1H-Imidazole-4-ethanamine, N-methyl-

Details

• Internal ID: b728ecd3-ccd3-4933-af77-31cf61c76675
• Taxonomy: Organic nitrogen compounds > Organonitrogen compounds > Amines > Aralkylamines
• IUPAC Name: 2-(1H-imidazol-5-yl)-N-methylethanamine
• SMILES (Canonical): CNCCC1=CN=CN1
• SMILES (Isomeric): CNCCC1=CN=CN1
• InChI: InChI=1S/C6H11N3/c1-7-3-2-6-4-8-5-9-6/h4-5,7H,2-3H2,1H3,(H,8,9)
• InChI Key: PHSPJQZRQAJPPF-UHFFFAOYSA-N
• Popularity: 888 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₁N₃
• Molecular Weight: 125.17 g/mol
• Exact Mass: 125.095297364 g/mol
• Topological Polar Surface Area (TPSA): 40.70 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.17
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 1H-Imidazole-4-ethanamine, N-methyl-
• N-alpha-methylhistamine
• 4-(2-Methylaminoethyl)imidazole
• Nalpha-Methylhistamine
• 2-(1H-imidazol-5-yl)-N-methylethanamine
• N'-Methylhistamine
• NAMH
• N(alpha)-methylhistamine
• N.alpha.-Methylhistamine
• Imidazole, 4-(2-(methylamino)ethyl)-
• Y7QR253130
• Imidazole, 4-[2-(methylamino)ethyl]-
• [2-(1H-imidazol-5-yl)ethyl](methyl)amine
• N(sup alpha)-Methylhistamine
• 2-(3H-imidazol-4-yl)-N-methylethanamine
• [3H]-Na-methylhistamine
• [3H]NAMH
• N-[3H]alpha-methylhistamine
• UNII-Y7QR253130
• N-alpha-MeHA
• Phosphorustribromide
• Tocris-0573
• SCHEMBL119179
• [3H]N-alpha-methyl histamine
• CHEMBL268490
• GTPL1239
• GTPL1240
• SCHEMBL2086409
• N(sup .alpha.)-Methylhistamine
• BDBM22530
• DTXSID00217671
• CHEBI:184982
• PHSPJQZRQAJPPF-UHFFFAOYSA-N
• N-Methyl-1h-imidazole-4-ethanamine
• PDSP1_000543
• PDSP2_000541
• AKOS006348059
• AKOS015906002
• N-alpha-methylhistamine-dihydrochloride
• NCGC00024660-01
• NCGC00024660-02
• NCGC00024660-03
• [2-(1H-imidazol-4-yl)ethyl](methyl)amine
• 4-(2-(N-METHYLAMINO)ETHYL)IMIDAZOLE
• 4-(2-METHYLAMINOETHYL)-1H-IMIDAZOLE
• FT-0632781
• 1H-IMIDAZOLE-5-ETHANAMINE, N-METHYL-
• EN300-170734
• N-[2-(1H-imidazol-5-yl)ethyl]-N-methylamine
• 2-(1H-IMIDAZOL-4-YL)-N-METHYLETHANAMINE
• L000451
• N-[2-(1H-Imidazol-4-yl)ethyl]-N-methylamine #
• IMIDAZOLE, 4(OR 5)-(2-(METHYLAMINO)ETHYL)-
• Q27078066

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9908	99.08%
Caco-2	+	0.7195	71.95%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.7857	78.57%
Subcellular localzation	Lysosomes	0.7951	79.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8980	89.80%
OATP1B3 inhibitior	+	0.9467	94.67%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.9392	93.92%
P-glycoprotein inhibitior	-	0.9872	98.72%
P-glycoprotein substrate	-	0.7005	70.05%
CYP3A4 substrate	-	0.6599	65.99%
CYP2C9 substrate	-	0.6061	60.61%
CYP2D6 substrate	-	0.6691	66.91%
CYP3A4 inhibition	-	0.9255	92.55%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9135	91.35%
CYP2C8 inhibition	-	0.7855	78.55%
CYP inhibitory promiscuity	-	0.9535	95.35%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6584	65.84%
Eye corrosion	-	0.9791	97.91%
Eye irritation	-	0.7042	70.42%
Skin irritation	-	0.5720	57.20%
Skin corrosion	-	0.5139	51.39%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6588	65.88%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8455	84.55%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6304	63.04%
Acute Oral Toxicity (c)	III	0.6491	64.91%
Estrogen receptor binding	-	0.8671	86.71%
Androgen receptor binding	-	0.8406	84.06%
Thyroid receptor binding	-	0.8520	85.20%
Glucocorticoid receptor binding	-	0.8736	87.36%
Aromatase binding	-	0.8365	83.65%
PPAR gamma	-	0.9033	90.33%
Honey bee toxicity	-	0.8774	87.74%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	-	0.9415	94.15%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL264	Q9Y5N1	Histamine H3 receptor	0.3981 nM	EC50	via Super-PRED
CHEMBL3759	Q9H3N8	Histamine H4 receptor	316.23 nM	Ki	via Super-PRED
CHEMBL1293224	P10636	Microtubule-associated protein tau	79.4 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL255	P29275	Adenosine A2b receptor	94.21%	98.59%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.14%	96.09%
CHEMBL3038469	P24941	CDK2/Cyclin A	90.35%	91.38%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.08%	89.34%
CHEMBL202	P00374	Dihydrofolate reductase	83.18%	89.92%
CHEMBL4296013	Q5VWK5	Interleukin-23 receptor	82.46%	88.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	82.40%	90.24%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.22%	96.90%

Plants that contains it

• Casimiroa edulis

Cross-Links

• PubChem: 912
• LOTUS: LTS0127937
• wikiData: Q27078066