N-Methylmescaline

Details

• Internal ID: c6cc3ac1-7615-4688-b723-6e26bf1a243d
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenethylamines
• IUPAC Name: N-methyl-2-(3,4,5-trimethoxyphenyl)ethanamine
• SMILES (Canonical): CNCCC1=CC(=C(C(=C1)OC)OC)OC
• SMILES (Isomeric): CNCCC1=CC(=C(C(=C1)OC)OC)OC
• InChI: InChI=1S/C12H19NO3/c1-13-6-5-9-7-10(14-2)12(16-4)11(8-9)15-3/h7-8,13H,5-6H2,1-4H3
• InChI Key: OTXANOLOOUNVSR-UHFFFAOYSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₉NO₃
• Molecular Weight: 225.28 g/mol
• Exact Mass: 225.13649347 g/mol
• Topological Polar Surface Area (TPSA): 39.70 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.47
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 4838-96-4
• N-Methyl-2-(3,4,5-trimethoxyphenyl)ethanamine
• Benzenethanamine, 3,4,5-trimethoxy-N-methyl-
• Benzenethanamine,3,4,5-trimethoxy-N-methyl-
• Benzeneethanamine, 3,4,5-trimethoxy-N-methyl-
• LNN57P8WGG
• CHEBI:7319
• Benzeneethanamine,3,4,5-trimethoxy-N-methyl-
• N-methyl-3,4,5-trimethoxyphenethylamine
• Phenethylamine, 3,4,5-trimethoxy-N-methyl-
• N-methyl Mescaline (hydrochloride)
• AC1L3CNA
• Mescaline, N-methyl-
• UNII-LNN57P8WGG
• C08310
• CHEMBL100531
• SCHEMBL4320087
• DTXSID00197505
• AKOS000277427
• N-Methyl-3,4,5-trimethoxybenzeneethanamine
• CS-0302462
• methyl[2-(3,4,5-trimethoxyphenyl)ethyl]amine
• EN300-1853035
• 3,4,5-TRIMETHOXY-N-METHYLBENZENEETHANAMINE
• N-Methyl-2-(3,4,5-trimethoxyphenyl)ethanamine #
• n-Methyl-2-(3,4,5-trimethoxyphenyl)ethan-1-amine
• Q15425805
• (METHYL)(2-(3,4,5-TRIMETHOXYPHENYL)ETHYL)AMINE
• N-methyl-N-[2-(3,4,5-trimethoxy-phenyl)-ethyl]-amine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8829	88.29%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5662	56.62%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9330	93.30%
OATP1B3 inhibitior	+	0.9526	95.26%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.9433	94.33%
P-glycoprotein inhibitior	-	0.9330	93.30%
P-glycoprotein substrate	-	0.5792	57.92%
CYP3A4 substrate	-	0.5141	51.41%
CYP2C9 substrate	-	0.5000	50.00%
CYP2D6 substrate	+	0.7507	75.07%
CYP3A4 inhibition	-	0.9315	93.15%
CYP2C9 inhibition	-	0.9606	96.06%
CYP2C19 inhibition	-	0.9375	93.75%
CYP2D6 inhibition	-	0.7064	70.64%
CYP1A2 inhibition	+	0.7024	70.24%
CYP2C8 inhibition	+	0.6732	67.32%
CYP inhibitory promiscuity	-	0.9582	95.82%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6600	66.00%
Carcinogenicity (trinary)	Non-required	0.7019	70.19%
Eye corrosion	-	0.8779	87.79%
Eye irritation	-	0.5219	52.19%
Skin irritation	+	0.5323	53.23%
Skin corrosion	-	0.8063	80.63%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3918	39.18%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.7609	76.09%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7626	76.26%
Acute Oral Toxicity (c)	II	0.4817	48.17%
Estrogen receptor binding	-	0.8160	81.60%
Androgen receptor binding	-	0.7608	76.08%
Thyroid receptor binding	-	0.5123	51.23%
Glucocorticoid receptor binding	-	0.7841	78.41%
Aromatase binding	-	0.6706	67.06%
PPAR gamma	-	0.8631	86.31%
Honey bee toxicity	-	0.7971	79.71%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	-	0.6656	66.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.34%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.42%	99.17%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.14%	95.17%
CHEMBL1255126	O15151	Protein Mdm4	86.34%	90.20%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.12%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.13%	86.33%
CHEMBL4302	P08183	P-glycoprotein 1	85.00%	92.98%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.52%	91.11%
CHEMBL2535	P11166	Glucose transporter	84.41%	98.75%
CHEMBL2581	P07339	Cathepsin D	84.35%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.73%	94.00%

Plants that contains it

• Alhagi maurorum
• Allium sativum
• Gymnocalycium bodenbenderianum
• Gymnocalycium monvillei
• Lophophora williamsii
• Senegalia berlandieri
• Turbinicarpus pseudopectinatus
• Vachellia rigidula

Cross-Links

• PubChem: 138365
• NPASS: NPC262641
• LOTUS: LTS0239088
• wikiData: Q15425805