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Amphetamine

Updated: Wikipedia source

Amphetamine

Amphetamine is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity; it is also used to treat binge eating disorder in the form of its inactive prodrug lisdexamfetamine. Amphetamine was discovered as a chemical in 1887 by Lazăr Edeleanu, and then as a drug in the late 1920s. It exists as two enantiomers: levoamphetamine and dextroamphetamine. Amphetamine properly refers to a specific chemical, the racemic free base, which is equal parts of the two enantiomers in their pure amine forms. The term is frequently used informally to refer to any combination of the enantiomers, or to either of them alone. Historically, it has been used to treat nasal congestion and depression. Amphetamine is also used as an athletic performance enhancer and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. It is a prescription drug in many countries, and unauthorized possession and distribution of amphetamine are often tightly controlled due to the significant health risks associated with recreational use. The first amphetamine pharmaceutical was Benzedrine, a brand which was used to treat a variety of conditions. Pharmaceutical amphetamine is prescribed as racemic amphetamine, Adderall, dextroamphetamine, or the inactive prodrug lisdexamfetamine. Amphetamine increases monoamine and excitatory neurotransmission in the brain, with its most pronounced effects targeting the norepinephrine and dopamine neurotransmitter systems. At therapeutic doses, amphetamine causes emotional and cognitive effects such as euphoria, change in desire for sex, increased wakefulness, and improved cognitive control. It induces physical effects such as improved reaction time, fatigue resistance, decreased appetite, elevated heart rate, and increased muscle strength. Larger doses of amphetamine may impair cognitive function and induce rapid muscle breakdown. Addiction is a serious risk with heavy recreational amphetamine use, but is unlikely to occur from long-term medical use at therapeutic doses. Very high doses can result in psychosis (e.g., hallucinations, delusions, and paranoia) which rarely occurs at therapeutic doses even during long-term use. Recreational doses are generally much larger than prescribed therapeutic doses and carry a far greater risk of serious side effects. Amphetamine belongs to the phenethylamine class. It is also the parent compound of its own structural class, the substituted amphetamines, which includes prominent substances such as bupropion, cathinone, MDMA, and methamphetamine. As a member of the phenethylamine class, amphetamine is also chemically related to the naturally occurring trace amine neuromodulators, specifically phenethylamine and N-methylphenethylamine, both of which are produced within the human body. Phenethylamine is the parent compound of amphetamine, while N-methylphenethylamine is a positional isomer of amphetamine that differs only in the placement of the methyl group.

Infobox

Pronunciation
/æmˈfɛtəmiːn/ ⓘ
Trade names
Evekeo, Adderall,[note 1] others
Other names
α-methylphenethylamine, β-phenylisopropylamine, thyramine
AHFS/Drugs.com
Monograph
MedlinePlus
a616004
License data
mw- US DailyMed: Amphetamine
Dependenceliability
Physical: NonePsychological: Moderate
Addictionliability
Moderate
Routes ofadministration
Medical: OralRecreational: Oral, insufflation, rectal, intramuscular, intravenous
Drug class
Stimulant, anorectic
ATC code
N06BA01 (WHO) N06BA02 (WHO) N06BA12 (WHO)
Receptors
TAAR1, VMAT2, 5HT1A
Metabolism
CYP2D6, DBH, FMO3
Legal status
AU: S8 (Controlled drug) BR: Class A3 (Psychoactive drugs) CA: Schedule I DE: Anlage III (Special prescription form required) NZ: Class B UK: Class B US: Schedule II UN: Psychotropic Schedule II SE: Förteckning II (in some forms, like Dextroamphetamine and Lisdexamfetamine)
Bioavailability
Oral: 90%
Protein binding
20%
Metabolites
4-hydroxyamphetamine, 4-hydroxynorephedrine, 4-hydroxyphenylacetone, benzoic acid, hippuric acid, norephedrine, phenylacetone
Onset of action
IR dosing: 30–60 minutesXR dosing: 1.5–2 hours
Elimination half-life
D-amph: 9–11 hoursL-amph: 11–14 hourspH-dependent: 7–34 hours
Duration of action
IR dosing: 3–6 hours XR dosing: 8–12 hours
Excretion
Primarily renal;pH-dependent range: 1–75%
CAS Number
300-62-9 Y
PubChem CID
3007
IUPHAR/BPS
4804
DrugBank
DB00182 Y
ChemSpider
13852819 Y
UNII
CK833KGX7E
KEGG
D07445 Y
ChEBI
CHEBI:2679 Y
ChEMBL
ChEMBL405 Y
NIAID ChemDB
018564
CompTox Dashboard (EPA)
DTXSID4022600
ECHA InfoCard
100.005.543
Formula
C9H13N
Molar mass
135.210 g·mol−1
3D model (JSmol)
Interactive image
Chirality
Racemic mixture
Density
936 g/cm3 at 25 °C
Melting point
146 °C (295 °F)
Boiling point
203 °C (397 °F) at 760 mmHg

Tables

Summary of addiction-related plasticity · Adverse effects › Reinforcement disorders › Biomolecular mechanisms › Behavioral treatments
Opiates
Opiates
Form of neuroplasticity or behavioral plasticity
Opiates
Type of reinforcer
Psychostimulants
Type of reinforcer
High fat or sugar food
Type of reinforcer
Sexual intercourse
Type of reinforcer
Physical exercise(aerobic)
Type of reinforcer
Environmentalenrichment
ΔFosB expression innucleus accumbens D1-type MSNsTooltip medium spiny neurons
ΔFosB expression innucleus accumbens D1-type MSNsTooltip medium spiny neurons
Form of neuroplasticity or behavioral plasticity
ΔFosB expression innucleus accumbens D1-type MSNsTooltip medium spiny neurons
Type of reinforcer
Type of reinforcer
Type of reinforcer
Type of reinforcer
Type of reinforcer
Type of reinforcer
Behavioral plasticity
Behavioral plasticity
Form of neuroplasticity or behavioral plasticity
Behavioral plasticity
Escalation of intake
Escalation of intake
Form of neuroplasticity or behavioral plasticity
Escalation of intake
Type of reinforcer
Yes
Type of reinforcer
Yes
Type of reinforcer
Yes
Psychostimulantcross-sensitization
Psychostimulantcross-sensitization
Form of neuroplasticity or behavioral plasticity
Psychostimulantcross-sensitization
Type of reinforcer
Yes
Type of reinforcer
Not applicable
Type of reinforcer
Yes
Type of reinforcer
Yes
Type of reinforcer
Attenuated
Type of reinforcer
Attenuated
Psychostimulantself-administration
Psychostimulantself-administration
Form of neuroplasticity or behavioral plasticity
Psychostimulantself-administration
Type of reinforcer
Type of reinforcer
Type of reinforcer
Type of reinforcer
Type of reinforcer
Psychostimulantconditioned place preference
Psychostimulantconditioned place preference
Form of neuroplasticity or behavioral plasticity
Psychostimulantconditioned place preference
Type of reinforcer
Type of reinforcer
Type of reinforcer
Type of reinforcer
Type of reinforcer
Type of reinforcer
Reinstatement of drug-seeking behavior
Reinstatement of drug-seeking behavior
Form of neuroplasticity or behavioral plasticity
Reinstatement of drug-seeking behavior
Type of reinforcer
Type of reinforcer
Type of reinforcer
Type of reinforcer
Neurochemical plasticity
Neurochemical plasticity
Form of neuroplasticity or behavioral plasticity
Neurochemical plasticity
CREBTooltip cAMP response element-binding protein phosphorylationin the nucleus accumbens
CREBTooltip cAMP response element-binding protein phosphorylationin the nucleus accumbens
Form of neuroplasticity or behavioral plasticity
CREBTooltip cAMP response element-binding protein phosphorylationin the nucleus accumbens
Type of reinforcer
Type of reinforcer
Type of reinforcer
Type of reinforcer
Type of reinforcer
Sensitized dopamine responsein the nucleus accumbens
Sensitized dopamine responsein the nucleus accumbens
Form of neuroplasticity or behavioral plasticity
Sensitized dopamine responsein the nucleus accumbens
Type of reinforcer
No
Type of reinforcer
Yes
Type of reinforcer
No
Type of reinforcer
Yes
Altered striatal dopamine signaling
Altered striatal dopamine signaling
Form of neuroplasticity or behavioral plasticity
Altered striatal dopamine signaling
Type of reinforcer
↓DRD2, ↑DRD3
Type of reinforcer
↑DRD1, ↓DRD2, ↑DRD3
Type of reinforcer
↑DRD1, ↓DRD2, ↑DRD3
Type of reinforcer
↑DRD2
Type of reinforcer
↑DRD2
Altered striatal opioid signaling
Altered striatal opioid signaling
Form of neuroplasticity or behavioral plasticity
Altered striatal opioid signaling
Type of reinforcer
No change or↑μ-opioid receptors
Type of reinforcer
↑μ-opioid receptors↑κ-opioid receptors
Type of reinforcer
↑μ-opioid receptors
Type of reinforcer
↑μ-opioid receptors
Type of reinforcer
No change
Type of reinforcer
No change
Changes in striatal opioid peptides
Changes in striatal opioid peptides
Form of neuroplasticity or behavioral plasticity
Changes in striatal opioid peptides
Type of reinforcer
↑dynorphinNo change: enkephalin
Type of reinforcer
↑dynorphin
Type of reinforcer
↓enkephalin
Type of reinforcer
↑dynorphin
Type of reinforcer
↑dynorphin
Mesocorticolimbic synaptic plasticity
Mesocorticolimbic synaptic plasticity
Form of neuroplasticity or behavioral plasticity
Mesocorticolimbic synaptic plasticity
Number of dendrites in the nucleus accumbens
Number of dendrites in the nucleus accumbens
Form of neuroplasticity or behavioral plasticity
Number of dendrites in the nucleus accumbens
Type of reinforcer
Type of reinforcer
Type of reinforcer
Dendritic spine density inthe nucleus accumbens
Dendritic spine density inthe nucleus accumbens
Form of neuroplasticity or behavioral plasticity
Dendritic spine density inthe nucleus accumbens
Type of reinforcer
Type of reinforcer
Type of reinforcer
Form of neuroplasticity or behavioral plasticity
Type of reinforcer
Ref.
Opiates
Psychostimulants
High fat or sugar food
Sexual intercourse
Physical exercise(aerobic)
Environmentalenrichment
ΔFosB expression innucleus accumbens D1-type MSNsTooltip medium spiny neurons
Behavioral plasticity
Escalation of intake
Yes
Yes
Yes
Psychostimulantcross-sensitization
Yes
Not applicable
Yes
Yes
Attenuated
Attenuated
Psychostimulantself-administration
Psychostimulantconditioned place preference
Reinstatement of drug-seeking behavior
Neurochemical plasticity
CREBTooltip cAMP response element-binding protein phosphorylationin the nucleus accumbens
Sensitized dopamine responsein the nucleus accumbens
No
Yes
No
Yes
Altered striatal dopamine signaling
↓DRD2, ↑DRD3
↑DRD1, ↓DRD2, ↑DRD3
↑DRD1, ↓DRD2, ↑DRD3
↑DRD2
↑DRD2
Altered striatal opioid signaling
No change or↑μ-opioid receptors
↑μ-opioid receptors↑κ-opioid receptors
↑μ-opioid receptors
↑μ-opioid receptors
No change
No change
Changes in striatal opioid peptides
↑dynorphinNo change: enkephalin
↑dynorphin
↓enkephalin
↑dynorphin
↑dynorphin
Mesocorticolimbic synaptic plasticity
Number of dendrites in the nucleus accumbens
Dendritic spine density inthe nucleus accumbens
Overdose symptoms by system · Overdose
Cardiovascular
Cardiovascular
System
Cardiovascular
Minor or moderate overdose
Abnormal heartbeat High or low blood pressure
Severe overdose
Cardiogenic shock (heart not pumping enough blood) Cerebral hemorrhage (bleeding in the brain) Circulatory collapse (partial or complete failure of the circulatory system)
Central nervoussystem
Central nervoussystem
System
Central nervoussystem
Minor or moderate overdose
Confusion Abnormally fast reflexes Severe agitation Tremor (involuntary muscle twitching)
Severe overdose
Acute amphetamine psychosis (e.g., delusions and paranoia) Compulsive and repetitive movement Serotonin syndrome (excessive serotonergic nerve activity) Sympathomimetic toxidrome (excessive adrenergic nerve activity)
Musculoskeletal
Musculoskeletal
System
Musculoskeletal
Minor or moderate overdose
Muscle pain
Severe overdose
Rhabdomyolysis (rapid muscle breakdown)
Respiratory
Respiratory
System
Respiratory
Minor or moderate overdose
Rapid breathing
Severe overdose
Pulmonary edema (fluid accumulation in the lungs) Pulmonary hypertension (high blood pressure in the arteries of the lung) Respiratory alkalosis (reduced blood CO2)
Urinary
Urinary
System
Urinary
Minor or moderate overdose
Painful urination Urinary retention (inability to urinate)
Severe overdose
No urine production Kidney failure
Other
Other
System
Other
Minor or moderate overdose
Elevated body temperature Mydriasis (dilated pupils)
Severe overdose
Elevated or low blood potassium Hyperpyrexia (extremely elevated core body temperature) Metabolic acidosis (excessively acidic bodily fluids)
System
Minor or moderate overdose
Severe overdose
Cardiovascular
Abnormal heartbeat High or low blood pressure
Cardiogenic shock (heart not pumping enough blood) Cerebral hemorrhage (bleeding in the brain) Circulatory collapse (partial or complete failure of the circulatory system)
Central nervoussystem
Confusion Abnormally fast reflexes Severe agitation Tremor (involuntary muscle twitching)
Acute amphetamine psychosis (e.g., delusions and paranoia) Compulsive and repetitive movement Serotonin syndrome (excessive serotonergic nerve activity) Sympathomimetic toxidrome (excessive adrenergic nerve activity)
Musculoskeletal
Muscle pain
Rhabdomyolysis (rapid muscle breakdown)
Respiratory
Rapid breathing
Pulmonary edema (fluid accumulation in the lungs) Pulmonary hypertension (high blood pressure in the arteries of the lung) Respiratory alkalosis (reduced blood CO2)
Urinary
Painful urination Urinary retention (inability to urinate)
No urine production Kidney failure
Other
Elevated body temperature Mydriasis (dilated pupils)
Elevated or low blood potassium Hyperpyrexia (extremely elevated core body temperature) Metabolic acidosis (excessively acidic bodily fluids)
Effects of amphetamine on membrane transport proteins in dopamine neurons[note 19] · Pharmacology › Pharmacodynamics › Dopamine
Unidentified
Unidentified
Biological target of amphetamine
Unidentified
Initial effector / G-protein
Unidentified intracellular effector
Second messenger(s)
IP₃-mediated intracellular Ca²⁺ release
Secondary effectorprotein kinase
CAMKIIαTooltip Calcium/calmodulin-dependent protein kinase II alpha
Phosphorylated transporter
DATTooltip Dopamine transporter
Effect on transporter function
Reverse transport of dopamine
Effect on neurotransmission
Dopamine efflux into synaptic cleft
TAAR1Tooltip Trace amine-associated receptor 1
TAAR1Tooltip Trace amine-associated receptor 1
Biological target of amphetamine
TAAR1Tooltip Trace amine-associated receptor 1
Initial effector / G-protein
G13
Second messenger(s)
RhoA–GTP
Secondary effectorprotein kinase
ROCK†
Phosphorylated transporter
DAT
Effect on transporter function
Transporter internalization
Effect on neurotransmission
Dopamine reuptake inhibition
TAAR1Tooltip Trace amine-associated receptor 1
TAAR1Tooltip Trace amine-associated receptor 1
Biological target of amphetamine
TAAR1Tooltip Trace amine-associated receptor 1
Initial effector / G-protein
G13
Second messenger(s)
RhoA–GTP
Secondary effectorprotein kinase
ROCK†
Phosphorylated transporter
EAAT3Tooltip Excitatory amino acid transporter 3
Effect on transporter function
Transporter internalization
Effect on neurotransmission
Glutamate reuptake inhibition
TAAR1Tooltip Trace amine-associated receptor 1
TAAR1Tooltip Trace amine-associated receptor 1
Biological target of amphetamine
TAAR1Tooltip Trace amine-associated receptor 1
Initial effector / G-protein
Gs
Second messenger(s)
↑ cAMPTooltip cyclic adenosine monophosphate
Secondary effectorprotein kinase
PKATooltip Protein kinase A
Phosphorylated transporter
DAT
Effect on transporter function
Transporter internalization
Effect on neurotransmission
Dopamine reuptake inhibition
TAAR1Tooltip Trace amine-associated receptor 1
TAAR1Tooltip Trace amine-associated receptor 1
Biological target of amphetamine
TAAR1Tooltip Trace amine-associated receptor 1
Initial effector / G-protein
Gs
Second messenger(s)
↑ cAMP
Secondary effectorprotein kinase
PKCTooltip Protein kinase C
Phosphorylated transporter
DAT
Effect on transporter function
Reverse transport of dopamineTransporter internalization
Effect on neurotransmission
Dopamine efflux into synaptic cleftDopamine reuptake inhibition
Unidentified
Unidentified
Biological target of amphetamine
Unidentified
Initial effector / G-protein
Unidentified intracellular effector
Second messenger(s)
IP₃/DAG pathway‡
Secondary effectorprotein kinase
PKCTooltip Protein kinase C
Phosphorylated transporter
DAT
Effect on transporter function
Reverse transport of dopamineTransporter internalization
Effect on neurotransmission
Dopamine efflux into synaptic cleftDopamine reuptake inhibition
†ROCK-mediated transporter internalization is transient due to the inactivation of RhoA (which activates ROCK) by PKA. ‡IP₃ binds to its receptors on the endoplasmic reticulum to release intracellular Ca²⁺ stores, and together with diacylglycerol activates conventional PKC isoforms.
†ROCK-mediated transporter internalization is transient due to the inactivation of RhoA (which activates ROCK) by PKA. ‡IP₃ binds to its receptors on the endoplasmic reticulum to release intracellular Ca²⁺ stores, and together with diacylglycerol activates conventional PKC isoforms.
Biological target of amphetamine
†ROCK-mediated transporter internalization is transient due to the inactivation of RhoA (which activates ROCK) by PKA. ‡IP₃ binds to its receptors on the endoplasmic reticulum to release intracellular Ca²⁺ stores, and together with diacylglycerol activates conventional PKC isoforms.
Biological target of amphetamine
Initial effector / G-protein
Second messenger(s)
Secondary effectorprotein kinase
Phosphorylated transporter
Effect on transporter function
Effect on neurotransmission
Sources
Unidentified
Unidentified intracellular effector
IP₃-mediated intracellular Ca²⁺ release
CAMKIIαTooltip Calcium/calmodulin-dependent protein kinase II alpha
DATTooltip Dopamine transporter
Reverse transport of dopamine
Dopamine efflux into synaptic cleft
TAAR1Tooltip Trace amine-associated receptor 1
G13
RhoA–GTP
ROCK†
DAT
Transporter internalization
Dopamine reuptake inhibition
TAAR1Tooltip Trace amine-associated receptor 1
G13
RhoA–GTP
ROCK†
EAAT3Tooltip Excitatory amino acid transporter 3
Transporter internalization
Glutamate reuptake inhibition
TAAR1Tooltip Trace amine-associated receptor 1
Gs
↑ cAMPTooltip cyclic adenosine monophosphate
PKATooltip Protein kinase A
DAT
Transporter internalization
Dopamine reuptake inhibition
TAAR1Tooltip Trace amine-associated receptor 1
Gs
↑ cAMP
PKCTooltip Protein kinase C
DAT
Reverse transport of dopamineTransporter internalization
Dopamine efflux into synaptic cleftDopamine reuptake inhibition
Unidentified
Unidentified intracellular effector
IP₃/DAG pathway‡
PKCTooltip Protein kinase C
DAT
Reverse transport of dopamineTransporter internalization
Dopamine efflux into synaptic cleftDopamine reuptake inhibition
†ROCK-mediated transporter internalization is transient due to the inactivation of RhoA (which activates ROCK) by PKA. ‡IP₃ binds to its receptors on the endoplasmic reticulum to release intracellular Ca²⁺ stores, and together with diacylglycerol activates conventional PKC isoforms.
Human carbonic anhydraseactivation potency · Pharmacology › Pharmacodynamics › Other neurotransmitters, peptides, hormones, and enzymes
hCA4
hCA4
Enzyme
hCA4
KA (nMTooltip nanomolar)
94
hCA5A
hCA5A
Enzyme
hCA5A
KA (nMTooltip nanomolar)
810
hCA5B
hCA5B
Enzyme
hCA5B
KA (nMTooltip nanomolar)
2560
hCA7
hCA7
Enzyme
hCA7
KA (nMTooltip nanomolar)
910
hCA12
hCA12
Enzyme
hCA12
KA (nMTooltip nanomolar)
640
hCA13
hCA13
Enzyme
hCA13
KA (nMTooltip nanomolar)
24100
hCA14
hCA14
Enzyme
hCA14
KA (nMTooltip nanomolar)
9150
Enzyme
KA (nMTooltip nanomolar)
Sources
hCA4
94
hCA5A
810
hCA5B
2560
hCA7
910
hCA12
640
hCA13
24100
hCA14
9150
Global estimates of drug users in 2016(in millions of users)[291] · History, society, and culture
Amphetamine-type stimulants
Amphetamine-type stimulants
Substance
Amphetamine-type stimulants
Bestestimate
34.16
Lowestimate
13.42
Highestimate
55.24
Cannabis
Cannabis
Substance
Cannabis
Bestestimate
192.15
Lowestimate
165.76
Highestimate
234.06
Cocaine
Cocaine
Substance
Cocaine
Bestestimate
18.20
Lowestimate
13.87
Highestimate
22.85
Ecstasy
Ecstasy
Substance
Ecstasy
Bestestimate
20.57
Lowestimate
8.99
Highestimate
32.34
Opiates
Opiates
Substance
Opiates
Bestestimate
19.38
Lowestimate
13.80
Highestimate
26.15
Opioids
Opioids
Substance
Opioids
Bestestimate
34.26
Lowestimate
27.01
Highestimate
44.54
Substance
Bestestimate
Lowestimate
Highestimate
Amphetamine-type stimulants
34.16
13.42
55.24
Cannabis
192.15
165.76
234.06
Cocaine
18.20
13.87
22.85
Ecstasy
20.57
8.99
32.34
Opiates
19.38
13.80
26.15
Opioids
34.26
27.01
44.54
Amphetamine pharmaceuticals · History, society, and culture › Pharmaceutical products
Adderall
Adderall
Brandname
Adderall
United StatesAdopted Name
(D:L) ratio
3:1 (salts)
Dosageform
tablet
Marketingstart date
1996
Adderall XR
Adderall XR
Brandname
Adderall XR
United StatesAdopted Name
(D:L) ratio
3:1 (salts)
Dosageform
capsule
Marketingstart date
2001
Mydayis
Mydayis
Brandname
Mydayis
United StatesAdopted Name
(D:L) ratio
3:1 (salts)
Dosageform
capsule
Marketingstart date
2017
Adzenys ER
Adzenys ER
Brandname
Adzenys ER
United StatesAdopted Name
amphetamine
(D:L) ratio
3:1 (base)
Dosageform
suspension
Marketingstart date
2017
Adzenys XR-ODT
Adzenys XR-ODT
Brandname
Adzenys XR-ODT
United StatesAdopted Name
amphetamine
(D:L) ratio
3:1 (base)
Dosageform
ODT
Marketingstart date
2016
Dyanavel XR
Dyanavel XR
Brandname
Dyanavel XR
United StatesAdopted Name
amphetamine
(D:L) ratio
3.2:1 (base)
Dosageform
suspension
Marketingstart date
2015
Evekeo
Evekeo
Brandname
Evekeo
United StatesAdopted Name
amphetamine sulfate
(D:L) ratio
1:1 (salts)
Dosageform
tablet
Marketingstart date
2012
Evekeo ODT
Evekeo ODT
Brandname
Evekeo ODT
United StatesAdopted Name
amphetamine sulfate
(D:L) ratio
1:1 (salts)
Dosageform
ODT
Marketingstart date
2019
Dexedrine
Dexedrine
Brandname
Dexedrine
United StatesAdopted Name
dextroamphetamine sulfate
(D:L) ratio
1:0 (salts)
Dosageform
capsule
Marketingstart date
1976
Zenzedi
Zenzedi
Brandname
Zenzedi
United StatesAdopted Name
dextroamphetamine sulfate
(D:L) ratio
1:0 (salts)
Dosageform
tablet
Marketingstart date
2013
Vyvanse
Vyvanse
Brandname
Vyvanse
United StatesAdopted Name
lisdexamfetamine dimesylate
(D:L) ratio
1:0 (prodrug)
Dosageform
capsule
Marketingstart date
2007
tablet
tablet
Brandname
tablet
Xelstrym
Xelstrym
Brandname
Xelstrym
United StatesAdopted Name
dextroamphetamine
(D:L) ratio
1:0 (base)
Dosageform
patch
Marketingstart date
2022
Brandname
United StatesAdopted Name
(D:L) ratio
Dosageform
Marketingstart date
Sources
Adderall
3:1 (salts)
tablet
1996
Adderall XR
3:1 (salts)
capsule
2001
Mydayis
3:1 (salts)
capsule
2017
Adzenys ER
amphetamine
3:1 (base)
suspension
2017
Adzenys XR-ODT
amphetamine
3:1 (base)
ODT
2016
Dyanavel XR
amphetamine
base)
suspension
2015
Evekeo
amphetamine sulfate
1:1 (salts)
tablet
2012
Evekeo ODT
amphetamine sulfate
1:1 (salts)
ODT
2019
Dexedrine
dextroamphetamine sulfate
1:0 (salts)
capsule
1976
Zenzedi
dextroamphetamine sulfate
1:0 (salts)
tablet
2013
Vyvanse
lisdexamfetamine dimesylate
1:0 (prodrug)
capsule
2007
tablet
Xelstrym
dextroamphetamine
1:0 (base)
patch
2022
Amphetamine base in marketed amphetamine medications · History, society, and culture › Pharmaceutical products
(g/mol)
(g/mol)
drug
(g/mol)
drug
(percent)
formula
(30 mg dose)
total
total
drug
total
drug
base
formula
total
molar mass
dextro-
molar mass
levo-
amphetamine base
dextro-
amphetamine base
levo-
dextroamphetamine sulfate
dextroamphetamine sulfate
drug
dextroamphetamine sulfate
drug
(C9H13N)2•H2SO4
formula
368.49
molar mass
270.41
molar mass
73.38%
amphetamine base
73.38%
amphetamine base
amphetamine base
22.0 mg
amphetamine basein equal doses
amphetamine basein equal doses
30.0 mg
amphetamine sulfate
amphetamine sulfate
drug
amphetamine sulfate
drug
(C9H13N)2•H2SO4
formula
368.49
molar mass
270.41
molar mass
73.38%
amphetamine base
36.69%
amphetamine base
36.69%
amphetamine base
11.0 mg
amphetamine basein equal doses
11.0 mg
amphetamine basein equal doses
30.0 mg
Adderall
Adderall
drug
Adderall
molar mass
62.57%
amphetamine base
47.49%
amphetamine base
15.08%
amphetamine base
14.2 mg
amphetamine basein equal doses
4.5 mg
amphetamine basein equal doses
35.2 mg
25%
25%
drug
25%
drug
dextroamphetamine sulfate
formula
(C9H13N)2•H2SO4
molar mass
368.49
molar mass
270.41
amphetamine base
73.38%
amphetamine base
73.38%
amphetamine base
25%
25%
drug
25%
drug
amphetamine sulfate
formula
(C9H13N)2•H2SO4
molar mass
368.49
molar mass
270.41
amphetamine base
73.38%
amphetamine base
36.69%
amphetamine base
36.69%
25%
25%
drug
25%
drug
dextroamphetamine saccharate
formula
(C9H13N)2•C6H10O8
molar mass
480.55
molar mass
270.41
amphetamine base
56.27%
amphetamine base
56.27%
amphetamine base
25%
25%
drug
25%
drug
amphetamine aspartate monohydrate
formula
(C9H13N)•C4H7NO4•H2O
molar mass
286.32
molar mass
135.21
amphetamine base
47.22%
amphetamine base
23.61%
amphetamine base
23.61%
lisdexamfetamine dimesylate
lisdexamfetamine dimesylate
drug
lisdexamfetamine dimesylate
drug
C15H25N3O•(CH4O3S)2
formula
455.49
molar mass
135.21
molar mass
29.68%
amphetamine base
29.68%
amphetamine base
amphetamine base
8.9 mg
amphetamine basein equal doses
amphetamine basein equal doses
74.2 mg
amphetamine base suspension
amphetamine base suspension
drug
amphetamine base suspension
drug
C9H13N
formula
135.21
molar mass
135.21
molar mass
100%
amphetamine base
76.19%
amphetamine base
23.81%
amphetamine base
22.9 mg
amphetamine basein equal doses
7.1 mg
amphetamine basein equal doses
22.0 mg
drug
formula
molar mass
amphetamine base
amphetamine basein equal doses
doses withequal basecontent
(g/mol)
(percent)
(30 mg dose)
total
base
total
dextro-
levo-
dextro-
levo-
dextroamphetamine sulfate
(C9H13N)2•H2SO4
368.49
270.41
73.38%
73.38%
22.0 mg
30.0 mg
amphetamine sulfate
(C9H13N)2•H2SO4
368.49
270.41
73.38%
36.69%
36.69%
11.0 mg
11.0 mg
30.0 mg
Adderall
62.57%
47.49%
15.08%
14.2 mg
4.5 mg
35.2 mg
25%
dextroamphetamine sulfate
(C9H13N)2•H2SO4
368.49
270.41
73.38%
73.38%
25%
amphetamine sulfate
(C9H13N)2•H2SO4
368.49
270.41
73.38%
36.69%
36.69%
25%
dextroamphetamine saccharate
(C9H13N)2•C6H10O8
480.55
270.41
56.27%
56.27%
25%
amphetamine aspartate monohydrate
(C9H13N)•C4H7NO4•H2O
286.32
135.21
47.22%
23.61%
23.61%
lisdexamfetamine dimesylate
C15H25N3O•(CH4O3S)2
455.49
135.21
29.68%
29.68%
8.9 mg
74.2 mg
amphetamine base suspension
C9H13N
135.21
135.21
100%
76.19%
23.81%
22.9 mg
7.1 mg
22.0 mg

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  4. The brand name Adderall is used throughout this article to refer to the amphetamine four-salt mixture it contains (dextr
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  10. According to one review, amphetamine can be prescribed to individuals with a history of abuse provided that appropriate
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