Details
Stereochemistry | RACEMIC |
Molecular Formula | 2C9H13N.H2O4S |
Molecular Weight | 368.491 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.CC(N)CC1=CC=CC=C1.CC(N)CC2=CC=CC=C2
InChI
InChIKey=PYHRZPFZZDCOPH-UHFFFAOYSA-N
InChI=1S/2C9H13N.H2O4S/c2*1-8(10)7-9-5-3-2-4-6-9;1-5(2,3)4/h2*2-6,8H,7,10H2,1H3;(H2,1,2,3,4)
Molecular Formula | H2O4S |
Molecular Weight | 98.078 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C9H13N |
Molecular Weight | 135.2062 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.caremark.com/portal/asset/FEP_Rationale_Amphetamine.pdf
https://www.ncbi.nlm.nih.gov/pubmed/23539642
http://www.cesar.umd.edu/cesar/drugs/amphetamines.asp
Curator's Comment: description was created based on several sources, including
https://www.caremark.com/portal/asset/FEP_Rationale_Amphetamine.pdf
https://www.ncbi.nlm.nih.gov/pubmed/23539642
http://www.cesar.umd.edu/cesar/drugs/amphetamines.asp
Amphetamine is a potent central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered in 1887 and exists as two enantiomers: levoamphetamine and dextroamphetamine. The mode of therapeutic action in ADHD is not known. Amphetamines are thought to block the reuptake of norepinephrine and dopamine into the presynaptic neuron and increase the release of these monoamines into the extraneuronal space. At higher dosages, they cause release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems. Amphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). In the periphery, amphetamines are believed to cause the release of noradrenaline by acting on the adrenergic nerve terminals and alpha- and beta-receptors. Modulation of serotonergic pathways may contribute to the calming affect. The drug interacts with VMAT enzymes to enhance release of DA and 5-HT from vesicles. It may also directly cause the reversal of DAT and SERT. Several currently prescribed amphetamine formulations contain both enantiomers, including Adderall, Dyanavel XR, and Evekeo, the last of which is racemic amphetamine sulfate. Amphetamine is also prescribed in enantiopure and prodrug form as dextroamphetamine and lisdexamfetamine respectively. Lisdexamfetamine is structurally different from amphetamine, and is inactive until it metabolizes into dextroamphetamine.
CNS Activity
Sources: https://nootropicscity.com/comprehensive-write-amphetamines-adderall-ritalin-vyvanse-concerta/
Curator's Comment: Amphetamines readily cross the blood-brain barrier to reach their primary sites of action in the brain. The acute administration of amphetamine produces a wide range of dose-dependent behavioral changes, including increased arousal or wakefulness, anorexia, hyperactivity, perseverative movements, and, in particular, a state of pleasurable affect, elation, and euphoria, which can lead to the abuse of the drug.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1893 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7751968 |
|||
Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=15602501 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DYANAVEL XR Approved UseINDICATIONS Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine Sulfate Tablets is indicated for the treatment of Attention Deficit Hyperactivity Disorder (ADHD) and Narcolepsy. Attention Deficit Hyperactivity Disorder (ADHD) A diagnosis of Attention Deficit Hyperactivity Disorder (ADHD; DSM-IV®) implies the presence of hyperactive-impulsive or inattentive symptoms that caused impairment and were present before age 7 years. The symptoms must cause clinically significant impairment, e.g., in social, academic, or occupational functioning, and be present in two or more settings, e.g., school (or work) and at home. The symptoms must not be better accounted for by another mental disorder. For the Inattentive Type, at least six of the following symptoms must have persisted for at least 6 months: lack of attention to details/careless mistakes; lack of sustained attention; poor listener; failure to follow through on tasks; poor organization; avoids tasks requiring sustained mental effort; loses things; easily distracted; forgetful. For the Hyperactive-Impulsive Type, at least six of the following symptoms must have persisted for at least 6 months: fidgeting/squirming; leaving seat; inappropriate running/climbing; difficulty with quiet activities; “on the go;” excessive talking; blurting answers; can't wait turn; intrusive. The Combined Type requires both inattentive and hyperactive-impulsive criteria to be met. Special Diagnostic Considerations: Specific etiology of this syndrome is unknown, and there is no single diagnostic test. Adequate diagnosis requires the use not only of medical but of special psychological, educational, and social resources. Learning may or may not be impaired. The diagnosis must be based upon a complete history and evaluation of the child and not solely on the presence of the required number of DSM-IV® characteristics. Need for Comprehensive Treatment Program: Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine Sulfate Tablets is indicated as an integral part of a total treatment program for ADHD that may include other measures (psychological, educational, social) for patients with this syndrome. Drug treatment may not be indicated for all children with this syndrome. Stimulants are not intended for use in the child who exhibits symptoms secondary to environmental factors and/or other primary psychiatric disorders, including psychosis. Appropriate educational placement is essential and psychosocial intervention is often helpful. When remedial measures alone are insufficient, the decision to prescribe stimulant medication will depend upon the physician's assessment of the chronicity and severity of the child's symptoms. Long-Term Use: The effectiveness of Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine Sulfate Tablets for long-term use has not been systematically evaluated in controlled trials. Therefore, the physician who elects to use Dextroamphetamine Saccharate, Amphetamine Aspartate, Dextroamphetamine Sulfate and Amphetamine Sulfate Tablets for extended periods should periodically re-evaluate the long-term usefulness of the drug for the individual patient. Launch Date2015 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
120 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28936175/ |
40.3 mg single, oral dose: 40.3 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1727 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28936175/ |
40.3 mg single, oral dose: 40.3 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28936175/ |
40.3 mg single, oral dose: 40.3 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMPHETAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
PubMed
Title | Date | PubMed |
---|---|---|
Effect of chronic amphetamine exposure on stereotyped behavior: implications for pathogenesis of l-dopa-induced dyskinesias. | 1975 |
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The behavioral pharmacology of butaclamol hydrochloride (AY-23,028), a new potent neuroleptic drug. | 1975 Apr 30 |
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Acute subarachnoid hemorrhage. | 1975 Jul 7 |
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The anticataleptic effect of 7-OH-DPAT: are dopamine D3 receptors involved? | 1999 |
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Enantiomer-specific high-performance liquid chromatography with fluorescence detection of methamphetamines in abusers' hair and urine. | 1999 Dec |
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Pharmacological properties of some xanthone derivatives. | 1999 Jul-Aug |
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5-HT2 receptor antagonism reduces hyperactivity induced by amphetamine, cocaine, and MK-801 but not D1 agonist C-APB. | 1999 Jun |
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Differential regional zif268 messenger RNA expression in an escalating dose/binge model of amphetamine-induced psychosis. | 2000 |
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Inhibition of amphetamine- and apomorphine-induced behavioural effects by neuropeptide Y Y(1) receptor antagonist BIBO 3304. | 2000 Apr 27 |
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Regulation of the human norepinephrine transporter by cocaine and amphetamine. | 2000 Dec |
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[Fatal intracerebral hemorrhage after amphetamine intake]. | 2000 Jul 31 |
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Amphetamine abuse during pregnancy: environmental factors and outcome after 14-15 years. | 2000 Jun |
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Effect of dopamine agonists and antagonists on the lorazepam withdrawal syndrome in rats. | 2000 Mar |
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Effects of repeated withdrawal from continuous amphetamine administration on brain reward function in rats. | 2000 Nov |
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Delivery of a GDNF gene into the substantia nigra after a progressive 6-OHDA lesion maintains functional nigrostriatal connections. | 2000 Nov |
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Amphetamine-induced toxicity in dopamine terminals in CD-1 and C57BL/6J mice: complex roles for oxygen-based species and temperature regulation. | 2001 |
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Behavioral sensitization in humans. | 2001 |
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Evaluation of the alpha2C-adrenoceptor as a neuropsychiatric drug target studies in transgenic mouse models. | 2001 Apr 6 |
|
Attention-deficit/hyperactivity disorder in adults: beyond controversy. | 2001 Aug |
|
Stability of Adderall in extemporaneously compounded oral liquids. | 2001 Aug 1 |
|
Developmental aspects of psychostimulant treatment in children and adolescents with attention-deficit/hyperactivity disorder. | 2001 Dec |
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Role of hypothalamic neuropeptide Y (NPY) in the change of feeding behavior induced by repeated treatment of amphetamine. | 2001 Dec 7 |
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[Myocardial infarction caused by amphetamine]. | 2001 Feb |
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Transcranial magnetic stimulation in an amphetamine hyperactivity model of mania. | 2001 Feb |
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Placebo-controlled evaluation of amphetamine mixture-dextroamphetamine salts and amphetamine salts (Adderall): efficacy rate and side effects. | 2001 Jan |
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Effects of drugs of abuse on response accuracy and bias under a delayed matching-to-sample procedure in squirrel monkeys. | 2001 Jul |
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Evaluation of nigrostriatal dopaminergic function in adult +/+ and +/- BDNF mutant mice. | 2001 Jul |
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Acute myocardial infarction caused by amphetamines: a case report and review of the literature. | 2001 Jun |
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Locomotor effects of acute and repeated threshold doses of amphetamine and methylphenidate: relative roles of dopamine and norepinephrine. | 2001 Mar |
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Short-term cardiovascular effects of methylphenidate and adderall. | 2001 May |
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Cholecystokinin2 receptor-deficient mice display altered function of brain dopaminergic system. | 2001 Nov |
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Double-blind, placebo-controlled study of single-dose amphetamine formulations in ADHD. | 2001 Nov |
|
Changes in the performance of schedule-induced polydipsia (SIP) in rats after arecoline and amphetamine treatments. | 2001 Oct |
|
Pilot randomized controlled study of dexamphetamine substitution for amphetamine dependence. | 2001 Sep |
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Differentially altered mGluR1 and mGluR5 mRNA expression in rat caudate nucleus and nucleus accumbens in the development and expression of behavioral sensitization to repeated amphetamine administration. | 2001 Sep 1 |
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Serotonin1B receptor ligands in the nucleus accumbens shell do not affect the discriminative stimulus effects of amphetamine in rats. | 2001 Sep-Oct |
|
Retrospective comparison of Adderall and methylphenidate in the treatment of attention deficit hyperactivity disorder. | 2001 Spring |
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D-amphetamine-induced behavioral sensitization: effect of lesioning dopaminergic terminals in the medial prefrontal cortex, the amygdala and the entorhinal cortex. | 2002 |
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The effects of delayed rewards, tokens, and stimulant medication on sportsmanlike behavior with ADHD-diagnosed children. | 2002 Apr |
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A randomized, double-blind, placebo-controlled, parallel-group study of SLI381 (Adderall XR) in children with attention-deficit/hyperactivity disorder. | 2002 Aug |
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Spontaneous novelty seeking and amphetamine-induced conditioning and sensitization in adult mice: evidence of dissociation as a function of age at weaning. | 2002 Aug |
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Assessment of silver and gold substrates for the detection of amphetamine sulfate by surface enhanced Raman scattering (SERS). | 2002 Feb |
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Effects of amphetamine on the plus-maze discriminative avoidance task in mice. | 2002 Feb |
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24-hour ambulatory blood pressure monitoring in male children receiving stimulant therapy. | 2002 Jul-Aug |
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Efficacy of Adderall and methylphenidate in attention deficit hyperactivity disorder: a drug-placebo and drug-drug response curve analysis of a naturalistic study. | 2002 Jun |
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CaMKII regulates amphetamine-induced ERK1/2 phosphorylation in striatal neurons. | 2002 Jun 12 |
|
The effect of nitrostyrene on cell proliferation and macrophage immune responses. | 2002 May |
|
The neurosteroid 3 alpha-hydroxy-5 alpha-pregnan-20-one affects dopamine-mediated behavior in rodents. | 2002 May |
|
Spatial and temporal profile of haloperidol-induced immediate-early gene expression and phosphoCREB binding in the dorsal and ventral striatum of amphetamine-sensitized rats. | 2002 Sep 15 |
|
Case series: Adderall augmentation of serotonin reuptake inhibitors in childhood-onset obsessive compulsive disorder. | 2002 Summer |
Sample Use Guides
DYANAVEL XR (R (amphetamine) extended-release oral suspension) should be orally administered once daily in the morning with or without food. The dose should be individualized according to the needs and responses of the patient. Before administering the dose, shake the bottle of DYANAVEL XR.
In children 6 years of age and older, start with 2.5 mg or 5 mg once daily in the morning. The dose may be increase
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24672014
Curator's Comment: Amph increases the effects induced by βPEA on the LGC-55, indicating that Amph potentiates the effects generated by the biogenic amine βPEA
β-Phenylethylamine (βPEA) activates the amine-gated chloride channel LGC-55 more efficiently than amphetamine (Amph) (Km = 9 and 152 μm, respectively)
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 14:58:17 GMT 2023
by
admin
on
Fri Dec 15 14:58:17 GMT 2023
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Record UNII |
6DPV8NK46S
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
600085
Created by
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NCI_THESAURUS |
C47795
Created by
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DEA NO. |
1100
Created by
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Code System | Code | Type | Description | ||
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2679
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100000085149
Created by
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C28822
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PRIMARY | |||
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200-457-8
Created by
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6DPV8NK46S
Created by
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51063
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SUB00438MIG
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CHEMBL405
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81952
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PRIMARY | RxNorm | ||
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6DPV8NK46S
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DBSALT001205
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60-13-9
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DTXSID4020082
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PA 003
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m1849
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PRIMARY | Merck Index | ||
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6055
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156-31-0
Created by
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SUPERSEDED |
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PARENT -> SALT/SOLVATE |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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