DEXTROAMPHETAMINE ADIPATE

First marketed in 1937

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H13N.C6H10O4
Molecular Weight	281.348
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]([H])(Cc1ccccc1)N.C(CCC(=O)O)CC(=O)O

InChI

InChIKey=OFCJKOOVFDGTLY-QRPNPIFTSA-N

InChI=1S/C9H13N.C6H10O4/c1-8(10)7-9-5-3-2-4-6-9;7-5(8)3-1-2-4-6(9)10/h2-6,8H,7,10H2,1H3;1-4H2,(H,7,8)(H,9,10)/t8-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C6H10O4
Molecular Weight	146.1414
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C9H13N
Molecular Weight	135.2066
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017078s048lbl.pdf
Curator's Comment:: description was created based on several sources, including https://blackpoppymag.wordpress.com/substances/dexedrine-dexamphetamine/

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. Dextroamphetamine is useful for those with ADHD and Narcolepsy. It improves self-control for people who have a hard time naturally controlling themselves. Dextroamphetamine aids a person learning and memory of words, and perhaps makes the brain stronger. When a person given dextroamphetamine is tested, their brain is extremely active in the brain parts required for the test and radically less active in other parts. Short practice sessions with dextroamphetamine have a greater effect on learning than sessions without dextroamphetamine. Dextroamphetamine raises decision-making scores, improves choices, and changes beliefs about rewards; at the same time, dextroamphetamine barely—if at all—affects guesses of time. Those who feel lower amounts of joy from dextroamphetamine have greater impulsivity improvements compared to those who feel extreme happiness. The drug should be avoided for those who have hypersensitivity to amphetamines, a history of drug abuse, cardiovascular diseases, hypertensive disease, hyperthyroidism, or in those with glaucoma. In 1935, the medical community became aware of the stimulant properties of amphetamine, specifically dextroamphetamine, and in 1937 Smith, Kline, and French introduced Dexedrine tablets, under the tradename Dexedrine. In the United States, Dexedrine tablets were approved to treat narcolepsy, attention disorders, depression, and obesity. Dexedrine, along with other sympathomimetic, was eventually classified as schedule II, the most restrictive category possible for a drug with recognized medical uses. The exact mechanism of action is not known. Dextroamphetamine stimulates the release of norepinephrine from central adrenergic receptors. At higher dosages, it causes release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems by reversal of the monoamine transporters. Dextroamphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). Modulation of serotonergic pathways may contribute to the calming effect.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Norepinephrine transporter 175 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17239355	Modulator 780
Synaptic vesicular amine transporter 48 Target ID: CHEMBL1893 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7751968	Inhibitor 7728
Dopamine transporter 164 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19244097	Modulator 780

Conditions

Condition	Modality	Targets	Highest Phase	Product
Attention deficit hyperactivity disorder 62 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/017078s048lbl.pdf	Primary		Approved 8043	DEXEDRINE Approved Use Narcolepsy. Attention Deficit Disorder with Hyperactivity. As an integral part of a total treatment program that typically includes other measures (psychological, educational, social) for patients (ages 6 years to 16 years) with this syndrome. A diagnosis of Attention Deficit Hyperactivity Disorder (ADHD; DSM-IV) implies the presence of the 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 2 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 6 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 6 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. Launch Date 3.15532804E11

C_max

Value	Dose	Co-administered	Analyte	Population
24.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9807980/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
36.6 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/040361Orig1s017lbl.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
431 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9807980/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
12.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9807980/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/040361Orig1s017lbl.pdf	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		DEXTROAMPHETAMINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		substrate 1118 inhibitor 1702

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1738	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017078s049lbl.pdf#page=4	likely

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1118	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017078s049lbl.pdf#page=4 Page: 4.0	likely		likely (co-administration study) Comment: Amphetamines and amphetamine derivatives are known to be metabolized, to some degree, by cytochrome P450 2D6 (CYP2D6) and display minor inhibition of CYP2D6 metabolism; concomitant use of DEXEDRINE and CYP2D6 inhibitors may increase the exposure of DEXEDRINE; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/017078s049lbl.pdf#page=4 Page: 4.0

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA00DRV1	https://www.aablocks.com/goods/Goods/detail?id=AA00DRV1
Aurora Fine Chemicals LLC	A17.876.402	http://online.aurorafinechemicals.com/info?ID=A17.876.402
Aurora Fine Chemicals LLC	K16.670.581	http://online.aurorafinechemicals.com/info?ID=K16.670.581
Avantor Inc	101096-690	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101096-690
Avantor Inc	75835-260	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
BioCrick	BCC5942	http://www.biocrick.com/D-Amphetamine-sulfate-BCC5942.html
LGC Standards	LGCFOR1359.00	https://www.lgcstandards.com/US/en/p/LGCFOR1359.00
LGC Standards	MM1359.00	https://www.lgcstandards.com/US/en/p/MM1359.00
Parchem	16880	http://www.parchem.com/chemical-supplier-distributor/DITAB-006880.aspx
Sigma-Aldrich	A3278_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/a3278?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	A5880_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/a5880?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1180004_USP	https://www.sigmaaldrich.com/catalog/product/usp/1180004?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S525797	http://www.smolecule.com/products/s525797
THE BioTek	bt-267390	https://www.thebiotek.com/product/inhibitors/bt-267390
Tocris	2813	https://www.tocris.com/products/d-amphetamine-sulfate_2813
iChemical	EBD2638102	http://www.ichemical.com/products/51-63-8.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Agonist and antagonist activity of low efficacy D2 dopamine receptor agonists in rats discriminating d-amphetamine from saline.	1992 Dec	11224162
Effect of amphetamine on the expression of the metabotropic glutamate receptor 5 mRNA in developing rat brain.	2000 Dec	11303782
Dopaminergic mRNA expression in the intact substantia nigra of unilaterally 6-OHDA-lesioned and grafted rats: an in situ hybridization study.	2001	11314769
Stimulation of metabotropic but not ionotropic glutamatergic receptors in the nucleus accumbens is required for the D-amphetamine-induced release of functional dopamine.	2001	11246154
No functional effects of embryonic neuronal grafts on motor deficits in a 3-nitropropionic acid rat model of advanced striatonigral degeneration (multiple system atrophy).	2001	11226695
Anorectic drugs and pulmonary hypertension from the bedside to the bench.	2001 Apr	11307870
Resolution of stroke deficits following contralateral grafts of conditionally immortal neuroepithelial stem cells.	2001 Apr	11283405
Determination of amphetamine in dog plasma by gas chromatography with mass selective detection.	2001 Apr	11268050
A nitric oxide-dopamine link pathway in organum vasculosum laminae terminalis of rat brain exerts control over blood pressure.	2001 Apr	11264246
Effect of 6-hydroxydopamine or repeated amphetamine treatment on mesencephalic mRNA levels for AMPA glutamate receptor subunits in the rat.	2001 Apr 20	11290405
Nicotine sensitization increases dendritic length and spine density in the nucleus accumbens and cingulate cortex.	2001 Apr 27	11311869
Interleukin-2 potentiates novelty- and GBR 12909-induced exploratory activity.	2001 Apr 27	11311862
Neural mechanisms of motion sickness.	2001 Feb	11286016
Tyrosine improves behavioral and neurochemical deficits caused by cold exposure.	2001 Feb	11274672
Differences in locomotor response to an inescapable novel environment predict sensitivity to aversive effects of amphetamine.	2001 Feb	11270513
Effects of acute D-amphetamine and ketamine on the performance of rats in a serial negative patterning procedure.	2001 Feb	11270512
The D3R partial agonist, BP 897, attenuates the discriminative stimulus effects of cocaine and D-amphetamine and is not self-administered.	2001 Feb	11270507
Chronic inositol increases striatal D(2) receptors but does not modify dexamphetamine-induced motor behavior. Relevance to obsessive-compulsive disorder.	2001 Feb	11267629
Transcranial magnetic stimulation in an amphetamine hyperactivity model of mania.	2001 Feb	11256461
Comparison of the effects of infant handling, isolation, and nonhandling on acoustic startle, prepulse inhibition, locomotion, and HPA activity in the adult rat.	2001 Feb	11256454
Conditioned activity to amphetamine in transgenic mice expressing an antisense RNA against the glucocorticoid receptor.	2001 Feb	11256444
Drugs used in the treatment of attention-deficit/hyperactivity disorder affect postsynaptic firing rate and oscillation without preferential dopamine autoreceptor action.	2001 Feb 15	11239905
Analysis of benzphetamine and its metabolites in rat urine by liquid chromatography-electrospray ionization mass spectrometry.	2001 Feb 25	11236083
Striatal dopamine sensitization to D-amphetamine in periadolescent but not in adult rats.	2001 Jan	11274716
Schedule-dependent effects of haloperidol and amphetamine: multiple-schedule task shows within-subject effects.	2001 Jan	11274708
Acute hydrocortisone administration does not affect subjective responses to d-amphetamine in humans.	2001 Jan	11271411
Distinct contributions of glutamate and dopamine receptors to temporal aspects of rodent working memory using a clinically relevant task.	2001 Jan	11271408
Modification of d-amphetamine-induced responses by baclofen in rats.	2001 Jan	11271399
[Analysis of the striato-pallidal interactions in regulation of avoidance behavior].	2001 Jan	11227866
Neonatal dexamethasone on day 7 in rats causes behavioral alterations reflective of hippocampal, but not cerebellar, deficits.	2001 Jan-Feb	11274876
Developmental exposure to methylmercury alters behavioral sensitivity to D-amphetamine and pentobarbital in adult rats.	2001 Jan-Feb	11274875
The weaver mutant mouse: a model to study the ontogeny of dopamine transmission systems and their role in drug addiction.	2001 Jun	11240309
Entopeduncular lesions facilitate and thalamic lesions depress spontaneous and drug-evoked motor behavior in the hemiparkinsonian rat.	2001 Jun 1	11304759
Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis.	2001 Mar	11300514
Effects of d-amphetamine on the performance of rats in an animal analogue of the A-X continuous performance test.	2001 Mar	11277604
Differential sensitivity to NaCl for inhibitors and substrates that recognize mutually exclusive binding sites on the neuronal transporter of dopamine in rat striatal membranes.	2001 Mar	11248372
Adrenergic hyperactivity and metanephrine excess in the nucleus accumbens after prefrontocortical dopamine depletion.	2001 Mar	11247995
Acute myocardial infarction associated with amphetamine use.	2001 Mar	11243281
Amphetamine selectively blocks inhibitory glutamate transmission in dopamine neurons.	2001 Mar	11224544
Sexual behavior induction of c-Fos in the nucleus accumbens and amphetamine-stimulated locomotor activity are sensitized by previous sexual experience in female Syrian hamsters.	2001 Mar 15	11245696
Dissociations between the effects of intra-accumbens administration of amphetamine and exposure to a novel environment on accumbens dopamine and cortical acetylcholine release.	2001 Mar 16	11251215
Serotonin transporter localization in the hamster suprachiasmatic nucleus.	2001 Mar 2	11222995
Amphetamine-stimulated cortical acetylcholine release: role of the basal forebrain.	2001 Mar 9	11245817
Glial cell line-derived neurotrophic factor (GDNF) gene delivery protects dopaminergic terminals from degeneration.	2001 May	11312561
Amphetamine normalizes the electrical activity of dopamine neurons in the ventral tegmental area following prenatal ethanol exposure.	2001 May	11303066
Chronic amphetamine exposure during the preweanling period does not affect avoidance learning or novelty-seeking of adult rats.	2001 May	11300739
The variable number of tandem repeats polymorphism of the dopamine transporter gene is not associated with significant change in dopamine transporter phenotype in humans.	2001 May	11282255
Cocaine and amphetamine increase extracellular dopamine in the nucleus accumbens of mice lacking the dopamine transporter gene.	2001 May 1	11312315
Genes in drug abuse.	2001 May 1	11295319
Post-training injections of catecholaminergic drugs do not modulate fear conditioning in rats and mice.	2001 May 4	11311508

Patents

Sample Use Guides

In Vivo Use Guide

Usual dose is 5 to 60 mg per day in divided doses, depending on the individual patient response. Narcolepsy seldom occurs in children under 12 years of age; however, when it does, DEXEDRINE may be used. The suggested initial dose for patients aged 6 to 12 is 5 mg daily; daily dose may be raised in increments of 5 mg at weekly intervals until an optimal response is obtained. In patients 12 years of age and older, start with 10 mg daily; daily dosage may be raised in increments of 10 mg at weekly intervals until an optimal response is obtained. If bothersome adverse reactions appear (e.g., insomnia or anorexia), dosage should be reduced. SPANSULE capsules may be used for once-a-day dosage wherever appropriate.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Jun 26 06:47:56 UTC 2021` Edited by `admin` on `Sat Jun 26 06:47:56 UTC 2021`
Record UNII	YYI1A8W4TQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEXTROAMPHETAMINE ADIPATE

Common Name

English

D-AMPHETAMINE ADIPATE

Common Name

English

DEXTROAMPHETAMINE ADIPATE COMPONENT OF DELCOBESE

Common Name

English

HEXANEDIOIC ACID, COMPD. WITH (.ALPHA.S)-.ALPHA.-METHYLBENZENEETHANAMINE (1:1)

Common Name

English

DEXTROAMPHETAMINE ADIPATE [ORANGE BOOK]

Common Name

English

DEXTROAMPHETAMINE ADIPATE [VANDF]

Common Name

English

BENZENEETHANAMINE, .ALPHA.-METHYL-, (S)-, HEXANEDIOATE (1:1)

Systematic Name

English

DELCOBESE COMPONENT DEXTROAMPHETAMINE ADIPATE

Common Name

English

Code System Code Type Description

PUBCHEM

49800024