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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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The interaction between tropomyosin-related kinase B receptors and presynaptic muscarinic receptors modulates transmitter release in adult rodent motor nerve terminals.

Neus Garcia et al.

The Journal of neuroscience : the official journal of the Society for Neuroscience, 30(49), 16514-16522 (2010-12-15)

The neurotrophin brain-derived neurotrophic factor (BDNF), neurotrophin-4 (NT-4) and the receptors tropomyosin-related kinase B (trkB) and p75(NTR) are present in the nerve terminals on the neuromuscular junctions (NMJs) of the levator auris longus muscle of the adult mouse. Exogenously added

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)

Increase of [Ca(2+)]i and release of arachidonic acid via activation of M2 receptor coupled to Gi and rho proteins in oesophageal muscle.

U D Sohn et al.

Cellular signalling, 12(4), 215-222 (2000-04-27)

We have previously shown that acetylcholine-induced contraction of oesophageal circular muscle depends on activation of phosphatidylcholine selective phospholipase C and D, which result in formation of diacylglycerol, and of phospholipase 2 which produces arachidonic acid. Diacylglycerol and arachidonic acid interact

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Global Trade Item Number

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