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Bifemelane

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Bifemelane
Clinical data

Trade names	Alnert, Celeport
Other names	MCl-2016
AHFS/Drugs.com	International Drug Names
ATC code	N06AX08 (WHO)
Identifiers
IUPAC name N-methyl-4-[2-(phenylmethyl)phenoxy]butan-1-amine
CAS Number	90293-01-9^Y
PubChem CID	2377
ChemSpider	2286^Y
UNII	Z4501GN13G
ChEMBL	ChEMBL1192517^N
CompTox Dashboard (EPA)	DTXSID1045663
ECHA InfoCard	100.220.566
Chemical and physical data
Formula	C₁₈H₂₃NO
Molar mass	269.388 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O(c1ccccc1Cc2ccccc2)CCCCNC
InChI 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^Y Key:QSQQPMHPCBLLGX-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Bifemelane (INN) (Alnert, Celeport), or bifemelane hydrochloride (JAN), also known as 4-(O-benzylphenoxy)-N-methylbutylamine, is an antidepressant and cerebral activator that was widely used in the treatment of cerebral infarction patients with depressive symptoms in Japan, and in the treatment of senile dementia as well.^[1]^[2] It also appears to be useful in the treatment of glaucoma.^[3] It has been discontinued in Japan since 1998, when it was removed from the market reportedly for lack of effectiveness.^[4]

Bifemelane acts as a monoamine oxidase inhibitor of both isoenzymes, with competitive (reversible) inhibition of MAO-A (K_i = 4.20 μM) (making it a reversible inhibitor of monoamine oxidase A (RIMA)) and non-competitive (irreversible) inhibition of MAO-B (K_i = 46.0 μM),^[5]^[6]^[7] and also acts (weakly) as a norepinephrine reuptake inhibitor.^[8] The drug has nootropic, neuroprotective, and antidepressant-like effects in animal models, and appears to enhance the cholinergic system in the brain.^[9]^[10]^[11]

References

[edit]

^ Koide S, Onishi H, Hashimoto H, Kai T, Katayama M, Yamagami S (1995). "Effects of bifemelane hydrochloride on plasma neuropeptide Y, 3-methoxy-4-hydroxyphenylethylene glycol and 5-hydroxy-indole acetic acid concentrations in patients with cerebral infarction". Drugs Under Experimental and Clinical Research. 21 (5): 175–80. PMID 8846747.

^ Triggle DJ (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. p. 265. ISBN 978-0-412-46630-4.

^ Shigemitsu T, Majima Y (1996). "Use of bifemelane hydrochloride in improving and maintaining the visual field of patients with glaucoma". Clinical Therapeutics. 18 (1): 106–13. doi:10.1016/S0149-2918(96)80183-4. PMID 8851457.

^ Hayashi K, Hashimoto K, Yanagi M, Umeda T, Hama R (August 1998). "Drug approval in Japan questioned". Lancet. 352 (9126): 491. doi:10.1016/S0140-6736(05)79232-1. PMID 9708787.

^ Naoi M, Nomura Y, Ishiki R, Suzuki H, Nagatsu T (January 1988). "4-(O-benzylphenoxy)-N-methylbutylamine (bifemelane) and other 4-(O-benzylphenoxy)-N-methylalkylamines as new inhibitors of type A and B monoamine oxidase". Journal of Neurochemistry. 50 (1): 243–7. doi:10.1111/j.1471-4159.1988.tb13256.x. PMID 3335842. S2CID 35543291.

^ Kovel'man IR, Tochilkin AI, Gorkin VZ (1991). "Structure and action of reversible monoamine oxidase inhibitors (review)". Pharmaceutical Chemistry Journal. 25 (8): 505–520. doi:10.1007/BF00777412. ISSN 0091-150X. S2CID 42477788.

^ Choe JY (4 March 2011). Drug Actions and Interactions. McGraw Hill Professional. p. 307. ISBN 978-0-07-176945-7.

^ Dostert P (1994). "Can our knowledge of monoamine oxidase (MAO) help in the design of better MAO inhibitors?". Journal of Neural Transmission. 41 (Supplementum): 269–279. doi:10.1007/978-3-7091-9324-2_35. ISBN 978-3-211-82521-1. PMID 7931236. For example, bifemelane [4-(O-benzylphenoxy)-N-methylbutylamine) is one of the few molecules in which both activities, reversible inhibition of MAO-A (Naoi et al., 1988) and inhibition of noradrenaline uptake (Egawa et al., 1983), although weak (IC50 = 10-6-10-7 M), coexist.

^ Kondo Y, Ogawa N, Asanuma M, Matsuura K, Nishibayashi K, Iwata E (March 1996). "Preventive effects of bifemelane hydrochloride on decreased levels of muscarinic acetylcholine receptor and its mRNA in a rat model of chronic cerebral hypoperfusion". Neuroscience Research. 24 (4): 409–14. doi:10.1016/0168-0102(95)01017-3. PMID 8861111. S2CID 34313096.

^ Egashira T, Takayama F, Yamanaka Y (September 1996). "Effects of bifemelane on muscarinic receptors and choline acetyltransferase in the brains of aged rats following chronic cerebral hypoperfusion induced by permanent occlusion of bilateral carotid arteries". Japanese Journal of Pharmacology. 72 (1): 57–65. doi:10.1254/jjp.72.57. PMID 8902600.

^ Moryl E, Danysz W, Quack G (June 1993). "Potential antidepressive properties of amantadine, memantine and bifemelane". Pharmacology & Toxicology. 72 (6): 394–7. doi:10.1111/j.1600-0773.1993.tb01351.x. PMID 8361950.

Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIsTooltip Selective serotonin reuptake inhibitors	Citalopram Escitalopram Fluoxetine^# Fluvoxamine Indalpine^‡ Paroxetine Sertraline Zimelidine^‡
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine
NRIsTooltip Norepinephrine reuptake inhibitors	Atomoxetine Reboxetine Viloxazine
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors	Amineptine^‡ Bupropion Nomifensine^‡
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants	Mianserin Mirtazapine Setiptiline
SARIsTooltip Serotonin antagonist and reuptake inhibitors	Etoperidone Nefazodone Trazodone
SMSTooltip Serotonin modulator and stimulators	Vilazodone Vortioxetine
Others	Agomelatine Amisulpride Dextromethorphan/bupropion Esketamine Etryptamine^‡ Gepirone Indeloxazine Flupentixol Ketamine^§ Medifoxamine^‡ Metryptamine^‡ Oxaflozane^‡ Pivagabine^‡ Tandospirone Teniloxazine Tianeptine