Compound: FENETHYLLINE
SMILES: O=c1n(c(=O)c2n(CCNC(Cc3ccccc3)C)cnc2n1C)C
InChIKey: NMCHYWGKBADVMK-UHFFFAOYSA-N
Synonyms: FENETHYLLINE, Fenetylline, Phenethylline, Amfetyline, Captagon, Fenetyllin, Amphetaminoethyltheophylline, Theophyllineethylamphetamine, Fenetylinum, Fenetilina, Fitton, Humburg 814, 3736-08-1, Fenetillina, Fenetyllinum, HOMBURG-814, YZ0N7VL5R3, Theophylline, 7-(2-((alpha-methylphenethyl)amino)ethyl)-, D323, DTXSID50859686, 7-(2-((alpha-Methylphenethyl)amino)ethyl)theophylline, 1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-1,3-DIMETHYL-7-(2-((1-METHYL-2-PHENYLETHYL)AMINO)ETHYL)-, 1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-7-[2-[(1-methyl-2-phenylethyl)amino]ethyl]-, RefChem:598868, 7-ethyltheophyllineamphetamine, DTXCID80197301, N06BA10, 1,3-dimethyl-7-(2-((1-phenylpropan-2-yl)amino)ethyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione, 609-418-3, Fenetylline, (+)-, Fenethylline, (+)-, Fenetylline, (-)-, Fenethylline, (-)-, 76284FBU6H, CP55WHR66R, UNII-76284FBU6H, Fenetylline (INN), FENETYLLINE [INN], 1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-7-(2-((1-methyl-2-phenylethyl)amino)ethyl)-, (+)-, 802018-96-8, 1H-Purine-2,6-dione, 3,7-dihydro-1,3-dimethyl-7-(2-((1-methyl-2-phenylethyl)amino)ethyl)-, (-)-, 765207-54-3, Fenetillina [DCIT], NCGC00247730-01, Fenetylline [INN:BAN], Fenetilina [INN-Spanish], Fenetyllinum [INN-Latin], Ethylteophylline amphetamine, DEA No. 1503, Fitton (TN), BRN 1169517, FENETHYLLINE [MI], UNII-CP55WHR66R, UNII-YZ0N7VL5R3, FENETYLLINE [WHO-DD], SCHEMBL149145, CHEMBL2111152, HSDB 8315, CHEBI:135451, NMCHYWGKBADVMK-UHFFFAOYSA-N, HY-A0238, 1,3-dimethyl-7-[2-(1-phenylpropan-2-ylamino)ethyl]purine-2,6-dione, CS-6600, DB01482, NS00002184, D07944, 5-26-14-00005 (Beilstein Handbook Reference), Q27887794, 7-[2-[(.alpha.-Methylphenethyl)amino]methyl]theophylline, 7-(2-((.ALPHA.-METHYLPHENETHYL)AMINO)ETHYL)THEOPHYLLINE, THEOPHYLLINE, 7-(2-((.ALPHA.-METHYLPHENETHYL)AMINO)ETHYL)-, 1,3-DIMETHYL-7-(2-(1-METHYL-2-PHENYLETHYLAMINO)ETHYL)XANTHINE, 1,3-dimethyl-7-{2-[(1-phenylpropan-2-yl)amino]ethyl}-3,7-dihydro-1H-purine-2,6-dione, 1,3-Dimethyl-7-(2-[(1-methyl-2-phenylethyl)amino]ethyl)-3,7-dihydro-1H-purine-2,6-dione #, 3,7-DIHYDRO-1,3-DIMETHYL-7-(2-((1-METHYL-2-PHENYLETHYL)AMINO)ETHYL)-1H-PURINE-2,6-DIONE
Theoretical properties:
molecular_formula: C18H23N5O2
molecular_weight: 341.4 g/mol
exact_mass: 341.18517499 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 6
heavy_atom_count: 25
topological_polar_surface_area: 70.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 227-229
Descriptions:
pubchem: Fenetylline is an oxopurine.
chembl: FENETHYLLINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Fenethylline (BAN, USAN) or fenetylline (INN) is a codrug of amphetamine and theophylline and so a mutual prodrug of both.  It is also spelled phenethylline; other names for it are amphetaminoethyltheophylline and amfetyline. The drug was marketed for use as a psychostimulant under the brand names Captagon, Biocapton, and Fitton. The brand name "Captagon" (or in lowercase as "captagon") is often used generically to describe illicitly produced fenethylline.
Fenethylline is illegal in most countries. It is produced primarily for illicit use, which takes place mainly in Syria. The illicit global market for the drug was estimated in 2023 to be worth approximately US$57 billion.
Smuggling of fenethylline became Syria's principal export, exceeding the total of all other exports under the Assad regime during the Syrian civil war (2011–2024). It was the world's largest producer of the drug, accounting for about 80% of the global supply. A large quantity of Captagon tablets, ready for clandestine export, was captured by anti-Assad forces that took control of Damascus in December 2024.