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M105

Methoctramine hydrate

Name: Methoctramine hydrate
Brand: SIGMA

≥97% (NMR), muscarinic receptor 2 antogonist, solid

Synonym(s):

Methoctramine tetrahydrochloride hydrate, N,N′-bis[6-[[(2-Methoxyphenyl)methyl]amino]hexyl]-1,8-octane diamine tetrahydrochloride hydrate

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About This Item

Empirical Formula (Hill Notation):

C₃₆H₆₂N₄O₂ · 4HCl · xH₂O

CAS Number:

104807-46-7

Molecular Weight:

728.75 (anhydrous basis)

UNSPSC Code:

12352116

PubChem Substance ID:

24277850

NACRES:

NA.32

MDL number:

MFCD11045942

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Properties

Product Name

Methoctramine hydrate, ≥97% (NMR), solid

Quality Level

100

assay

≥97% (NMR)

form

solid

color

white

solubility

H₂O: >20 mg/mL

storage temp.

2-8°C

SMILES string

O.Cl.Cl.Cl.Cl.COc1ccccc1CNCCCCCCNCCCCCCCCNCCCCCCNCc2ccccc2OC.COc3ccccc3CNCCCCCCNCCCCCCCCNCCCCCCNCc4ccccc4OC

InChI

1S/2C36H62N4O2.4ClH.H2O/c2*1-41-35-23-13-11-21-33(35)31-39-29-19-9-7-17-27-37-25-15-5-3-4-6-16-26-38-28-18-8-10-20-30-40-32-34-22-12-14-24-36(34)42-2;;;;;/h2*11-14,21-24,37-40H,3-10,15-20,25-32H2,1-2H3;4*1H;1H2

InChI key

XIIINYPADNNZHA-UHFFFAOYSA-N

Gene Information

human ... CHRM2(1129)

Description

General description

Methoctramine (N, N′-bis [6-[[(2-methoxyphenyl)-methyl] hexyl]-1, 8-octane] diamine) is a derivative of polymethylene tetramine.

Application

Methoctramine hydrate has been used:

As a muscarinic receptor 2 antogonist.
As a test molecule to check its effect on premature osteogenic differentiation of HGPS (Hutchinson-Gilford progeria syndrome) iPS (induced pluripotent)-derived mesenchymal stem cells.

Biochem/physiol Actions

Methoctramine is a selective M2 muscarinic receptor antagonist at nM concentrations. At mM concentrations, methoctramine directly inhibits the high affinity GTPase activity of G proteins. In oesophageal muscle, acetylcholine-mediated increase in calcium and arachidonic acid release were reduced by the M2 receptor antagonist, methoctramine. Methoctramine infused bilaterally in the dorsolateral striatum, considerably enhanced memory in cognitively impaired aged rats. Methoctramine plays a vital role in muscarinic receptor classification.

Methoctramine is a selective M2 muscarinic receptor antagonist at nM concentrations. At mM concentrations, methoctramine directly inhibits the high affinity GTPase activity of G proteins. The increase in calcium and arachidonic acid release were attenuated by the M2 receptor antagonist methoctramine, but not by the M3 receptor antagonist p-fluoro-hexahydro siladifenidol.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Presynaptic Muscarinic Acetylcholine Receptors and TrkB Receptor Cooperate in the Elimination of Redundant Motor Nerve Terminals during Development.

Nadal L

Frontiers in Aging Neuroscience, 9, 24-24 (2017)

Intrastriatal infusions of methoctramine improve memory in cognitively impaired aged rats.

Lazaris A

Neurobiology of Aging, 24(2), 379-383 (2003)

Inhibition of GTPase activity of Gi proteins and decreased agonist affinity at M2 muscarinic acetylcholine receptors by spermine and methoctramine.

L Daeffler et al.

British journal of pharmacology, 127(4), 1021-1029 (1999-08-05)

1. The effects of spermine and methoctramine, a selective M2 muscarinic receptor antagonist, were studied on the high-affinity GTPase activity of G proteins, and on ligand binding to M2 muscarinic receptors in pig heart sarcolemma. 2. The spontaneous GTP hydrolysis

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Global Trade Item Number

SKU	GTIN
M105-100MG	04061833007549
M105-25MG	04061834037811
M105-10MG	04061834037798