMed
Pharmacological evaluation of 2-(4-methylaminobutoxy)diphenylmethane hydrochloride (MCI-2016), a new psychotropic drug with antidepressant activity.	1981	7197535
4-(O-benzylphenoxy)-N-methylbutylamine (bifemelane) and other 4-(O-benzylphenoxy)-N-methylalkylamines as new inhibitors of type A and B monoamine oxidase.	1988 Jan	3335842
A novel effect of bifemelane, a nootropic drug, on intracellular Ca2+ levels in rat cerebral astrocytes.	2006 Feb	16474207
Effects of bifemelane on the calcium level and ATP release of the human origin astrocyte clonal cell.	2006 Sep	16974067

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 `Fri Dec 15 15:59:03 GMT 2023` Edited by `admin` on `Fri Dec 15 15:59:03 GMT 2023`
Record UNII	2N52S01UFY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIFEMELANE HYDROCHLORIDE

Common Name

English

BIFEMELANE HCL

Common Name

English

BIFEMELANE HYDROCHLORIDE [MI]

Common Name

English

BIFEMELANE HYDROCHLORIDE [JAN]

Common Name

English

4-(O-BENZYLPHENOXY)-N-METHYLBUTYLAMINE HYDROCHLORIDE

Common Name

English

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

Systematic Name

English

2-(4-METHYLAMINOBUTOXY)DIPHENYLMETHANE HYDROCHLORIDE

Common Name

English

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

Systematic Name

English

Bifemelane hydrochloride [WHO-DD]

Common Name

English

Code System Code Type Description

MERCK INDEX

m2480