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Details

Stereochemistry UNKNOWN
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

Molecular Formula C18H23N5O2
Molecular Weight 341.4075
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:10:10 UTC 2023
Edited
by admin
on Sat Dec 16 18:10:10 UTC 2023
Record UNII
HK6XYT4SE5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FENETHYLLINE HYDROCHLORIDE, (-)-
Common Name English
THEOPHYLLINE, 7-(2-((.ALPHA.-METHYLPHENETHYL)AMINO)ETHYL)-, MONOHYDROCHLORIDE, (-)-
Common Name English
1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-1,3-DIMETHYL-7-(2-((1-METHYL-2-PHENYLETHYL)AMINO)ETHYL)-, MONOHYDROCHLORIDE, (-)-
Systematic Name English
FENETYLLINE HYDROCHLORIDE, (-)-
Common Name English
Code System Code Type Description
CAS
22256-65-1
Created by admin on Sat Dec 16 18:10:10 UTC 2023 , Edited by admin on Sat Dec 16 18:10:10 UTC 2023
PRIMARY
FDA UNII
HK6XYT4SE5
Created by admin on Sat Dec 16 18:10:10 UTC 2023 , Edited by admin on Sat Dec 16 18:10:10 UTC 2023
PRIMARY