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Namespace Prefixes

PrefixIRI
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n11http://linked.opendata.cz/resource/drugbank/drug/DB01546/identifier/chemspider/
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Statements

Subject Item
n2:DB01546
rdf:type
n3:Drug
n3:description
In the 1960's, alpha-ethyltryptamine (αET), a non hydrazine reversible monoamine oxidase inhibitor, was developed in the United States by the Upjohn chemical company for use as an antidepressant. αET was an FDA approved antidepressant under the name Monase. However, in 1962, after the discovery of an unacceptable incidence of agranulocytosis, the development of Monase was halted and the drug was withdrawn from potential market use. In 1993, the US Drug Enforcement Administration added αET to Schedule I of its Schedules of Controlled Substances, after an increasing incidence of its use as a recreational drug in the 1980's. Currently, αET is an illegal substance; however, it's activity is still under scientific investigation. αET is a stimulant and hallucinogen, but it is less stimulating and hallucinogenic than alpha-methyltryptamine, a closely related compound. Instead, the effects of αET, a tryptamine derivative, more closely resemble the amphetamine derived drug 3,4-methylenedioxy-N-methylamphetamine (MDMA). Similarly to MDMA, αET has been shown to release serotonin pre-synaptically, as well as lesser amounts of norepinephrine and dopamine. Like MDMA, increases in locomotor activity and mood elevation can be seen post administration.
n3:generalReferences
1. Huang, Xuemei, Michael P. Johnson, and David E. Nichols. "Reduction in brain serotonin markers by α-ethyltryptamine (Monase)." European journal of pharmacology 200.1 (1991): 187-190. 2. Krebs, Kirsten M., and Mark A. Geyer. "Behavioral characterization of alpha-ethyltryptamine, a tryptamine derivative with MDMA-like properties in rats." Psychopharmacology 113.2 (1993): 284-287. 3. Martinez, Diana L., and Mark A. Geyer. "Characterization of the disruptions of prepulse inhibition and habituation of startle induced by α-ethyltryptamine." Neuropsychopharmacology 16.3 (1997): 246-255. 4. Steiner, Wm G., et al. "α-Ethyltryptamine (etryptamine): An electroencephalographic, behavioral and neurochemical analysis." Psychopharmacology 4.5 (1963): 354-366. 5. α-ET TiHKAL entry • Isomer Design: http://isomerdesign.com/PiHKAL/read.php?domain=tk&id=11
n3:group
illicit investigational withdrawn
n3:indication
Developed in the 1960's for use as an antidepressant before market withdrawal in 1962.
owl:sameAs
n7:DB01546 n15:DB01546
dcterms:title
Alpha-ethyltryptamine
adms:identifier
n9:DB01546 n10:C06213 n11:8064 n12:46507084 n13:D04092 n14:8367 n16:Alpha-ethyltryptamine
n3:mechanismOfAction
The mechanism of action responsible for its antidepressant activity was believed to lie in its ability to inhibit monoamine oxidase, while its stimulant activity on the central nervous system appeared to result from its structural similarity to indole-based psychedelics. [5] Research discovered αET to be both a monoamine oxidase inhibitor and a potent monoamine releasing agent capable of serotonergic neurotoxicity. [3] The ability to release serotonin was linked to αET's MDMA like properties. [2] αET has been shown to release serotonin pre-synaptically, as well as lesser amounts of norepinephrine and dopamine.
n3:synonym
αET Etryptamine α-ethyltryptamine
n3:salt
n3:synthesisReference
α-ET TiHKAL entry • Isomer Design: http://isomerdesign.com/PiHKAL/read.php?domain=tk&id=11
n3:IUPAC-Name
n4:271B5415-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B541B-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B541A-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B5417-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B5418-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5419-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5413-363D-11E5-9242-09173F13E4C5 n4:271B542B-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5411-363D-11E5-9242-09173F13E4C5 n4:271B5414-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B542D-363D-11E5-9242-09173F13E4C5 n4:271B5412-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Acceptor-Count
n4:271B5421-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5422-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B541C-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B541D-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B541F-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B541E-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5420-363D-11E5-9242-09173F13E4C5
n3:casRegistryNumber
2235-90-7
n3:category
n3:Bioavailability
n4:271B5427-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5429-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B542A-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B542C-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5426-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B5425-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5428-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B5416-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B5423-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B5424-363D-11E5-9242-09173F13E4C5