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Details

Stereochemistry RACEMIC
Molecular Formula C18H23N5O2.ClH
Molecular Weight 377.868
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FENETHYLLINE HYDROCHLORIDE

SMILES

Cl.CC(CC1=CC=CC=C1)NCCN2C=NC3=C2C(=O)N(C)C(=O)N3C

InChI

InChIKey=MVXGSLGVWBVZCA-UHFFFAOYSA-N
InChI=1S/C18H23N5O2.ClH/c1-13(11-14-7-5-4-6-8-14)19-9-10-23-12-20-16-15(23)17(24)22(3)18(25)21(16)2;/h4-8,12-13,19H,9-11H2,1-3H3;1H

HIDE SMILES / InChI
Fenethylline (generic name Captagon) is a codrug of amphetamine and theophylline. In the fenetylline molecule, theophylline is covalently linked with amphetamine via an alkyl chain. It was formerly used to treat conditions such as ADHD, narcolepsy, and depression, but its use has been banned because of the potential for abuse. Amphetamine, an agonist for trace amine-associated receptor 1 (TAAR1) with enhancing dopamine signaling (an increase of irritability, aggression, etc.), is the main cause of Captagon addiction. Theophylline, an antagonist that blocks adenosine receptors (e.g. A2aR) in the brain responsible for restlessness and painlessness, may attenuate the behavioral sensitization caused by amphetamine. Fenethylline is included in a list of compounds to be considered by a World Health Organization (WHO) Expert Committee in April 1985 for possible international scheduling under the Convention on Psychotropic Substances, 1971. Fenethylline re-emerged because of its widespread abuse by Middle Eastern young adults. Terrorist groups such as the Islamic State to enhance what they consider desirable characteristics - aggressiveness, alertness, and fearlessness - in their recruits, promote it.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q96RJ0
Gene ID: 134864.0
Gene Symbol: TAAR1
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
Fenethylline as a possible etiology for retinal vein occlusion.
2009 Fall-Winter
Patents
Name Type Language
FENETHYLLINE HYDROCHLORIDE
MI   USAN  
USAN  
Official Name English
1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-1,3-DIMETHYL-7-(2-((1-METHYL-2-PHENYLETHYL)AMINO)ETHYL)-, MONOHYDROCHLORIDE
Common Name English
FENETHYLLINE HYDROCHLORIDE [USAN]
Common Name English
AMFETYLINE HYDROCHLORIDE
Common Name English
FENETYLLINE HYDROCHLORIDE
MART.   WHO-DD  
Common Name English
H-814
Code English
FENETYLLINE HYDROCHLORIDE [MART.]
Common Name English
NSC-169872
Code English
7-[2-[(α-Methylphenethyl)amino]ethyl]theophylline monohydrochloride
Systematic Name English
BIOCAPTON
Brand Name English
FENETHYLLINE HYDROCHLORIDE [MI]
Common Name English
THEOPHYLLINE, 7-(2-((.ALPHA.-METHYLPHENETHYL)AMINO)ETHYL)-, MONOHYDROCHLORIDE
Common Name English
FENETHYLLINE HCL
Common Name English
Fenetylline hydrochloride [WHO-DD]
Common Name English
CAPTAGON HYDROCHLORIDE
Brand Name English
1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-1,3-DIMETHYL-7-(2-((1-METHYL-2-PHENYLETHYL)AMINO)ETHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
7-(2-(1-METHYL-2-PHENYLETHYLAMINO)ETHYL)THEOPHYLLINE HYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Fri Dec 15 16:10:25 UTC 2023 , Edited by admin on Fri Dec 15 16:10:25 UTC 2023
Code System Code Type Description
MERCK INDEX
m5273
Created by admin on Fri Dec 15 16:10:25 UTC 2023 , Edited by admin on Fri Dec 15 16:10:25 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C81052
Created by admin on Fri Dec 15 16:10:25 UTC 2023 , Edited by admin on Fri Dec 15 16:10:25 UTC 2023
PRIMARY
ECHA (EC/EINECS)
217-580-8
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PRIMARY
ChEMBL
CHEMBL2111152
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PRIMARY
DRUG BANK
DBSALT002869
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PRIMARY
FDA UNII
YA7K8ADZ2V
Created by admin on Fri Dec 15 16:10:25 UTC 2023 , Edited by admin on Fri Dec 15 16:10:25 UTC 2023
PRIMARY
PUBCHEM
102710
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PRIMARY
SMS_ID
100000087503
Created by admin on Fri Dec 15 16:10:25 UTC 2023 , Edited by admin on Fri Dec 15 16:10:25 UTC 2023
PRIMARY
NSC
169872
Created by admin on Fri Dec 15 16:10:25 UTC 2023 , Edited by admin on Fri Dec 15 16:10:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID3048869
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PRIMARY
RXCUI
236651
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PRIMARY RxNorm
EVMPD
SUB02114MIG
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PRIMARY
CAS
1892-80-4
Created by admin on Fri Dec 15 16:10:25 UTC 2023 , Edited by admin on Fri Dec 15 16:10:25 UTC 2023
PRIMARY