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Levoamphetamine

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Levoamphetamine
Systematic name

(2R)-1-Phenylpropan-2-amine[1]
Identifiers
CAS number 156-34-3 N
PubChem 32893
ChemSpider 30477 YesY
EC number 205-850-8
ChEBI CHEBI:42724 YesY
ChEMBL CHEMBL19393 YesY
Beilstein Reference 2432739
Gmelin Reference 1125855
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C9H13N
Molar mass 135.21 g mol−1
Exact mass 135.104799421 g mol-1
log P 1.789
Pharmacology
Routes of
administration		 Oral
Legal status


℞-only(US)
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Levoamphetamine (or levamfetamine) is a psychostimulant known to increase wakefulness and focus in association with decreased appetite and fatigue. Levoamphetamine is the levorotary stereoisomer of the amphetamine molecule. It possesses much weaker dopaminergic activity than the dextrorotary isomer (dextroamphetamine) and acts as a selective releasing agent of norepinephrine, similarly to levomethamphetamine.

Contents

[edit] Chemistry

Levoamphetamine is the levorotary stereoisomer of the amphetamine molecule. The amphetamine racemate contains two stereoisomers, dextroamphetamine and levoamphetamine, both exhibiting amphetaminergic (amphetamine-like) effects.

[edit] Formulations

[edit] Adderall

Levoamphetamine is approximately 25% of the drug Adderall (racemic amphetamine salt mixture), while 75% of the drug is dextroamphetamine.

[edit] Benzedrine

Benzedrine was a racemic (1:1 racemate) mixture of dextroamphetamine and levoamphetamine introduced in the United States delivered by an inhaler in 1928 for decongestant uses. Benzedrine was converted into tablet form in 1938 after it was discovered that amphetamine could treat narcolepsy and behavioral disorders.

[edit] See also

[edit] References

  1. ^ "Amphetamine - PubChem Public Chemical Project". The PubChem Project. USA: National Center for Biotechnology Information. 08 August 2005. Descriptors Computed from Structure. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=32893&loc=ec_rcs. Retrieved 26 September 2011. 


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Eugeroics / Benzhydryl compounds
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α7 nicotinic agonists / PAMs
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Other psychostimulants and nootropics

M: PSO/PSI

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc(eval/thrp), drug(N5A/5B/5C/6A/6B/6D)
v · d · eAntiobesity agents/Anorectics (A08)
Central
4-Methylamphetamine • Amfecloral • Amfepentorex • Amfepramone • Aminorex • Amphetamine • Amphetaminil • Atomoxetine • Benfluorex‡ • Benzphetamine • Bupropion • Cathine • Cathinone • Chlorphentermine • Ciclazindol • Clobenzorex • Cloforex • Clominorex • Clortermine • Dexfenfluramine • Dextroamphetamine • Dextromethamphetamine • Dexmethylphenidate • Difemetorex • Dimethylcathinone • Diphemethoxidine • Ephedrine • Ephedra • Ethylamphetamine • Etolorex • Fenbutrazate • Fencamfamine • Fenethylline • Fenfluramine (+phentermine) • Fenproporex • Fludorex • Fluminorex • Furfenorex • Indanorex • Khat • Levopropylhexedrine • Lisdexamfetamine • Manifaxine • Mazindol • Mefenorex • Methamphetamine • Methylphenidate • Norfenfluramine • Pemoline • Pentorex (Phenpentermine) • Phendimetrazine • Phenethylamine • Phenmetrazine • Phentermine • Phenylpropanolamine • Pipradrol • Prolintane • Propylhexedrine • Pseudoephedrine • Pyrovalerone • Radafaxine • Reboxetine • Setazindol • Sibutramine • Synephrine • Tesofensine • Viloxazine • Xylopropamine • Zylofuramine
Others
Peripheral

M: NUT

cof, enz, met

drug(A8/11/12)
v · d · ePhenethylamines
Phenethylamines
Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-P • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • Allylescaline • DESOXY • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2
Stimulants: 2-OH-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA)
Entactogens: Lophophine • MDPEA • MDMPEA
Others: BOH • DMPEA
Amphetamines
Phenylisopropylamines
Psychedelics: 3C-BZ • 3C-E • 3C-P • Aleph • Beatrice • Bromo-DragonFLY • D-Deprenyl • DMA • DMCPA • DMMDA • DOB • DOC • DOEF • DOET • DOI • DOM • DON • DOPR • DOTFM • Ganesha • MMDA • MMDA-2 • Psi-DOM • TMA • TeMA
Stimulants: 4-MA • 4-MMA • 4-MTA • 5-IT • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Lefetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methoxyphenamine • MMA • Norfenfluramine • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine
Entactogens: 5-APDB • 6-APB • 6-APDB • EDA • IAP • MDA • MDEA • MDHMA (FLEA) • MDMA ("Ecstasy") • MDOH • MMDMA • NAP • TAP
Others: Amiflamine • DFMDA • D-Deprenyl • L-Deprenyl (Selegiline)
Phentermines
Stimulants: Chlorphentermine • Cloforex • Clortermine • Etolorex • Mephentermine • Pentorex (Phenpentermine) • Phentermine
Entactogens: MDPH • MDMPH
Cathinones
Stimulants: Amfepramone • Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone
Entactogens: Ethylone • Methylone
Phenylisobutylamines
Entactogens: 4-CAB • 4-MAB • Ariadne (α-Et-DOM) • BDB (J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • Eutylone (bk-EBDB) • MBDB (Methyl-J)
Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines
Stimulants: α-PBP • α-PPP • α-PVP • MDPBP • MDPPP • MDPV • MOPPP • MPBP • MPHP • MPPP • Naphyrone • PEP • Prolintane • Pyrovalerone
Catecholamines
(and relatives..)
6-FNE • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • Ciladopa • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • meta-Octopamine • meta-Tyramine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • para-Octopamine • para-Tyramine
Miscellaneous
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