Amphetamine

Details

• Internal ID: 35fd1d8b-ab9a-40c1-8d88-5207057d54ca
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenethylamines > Amphetamines and derivatives
• IUPAC Name: 1-phenylpropan-2-amine
• SMILES (Canonical): CC(CC1=CC=CC=C1)N
• SMILES (Isomeric): CC(CC1=CC=CC=C1)N
• InChI: InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3
• InChI Key: KWTSXDURSIMDCE-UHFFFAOYSA-N
• Popularity: 36,966 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₃N
• Molecular Weight: 135.21 g/mol
• Exact Mass: 135.104799419 g/mol
• Topological Polar Surface Area (TPSA): 26.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.58
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• Amfetamine
• 1-phenylpropan-2-amine
• dl-Amphetamine
• Desoxynorephedrine
• Norephedrane
• 1-Phenyl-2-aminopropane
• 300-62-9
• alpha-Methylphenethylamine
• Elastonon
• Fenopromin
• Phenedrine
• Mydrial
• beta-Aminopropylbenzene
• Actedron
• Adderall
• Allodene
• Anorexide
• Anorexine
• Benzebar
• Benzolone
• Isoamyne
• Mecodrin
• Novydrine
• Oktedrin
• Ortedrine
• Percomon
• Profamina
• Simpatina
• Adipan
• Finam
• Isomyn
• 1-Methyl-2-phenylethylamine
• 1-Phenyl-2-propylamine
• Protioamphetamine
• amfetaminum
• alpha-Methylbenzeneethaneamine
• 3-Phenyl-2-propylamine
• Fenylo-izopropylaminyl
• (Phenylisopropyl)amine
• dl-alpha-Methylphenethylamine
• 1-Phenyl-2-propanamine
• 2-Amino-1-phenylpropane
• Psychedrine
• (+-)-Benzedrine
• racemic-Desoxynor-ephedrine
• Amfetamin
• Amfetamina
• Amphetamin
• Anfetamina
• Dyanavel
• rac-Amphetamine
• dl-Benzedrine
• Benzedrine
• Desoxynorephedrin
• Propisamine
• Raphetamine
• Rhinalator
• Simpatedrin
• Sympatedrine
• beta-Phenylisopropylamin
• Sympamine
• Weckamine
• Dyanavel XR
• Adzenys ER
• Amphetamine, dl-
• 1-Phenyl-2-amino-propan
• (+-)-alpha-Methylphenylethylamine
• Amfetamina [Italian]
• Anfetamina [Spanish]
• beta-Phenylisopropylamine
• 60-15-1
• Amfetamine [INN:BAN]
• (+-)-alpha-Methylphenethylamine
• HSDB 3287
• .beta.-Aminopropylbenzene
• Amfetaminum [INN-Latin]
• Adderall XR
• Benzeneethanamine, alpha-methyl-, (+-)-
• Amfetamina [INN-Spanish]
• (+-)-alpha-Methylbenzeneethanamine
• (+/-)-Desoxynorephedrine
• Benzeneethanamine, .alpha.-methyl-
• UNII-CK833KGX7E
• EINECS 200-458-3
• EINECS 206-096-2
• CK833KGX7E
• dl-1-Phenyl-2-aminopropane
• Adzenys XR-ODT
• NSC 27159
• NSC-27159
• Phenethylamine, alpha-methyl-
• beta-Aminopropylbenzene (VAN)
• .alpha.-Methylbenzeneethanamine
• DELCOBESE
• Phenethylamine, alpha-methyl-, (+-)-
• Norephedrine, deoxy-
• Fenylo-izopropylaminyl [Polish]
• 3-AMINO-1-PROPYLBENZENE
• Benzeneethanamine, alpha-methyl-
• 1-Phenyl-2-aminopropane (VAN)
• AI3-02438
• beta-Phenylisopropylamin [German]
• 1-Phenylpropan-2-amin
• 1-Phenyl-2-amino-propan [German]
• alpha-Methylphenylethylamine
• Dexedrine
• CHEBI:2679
• DTXSID4022600
• 1-benzylethylamine
• Amfetamine (INN)
• NSC27159
• NT-0201
• AMFETAMINE [INN]
• beta-phenyl-isopropylamine
• Phenethylamine, .alpha.-methyl-, (.+/-.)-
• AMFETAMINE (MART.)
• AMFETAMINE [MART.]
• Benzeneethanamine, .alpha.-methyl-, (.+/-.)-
• Isoamycin
• DEA No. 1100
• (+/-)-1-Phenyl-2-aminopropane
• Thyramine
• S(+)-Amphetamine
• levo-Amphetamine
• (+/-)-Benzedrine
• alpha-Methylbenzeneethanamine
• (+/-)-beta-Phenylisopropylamine
• amphetaminium
• Amphetamine Sulfate (2:1)
• (+)-.alpha.-Methylphenethylamine
• Adderal
• Adzenys
• amphetamine-
• NSC73713
• DEXTROAMP SACCHARATE, AMP ASPARTATE, DEXTROAMP SULFATE AND AMP SULFATE
• Amfetamin (TN)
• Dyanavel (TN)
• component of Amodex
• Phenethylamine, d-
• (+-)-amphetamine
• Adzenys (TN)
• (plusmn)-amphetamine
• Benzeneethanamine, .alpha.-methyl-, (S)-
• Noclon (Salt/Mix)
• ACETEDRON
• Fenamin (Salt/Mix)
• Ortenal (Salt/Mix)
• Zedrine (Salt/Mix)
• Euphodyn (Salt/Mix)
• Stimulan (Salt/Mix)
• Fabedrine (Salt/Mix)
• Oraldrina (Salt/Mix)
• Vapedrine (Salt/Mix)
• Sympametin (Salt/Mix)
• alpha-methylphenethylamin
• component of Biphetamine
• Phenethylamine, (+)-
• 3-phenylpropan-2-amine
• AMPHETAMINE [MI]
• (.+/-.)-Benzedrine
• Benzeneethanamine, (S)-
• RACEMIC AMPHETAMINE
• .beta.-Phenylisopropylamin
• alpha-methyl phenethylamine
• AMPHETAMINE, (D)
• Amphetamine; (Benzedrine)
• (+-)-desoxynor-ephedrine
• AMPHETAMINE [HSDB]
• CHEMBL405
• D05BMG
• .beta.-Phenylisopropylamine
• AMPHETAMINE [VANDF]
• SCHEMBL8858
• .alpha.-Methylphenethylamine
• AMFETAMINE [WHO-DD]
• Oprea1_447423
• alpha-Methylbenzeneethan-amine
• d/l-Amphetamine hydrochloride
• (.+/-.)-Desoxynorephedrine
• .alpha.-Methylphenylethylamine
• Bencenoetanamina, Alfa-metil-
• DivK1c_000991
• WLN: ZY1&1R
• (S)-.alpha.-Phenylethylamine
• d-.alpha.-Methylphenethylamine
• DTXCID402600
• GTPL4804
• WLN: ZY1&1R -D
• .alpha.-Methylbenzeneethaneamine
• DL-.alpha.-Methylphenethylamine
• (+-)-DESOXYNOREPHEDRINE
• HMS503G03
• KBio1_000991
• Phenethylamine, .alpha.-methyl-
• alpha-methyl-beta-phenylethylamine
• AMPHETAMINE [ORANGE BOOK]
• N06BA01
• (+-)-alpha-methyl phenethylamine
• (+-)-PHENYLISOPROPYLAMINE
• (+/-)-alpha-Methylphenethylamine
• CHEBI:132233
• NINDS_000991
• rac-(2R)-1-phenylpropan-2-amine
• (+)-.alpha.-Methylphenylethylamine
• PHENETHYLAMINE, ALPHA-METHYL
• RACEMIC DESOXY-NOR-EPHEDRINE
• .alpha.-Methylphenethylamine, d-form
• BDBM50005246
• (S)-(+)-.beta.-Phenylisopropylamine
• Phenethylamine, alpha-methyl, (+-)-
• (+-)-BETA-PHENYLISOPROPYLAMINE
• (.+/-.)-.beta.-Phenylisopropylamine
• AB07478
• DB00182
• LS-1148
• LS-1428
• (+-)-1-PHENYL-2-AMINOPROPANE
• (.+/-.)-.alpha.-Methylphenethylamine
• IDI1_000991
• rac-Amphetamine 1.0 mg/ml in Methanol
• (.+/-.)-.alpha.-Methylphenylethylamine
• (+-)-ALPHA-METHYLBENZENE-ETHANAMINE
• (+-)-ALPHA-METHYLPHENYL ETHYLAMINE
• Benzeneethanamine, alpha-methyl-, (+/-)-
• (+/-)-.ALPHA.-METHYLPHENETHYLAMINE
• BENZENEETHANAMINE, ALPHA-METHYL-,(+-)
• C07514
• D03740
• D07445
• L000864
• Q179452
• BENZENEETHANAMINE, .ALPHA.-METHYL-, (+/-)-
• PF-08 (Bio-MD/MPAR/prodrug/oral, ADHD), PharmacoFore
• SELEGILINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
• Amphetamine (tamper and abuse-resistant, Bio-MD/MPAR, ADHD)
• ALPHA-METHYL-BENZENEETHANAMIDE (SEE ALSO DL-AMPHETAMINE SULFATE)
• Amphetamine (tamper and abuse-resistant, Bio-MD/MPAR, ADHD), PharmacoFore
• AMPHETAMINE (SEE ALSO: D-AMPHETAMINE (51-64-9) & AMPHETAMINE SULFATE (60-13-9))

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9594	95.94%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.9286	92.86%
Subcellular localzation	Lysosomes	0.9263	92.63%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9743	97.43%
OATP1B3 inhibitior	+	0.9580	95.80%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.9034	90.34%
P-glycoprotein inhibitior	-	0.9935	99.35%
P-glycoprotein substrate	-	0.8754	87.54%
CYP3A4 substrate	-	0.8047	80.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6122	61.22%
CYP3A4 inhibition	-	0.8709	87.09%
CYP2C9 inhibition	-	0.9313	93.13%
CYP2C19 inhibition	-	0.8445	84.45%
CYP2D6 inhibition	+	0.6570	65.70%
CYP1A2 inhibition	-	0.5697	56.97%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.8732	87.32%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5300	53.00%
Carcinogenicity (trinary)	Non-required	0.7287	72.87%
Eye corrosion	-	0.9593	95.93%
Eye irritation	-	0.9541	95.41%
Skin irritation	+	0.8532	85.32%
Skin corrosion	+	0.9740	97.40%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7106	71.06%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.5068	50.68%
skin sensitisation	+	0.6957	69.57%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	-	0.7000	70.00%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7394	73.94%
Acute Oral Toxicity (c)	I	0.7687	76.87%
Estrogen receptor binding	-	0.9577	95.77%
Androgen receptor binding	-	0.8437	84.37%
Thyroid receptor binding	-	0.8907	89.07%
Glucocorticoid receptor binding	-	0.8554	85.54%
Aromatase binding	-	0.8997	89.97%
PPAR gamma	-	0.9201	92.01%
Honey bee toxicity	-	0.9686	96.86%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	-	0.4224	42.24%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5282	P11509	Cytochrome P450 2A6	3500 nM	IC50	PMID: 15658857
CHEMBL238	Q01959	Dopamine transporter	24.8 nM	EC50	via Super-PRED
CHEMBL222	P23975	Norepinephrine transporter	7.1 nM	EC50	via Super-PRED
CHEMBL5857	Q96RJ0	Trace amine-associated receptor 1	250 nM; 140 nM	EC50; EC50	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.61%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	96.08%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.17%	96.09%
CHEMBL1907	P15144	Aminopeptidase N	91.27%	93.31%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.41%	95.56%
CHEMBL3492	P49721	Proteasome Macropain subunit	88.97%	90.24%
CHEMBL3401	O75469	Pregnane X receptor	85.86%	94.73%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	83.18%	97.23%
CHEMBL1255126	O15151	Protein Mdm4	82.01%	90.20%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.30%	86.33%

Plants that contains it

• Senegalia berlandieri
• Tetradium ruticarpum
• Vachellia rigidula

Cross-Links

• PubChem: 3007
• NPASS: NPC112609
• ChEMBL: CHEMBL405
• LOTUS: LTS0228132
• wikiData: Q179452