Mecamylamine

Details

• Internal ID: d770b620-373f-47ef-b37d-f16066c40b65
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine
• SMILES (Canonical): CC1(C2CCC(C2)C1(C)NC)C
• SMILES (Isomeric): CC1(C2CCC(C2)C1(C)NC)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
• InChI Key: IMYZQPCYWPFTAG-UHFFFAOYSA-N
• Popularity: 3,987 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₂₁N
• Molecular Weight: 167.29 g/mol
• Exact Mass: 167.167399674 g/mol
• Topological Polar Surface Area (TPSA): 12.00 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.42
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• Versamine
• Revertina
• Mecamine
• Mecamilamina
• Mekamine
• 60-40-2
• 2-Methylaminoisocamphane
• Mecamylaminum
• 3-Methylaminoisocamphane
• Mevasine
• N-Methyl-2-isocamphanamine
• N,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-amine
• 2-Methylamino-2,3,3-trimethylnorbornane
• 3-Methylaminoisokamfan
• N,2,3,3-Tetramethyl-2-norbornamine
• Mecamylaminum [INN-Latin]
• N,2,3,3-Tetramethyl-2-norcamphanamine
• EINECS 200-476-1
• DTXSID0023240
• 2-Norbornanamine, N,2,3,3-tetramethyl-
• Bicyclo(2.2.1)heptan-2-amine, N,2,3,3-tetramethyl-
• 3-beta-Methylamino-2,2,3-trimethylbicyclo(2.2.1)heptane
• CHEBI:6706
• CHEMBL267936
• DTXCID903240
• Bicyclo[2.2.1]heptan-2-amine, N,2,3,3-tetramethyl-
• NCGC00015703-03
• Mecamilamina [DCIT]
• Mecamilamina [Italian]
• Mecamylaminum (INN-Latin)
• Mecamylamine [INN:BAN]
• 3-Methylaminoisokamfan [Czech]
• CAS-60-40-2
• Inversine (Salt/Mix)
• Spectrum_000304
• SpecPlus_000736
• Prestwick0_001111
• Prestwick1_001111
• Prestwick2_001111
• Prestwick3_001111
• Spectrum3_000736
• Spectrum4_001257
• Spectrum5_001616
• Lopac0_000841
• SCHEMBL34252
• BSPBio_001242
• BSPBio_002292
• KBioGR_001814
• KBioSS_000784
• DivK1c_006832
• SPBio_003111
• BPBio1_001367
• GTPL3990
• HY-B1395A
• KBio1_001776
• KBio2_000784
• KBio2_003352
• KBio2_005920
• KBio3_001512
• C02BB01
• HMS3604D12
• Tox21_110198
• BDBM50061565
• AKOS003662515
• Tox21_110198_1
• CCG-204924
• DB00657
• SDCCGSBI-0050817.P005
• NCGC00015703-02
• NCGC00015703-04
• NCGC00015703-06
• NCGC00015703-12
• NCGC00162272-01
• NCGC00162272-02
• SBI-0050817.P004
• AB00053764
• CS-0013657
• C07511
• EN300-267821
• AB00053764_03
• Q3332124
• BRD-A20119038-001-01-5
• BRD-A20119038-003-01-1
• N,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-amine #
• Methyl-(2,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-amine
• (+)Methyl-(2,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-amine
• (-)Methyl-(2,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-amine
• 3-.beta.-Methylamino-2,2,3-trimethylbicyclo(2.2.1)heptane
• (+/-)Methyl-(2,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-amine
• Methyl-(2,3,3-trimethyl-bicyclo[2.2.1]hept-2-yl)-amine(Mecamylamine)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9809	98.09%
Caco-2	+	0.6975	69.75%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.9143	91.43%
Subcellular localzation	Lysosomes	0.8477	84.77%
OATP2B1 inhibitior	-	0.8529	85.29%
OATP1B1 inhibitior	+	0.9541	95.41%
OATP1B3 inhibitior	+	0.9442	94.42%
MATE1 inhibitior	-	0.6400	64.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.9388	93.88%
P-glycoprotein inhibitior	-	0.9665	96.65%
P-glycoprotein substrate	-	0.8790	87.90%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.8090	80.90%
CYP2D6 substrate	+	0.4424	44.24%
CYP3A4 inhibition	-	0.9054	90.54%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.8945	89.45%
CYP inhibitory promiscuity	-	0.7435	74.35%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8120	81.20%
Carcinogenicity (trinary)	Non-required	0.6171	61.71%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.6894	68.94%
Skin irritation	-	0.5713	57.13%
Skin corrosion	-	0.6108	61.08%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6550	65.50%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6583	65.83%
skin sensitisation	+	0.4743	47.43%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5333	53.33%
Acute Oral Toxicity (c)	III	0.5675	56.75%
Estrogen receptor binding	-	0.5252	52.52%
Androgen receptor binding	-	0.8513	85.13%
Thyroid receptor binding	-	0.7591	75.91%
Glucocorticoid receptor binding	-	0.7901	79.01%
Aromatase binding	-	0.6232	62.32%
PPAR gamma	-	0.7188	71.88%
Honey bee toxicity	-	0.7925	79.25%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9261	92.61%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1907588	P02708	Acetylcholine receptor; alpha1/beta1/delta/gamma	300 nM; 600 nM	IC50; IC50	via Super-PRED; via Super-PRED
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	700 nM; 91 nM; 50 nM; 200 nM	IC50; IC50; IC50; IC50	via Super-PRED; via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL1907589	P17787	Neuronal acetylcholine receptor; alpha4/beta2	600 nM; 500 nM; 500 nM; 600 nM	IC50; IC50; IC50; IC50	via Super-PRED; via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	10 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	90.06%	91.79%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.60%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.17%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	87.31%	83.82%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.52%	82.69%
CHEMBL221	P23219	Cyclooxygenase-1	85.61%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.27%	97.09%
CHEMBL4482	O96013	Serine/threonine-protein kinase PAK 4	84.15%	95.42%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.27%	97.25%
CHEMBL3045	P05771	Protein kinase C beta	83.22%	97.63%
CHEMBL2996	Q05655	Protein kinase C delta	81.15%	97.79%
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	80.98%	88.81%
CHEMBL3920	Q04759	Protein kinase C theta	80.30%	97.69%

Plants that contains it

• Wettsteinia inversa

Cross-Links

• PubChem: 4032
• LOTUS: LTS0147594
• wikiData: Q3332124