Amphetamine

Summary

Amphetamine (CHEMBL405) is an approved small molecule (ATC N06BA01) targeting CA7 and CA5A; indicated across 3 conditions including attention deficit-hyperactivity disorder and cocaine dependence.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: N06BA01
• Targets: 2 (CA7, CA5A)
• Indications: 3 conditions
• Clinical trials: 13
• Chemistry: 135.21 Da · C9H13N

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL405
Name	Amphetamine
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	3007
ChEBI	CHEBI:132233
ATC	N06BA01
Molecular formula	C9H13N
Molecular weight	135.21
InChIKey	KWTSXDURSIMDCE-UHFFFAOYSA-N

SMILES: CC(CC1=CC=CC=C1)N

IUPAC name: 1-phenylpropan-2-amine

ChEBI definition: A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.

Also known as: Adzenys er, Adzenys xr-odt, Amfetamin, Amfetamine, Amphetamine, Amphetamine resin complex, dl-, Anfetamina, Dyanavel, Dyanavel xr, Mydayis (mixed salts of a single entity), Norephedrane

Parent form; salt/anhydrous children: CHEMBL501, CHEMBL554211, CHEMBL1200377, CHEMBL1200387, CHEMBL3250770, CHEMBL3250771, CHEMBL3250772, CHEMBL3250773, CHEMBL3250774, CHEMBL3250775

Patent coverage: 20,104 distinct patent families (68,439 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
CA7	carbonic anhydrase 7	Activation		1.6%	P43166
CA5A	carbonic anhydrase 5A	Activation		29.6%	P35218

Broader ChEMBL bioactivity targets: 13 (assay-derived). Sample: Solute carrier family 22 member 3, Serotonin 2 (5-HT2) receptor, Serotonin (5-HT) receptor, Serotonin 1 (5-HT1) receptor, Sodium-dependent noradrenaline transporter, Adenosine receptor A1, Sodium-dependent noradrenaline transporter, Adenosine receptor A2a, 5-hydroxytryptamine receptor 2B, Sodium-dependent dopamine transporter.

Bioactivity

ChEMBL activities: 11 potent at pChembl ≥ 5 of 17 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
P23977	6.02	IC50	960	nM	CHEMBL_ACT_14683741
O55192	6	IC50	1000	nM	CHEMBL_ACT_14626043
P20852	5.54	IC50	2850	nM	CHEMBL_ACT_1514645
CYP2A6	5.46	IC50	3500	nM	CHEMBL_ACT_1514644
P30994	5.27	Kd	5370	nM	CHEMBL_ACT_1113855
P08909	5.27	Kd	5370	nM	CHEMBL_ACT_1211362
P08909	5.27	Kd	5370	nM	CHEMBL_ACT_232896
P08909	5.27	Kd	5370	nM	CHEMBL_ACT_241872
P19327	5.12	Ki	7660	nM	CHEMBL_ACT_234104
P19327	5.12	Ki	7660	nM	CHEMBL_ACT_796054
SLC6A2	5.05	AC50	8840	nM	CHEMBL_ACT_25145289

Target pathways

Aggregated over 2 target gene(s): CA7, CA5A.

Top Reactome pathways

2 total, by targets touching each:

Pathway	Targets	Genes
Metabolism	2	CA5A, CA7
Reversible hydration of carbon dioxide	2	CA5A, CA7

Dominant GO biological processes

GO term	Targets
positive regulation of synaptic transmission, GABAergic	1
obsolete positive regulation of cellular pH reduction	1
regulation of intracellular pH	1
neuron cellular homeostasis	1
regulation of chloride transport	1

Indications & clinical

Indications

3 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
attention deficit-hyperactivity disorder	4	MONDO:0007743	EFO:0003888
cocaine dependence	1	MONDO:0005186	EFO:0002610

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 13.

Phase distribution

Phase	Trials
Not specified	4
PHASE4	3
PHASE2	2
PHASE1	2
PHASE1/PHASE2	1
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT06248229	PHASE4	RECRUITING	A Trial of Dyanavel XR in Treating Co-occurring Fatigue Symptoms in Adults With Attention Deficit Hyperactivity Disorder (ADHD).
NCT02020408	PHASE4	COMPLETED	Monoamine Contributions to Neurocircuitry in Eating Disorders
NCT07169162	PHASE4	WITHDRAWN	ADZENYS XR-ODT™ in Children (4 to <6 Years) Diagnosed With Attention-deficit/Hyperactivity Disorder
NCT00151996	PHASE2	COMPLETED	Safety and Tolerability of SPD503 and Psychostimulants in Children and Adolescents Aged 6-17 With Attention-Deficit/Hyperactivity Disorder (ADHD)
NCT00733993	PHASE1/PHASE2	COMPLETED	Caffeine and Cocaine
NCT03242772	PHASE2	TERMINATED	Impact of Combined Medication and Behavioral Treatment for ASD & ADHD
NCT02959892	PHASE1	COMPLETED	A Single-Dose Positron Emission Tomography (PET) Study to Determine the Effect of TAK-041 on Amphetamine-Induced Dopamine Release in the Central Nervous System (CNS)
NCT03103750	PHASE1	COMPLETED	Vitamin D as a Therapeutic Adjunct in the Stimulant Treatment of ADHD
NCT03019822	EARLY_PHASE1	COMPLETED	Role of Dopamine, Serotonin and 5-HT2A Receptors in Emotion Processing
NCT01699607	Not specified	COMPLETED	Test-retest Reproducibility of [11C]PHNO PET Using the Constant Infusion Paradigm
NCT02348385	Not specified	COMPLETED	Imaging Extrastriatal Dopamine Release in Tobacco Smokers and Nonsmokers
NCT04132557	Not specified	COMPLETED	A Study on Suicidality, Psychosis or Substance Abuse With Methylphenidate, Atomoxetine, Amphetamine/Dextroamphetamine or Lisdexamfetamine
NCT04577417	Not specified	COMPLETED	Stimulant Medication Effects on Auditory Sensitivity in Teens With ADHD

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 4 clinical and 9 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

67 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
ACETAMINOPHEN	ChEMBL + PubChem	Phase 4 (approved)	CA5A, CA7
ACETAZOLAMIDE	ChEMBL + PubChem	Phase 4 (approved)	CA5A, CA7
BORTEZOMIB	ChEMBL	Phase 4 (approved)	CA5A, CA7
BRINZOLAMIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
CELECOXIB	ChEMBL	Phase 4 (approved)	CA5A, CA7
CHLORTHALIDONE	ChEMBL	Phase 4 (approved)	CA5A, CA7
COUMARIN	ChEMBL	Phase 4 (approved)	CA5A, CA7
DICHLORPHENAMIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
DOBUTAMINE	ChEMBL	Phase 4 (approved)	CA5A, CA7
DORZOLAMIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
ETHOXZOLAMIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
FAMOTIDINE	ChEMBL	Phase 4 (approved)	CA5A, CA7
FUROSEMIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
IMATINIB	ChEMBL	Phase 4 (approved)	CA5A, CA7
INDAPAMIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
LACOSAMIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
LEVETIRACETAM	ChEMBL	Phase 4 (approved)	CA5A, CA7
MAFENIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
METHAZOLAMIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
NILOTINIB	ChEMBL	Phase 4 (approved)	CA5A, CA7
PYRITHIONE ZINC	ChEMBL	Phase 4 (approved)	CA5A, CA7
SULFANILAMIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
SULPIRIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
TOPIRAMATE	ChEMBL	Phase 4 (approved)	CA5A, CA7
TRICHLORMETHIAZIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
TRIENTINE	ChEMBL	Phase 4 (approved)	CA5A, CA7
VALDECOXIB	ChEMBL	Phase 4 (approved)	CA5A, CA7
VERALIPRIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
ZONISAMIDE	ChEMBL	Phase 4 (approved)	CA5A, CA7
CAFFEIC ACID	ChEMBL	Phase 3	CA5A, CA7
CURCUMIN	ChEMBL	Phase 3	CA5A, CA7
P-TOLUENESULFONAMIDE	ChEMBL	Phase 3	CA5A, CA7
QUERCETIN	ChEMBL	Phase 3	CA5A, CA7
RESVERATROL	ChEMBL	Phase 3	CA5A, CA7
SACCHARIN	ChEMBL	Phase 3	CA5A, CA7
SPERMIDINE	ChEMBL	Phase 3	CA5A, CA7
THIMEROSAL	ChEMBL	Phase 3	CA5A, CA7
CARZENIDE	ChEMBL	Phase 2	CA5A, CA7
COUMAPHOS	ChEMBL	Phase 2	CA5A, CA7
ELLAGIC ACID	ChEMBL	Phase 2	CA5A, CA7
GALLIC ACID	ChEMBL	Phase 2	CA5A, CA7
INDISULAM	ChEMBL	Phase 2	CA5A, CA7
IROSUSTAT	ChEMBL	Phase 2	CA5A, CA7
PCI-27483	ChEMBL	Phase 2	CA5A, CA7
SONEPIPRAZOLE	ChEMBL	Phase 2	CA5A, CA7
Sildenafil	PubChem	Approved	CA5A, CA7
Sulfuric Acid	PubChem	Approved	CA5A, CA7
RUFINAMIDE	ChEMBL + PubChem	Phase 4 (approved)	CA5A
FLUDARABINE	ChEMBL	Phase 4 (approved)	CA5A
HYDROQUINONE	ChEMBL	Phase 4 (approved)	CA5A
HYDROXYUREA	ChEMBL	Phase 4 (approved)	CA5A
LENVATINIB	ChEMBL	Phase 4 (approved)	CA5A
METOLAZONE	ChEMBL	Phase 4 (approved)	CA7
SALICYLIC ACID	ChEMBL	Phase 4 (approved)	CA7
SORAFENIB	ChEMBL	Phase 4 (approved)	CA7
SULTHIAME	ChEMBL	Phase 4 (approved)	CA7
NITRIC ACID	ChEMBL	Phase 3	CA5A
PRITELIVIR	ChEMBL	Phase 3	CA5A
DAIDZEIN	ChEMBL	Phase 2	CA7
ISOQUERCETIN	ChEMBL	Phase 2	CA7