Levamfetamine
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Also known as Amfetamine, (r)-Amphetamine l-formLevanfetaminaL-amphetamine(R)-Amphetamine(R)-(+)-amphetamine(-)-(R)-Amphetamine(L)-AmphetamineDEXTROAMPHETAMINE
Summary
Levamfetamine (CHEMBL19393) is an approved small molecule targeting TAAR1.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- Targets: 1 (TAAR1)
- Clinical trials: 17
- Chemistry: 135.21 Da · C9H13N
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL19393 |
| Name | Levamfetamine |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 32893 |
| ChEBI | CHEBI:42724 |
| Molecular formula | C9H13N |
| Molecular weight | 135.21 |
| InChIKey | KWTSXDURSIMDCE-MRVPVSSYSA-N |
SMILES: C[C@H](CC1=CC=CC=C1)N
IUPAC name: (2R)-1-phenylpropan-2-amine
ChEBI definition: A 1-phenylpropan-2-amine that has R configuration.
Also known as: Amfetamine, (r)-, Amphetamine l-form, Levamfetamine, Levanfetamina, L-amphetamine, (R)-Amphetamine, (R)-(+)-amphetamine, (-)-(R)-Amphetamine, (L)-Amphetamine, DEXTROAMPHETAMINE, LEVAMFETAMINE
Parent form; salt/anhydrous children: CHEMBL1788294, CHEMBL2106371
Patent coverage: 706 distinct patent families (2,668 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 |
|---|---|---|---|---|---|
| TAAR1 | TA1 receptor | Full agonist | 6.6 | 0% | Q96RJ0 |
Broader ChEMBL bioactivity targets: 6 (assay-derived). Sample: Trace amine-associated receptor 1, Serotonin (5-HT) receptor, Sigma non-opioid intracellular receptor 1, Trace amine-associated receptor 1, Trace amine-associated receptor 1, Trace amine-associated receptor 1.
Bioactivity
ChEMBL activities: 17 potent at pChembl ≥ 5 of 18 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| Q923Y9 | 7.47 | EC50 | 33.9 | nM | CHEMBL_ACT_13895570 |
| Q923Y8 | 7.19 | EC50 | 65 | nM | CHEMBL_ACT_7968718 |
| Q923Y8 | 6.98 | EC50 | 104.5 | nM | CHEMBL_ACT_13895545 |
| Q923Y8 | 6.92 | EC50 | 121 | nM | CHEMBL_ACT_13895555 |
| Q923Y9 | 6.77 | EC50 | 169.9 | nM | CHEMBL_ACT_13895550 |
| Q923Y9 | 6.68 | EC50 | 210 | nM | CHEMBL_ACT_7968704 |
| Q923Y9 | 6.67 | EC50 | 214.4 | nM | CHEMBL_ACT_13895560 |
| TAAR1 | 6.6 | EC50 | 250 | nM | CHEMBL_ACT_7968731 |
| Q923Y9 | 6.55 | EC50 | 280 | nM | CHEMBL_ACT_7968698 |
| Q923Y8 | 6.11 | EC50 | 785.5 | nM | CHEMBL_ACT_13895565 |
| TAAR1 | 6.04 | EC50 | 920 | nM | CHEMBL_ACT_2558467 |
| TAAR1 | 5.89 | EC50 | 1300 | nM | CHEMBL_ACT_7967444 |
| Q923Y9 | 5.85 | EC50 | 1400 | nM | CHEMBL_ACT_7968708 |
| TAAR1 | 5.77 | EC50 | 1700 | nM | CHEMBL_ACT_7968727 |
| Q8HZ64 | 5.73 | EC50 | 1860 | nM | CHEMBL_ACT_7968677 |
| Q923Y8 | 5.3 | EC50 | 4960 | nM | CHEMBL_ACT_7968712 |
| P08909 | 5.16 | Kd | 6918 | nM | CHEMBL_ACT_232897 |
Target pathways
Aggregated over 1 target gene(s): TAAR1.
Top Reactome pathways
7 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Signal Transduction | 1 | TAAR1 |
| Signaling by GPCR | 1 | TAAR1 |
| Class A/1 (Rhodopsin-like receptors) | 1 | TAAR1 |
| Amine ligand-binding receptors | 1 | TAAR1 |
| GPCR downstream signalling | 1 | TAAR1 |
| G alpha (s) signalling events | 1 | TAAR1 |
| GPCR ligand binding | 1 | TAAR1 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| G protein-coupled receptor signaling pathway | 1 |
| adenylate cyclase-activating G protein-coupled receptor signaling pathway | 1 |
| adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway | 1 |
| phospholipase C-activating G protein-coupled receptor signaling pathway | 1 |
| signal transduction | 1 |
Indications & clinical
Indications
0 indications (0 at ChEMBL trial phase 4).
Clinical trials
Total trials: 17.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE2 | 7 |
| PHASE4 | 4 |
| Not specified | 4 |
| PHASE1 | 2 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00228046 | PHASE4 | COMPLETED | Medication Strategies for Treating Aggressive Behavior in Youth With Attention Deficit Hyperactivity Disorder |
| NCT00254033 | PHASE4 | COMPLETED | Apathy Associated With Alzheimer’s Disease |
| NCT00296686 | PHASE4 | TERMINATED | Sequential Tranylcypromine (TC), TC + Dextroamphetamine and TC + Triiodothyronine for Refractory Depression |
| NCT01220440 | PHASE4 | COMPLETED | Comparing the Efficacy of Methylphenidate, Dextroamphetamine and Placebo in Children Diagnosed With ADHD |
| NCT00000304 | PHASE2 | COMPLETED | Dextroamphetamine as an Adjunct in Cocaine Treatment - 1 |
| NCT00000306 | PHASE2 | COMPLETED | Dextroamphetamine as Adjunct in Cocaine/Opiate Dependent Patients - 3 |
| NCT00000308 | PHASE2 | COMPLETED | Dextroamphetamine-Cocaine Behavioral Intervention - 5 |
| NCT00630682 | PHASE2 | COMPLETED | A Pilot Trial of Dextroamphetamine for Methamphetamine Dependence |
| NCT01215929 | PHASE2 | COMPLETED | Studying Amphetamine Withdrawal in Humans |
| NCT01905371 | PHASE2 | COMPLETED | Amphetamine-Enhanced Stroke Recovery |
| NCT02634684 | PHASE2 | COMPLETED | Pharmacologically-augmented Cognitive Therapies (PACTs) for Schizophrenia. |
| NCT00000305 | PHASE1 | TERMINATED | Amphetamine Cocaine Interaction Study - 2 |
| NCT03512171 | PHASE1 | COMPLETED | Decision Making Study in Young and Middle-Aged Adults: Part II |
| NCT01577706 | Not specified | TERMINATED | Spectroscopic Imaging at 4T: A Drug Challenge Study |
| NCT03999190 | Not specified | WITHDRAWN | Imaging Dopamine D2 Agonist Binding Sites in Schizophrenia |
| 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 PharmGKB pharmacogenomic data curated for this drug.
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.
22 molecules share ≥1 primary target. Top 22 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| DEXTROAMPHETAMINE | ChEMBL + PubChem | Phase 4 (approved) | TAAR1 |
| DOPAMINE | ChEMBL + PubChem | Phase 4 (approved) | TAAR1 |
| METHAMPHETAMINE | ChEMBL + PubChem | Phase 4 (approved) | TAAR1 |
| PHENTERMINE | ChEMBL + PubChem | Phase 4 (approved) | TAAR1 |
| TOLAZOLINE | ChEMBL + PubChem | Phase 4 (approved) | TAAR1 |
| FENOLDOPAM | ChEMBL | Phase 4 (approved) | TAAR1 |
| GUANABENZ | ChEMBL | Phase 4 (approved) | TAAR1 |
| HYDROXYAMPHETAMINE | ChEMBL | Phase 4 (approved) | TAAR1 |
| NAPHAZOLINE | ChEMBL | Phase 4 (approved) | TAAR1 |
| TETRAHYDROZOLINE | ChEMBL | Phase 4 (approved) | TAAR1 |
| SEROTONIN | ChEMBL + PubChem | Phase 3 (approved) | TAAR1 |
| ANTAZOLINE | ChEMBL | Phase 3 | TAAR1 |
| TYRAMINE | ChEMBL | Phase 3 | TAAR1 |
| ULOTARONT | ChEMBL | Phase 3 | TAAR1 |
| LEVMETAMFETAMINE | ChEMBL + PubChem | Phase 2 (approved) | TAAR1 |
| AZAQUINZOLE | ChEMBL | Phase 2 | TAAR1 |
| FORMETOREX | ChEMBL | Phase 2 | TAAR1 |
| RALMITARONT | ChEMBL | Phase 2 | TAAR1 |
| Amiodarone | PubChem | Approved | TAAR1 |
| Octopamine | PubChem | Approved | TAAR1 |
| Pyrimethamine | PubChem | Approved | TAAR1 |
| Trimethoprim | PubChem | Approved | TAAR1 |