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M9020

Sigma-Aldrich

Mecamylamine hydrochloride

≥98% (TLC), powder, nAChR antagonist

Synonym(s):

2-(Methylamino)isocamphane hydrochloride, Inversine, N,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-amine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C11H21N · HCl
CAS Number:
826-39-1
Molecular Weight:
203.75
EC Number:
212-555-8
MDL number:
MFCD00151462
UNSPSC Code:
12352116
PubChem Substance ID:
24277851
NACRES:
NA.77

product name

Mecamylamine hydrochloride,

form

powder

Quality Level

200

solubility

ethanol: 122 mg/mL
H2O: 47 mg/mL
isopropanol: 476 mg/mL
glycerol: 95 mg/mL

originator

AstraZeneca

SMILES string

Cl.[H][C@@]12CC[C@@]([H])(C1)C(C)(NC)C2(C)C

InChI

1S/C11H21N.ClH/c1-10(2)8-5-6-9(7-8)11(10,3)12-4;/h8-9,12H,5-7H2,1-4H3;1H/t8-,9+,11?;/m1./s1

InChI key

PKVZBNCYEICAQP-CIISUUNXSA-N

Gene Information

human ... CHRNA1(1134) , CHRNA10(57053) , CHRNA2(1135) , CHRNA3(1136) , CHRNA4(1137) , CHRNA5(1138) , CHRNA6(8973) , CHRNA7(1139) , CHRNA9(55584) , CHRNB1(1140) , CHRNB2(1141) , CHRNB3(1142) , CHRNB4(1143)

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Application

Mecamylamine hydrochloride has been used as an additive in extracellular saline during current-clamp recordings to reduce synaptic input. It has also been used as a non-selective nicotinic acetyl choline receptor blocker in aortic body neurons and in MLO-Y4 cells.

Biochem/physiol Actions

Noncompetitive nicotinic acetylcholine receptor antagonist; preferentially blocks nicotinic receptors at autonomic ganglia; crosses blood-brain barrier.

Features and Benefits

This compound is featured on the Acetylcholine Receptors (Nicotinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Caution

Solutions are stable to autoclaving.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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’.

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Acetylcholine affects osteocytic MLO-Y4 cells via acetylcholine receptors
Ma Y, et al.
Molecular and cellular endocrinology, 384(1-2), 155-164 (2014)
G Panagis et al.
Synapse (New York, N.Y.), 35(1), 15-25 (1999-12-01)
In the present study the neuronal expression of Fos, the protein product of c-fos, was used to study changes in neuronal activity in nerve terminal regions of the ascending dopaminergic system during nicotine withdrawal. Rats were infused for 14 days
M I Damaj et al.
The Journal of pharmacology and experimental therapeutics, 291(3), 1284-1291 (1999-11-24)
Pharmacological mechanisms involved in nicotine-induced seizures were investigated in mice by testing the ability of several nicotinic agonists in producing seizures after peripheral administration. In addition, nicotinic antagonists such as hexamethonium, mecamylamine, dihydro-beta-erythroidine, and methyllycaconitine citrate (MLA) were used in
Potential roles of ATP and local neurons in the monitoring of blood O2 content by rat aortic bodies
Piskuric NA, et al.
Experimental Physiology, 99(1), 248-261 (2014)
Olena Riabinina et al.
Genetics, 212(1), 53-63 (2019-03-14)
The Q-system is a binary expression system that works well across species. Here, we report the development and demonstrate the applications of a split-QF system that drives strong expression in Drosophila, is repressible by QS, and is inducible by a
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