Bifemelane HCl | CAS#62232-46-6 | MAO inhibitor

MedKoo Cat#: 329219 | Name: Bifemelane HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bifemelane, also known as MCI-2016, is Antidepressant MAO inhibitor used to treat cerebral infarction and Alzheimer's disease. At concentrations of 10 - 30 microM, Bifemelane induced a slow onset and small increase in the [Ca2+]i, while at higher concentrations (100 - 300 microM), it induced a rapid transient increase in the [Ca2+]i during administration and a second large increase was seen during drug washout.

Chemical Structure

Bifemelane HCl

CAS#62232-46-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 329219

Name: Bifemelane HCl

CAS#: 62232-46-6 (HCl)

Chemical Formula: C18H24ClNO

Exact Mass: 0.0000

Molecular Weight: 305.85

Elemental Analysis: C, 70.69; H, 7.91; Cl, 11.59; N, 4.58; O, 5.23

Price and Availability

Size	Price	Availability
10mg	USD 350.00	2 Weeks
25mg	USD 550.00	2 Weeks
50mg	USD 750.00	2 Weeks
100mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,850.00	2 Weeks
2g	USD 6,450.00	2 Weeks

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Related CAS #

62232-46-6 (HCl) 90293-01-9 (free base)

Synonym

Bifemelane; MCI-2016; MCI 2016; MCI2016; Bifemelanum, Bifemelane HCl

IUPAC/Chemical Name

4-(2-benzylphenoxy)-N-methylbutan-1-amine hydrochloride

InChi Key

MEAHDXWXNNDSAK-UHFFFAOYSA-N

InChi Code

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

SMILES Code

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

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Bifemelane hydrochloride (MCI-2016) is an inhibitor of monoamine oxidase A (MAO-A), with a Ki of 4.20 μM. Bifemelane hydrochloride also inhibits MAO-B noncompetitively with a Ki of 46.0 μM.

In vitro activity:

Bifemelane (125 - 1,000 microM) induced a dose-dependent increase in the intracellular calcium concentration ([Ca(2+)](i)). In the highest concentration (1,000 microM), the drug caused the second large increase in [Ca(2+)](i) during the washing. Reference: J Pharmacol Sci. 2006 Sep;102(1):121-8. https://pubmed.ncbi.nlm.nih.gov/16974067/

In vivo activity:

Long-term potentiation was significantly reduced in both the Schaffer collateral-CA1 and perforant path-dentate gyrus synapses in the saline-injected group. However bifemelane decreased the ischaemia-induced reduction of long-term potentiation in perforant path-dentate gyrus synapses, but not in Schaffer collateral-CA1 synapses. The findings suggest that bifemelane deserves further attention with regard to possible protective role in ischaemia. Reference: Pharmacol Toxicol. 1999 Aug;85(2):98-102. https://pubmed.ncbi.nlm.nih.gov/10488692/

	Solvent	mg/mL	mM
Solubility
	DMSO	30.6	100.00
	Water	30.6	100.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 305.85 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Yoshida Y, Kumagai H, Ohkubo Y, Tsuchiya R, Morita M, Miyakawa H, Kudo Y. Effects of bifemelane on the calcium level and ATP release of the human origin astrocyte clonal cell. J Pharmacol Sci. 2006 Sep;102(1):121-8. doi: 10.1254/jphs.fp0060471. Epub 2006 Sep 15. PMID: 16974067. 2. Yoshida Y, Nakane A, Morita M, Kudo Y. A novel effect of bifemelane, a nootropic drug, on intracellular Ca2+ levels in rat cerebral astrocytes. J Pharmacol Sci. 2006 Feb;100(2):126-32. doi: 10.1254/jphs.fp0050926. Epub 2006 Feb 11. PMID: 16474207. 3. Mori K, Suda N, Togashi H, Matsumoto M, Saito H, Yoshioka M. Effects of bifemelane on incomplete cerebral ischaemia-induced reduction of long-term potentiation in rat hippocampal neurones in vivo. Pharmacol Toxicol. 1999 Aug;85(2):98-102. doi: 10.1111/j.1600-0773.1999.tb00073.x. PMID: 10488692. 4. Yasui M, Ota K, Oshima A. Effects of bifemelane hydrochloride on atherosclerosis in aged rats fed low-calcium diets. J Int Med Res. 1996 Nov-Dec;24(6):454-65. doi: 10.1177/030006059602400602. PMID: 8959529.

In vitro protocol:

In vivo protocol:

1. Mori K, Suda N, Togashi H, Matsumoto M, Saito H, Yoshioka M. Effects of bifemelane on incomplete cerebral ischaemia-induced reduction of long-term potentiation in rat hippocampal neurones in vivo. Pharmacol Toxicol. 1999 Aug;85(2):98-102. doi: 10.1111/j.1600-0773.1999.tb00073.x. PMID: 10488692. 2. Yasui M, Ota K, Oshima A. Effects of bifemelane hydrochloride on atherosclerosis in aged rats fed low-calcium diets. J Int Med Res. 1996 Nov-Dec;24(6):454-65. doi: 10.1177/030006059602400602. PMID: 8959529.

1: Ueda M, Fujii T, Kuraishi Y, Satoh M. Bifemelane enhances high K(+)-evoked release of glutamate from mossy fiber synaptosomes of guinea-pig hippocampus. Eur J Pharmacol. 1992 Aug 25;219(2):271-7. doi: 10.1016/0014-2999(92)90305-n. PMID: 1358642. 2: Yasui M, Tsuda T, Ota K. Effects of bifemelane on calcium and magnesium deposition in the central nervous system tissues of rats maintained on low- calcium diets. J Int Med Res. 1991 Nov-Dec;19(6):471-8. doi: 10.1177/030006059101900607. Erratum in: J Int Med Res 1993 Jan- Feb;21(1):following 65. PMID: 1845351. 3: Fujii T, Kuraishi Y, Ueda M, Satoh M. Specific binding sites for bifemelane in the hippocampus of the guinea pig, relevant to its pharmacological actions. Neuropharmacology. 1991 Dec;30(12A):1291-5. doi: 10.1016/0028-3908(91)90025-7. PMID: 1787882. 4: Fujii T, Kuraishi Y, Okada T, Satoh M. Bifemelane induces translocation of protein kinase C in the CA3, but not the CA1, region of guinea-pig hippocampus. Can J Physiol Pharmacol. 1990 Mar;68(3):413-8. doi: 10.1139/y90-058. PMID: 2322898. 5: Mitsuma T, Hirooka Y, Yuasa K, Nogimori T. Bifemelane hydrochloride reduces plasma beta-endorphin-like immunoreactivity levels in rats. Exp Clin Endocrinol. 1990 Aug;95(3):301-5. doi: 10.1055/s-0029-1210969. PMID: 2245819. 6: Miyazaki I, Iwata-Ichikawa E, Asanuma M, Iida M, Ogawa N. Bifemelane hydrochloride protects against cytotoxicity of hydrogen peroxide on cultured rat neuroblastoma cell line. Neurochem Res. 1999 Jul;24(7):857-60. doi: 10.1023/a:1020953913490. PMID: 10403625. 7: Yoshida Y, Kumagai H, Ohkubo Y, Tsuchiya R, Morita M, Miyakawa H, Kudo Y. Effects of bifemelane on the calcium level and ATP release of the human origin astrocyte clonal cell. J Pharmacol Sci. 2006 Sep;102(1):121-8. doi: 10.1254/jphs.fp0060471. Epub 2006 Sep 15. PMID: 16974067. 8: Egashira T, Takayama F, Yamanaka Y. 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. Jpn J Pharmacol. 1996 Sep;72(1):57-65. doi: 10.1254/jjp.72.57. PMID: 8902600. 9: Nomoto M, Irifune M, Fukuzaki K, Fukuda T. Effects of bifemelane on parkinsonism induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) in the common marmoset. Neurosci Lett. 1994 Aug 29;178(1):95-8. doi: 10.1016/0304-3940(94)90298-4. PMID: 7816348. 10: Adachi M, Takahashi K, Yuge K, Nishikawa M, Miki H, Uyama M. Treatment with bifemelane for optic nerve damage following high intraocular pressure in rat eyes. Eur J Ophthalmol. 1996 Oct-Dec;6(4):415-20. doi: 10.1177/112067219600600413. PMID: 8997585. 11: Egawa M, Ikegami S, Hanada Y, Tobe A. Effects of bifemelane hydrochloride on cortical neuronal activity in cats. Neuropharmacology. 1987 Apr;26(4):379-84. doi: 10.1016/0028-3908(87)90192-4. PMID: 2884591. 12: Moryl E, Danysz W, Quack G. Potential antidepressive properties of amantadine, memantine and bifemelane. Pharmacol Toxicol. 1993 Jun;72(6):394-7. doi: 10.1111/j.1600-0773.1993.tb01351.x. PMID: 8361950. 13: Asanuma M, Ogawa N, Hirata H, Chou HH, Kondo Y, Mori A. Ischemia-induced changes in alpha-tubulin and beta-actin mRNA in the gerbil brain and effects of bifemelane hydrochloride. Brain Res. 1993 Jan 15;600(2):243-8. doi: 10.1016/0006-8993(93)91379-7. PMID: 8435749. 14: Hirayama Y, Matsunaga N, Tashiro J, Amemiya T, Iwasaki M. Bifemelane in the treatment of central retinal artery or vein obstruction. Clin Ther. 1990 May- Jun;12(3):230-5. PMID: 2379227. 15: Yoshida Y, Nakane A, Morita M, Kudo Y. A novel effect of bifemelane, a nootropic drug, on intracellular Ca2+ levels in rat cerebral astrocytes. J Pharmacol Sci. 2006 Feb;100(2):126-32. doi: 10.1254/jphs.fp0050926. Epub 2006 Feb 11. PMID: 16474207. 16: Shibata S, Ono M, Minamoto Y, Watanabe S. Attenuating effect of bifemelane on an impairment of mealtime-associated activity rhythm in aged and MK-801-treated rats. Pharmacol Biochem Behav. 1995 Feb;50(2):207-10. doi: 10.1016/0091-3057(94)00292-q. PMID: 7740059. 17: Ogawa N, Haba K, Sora YH, Higashida A, Sato H, Ogawa S. Comparison of the effects of bifemelane hydrochloride and indeloxazine hydrochloride on scopolamine hydrobromide-induced impairment in radial maze performance. Clin Ther. 1988;10(6):704-11. PMID: 3219685. 18: Goto Y, Taki W, Kikuchi H. [Effects of bifemelane on the free fatty acid levels during ischemia]. No To Shinkei. 1988 Nov;40(11):1045-9. Japanese. PMID: 3219239. 19: Ogawa N, Mizukawa K, Haba K, Asanuma M, Mori A. Chronic bifemelane hydrochloride administration enhances muscarinic cholinergic receptor binding in the senescent rat brain. J Med. 1991;22(1):17-27. PMID: 2072048. 20: Hata R, Matsumoto M, Kitagawa K, Tagaya M, Matsuyama T, Sugita M, Kamada T. Therapeutic effect of bifemelane on unilateral cerebral ischemia in gerbils. Life Sci. 1995;57(4):379-86. doi: 10.1016/0024-3205(95)00297-j. PMID: 7603310.