Hallucinogens, potential endogenous psychotogens, and related biochemicals sorted by E-state value of N1 and/or Scar2
| Compound | E-state of key N1 | Scar2 | Ratio* Scar to E-state of N | Evidence for effective dose (µg) |
|---|---|---|---|---|
| Adrenochrome | 1.765 | 4.25 | 2.41 | n.d. |
| 5-methyl-THF | 1.815 | 5.66 | 3.12 | mixed3 |
| LSD | 1.945 | 27.60 | 14.19 | 100 |
| Psilocybin | 2.043 | 14.04 | 6.87 | 4,000 |
| N-methyl-norsalsolinol | 2.193 | 10.40 | 4.74 | n.d. |
| N-acetylmescaline** | 2.208 | 5.67 | 2.57 | n.d. |
| Dimethyltryptamine | 2.211 | 21.00 | 9.50 | 14,000 |
| N-methyl-salsolinol | 2.235 | 11.99 | 5.36 | n.d. |
| Rows above sorted4 on E-state of key N1, rows below sorted on E-state of key N1 (+) Scar | ||||
| PCP | 2.811 | 27.11 | 9.64 | 1,000 |
| Ketamine | 3.197 | 14.29 | 4.47 | 70,000 |
| Tryptamine | 5.500 | 15.79 | 2.87 | none |
| Mescaline | 5.500 | 13.02 | 2.37 | 200,000 |
| Serotonin | 3.134 | 12.26 | 3.91 | none |
| Tryptophan | 3.084 | 11.09 | 3.60 | none |
| Salsolinol | 3.292 | 9.60 | 2.92 | n.d. |
| N-methyldopamine | 3.006 | 9.36 | 3.11 | n.d. |
| Phenylalanine | 5.349 | 8.92 | 1.67 | none |
| Norsalsolinol | 3.195 | 8.07 | 2.53 | n.d. |
| Dopamine | 5.305 | 6.73 | 1.27 | none |
| Epinephrine | 2.806 | 5.90 | 2.10 | none |
| Tyrosine | 5.325 | 5.64 | 1.06 | none |
| Norepinehrine | 5.198 | 3.43 | 0.66 | none |
| Arginine | 3.680 | –0.43 | –0.12 | n.d. |
| Homocysteine | 5.079 | –0.75 | –0.15 | none |
1 N represents the amide, tertiary, secondary or primary amine identified as the most conformationally flexible [266]. 2 Scar represents the total E-state value for carbons in the molecule. 3 In the presence of a B12 deficiency, administration of ≥ 1,000 µg/day of 5-methyl-THF or other folates could be problematic in otherwise normal individuals or those with psychosis [136, 221]. 4 The compounds were sorted from low to high values of the E-state of key N up to values < 2.5; from values of 2.5 to 3.2 they were sorted on E-state and then from high to low values of Scar; from values of E-state of 3.2 and above, they were sorted on Scar only (see text). * The ratio of Scar to E-state of N is of interest because of the potential interaction between the two variables. ** The E-state value of N for N-acetylmescaline predicted by ChemSAR (http://chemsar.scbdd.com/calcdes/index/) involved 3 possibilities: tertiary amine, double-stranded, and an aromatic component; the results were averaged to represent all 3 characteristics