Skip to Content
Merck
All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing


About This Item

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

Quality Level

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.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service