Etilamfetamine
Etilamfetamine
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Clinical data |
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Routes of administration |
Oral, sublingual, insufflated, inhaled (vaporized), intravenous, rectal |
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ATC code |
A08AA06 (WHO) |
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Legal status |
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Legal status |
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Pharmacokinetic data |
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Metabolism |
Hepatic |
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Excretion |
Renal |
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Identifiers |
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- N-ethyl-1-phenyl-propan-2-amine
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CAS Number |
457-87-4 Y |
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PubChem (CID) |
9982 |
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ChemSpider |
9588 Y |
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KEGG |
D07114 Y |
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ChEMBL |
CHEMBL276443 Y |
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ECHA InfoCard |
100.230.711 |
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Chemical and physical data |
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Formula |
C11H17N |
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Molar mass |
163.259 g/mol |
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3D model (Jmol) |
Interactive image |
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InChI=1S/C11H17N/c1-3-12-10(2)9-11-7-5-4-6-8-11/h4-8,10,12H,3,9H2,1-2H3 YKey:YAGBSNMZQKEFCO-UHFFFAOYSA-N Y
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Etilamfetamine (Apetinil, Adiparthrol), also known as N-ethylamphetamine, is a stimulant drug of the phenethylamine and amphetamine chemical classes. It was invented in the early 20th century and was subsequently used as an anorectic or appetite suppressant in the 1950s,[1] but was not as commonly used as other amphetamines such as amphetamine, methamphetamine, and benzphetamine, and was largely discontinued once newer drugs such as phenmetrazine were introduced.
Chemistry
The molecular structure of ethylamphetamine is analogous to amphetamine's.[Note 1] It is a substituted amphetamine, with an ethyl group on the amphetamine backbone.[Note 2][Note 3]
Recreational use
Ethylamphetamine can be used as a recreational drug and, while its prevalence is less than amphetamine's, it is still encountered as a substance taken for recreational purposes.
Ethylamphetamine produces effects similar to amphetamine and methamphetamine, its potency being slightly greater than amphetamine's and lesser than methamphetamine's.[Note 4][Note 5]
See also
References
- ↑ Junet, R. (1956). "Ethylamphetamine in the treatment of obesity". Praxis. 45 (43): 986–988. PMID 13389142.
Notes
- ↑ Amphetamine is a substituted phenethylamine with a methyl group at RA position.
- ↑ The ethyl group of ethylamphetamine is at RN position, hence the name N-ethylamphetamine.
- ↑ Ethylamphetamine is structurally similar to N-methylamphetamine (methamphetamine), the ethyl group being replaced in methamphetamine with a methyl group.
- ↑ Ethylamphetamine's higher potency may make its risk of causing abuse, dependence and/or addiction greater compared to amphetamine.
- ↑ A cohort of Australian users in the 1990s found single 40 mg doses of commercially produced racemic ethylamphetamine hydrochloride substantially less effective recreationally than 40 mg doses of either racemic amphetamine sulphate, d-methylamphetamine hydrochloride or racemic fenethylline hydrochloride.
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Alkylamines | |
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Ampakines | |
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Arylcyclohexylamines | |
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Benzazepines | |
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Cholinergics | |
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Convulsants | |
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Eugeroics | |
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Oxazolines | |
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Phenethylamines |
- 1-(4-Methylphenyl)-2-aminobutane
- 1-Phenyl-2-(piperidin-1-yl)pentan-3-one
- 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane
- 2-Fuoroamphetamine
- 2-Fuoromethamphetamine
- 2-OH-PEA
- 2-Phenyl-3-aminobutane
- 2-Phenyl-3-methylaminobutane
- 2,3-MDA
- 3-Fuoroamphetamine
- 3-Fluoroethamphetamine
- 3-Fluoromethcathinone
- 3-Methoxyamphetamine
- 3-Methylamphetamine
- 3,4-DMMC
- 4-BMC
- 4-CMC
- 4-Ethylamphetamine
- 4-Fluoroamphetamine
- 4-Fluoromethamphetamine
- 4-MA
- 4-Methylbuphedrone
- 4-Methylcathinone
- 4-MMA
- 4-Methylpentedrone
- 4-MTA
- 6-FNE
- AL-1095
- Alfetamine
- a-Ethylphenethylamine
- Amfecloral
- Amfepentorex
- Amfepramone
- Amidephrine
- 2-Amino-1,2-dihydronaphthalene
- 2-Aminoindane
- 5-(2-Aminopropyl)indole
- 2-Aminotetralin
- Acridorex
- Amphetamine (Dextroamphetamine, Levoamphetamine)
- Amphetaminil
- Arbutamine
- β-Methylphenethylamine
- β-Phenylmethamphetamine
- Benfluorex
- Benzedrone
- Benzphetamine
- BDB
- BOH
- 3-Benzhydrylmorpholine
- BPAP
- Buphedrone
- Bupropion
- Butylone
- Camfetamine
- Cathine
- Cathinone
- Chlorphentermine
- Cilobamine
- Cinnamedrine
- Clenbuterol
- Clobenzorex
- Cloforex
- Clortermine
- Cypenamine
- D-Deprenyl
- Denopamine
- Dimethoxyamphetamine
- Dimethylamphetamine
- Dimethylcathinone
- Dobutamine
- DOPA (Dextrodopa, Levodopa)
- Dopamine
- Dopexamine
- Droxidopa
- EBDB
- Ephedrine
- Epinephrine
- Epinine
- Etafedrine
- Ethcathinone
- Ethylnorepinephrine
- Ethylone
- Etilamfetamine
- Etilefrine
- Famprofazone
- Fencamfamine
- Fencamine
- Fenethylline
- Fenfluramine (Dexfenfluramine, Levofenfluramine)
- Fenproporex
- Feprosidnine
- Flephedrone
- Fludorex
- Formetorex
- Furfenorex
- Gepefrine
- Hexapradol
- Hexedrone
- HMMA
- Hordenine
- 4-Hydroxyamphetamine
- 5-Iodo-2-aminoindane
- Ibopamine
- IMP
- Indanylamphetamine
- Iofetamine
- Isoetarine
- Isoethcathinone
- Isoprenaline
- L-Deprenyl (Selegiline)
- Lefetamine
- Lisdexamfetamine
- Lophophine
- MBDB
- MDA
- MDBU
- MDEA
- MDMA
- MDMPEA
- MDOH
- MDPR
- MDPEA
- Mefenorex
- Mephedrone
- Mephentermine
- Metanephrine
- Metaraminol
- Mesocarb
- Methamphetamine (Dextromethamphetamine, Levomethamphetamine)
- Methoxamine
- Methoxyphenamine
- MMA
- Methcathinone
- Methedrone
- Methoxyphenamine
- Methylenedioxycathinone
- Methylone
- Mexedrone
- MMDA
- MMDMA
- MMMA
- Morforex
- N,alpha-Diethylphenylethylamine
- N-Benzyl-1-phenethylamine
- N-Ethylbuphedrone
- N-Ethylhexedrone
- N,N-Dimethylphenethylamine
- Naphthylamphetamine
- Nisoxetine
- Norepinephrine
- Norfenefrine
- Norfenfluramine
- Normetanephrine
- L-Norpseudoephedrine
- Octopamine (drug)
- Orciprenaline
- Ortetamine
- Oxifentorex
- Oxilofrine
- PBA
- PCA
- PCMA
- PHA
- Pentorex
- Pentedrone
- Pentylone
- Phenatine
- Phenpromethamine
- Phentermine
- Phenylalanine
- Phenylephrine
- Phenylpropanolamine
- Pholedrine
- PIA
- PMA
- PMEA
- PMMA
- PPAP
- Phthalimidopropiophenone
- Prenylamine
- Propylamphetamine
- Pseudoephedrine
- Ropinirole
- Salbutamol (Levosalbutamol)
- Sibutramine
- Synephrine
- Theodrenaline
- Tiflorex
- Tranylcypromine
- Tyramine
- Tyrosine
- Xylopropamine
- Zylofuramine
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Piperidines | |
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Pyrrolidines | |
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Racetams | |
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Tropanes | |
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Tryptamines | |
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Others | |
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α1 | | |
- Antagonists
- Abanoquil
- Adimolol
- Ajmalicine
- Alfuzosin
- Amosulalol
- Anisodamine
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- Benoxathian
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- Domesticine
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- Hydroxyzine
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- Ketanserin
- L-765,314
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- Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin)
- Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine)
- Trimazosin
- Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine)
- Urapidil
- WB-4101
- Zolertine
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α2 | | |
- Antagonists
- 1-PP
- Adimolol
- Aptazapine
- Atipamezole
- Atypical antipsychotics (e.g., asenapine, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine)
- Azapirones (e.g., buspirone, tandospirone)
- BRL-44408
- Buflomedil
- Cirazoline
- Efaroxan
- Esmirtazapine
- Fenmetozole
- Fluparoxan
- Idazoxan
- mCPP
- Mianserin
- Mirtazapine
- NAN-190
- Olanzapine
- Pardoprunox
- Phentolamine
- Phenoxybenzamine
- Piperoxan
- Piribedil
- Rauwolscine
- Rotigotine
- SB-269970
- Setiptiline
- Spiroxatrine
- Sunepitron
- Tolazoline
- Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine)
- Yohimbine
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β | |
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- See also: Dopaminergics
- Melatonergics
- Serotonergics
- Monoamine reuptake and release modulators
- Monoamine metabolism modulators
- Monoamine neurotoxins
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