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

Product Name

Methoctramine hydrate, ≥97% (NMR), solid

SMILES string

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

InChI key

XIIINYPADNNZHA-UHFFFAOYSA-N

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

assay

≥97% (NMR)

form

solid

color

white

solubility

H₂O: >20 mg/mL

storage temp.

2-8°C

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. 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.

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.

General description

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

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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Certificates of Analysis (COA)

Lot/Batch Number

0000494870

0000470540

0000470541

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Bronchodilator activity of (3R)-3-[[[(3-fluorophenyl)[(3,4,5-trifluorophenyl)methyl]amino] carbonyl]oxy]-1-[2-oxo-2-(2-thienyl)ethyl]-1-azoniabicyclo[2.2.2]octane bromide (CHF5407), a potent, long-acting, and selective muscarinic M3 receptor antagonist.

G Villetti et al.

The Journal of pharmacology and experimental therapeutics, 335(3), 622-635 (2010-09-02)

The novel quaternary ammonium salt (3R)-3-[[[(3-fluorophenyl)[(3,4,5-trifluorophenyl)methyl]amino]carbonyl]oxy]-1-[2-oxo-2-(2-thienyl)ethyl]-1-azoniabicyclo[2.2.2]octane bromide (CHF5407) showed subnanomolar affinities for human muscarinic M1 (hM1), M2 (hM2), and M3 (hM3) receptors and dissociated very slowly from hM3 receptors (t(½) = 166 min) with a large part of the receptorial

Synergistic Action of Presynaptic Muscarinic Acetylcholine Receptors and Adenosine Receptors in Developmental Axonal Competition at the Neuromuscular Junction.

Laura Nadal et al.

Developmental neuroscience, 38(6), 407-419 (2017-04-27)

The development of the nervous system involves the initial overproduction of synapses, which promotes connectivity. Hebbian competition between axons with different activities leads to the loss of roughly half of the overproduced elements and this refines connectivity. We used quantitative

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

A High Throughput Phenotypic Screening reveals compounds that counteract premature osteogenic differentiation of HGPS iPS-derived mesenchymal stem cells.

Lo Cicero A

Scientific Reports, 6:34798 (2016)

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

Lazaris A

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

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