4-Methoxyamphetamine

Details

• Internal ID: 9606635e-d380-4872-9657-d018f142ac0c
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenethylamines > Amphetamines and derivatives
• IUPAC Name: 1-(4-methoxyphenyl)propan-2-amine
• SMILES (Canonical): CC(CC1=CC=C(C=C1)OC)N
• SMILES (Isomeric): CC(CC1=CC=C(C=C1)OC)N
• InChI: InChI=1S/C10H15NO/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3
• InChI Key: NEGYEDYHPHMHGK-UHFFFAOYSA-N
• Popularity: 287 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23 g/mol
• Exact Mass: 165.115364102 g/mol
• Topological Polar Surface Area (TPSA): 35.20 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.58
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 64-13-1
• paramethoxyamphetamine
• 1-p-Methoxyphenyl-2-aminopropane
• 2-Amino-1-(4'-methoxyphenyl)propane
• P-methoxyamfetamine
• 4-methoxyamfetamine
• (+-)-p-Methoxyamphetamine
• p-Methoxy-alpha-methylphenethylamine
• (+-)-4-Methoxyamphetamine
• OVB8F8P39Q
• DL-p-Methoxy-alpha-methylphenethylamine
• DTXSID7040578
• (+-)-1-(p-Methoxyphenyl)-2-aminopropane
• alpha-Methyl-beta-(p-methoxyphenyl)ethylamine
• NSC-32757
• (2RS)-1-(4-methoxyphenyl)propan-2-amine
• (+-)-p-Methoxy-alpha-methylphenylethylamine
• J213.549C
• J434.573H
• RefChem:524704
• DTXCID5020578
• 200-577-0
• p-Methoxyamphetamine
• 1-(4-methoxyphenyl)propan-2-amine
• para-methoxyamphetamine
• 1-(4-Methoxybenzyl)ethylamine
• beta-methoxyamphetamine
• 1-p-Methoxyphenyl-2-propylamine
• 23239-32-9
• 2-(4-Methoxy-phenyl)-1-methyl-ethylamine
• D,L-p-methoxyamphetamine
• NSC 32757
• benzeneethanamine, 4-methoxy-alpha-methyl-
• CHEMBL278663
• 2-(4-Methoxyphenyl)-1-methylethylamine
• Phenethylamine, p-methoxy-.alpha.-methyl-
• Benzeneethanamine, 4-methoxy-.alpha.-methyl-
• .alpha.-Methyl-.beta.-(p-methoxyphenyl)ethylamine
• Benzenethanamine,4-methoxy-.alpha.-methyl-(.+/-.)-
• Phenethylamine, p-methoxy-.alpha.-methyl-, (.+/-.)-
• 1-(4-methoxyphenyl)prop-2-ylamine
• DEA No. 7411
• Death [Street Name]
• UNII-OVB8F8P39Q
• Chicken Powder [Street Name]
• Chicken Yellow [Street Name]
• HSDB 7594
• alpha-methyl-4-methoxyphenethylamine
• 4-Methoxy-alpha-methylphenethylamine
• EINECS 200-577-0
• DEATH
• DR. DEATH
• Formoterol EP Impurity G
• PMA (PSYCHEDELIC)
• (1S)-2-(4-METHOXYPHENYL)-1-METHYLETHYLAMINE
• (d,l)-4-Methoxyamphetamine
• (+/-)-p-Methoxyamphetamine
• (+/-)-4-Methoxyamphetamine
• SCHEMBL264634
• SCHEMBL721008
• SCHEMBL8851613
• (.+/-.)-p-Methoxyamphetamine
• (.+/-.)-4-Methoxyamphetamine
• NSC32757
• 1-(4-Methoxyphenyl)-2-propanamine
• 4-METHOXYAMFETAMINE [MART.]
• 1-(4-methoxyphenyl)-2-aminopropane
• BDBM50024209
• MFCD00869435
• SBB072264
• STK664902
• AKOS005536031
• p-Methoxy-.alpha.-methylphenethylamine
• 4-Methoxy-alpha-methylbenzeneethanamine
• AB51426
• AB70588
• DB01472
• FP26760
• MB01555
• Phenethylamine, p-methoxy-alpha-methyl-
• benzene, 1-(2-amino)propyl-4-methoxy-
• NCGC00168268-01
• DL-p-Methoxy-.alpha.-methylphenethylamine
• NCI60_002842
• DB-225703
• DB-345339
• ST4128921
• (+/-)-1-(p-Methoxyphenyl)-2-aminopropane
• (-)-2-(p-methoxyphenyl)-1-methylethylamine
• N-(2-(p-methoxyphenyl)-1-methylethyl)amine
• NS00005326
• (+/-)-p-Methoxy-alpha-methylphenylethylamine
• [2-(4-methoxyphenyl)-1-methyl-ethyl]-amine
• (-)2-(4-Methoxy-phenyl)-1-methyl-ethylamine
• (.+/-.)-1-(p-Methoxyphenyl)-2-aminopropane
• C22811
• (.+/-.)-p-Methoxy-.alpha.-methylphenethylamine
• 2-(4-Methoxy-phenyl)-1-methyl-ethylamine(PMA)
• (+/-)2-(4-Methoxy-phenyl)-1-methyl-ethylamine
• Benzeneethanamine, 4-methoxy-alpha-methyl- (9CI)
• Q230005
• (R)-(-)2-(4-Methoxy-phenyl)-1-methyl-ethylamine
• (S)-(+)2-(4-Methoxy-phenyl)-1-methyl-ethylamine
• Phenethylamine, p-methoxy-alpha-methyl- (6CI,7CI,8CI)
• A4070/0173407
• Benzeneethanamine, 4-methoxy-.alpha.-methyl-, (.+/-.)-
• FORMOTEROL FUMARATE DIHYDRATE IMPURITY G [EP IMPURITY]
• (a-R)-4-Methoxy-a-methyl-benzeneethanamine hydrochloride;(R)-4-Methoxy-a-methyl-benzeneethanamine hydrochloride

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9514	95.14%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Lysosomes	0.6698	66.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9744	97.44%
OATP1B3 inhibitior	+	0.9616	96.16%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.8239	82.39%
P-glycoprotein inhibitior	-	0.9874	98.74%
P-glycoprotein substrate	-	0.8356	83.56%
CYP3A4 substrate	-	0.7142	71.42%
CYP2C9 substrate	-	0.8228	82.28%
CYP2D6 substrate	+	0.6621	66.21%
CYP3A4 inhibition	-	0.9431	94.31%
CYP2C9 inhibition	-	0.9747	97.47%
CYP2C19 inhibition	-	0.6537	65.37%
CYP2D6 inhibition	+	0.8492	84.92%
CYP1A2 inhibition	+	0.6567	65.67%
CYP2C8 inhibition	-	0.9638	96.38%
CYP inhibitory promiscuity	-	0.8424	84.24%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6463	64.63%
Carcinogenicity (trinary)	Non-required	0.5931	59.31%
Eye corrosion	-	0.9361	93.61%
Eye irritation	-	0.8729	87.29%
Skin irritation	-	0.5192	51.92%
Skin corrosion	+	0.5943	59.43%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4767	47.67%
Micronuclear	+	0.5385	53.85%
Hepatotoxicity	-	0.6621	66.21%
skin sensitisation	-	0.7925	79.25%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.7997	79.97%
Acute Oral Toxicity (c)	II	0.5316	53.16%
Estrogen receptor binding	-	0.9099	90.99%
Androgen receptor binding	-	0.6500	65.00%
Thyroid receptor binding	-	0.8490	84.90%
Glucocorticoid receptor binding	-	0.8216	82.16%
Aromatase binding	-	0.8538	85.38%
PPAR gamma	-	0.8689	86.89%
Honey bee toxicity	-	0.9484	94.84%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	-	0.7219	72.19%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL228	P31645	Serotonin transporter	1071519.31 nM; 32359.37 nM	EC50; EC50	PMID: 19717215; PMID: 19717215

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.03%	96.09%
CHEMBL3492	P49721	Proteasome Macropain subunit	96.77%	90.24%
CHEMBL1907	P15144	Aminopeptidase N	96.29%	93.31%
CHEMBL2581	P07339	Cathepsin D	94.01%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	91.54%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.44%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.00%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.99%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.11%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.98%	94.00%
CHEMBL4581	P52732	Kinesin-like protein 1	82.51%	93.18%
CHEMBL2535	P11166	Glucose transporter	82.37%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.32%	95.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.83%	99.15%
CHEMBL4208	P20618	Proteasome component C5	80.57%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.38%	97.09%

Plants that contains it

• Senegalia berlandieri
• Thymus quinquecostatus
• Thymus vulgaris
• Vachellia rigidula

Cross-Links

• PubChem: 31721
• NPASS: NPC97811
• ChEMBL: CHEMBL278663
• LOTUS: LTS0137145
• wikiData: Q230005