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
Declarations
Acknowledgments
I would like to extend my deep gratitude to Sebastian Colwell and to Spencer Pittman (Technologic Computer Services) for their assistance with computer program selection and performance.
The author has no conflict of interest to declare, has no commercial product related to this work, and holds no patents related to this work, nor are any under development at this time.
Ethical approval
Not applicable.
Consent to participate
Not applicable.
Consent to publication
Not applicable.
Availability of data and materials
Where relevant, the site for availability of analytical tools is listed in the text.
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