U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H23N5O2
Molecular Weight 341.4075
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FENETHYLLINE

SMILES

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

InChI

InChIKey=NMCHYWGKBADVMK-UHFFFAOYSA-N
InChI=1S/C18H23N5O2/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

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 ( + / - )

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
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:48:32 GMT 2023
Edited
by admin
on Sat Dec 16 15:48:32 GMT 2023
Record UNII
YZ0N7VL5R3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FENETHYLLINE
MI  
Common Name English
1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-1,3-DIMETHYL-7-(2-((1-METHYL-2-PHENYLETHYL)AMINO)ETHYL)-
Systematic Name English
Fenetylline [WHO-DD]
Common Name English
THEOPHYLLINEETHYLAMPHETAMINE
Common Name English
FITTON
Brand Name English
HOMBURG-814
Code English
3,7-DIHYDRO-1,3-DIMETHYL-7-(2-((1-METHYL-2-PHENYLETHYL)AMINO)ETHYL)-1H-PURINE-2,6-DIONE
Systematic Name English
FENETHYLLINE [MI]
Common Name English
7-(2-((.ALPHA.-METHYLPHENETHYL)AMINO)ETHYL)THEOPHYLLINE
Systematic Name English
BZT
Common Name English
FENETYLLINE
INN   WHO-DD  
INN  
Official Name English
AMPHETAMINOETHYLTHEOPHYLLINE
Common Name English
AMFETYLINE
Brand Name English
THEOPHYLLINE, 7-(2-((.ALPHA.-METHYLPHENETHYL)AMINO)ETHYL)-
Systematic Name English
fenetylline [INN]
Common Name English
1,3-DIMETHYL-7-(2-(1-METHYL-2-PHENYLETHYLAMINO)ETHYL)XANTHINE
Systematic Name English
Captagon
Brand Name English
PHENETHYLLINE
Common Name English
Classification Tree Code System Code
DEA NO. 1503
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
WHO-ATC N06BA10
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
NCI_THESAURUS C47795
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
WHO-VATC QN06BA10
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
Code System Code Type Description
CAS
3736-08-1
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
HSDB
8315
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
MESH
C004518
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
RXCUI
24840
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY RxNorm
FDA UNII
YZ0N7VL5R3
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
INN
1554
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
MERCK INDEX
m5273
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C81051
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
EPA CompTox
DTXSID50859686
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
DRUG BANK
DB01482
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
PUBCHEM
19527
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
EVMPD
SUB07560MIG
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
ChEMBL
CHEMBL2111152
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
SMS_ID
100000081273
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
WIKIPEDIA
FENETHYLLINE
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
DRUG CENTRAL
1149
Created by admin on Sat Dec 16 15:48:32 GMT 2023 , Edited by admin on Sat Dec 16 15:48:32 GMT 2023
PRIMARY
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