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Merck

M105

Methoctramine hydrate

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

Sinónimos:

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

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Acerca de este artículo

Fórmula empírica (notación de Hill):
C36H62N4O2 · 4HCl · xH2O
Número CAS:
104807-46-7
Peso molecular:
728.75 (anhydrous basis)
UNSPSC Code:
12352116
PubChem Substance ID:
24277850
NACRES:
NA.32
MDL number:
MFCD11045942

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Nombre del producto

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

Quality Level

100

Gene Information

human ... CHRM2(1129)

Categorías relacionadas

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. 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.

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
0000494870
0000494870
0000470540
0000470541
0000470541

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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)
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
Maddalena Zini et al.
Chemico-biological interactions, 181(3), 409-416 (2009-07-07)
Methoctramine and its analogues are polymethylene tetramines that selectively bind to a variety of receptor sites. Although these compounds are widely used as pharmacological tools for receptor characterization, the toxicological properties of these polyamine-based structures are largely unknown. We have
Intrastriatal infusions of methoctramine improve memory in cognitively impaired aged rats.
Lazaris A
Neurobiology of Aging, 24(2), 379-383 (2003)
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
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