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
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
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Q96RJ0 Gene ID: 134864.0 Gene Symbol: TAAR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/30783122 |
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Target ID: CHEMBL2111329 Sources: https://www.ncbi.nlm.nih.gov/pubmed/30783122 |
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Classification Tree | Code System | Code | ||
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DEA NO. |
1503
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WHO-ATC |
N06BA10
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NCI_THESAURUS |
C47795
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WHO-VATC |
QN06BA10
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3736-08-1
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8315
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C004518
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24840
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YZ0N7VL5R3
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1554
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m5273
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C81051
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DTXSID50859686
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DB01482
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19527
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SUB07560MIG
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CHEMBL2111152
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100000081273
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FENETHYLLINE
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1149
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ACTIVE MOIETY
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