Table 4.
Structure–activity relationships
| Structure | Present in | Not present in | Pharmacolocial (clinical) activity |
|---|---|---|---|
| 3,4-Substitution on benzene ring (methylenedioxy or furan) | MDMA, 5-MAPDB, 5-EAPB | Methamphetamine | Reduced DAT/SERT inhibition ratio, aincreased potency to release 5-HT, areduced potency to release dopamine (more entactogenic, less stimulant) |
| MDA, 5-APB, 6-APB, 5-APDB, 6-APDB, 7-APB, β-keto-MDA | aAmphetamine | ||
| Oxygen in para-(4)-position | 5-APB, 5-APDB, 5-MAPDB | 7-APB, 4-APB, 6-APB, 6-APDB | Reduced DAT/SERT inhibition ratio (more serotonergic) |
| Dihydrobenzofuran | 5-APDB, 6-APDB, 5-MAPDB | 5-APB, 6-APB, 4-APB, 7-APB | Reduced DAT/SERT inhibition ratio (more 5-hydroxytryptaminergic) |
| N-Alkyl group | MDMA, 5-EAPB, 5-MAPDB | MDA, 5-APB, 5-APDB | Reduced 5-HT2A/B receptor activation and 5-HT2C receptor-binding potency (less hallucinogenic) |
| 2,5-Oxy-substitution on benzene ring | 2C-B-FLY | All other compounds | Strongly increased 5-HT2A/B receptor activation, strongly increased 5-HT2C receptor-binding potency (more hallucinogenic) |
| β-Keto group | β-Keto MDA | MDA | a,bIncreased DAT/SERT ratio (more dopaminergic) |