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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
¥2,686.42
25 MG
¥3,771.50
100 MG
¥14,449.04

¥2,686.42

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10 MG
¥2,686.42
25 MG
¥3,771.50
100 MG
¥14,449.04

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

¥2,686.42

Please contact Customer Service for Availability
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)

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M105

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assay

≥97% (NMR)

assay

≥99.0% (AT)

assay

-

assay

-

Quality Level

100

Quality Level

300

Quality Level

300

Quality Level

200

form

solid

form

powder or crystals

form

solid

form

powder or crystals

Gene Information

human ... CHRM2(1129)

Gene Information

-

Gene Information

-

Gene Information

human ... GRIN1(2902)

storage temp.

2-8°C

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

color

white

color

-

color

-

color

-

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 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

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    Lot/Batch Number
    0000355441
    0000355441
    0000110655
    0000110655
    0000131793

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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
    Intrastriatal infusions of methoctramine improve memory in cognitively impaired aged rats.
    Lazaris A
    Neurobiology of Aging, 24(2), 379-383 (2003)
    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)
    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
    Wei Wu et al.
    Neurobiology of learning and memory, 98(1), 41-46 (2012-05-09)
    Microinfusions of the nonselective muscarinic antagonist scopolamine into perirhinal cortex impairs performance on visual recognition tasks, indicating that muscarinic receptors in this region play a pivotal role in recognition memory. To assess the mnemonic effects of selective blockade in perirhinal
    View All Related Papers

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