MECAMYLAMINE

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Search structure


Synonyms	Mecamylamine
Status
Molecule Category	Free-form
ATC	C02BB01
UNII	6EE945D3OK
EPA CompTox	DTXSID0023240


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	IMYZQPCYWPFTAG-UHFFFAOYSA-N
Smiles	CNC1(C)C2CCC(C2)C1(C)C
InChI	InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C11H21N
Molecular Weight	167.3
AlogP	2.42
Hydrogen Bond Acceptor	1.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	1.0
Polar Surface Area	12.03
Molecular species	BASE
Aromatic Rings	0.0
Heavy Atoms	12.0

Assay Description	Organism	Bioactivity	Reference
Compound was evaluated for functional potency and efficacy at rat Nicotinic acetylcholine receptor in PC12 cells (ganglionic)	Rattus norvegicus	200.0 nM
Inhibitory activity against nicotinic acetylcholine receptor alpha3-beta4	None	100.0 nM
Inhibitory concentration against Nicotinic acetylcholine receptor alpha3-beta2	Homo sapiens	280.0 nM
Displacement of [3H]alpha-BGT from nAChR in Torpedo nobiliana electric organs membranes at 1000 uM by scintillation counting method	Torpedo nobiliana	0.0 %
Displacement of [3H]PCP from nAChR in Torpedo nobiliana electric organs membranes in presence of 100 uM carbachol by scintillation counting method	Torpedo nobiliana	596.0 nM
Antagonist activity at human recombinant alpha4beta2 nAChR expressed in human HEKtsA201 cells assessed as inhibition of epibatidine-stimulated calcium accumulation at 10 uM pretreated and cotreated with epibatidine by fluorescence plate reader analysis	Homo sapiens	91.8 %
Antagonist activity at human recombinant alpha3beta4 nAChR expressed in human HEKtsA201 cells assessed as inhibition of epibatidine-stimulated calcium accumulation at 10 uM pretreated and cotreated with epibatidine by fluorescence plate reader analysis	Homo sapiens	88.3 %
Antagonist activity at human alpha3beta4 nAChR expressed in HEK-tsA201 cells assessed as inhibition of epibatidine-induced intracellular calcium level by fluorescence plate reader analysis	Homo sapiens	700.0 nM
Antagonist activity at human alpha4beta2 nAChR expressed in HEK-tsA201 cells assessed as inhibition of epibatidine-induced intracellular calcium level by fluorescence plate reader analysis	Homo sapiens	600.0 nM
Antagonist activity at nAChR in Sprague-Dawley rat striatal slices assessed as inhibition of nicotine-induced [3H]-dopamine release	Rattus norvegicus	300.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	16.11 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.56 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.56 %

Cross References

Resources	Reference
ChEBI	6706
ChEMBL	CHEMBL267936
DrugBank	DB00657
DrugCentral	1646
FDA SRS	6EE945D3OK
Human Metabolome Database	HMDB0014795
Guide to Pharmacology	3990
KEGG	C07511
PharmGKB	PA450334
SureChEMBL	SCHEMBL34252

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).