Compound Detail

CHEMBL612

DEXTROAMPHETAMINE

💊 Approved Drug

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💊 Approved Drug

C[C@H](N)Cc1ccccc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL612
Name	DEXTROAMPHETAMINE
Phase	Approved
Structure Type	MOL
InChI Key	KWTSXDURSIMDCE-QMMMGPOBSA-N
Therapeutic	✓ Yes

Known Names

Amfetamine, (s)- Amphetamine, d- D-amphetamine Dexamfetamine Dexamphetamine Dexanfetamina Dexidrine Dextroamphetamine Dextroamphetamine resin complex NSC-73713 Xelstrym

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

135.2

MW (Da)

1.58

ALogP

HBA

HBD

26.0

PSA (Å²)

0.65

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1955
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Topical

Flags

Black Box Warning Natural Product

USAN Year

1964

Extended Properties

Molecular Formula	C9H13N
MW	135.21
Aromatic Rings	1
Heavy Atoms	10
NP-Likeness	-0.02

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Dopamine transporter releasing agent	RELEASING AGENT	Sodium-dependent dopamine transporter	✓	✓
Norepinephrine transporter releasing agent	RELEASING AGENT	Sodium-dependent noradrenaline transporter	✓	✓
Synaptic vesicular amine transporter inhibitor	INHIBITOR	Synaptic vesicular amine transporter	✓	✓

Indications

Arteriosclerosis Attention Deficit Disorder with Hyperactivity Narcolepsy Substance-Related Disorders Paraganglioma Amphetamine-Related Disorders Cocaine-Related Disorders Multiple Sclerosis Opioid-Related Disorders Schizophrenia Stress Disorders, Post-Traumatic Stroke Bipolar Disorder

ATC Classification

N06BA02

dexamfetamine

Level 1: NERVOUS SYSTEM

Level 2: PSYCHOANALEPTICS

Drug Warnings

Black Box Warning

neurotoxicity

Country: United States

Black Box Warning

misuse

Country: United States

Activity Summary

EC50 28 meas. best 8.7

Ki 16 meas. best 7.0

IC50 5 meas. best 6.7

Kd 1 meas. best 5.35

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Trace amine-associated receptor 1 CHEMBL4908	EC50	8.7	7.502	2.0	5
Unchecked CHEMBL612545	EC50	8.15	7.4167	7.0	3
Sodium-dependent noradrenaline transporter CHEMBL222	EC50	8.15	8.15	7.1	1
Trace amine-associated receptor 1 CHEMBL3833	EC50	7.86	6.6083	13.9	6
Sodium-dependent dopamine transporter CHEMBL238	EC50	7.61	7.61	24.8	1
Sodium-dependent dopamine transporter CHEMBL338	EC50	7.61	7.605	24.8	2
Sodium-dependent noradrenaline transporter CHEMBL222	Ki	7.0	7.0	101.0	1
Sodium-dependent dopamine transporter CHEMBL238	Ki	6.96	6.96	109.0	1
Trace amine-associated receptor 1 CHEMBL5857	EC50	6.85	6.275	140.0	4
Rattus norvegicus CHEMBL376	IC50	6.7	6.7	200.0	1
Sodium-dependent dopamine transporter CHEMBL238	IC50	6.54	6.54	288.4	1
Sodium-dependent noradrenaline transporter CHEMBL222	IC50	6.2	6.2	631.0	1
Rattus norvegicus CHEMBL376	EC50	6.1	5.53	800.0	2
Unchecked CHEMBL612545	Ki	6.0	5.17	1000.0	2
Trace amine-associated receptor 1 CHEMBL1926495	EC50	6.0	6.0	1010.0	1
Sodium-dependent serotonin transporter CHEMBL313	EC50	5.75	5.75	1765.0	2
Sodium-dependent serotonin transporter CHEMBL228	EC50	5.75	5.75	1770.0	1
Serotonin (5-HT) receptor CHEMBL2094123	Kd	5.35	5.35	4466.8	1
Sodium-dependent dopamine transporter CHEMBL338	IC50	5.31	5.31	4900.0	1
Sodium-dependent serotonin transporter CHEMBL228	Ki	5.24	5.24	5728.0	1
Amine oxidase [flavin-containing] A CHEMBL3358	Ki	4.91	4.91	12200.0	1
Amine oxidase [flavin-containing] A CHEMBL1951	Ki	4.84	4.84	14400.0	1
Sodium-dependent serotonin transporter CHEMBL228	IC50	4.78	4.78	16595.9	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	10.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Trace amine-associated receptor 1	EC50	=	2.0	nM	8.7	Activation of mouse TAAR1 expressed in human HEK293 cells assessed as accumulati...	22037049
Trace amine-associated receptor 1	EC50	=	3.98	nM	8.4	Activation of mouse TAAR1 transmembrane domain 6 Thr268(6.55)Met mutant expresse...	24354319
Sodium-dependent noradrenaline transporter	EC50	=	7.1	nM	8.15	Inhibition of [3H]norepinephrine reuptake at human NET cloned in rat brain synap...	22037049
Unchecked	EC50	=	7.1	nM	8.15	Activity at NET in rat synaptosomes obtained from whole brain minus striatum and...	-
Unchecked	EC50	=	7.0	nM	8.15	Activity at NET in rat synaptosomes assessed as release of [3H]NE after 30 mins ...	28244748
Trace amine-associated receptor 1	EC50	=	13.9	nM	7.86	Activation of rat TAAR1 transmembrane domain 7 Asn287(7.39)Tyr mutant expressed ...	24354319
Sodium-dependent dopamine transporter	EC50	=	24.8	nM	7.61	Inhibition of [3H]dopamine reuptake at human DAT cloned in rat brain synaptosome...	22037049
Sodium-dependent dopamine transporter	EC50	=	24.8	nM	7.61	Activity at DAT in rat synaptosomes obtained from striatum assessed as release o...	-
Sodium-dependent dopamine transporter	EC50	=	25.0	nM	7.6	Activity at DAT in rat synaptosomes assessed as release of [3H]DA after 5 mins b...	28244748
Trace amine-associated receptor 1	EC50	=	55.6	nM	7.25	Activation of rat wild type TAAR1 expressed in HEK293 cells assessed as stimulat...	24354319
Trace amine-associated receptor 1	EC50	=	84.6	nM	7.07	Activation of mouse wild type TAAR1 expressed in HEK293 cells assessed as stimul...	24354319
Sodium-dependent noradrenaline transporter	Ki	=	101.0	nM	7.0	Inhibition of [3H]norepinephrine uptake at human NET expressed in HEK293 cells p...	23602445
Sodium-dependent dopamine transporter	Ki	=	109.0	nM	6.96	Inhibition of [3H]dopamine uptake at human DAT expressed in HEK293 cells preincu...	23602445
Trace amine-associated receptor 1	EC50	=	140.0	nM	6.85	Activation of human TAAR1 expressed in human HEK293T cells assessed as cAMP accu...	22037049
Rattus norvegicus	IC50	=	200.0	nM	6.7	Inhibitory concentration against uptake of [3H]NE into chopped cerebral cortical...	7392028
Trace amine-associated receptor 1	EC50	=	210.0	nM	6.68	Activation of mouse TAAR1 expressed in human HEK293 cells assessed as accumulati...	22037049
Trace amine-associated receptor 1	EC50	=	218.8	nM	6.66	Activation of mouse TAAR1 transmembrane domain 7 Tyr287(7.39)Asn mutant expresse...	24354319
Sodium-dependent dopamine transporter	IC50	=	288.4	nM	6.54	Inhibition of [3H]dopamine uptake at human DAT expressed in HEK293 cells preincu...	23602445
Trace amine-associated receptor 1	EC50	=	440.0	nM	6.36	Activation of rat TAAR1 expressed in HEK293 cells assessed as accumulation of [3...	22037049
Trace amine-associated receptor 1	EC50	=	600.0	nM	6.22	Activation of C-terminal HA epitope tagged human TAAR1 expressed in RD-HGA16 cel...	22037049

Literature References

PubMed	DOI	Target Context	# Activities
24354319	10.1021/jm401316v	Trace amine-associated receptor 1	14
22037049	10.1016/j.bmc.2011.10.007	Trace amine-associated receptor 1	9
28244748	10.1021/acs.jmedchem.7b00085	Rattus norvegicus	8
7265121	10.1021/jm00135a020	Mus musculus	6
6716406	10.1021/jm00371a023	Mus musculus	5
2563772	10.1021/jm00123a004	Mus musculus	3
3397993	10.1021/jm00403a012	Amine oxidase [flavin-containing] B	3
7392028	10.1021/jm00180a006	Rattus norvegicus	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
20123154	10.1016/j.bmc.2010.01.029	Unchecked	2
23602445	10.1016/j.bmcl.2013.03.066	Sodium-dependent serotonin transporter	2
20123154	10.1016/j.bmc.2010.01.029	Amine oxidase [flavin-containing] B	2
20123154	10.1016/j.bmc.2010.01.029	Amine oxidase [flavin-containing] A	2
19345586	10.1016/j.bmc.2009.03.025	Glutamate NMDA receptor	2
18602830	10.1016/j.bmc.2008.06.009	Trace amine-associated receptor 1	2
8676127	10.1021/np50124a001	Unchecked	2
7143356	10.1021/jm00352a020	Phenylethanolamine N-methyltransferase	2
23602445	10.1016/j.bmcl.2013.03.066	Sodium-dependent noradrenaline transporter	2
6123601	10.1021/jm00347a011	Rattus norvegicus	2
23602445	10.1016/j.bmcl.2013.03.066	Sodium-dependent dopamine transporter	2

Data from ChEMBL 36 via Core Engine