etilamfetamine

Etilamfetamine
Systematic (IUPAC) name
	N-ethyl-1-phenyl-propan-2-amine
Clinical data
Legal status	DE: Anlage II; UK: Class C; US: Schedule I;
Routes of; administration	Oral, sublingual, insufflated, inhaled (vaporized), intravenous, rectal
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
CAS Number	457-87-4
ATC code	A08AA06
PubChem	CID: 9982
ChemSpider	9588
KEGG	D07114
ChEMBL	CHEMBL276443
Chemical data
Formula	C11H17N
Molecular mass	163.259 g/mol
	SMILES N(C(Cc1ccccc1)C)CC ;
	InChI InChI=1S/C11H17N/c1-3-12-10(2)9-11-7-5-4-6-8-11/h4-8,10,12H,3,9H2,1-2H3 ; Key:YAGBSNMZQKEFCO-UHFFFAOYSA-N ;
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エチルアンフェタミン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/24 19:16:12」(JST)

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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]}

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 R^A position.
^ The ethyl group of ethylamphetamine is at R^N 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.

English Journal

The influence of diuretics on the excretion and metabolism of doping agents. III. Etilamfetamine.

Delbeke FT, Debackere M.AbstractThe urinary excretion of etilamfetamine (ethylamphetamine) and its major metabolite amphetamine in humans was followed over a period of several days after the oral administration of two formulations. The excretion of both substances was affected by urinary pH. Excretion peaks were observed 3-4 h after the ingestion of etilamfetamine in a capsule and the proportion of etilamfetamine excreted during 72 h was 22.2 to 54.4%. Excepting a shift in the peak excretion time to 4-5 h, no meaningful pharmacokinetic differences were found when Apetinil-Depot, a retard formulation, was administered. The intake of acetozolamide shortly after etilamfetamine resulted in a decrease of the etilamfetamine excretion during one day and a suppression below the detection limit for periods varying from 2-7 h post-dosing. Although the etilamfetamine excretion was suppressed from 2 to at least 10 h post-dosing, the action of the diuretic clofenamide on the etilamfetamine excretion is generally not so obvious as that of acetazolamide. The administration of furosemide only reduced the etilamfetamine concentrations by a factor of 4 to 5 during a 2-h period.
Arzneimittel-Forschung.Arzneimittelforschung.1986 Sep;36(9):1413-6.
The urinary excretion of etilamfetamine (ethylamphetamine) and its major metabolite amphetamine in humans was followed over a period of several days after the oral administration of two formulations. The excretion of both substances was affected by urinary pH. Excretion peaks were observed 3-4 h aft
PMID 3790195

Related Pictures

[1] Junet, R. (1956). "Ethylamphetamine in the treatment of obesity". Praxis 45 (43): 986–988. PMID 13389142.

[2] Amphetamine is a substituted phenethylamine with a methyl group at R^A position.

[3] The ethyl group of ethylamphetamine is at R^N position, hence the name N-ethylamphetamine.

[4] Ethylamphetamine is structurally similar to N-methylamphetamine (methamphetamine), the ethyl group being replaced in methamphetamine with a methyl group.

[5] Ethylamphetamine's higher potency may make its risk of causing abuse, dependence and/or addiction greater compared to amphetamine.

[6] 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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