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Details

Stereochemistry RACEMIC
Molecular Formula C9H13N.ClH
Molecular Weight 171.667
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Amphetamine hydrochloride

SMILES

Cl.CC(N)CC1=CC=CC=C1

InChI

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

HIDE SMILES / InChI

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 ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
[Intracerebral hemorrhage following amphetamine use].
1998 Nov-Dec
Atrioventricular nodal re-entrant tachycardia associated with stimulant treatment.
1999
The potentiating effect of sertraline and fluoxetine on amphetamine-induced locomotor activity is not mediated by serotonin.
1999 Apr
5-HT2 receptor antagonism reduces hyperactivity induced by amphetamine, cocaine, and MK-801 but not D1 agonist C-APB.
1999 Jun
Differential regulation of calmodulin content and calmodulin messenger RNA levels by acute and repeated, intermittent amphetamine in dopaminergic terminal and midbrain areas.
2000
Selective lesions of the entorhinal cortex, the hippocampus, or the fimbria-fornix in rats: a comparison of effects on spontaneous and amphetamine-induced locomotion.
2000 Apr
Activation of neostriatal dopaminergic system in rats prevents toxic effects of picrotoxin administered into globus pallidus.
2000 Aug
A comparison of the patterns of striatal Fos-like immunoreactivity induced by various dopamine agonists in rats.
2000 Aug 4
Lack of effect of repeated treatment with a glycineB receptor partial agonist on the amphetamine-induced hyperactivity in rats.
2000 May-Jun
Delivery of a GDNF gene into the substantia nigra after a progressive 6-OHDA lesion maintains functional nigrostriatal connections.
2000 Nov
Present and future pharmacotherapeutic options for adult attention deficit/hyperactivity disorder.
2001 Apr
Attention-deficit/hyperactivity disorder in adults: beyond controversy.
2001 Aug
Behavioural and anti-psychotic effects of Ca2+ channel blockers in rhesus monkey.
2001 Jan 26
Evaluation of nigrostriatal dopaminergic function in adult +/+ and +/- BDNF mutant mice.
2001 Jul
Induction of tolerance to the suppressant effect of the neurotensin analogue NT69L on amphetamine-induced hyperactivity.
2001 Jun 22
Double-blind, placebo-controlled study of single-dose amphetamine formulations in ADHD.
2001 Nov
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
Maturational increases in c-fos expression in the ascending dopamine systems.
2001 Sep 15
Retrospective comparison of Adderall and methylphenidate in the treatment of attention deficit hyperactivity disorder.
2001 Spring
D-amphetamine-induced behavioral sensitization: effect of lesioning dopaminergic terminals in the medial prefrontal cortex, the amygdala and the entorhinal cortex.
2002
The effects of delayed rewards, tokens, and stimulant medication on sportsmanlike behavior with ADHD-diagnosed children.
2002 Apr
Adderall and seizures.
2002 Apr
Cocaine and amphetamine depress striatal GABAergic synaptic transmission through D2 dopamine receptors.
2002 Feb
The effect of nitrostyrene on cell proliferation and macrophage immune responses.
2002 May
Effect of amphetamine repeated treatment on the feeding behavior in neuropeptide Y-overexpressing mice.
2002 Sep 6
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 Fri Dec 15 16:35:09 UTC 2023
Edited
by admin
on Fri Dec 15 16:35:09 UTC 2023
Record UNII
70DMY940ZG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Amphetamine hydrochloride
Common Name English
Benzeneethanamine, α-methyl-, hydrochloride (1:1)
Systematic Name English
AMPHETAMINE HCL
Common Name English
Psychedrine hydrochloride
Common Name English
Phenethylamine, α-methyl-, hydrochloride, (±)-
Systematic Name English
DL-AMPHETAMINE HYDROCHLORIDE
Common Name English
(±)-Amphetamine hydrochloride
Common Name English
AMFETAMINE HYDROCHLORIDE [INCB GREEN LIST]
Common Name English
AMPHETAMINE HYDROCHLORIDE, DL-
Common Name English
AMFETAMINE HYDROCHLORIDE
INCB:GREEN LIST  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
Code System Code Type Description
CAS
2706-50-5
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
EVMPD
SUB181755
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
NCI_THESAURUS
C77844
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
FDA UNII
70DMY940ZG
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
INCB IDS CODE
PA 003
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
SMS_ID
100000167498
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
PUBCHEM
92939
Created by admin on Fri Dec 15 16:35:09 UTC 2023 , Edited by admin on Fri Dec 15 16:35:09 UTC 2023
PRIMARY
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ACTIVE MOIETY