Bifemelane HCl
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MedKoo CAT#: 329219

CAS#: 62232-46-6 (HCl)

Description: 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

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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: 269.178
Molecular Weight: 305.846
Elemental Analysis: C, 70.69; H, 7.91; Cl, 11.59; N, 4.58; O, 5.23

Price and Availability

Size Price Availability Quantity
50.0mg USD 350.0 2 Weeks
100.0mg USD 550.0 2 Weeks
200.0mg USD 950.0 2 Weeks
500.0mg USD 1850.0 2 Weeks
1.0g USD 2950.0 2 Weeks
2.0g USD 5250.0 2 Weeks
5.0g USD 7850.0 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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Water 30.58 100.0
DMSO 30.58 100.0

Preparing Stock Solutions

The following data is based on the product molecular weight 305.846 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.

Recalculate based on batch purity %
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

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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. PubMed 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. PubMed PMID: 16474207.

3: 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. PubMed PMID: 10403625.

4: Kinoshita M, Kaneko S, Yasuno T, Yada N, Akaike A, Satoh M. Inhibitory effects of bifemelane on brain Ca2+ channel subtypes expressed in Xenopus oocytes. Jpn J Pharmacol. 1998 Sep;78(1):39-44. PubMed PMID: 9804060.

5: 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. PubMed PMID: 10488692.

6: Akaike A, Maeda T, Kume T, Kaneko S. Bifemelane protects cultured cortical neurons against N-methyl-D-aspartate receptor-mediated glutamate cytotoxicity. Jpn J Pharmacol. 1998 Mar;76(3):313-6. PubMed PMID: 9593226.

7: Yoneda Y, Kuramoto N, Azuma Y, Inoue K, Ogita K, Mitani A, Yanase H, Masuda S, Zhang L, Kataoka K. Prolongation by bifemelane of potentiation of AP1 DNA binding in hippocampal CA1 subfield of gerbils with transient forebrain ischemia. J Neurosci Res. 1998 Mar 1;51(5):574-82. PubMed PMID: 9512001.

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. PubMed PMID: 8902600.

9: Ozaki S, Ohkawa I, Nakamura T, Tajima T. [Effect of bifemelane hydrochloride in rats on the improvement of the learning and memory impairments and prevention of neuronal damage following transient forebrain ischemia]. Nihon Yakurigaku Zasshi. 1994 Dec;104(6):469-80. Japanese. PubMed PMID: 7851820.

10: 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. PubMed PMID: 8959529.

11: 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. PubMed PMID: 8997585.

12: 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. PubMed PMID: 7603310.

13: 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. PubMed PMID: 7740059.

14: Shigemitsu T, Majima Y. Use of bifemelane hydrochloride in improving and maintaining the visual field of patients with glaucoma. Clin Ther. 1996 Jan-Feb;18(1):106-13. PubMed PMID: 8851457.

15: Kabasawa H, Matsubara M, Kamimoto K, Hibino H, Banno T, Nagai H. Effects of bifemelane hydrochloride on cerebral circulation and metabolism in patients with aphasia. Clin Ther. 1994 May-Jun;16(3):471-82. PubMed PMID: 7923314.