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M105

Sigma-Aldrich

Methoctramine hydrate

≥97% (NMR), 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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10 MG
$217.55
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$456.00
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$1,550.00

$217.55

List Price$229.00

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10 MG
$217.55
25 MG
$456.00
100 MG
$1,550.00

About This Item

Empirical Formula (Hill Notation):
C36H62N4O2 · 4HCl · xH2O
CAS Number:
104807-46-7
Molecular Weight:
728.75 (anhydrous basis)
MDL number:
MFCD11045942
UNSPSC Code:
12352116
PubChem Substance ID:
24277850
NACRES:
NA.32

$217.55

List Price$229.00

In StockDetails

Request a Bulk Order

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)

General description

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

Application

Methoctramine hydrate has been used:
  • As a muscarinic receptor 2 antogonist.[2]
  • 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.[3]

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.[4] In oesophageal muscle, acetylcholine-mediated increase in calcium and arachidonic acid release were reduced by the M2 receptor antagonist, methoctramine.[5] Methoctramine infused bilaterally in the dorsolateral striatum, considerably enhanced memory in cognitively impaired aged rats.[6] Methoctramine plays a vital role in muscarinic receptor classification.[7]

Storage Class

11 - Combustible Solids

wgk_germany

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
0000110655
0000131793
119K4617
058K47122
058K47121

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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
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)
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
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
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
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