U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C9H13N
Molecular Weight 135.2066
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMPHETAMINE

SMILES

CC(Cc1ccccc1)N

InChI

InChIKey=KWTSXDURSIMDCE-UHFFFAOYSA-N
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3

HIDE SMILES / InChI

Molecular Formula C9H13N
Molecular Weight 135.2066
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
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

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.

Originator

Curator's Comment:: Although a Japanese scientist called Mr. A Ogata, was the first to synthesize methamphetamine in 1919, it wasn’t until 1930 that it was realized that amphetamines raised the blood pressure. https://blackpoppymag.wordpress.com/substances/dexedrine-dexamphetamine/

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DYANAVEL XR

Approved Use

INDICATIONS 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 Date

1.44521285E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
120 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
1727 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
7.9 h
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​Drug as victim

Drug as victim

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Acute subarachnoid hemorrhage.
1975 Jul 7
[Amphetamine-induced psychosis].
1998
Behavioral studies of the effects of moderate oligemic hypoxia caused by bilateral clamping of carotid arteries in mice. Impairment of spatial working memory.
1998 Jul-Oct
[Intracerebral hemorrhage following amphetamine use].
1998 Nov-Dec
The anticataleptic effect of 7-OH-DPAT: are dopamine D3 receptors involved?
1999
HPLC with fluorescence detection of methamphetamine and amphetamine in segmentally analyzed human hair.
1999 Apr
Comparison of dopamine receptor antagonists on hyperlocomotion induced by cocaine, amphetamine, MK-801 and the dopamine D1 agonist C-APB in mice.
1999 Aug
Cocaine-seeking produced by experimenter-administered drug injections: dose-effect relationships in rats.
1999 Dec
Enantiomer-specific high-performance liquid chromatography with fluorescence detection of methamphetamines in abusers' hair and urine.
1999 Dec
The promotion effect of anorectic drugs on aflatoxin B(1)-induced hepatic preneoplastic foci.
1999 Sep
Differential regulation of calmodulin content and calmodulin messenger RNA levels by acute and repeated, intermittent amphetamine in dopaminergic terminal and midbrain areas.
2000
Profiles of cognitive dysfunction in chronic amphetamine and heroin abusers.
2000 Aug
[Fatal intracerebral hemorrhage after amphetamine intake].
2000 Jul 31
Effect of dopamine agonists and antagonists on the lorazepam withdrawal syndrome in rats.
2000 Mar
Effects of repeated withdrawal from continuous amphetamine administration on brain reward function in rats.
2000 Nov
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
Developmental aspects of psychostimulant treatment in children and adolescents with attention-deficit/hyperactivity disorder.
2001 Dec
Role of hypothalamic neuropeptide Y (NPY) in the change of feeding behavior induced by repeated treatment of amphetamine.
2001 Dec 7
Placebo-controlled evaluation of amphetamine mixture-dextroamphetamine salts and amphetamine salts (Adderall): efficacy rate and side effects.
2001 Jan
Behavioural and anti-psychotic effects of Ca2+ channel blockers in rhesus monkey.
2001 Jan 26
Effects of drugs of abuse on response accuracy and bias under a delayed matching-to-sample procedure in squirrel monkeys.
2001 Jul
Adderall and the FDA.
2001 Jul
Acute myocardial infarction caused by amphetamines: a case report and review of the literature.
2001 Jun
Short-term cardiovascular effects of methylphenidate and adderall.
2001 May
Cholecystokinin2 receptor-deficient mice display altered function of brain dopaminergic system.
2001 Nov
Double-blind, placebo-controlled study of single-dose amphetamine formulations in ADHD.
2001 Nov
The effects of delayed rewards, tokens, and stimulant medication on sportsmanlike behavior with ADHD-diagnosed children.
2002 Apr
A randomized, double-blind, placebo-controlled, parallel-group study of SLI381 (Adderall XR) in children with attention-deficit/hyperactivity disorder.
2002 Aug
Synthesis and D(2)-like binding affinity of new derivatives of N-(1-ethyl-2-pyrrolidinylmethyl)-4,5-dihydro-1H-benzo[g]indole-3-carboxamide and related 4H-[1]benzothiopyrano[4,3-b]pyrrole and 5,6-dihydro-4H-benzo[6,7]cyclohepta[b]pyrrole-3-carboxamide analogues.
2002 Aug
Effects of amphetamine on the plus-maze discriminative avoidance task in mice.
2002 Feb
Cocaine and amphetamine depress striatal GABAergic synaptic transmission through D2 dopamine receptors.
2002 Feb
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
The ability of amphetamine to evoke arc (Arg 3.1) mRNA expression in the caudate, nucleus accumbens and neocortex is modulated by environmental context.
2002 Mar 15
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
Patents

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
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 Sat Jun 26 09:16:41 UTC 2021
Edited
by admin
on Sat Jun 26 09:16:41 UTC 2021
Record UNII
CK833KGX7E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMPHETAMINE
HSDB   MI   VANDF  
Systematic Name English
NSC-27159
Code English
ADZENYS XR-ODT
Brand Name English
AMFETAMINE [INN]
Common Name English
(+/-)-.ALPHA.-METHYLPHENETHYLAMINE
Systematic Name English
NOREPHEDRANE
Common Name English
AMFETAMIN
Brand Name English
AMFETAMINE [MART.]
Common Name English
SELEGILINE HYDROCHLORIDE IMPURITY B [EP]
Common Name English
1-PHENYL-2-AMINOPROPANE
Systematic Name English
AMFETAMINE [WHO-DD]
Common Name English
.BETA.-AMINOPROPYLBENZENE
Systematic Name English
BENZENEETHANAMINE, .ALPHA.-METHYL-, (+/-)-
Systematic Name English
DYANAVEL
Brand Name English
AMPHETAMINE [VANDF]
Common Name English
AMFETAMINE
INN   MART.   WHO-DD  
INN  
Official Name English
AMPHETAMINE, DL-
Common Name English
AMPHETAMINE [ORANGE BOOK]
Common Name English
MYDAYIS (MIXED SALTS OF A SINGLE ENTITY)
Brand Name English
ADZENYS ER
Brand Name English
AMPHETAMINE [HSDB]
Common Name English
AMPHETAMINE [MI]
Common Name English
(+/-)-DESOXYNOREPHEDRINE
Common Name English
Classification Tree Code System Code
CFR 21 CFR 250.101
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
LIVERTOX 50
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
NDF-RT N0000175729
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
WHO-VATC QN06BA01
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
NCI_THESAURUS C47795
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
DEA NO. 1100
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
WHO-ATC N06BA01
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
CFR 21 CFR 862.3100
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
FDA ORPHAN DRUG 405313
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
DEA NO. 7401
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
NDF-RT N0000175739
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
CFR 21 CFR 310.502
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C62006
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
DRUG CENTRAL
195
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
CAS
300-62-9
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
EPA CompTox
300-62-9
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
MESH
D000661
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
HSDB
3287
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
WIKIPEDIA
AMPHETAMINE
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
MERCK INDEX
M1849
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00182
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
IUPHAR
4804
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
PUBCHEM
3007
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
LACTMED
Amphetamine
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
INN
377
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
EVMPD
SUB05418MIG
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-096-2
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
FDA UNII
CK833KGX7E
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
INCB IDS CODE
PA 003
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
ChEMBL
CHEMBL405
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY
RXCUI
725
Created by admin on Sat Jun 26 09:16:43 UTC 2021 , Edited by admin on Sat Jun 26 09:16:43 UTC 2021
PRIMARY RxNorm
Related Record Type Details
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
DERIVATIVE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Related Record Type Details
METABOLITE ACTIVE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
PARENT -> METABOLITE
METABOLITE -> PARENT
METABOLITE ACTIVE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
UNSPECIFIED
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC