Psychedelic Alkaloids Chemical and Physical Properties

Psychedelic Compounds Chemical and Physical Properties

DMT

N,N-Dimethyltryptamine

Freebase DMT

• Appearance: White/Transparent crystals
• Composition: C12H16N2
• Molecular Weight: 188.26884 g/mol
• Melting point: 44-68°C (Conflicting reports in literature, as mentioned in TIHKAL)
• Boiling point:
• XLogP: 2.0
• XLogP3: 2.5
• pKa: 8.68
• Stability/Degradation: Oxidation to DMT N-Oxide (yellow oil) in extended presence of oxygen (specialy in evaporation of dmt-containing solvents with heat and/or fan or generally in prolonged exposure to open air). N-oxide may be reverted back to the parent compound by reduction, as described here.
• Solubility:

Very Soluble in Xylene, Toluene, Limonene, acetone, IPA, methanol, ethanol, DCM, chloroform, ether, MEK, butanol Soluble in naphtha, hexane, heptane but almost insoluble in these solvents at freezing temperatures Almost insoluble in water.

DMT N-Oxide

• Appearance: Yellow oil
• XLogP3: 2
• Solubility:

Soluble in Xylene, Toluene, Limonene Slightly soluble in basic water Insoluble in naphtha

DMT Fumarate

• Molecular Weight: 492.608 g/mol
• Solubility:

Soluble in water, boiling IPA Insoluble in freeze-cold IPA Insoluble in freeze-cold acetone Insoluble in FASI (Fumaric Acid Saturated IPA) Insoluble in FASA (Fumaric Acid Saturated Acetone)

5-MeO-DMT

5-methoxy-N,N-dimethyl-tryptamine

Freebase 5-MeO-DMT

• Appearance: Off-white crystals (Sigma Aldrich)
• Composition: C13H18N20
• Molecular Weight: 218.298 g/mol
• Melting Point: 69-70°C (TIHKAL)
• XLogP: 1.9
• XLogP3: 1.5 (pubchem)

5-MeO-DMT Hydrochloride

• Melting Point: 145-146°C (TIHKAL)

Bufotenine

5-HO-DMT - 5-hydroxy-N,N-dimethyl-tryptamine

Freebase Bufotenine

• Composition: C12H16N2O
• Molecular Weight: 204.268 g/mol
• Melting point:146–147 °C (295–297 °F)
• Boiling point: 320 °C (608 °F)
• XLogP: 1.6
• XLogP3: 1.2 (PubChem)
• pKa:
• Solubility:

Acetone @ 20 C: soluble (5 g/100 ml)

Chloroform @ 20 C: soluble

Dichloromethane @ 20 C: soluble

Dimethyl sulfoxide (DMSO) @ 20 C: soluble (6 g/100 ml)

D-Limonene (Orange Oil) @ 20 C: insoluble

D-Limonene (Orange Oil) @ 176 C: soluble (more than 1.7 g/100 ml)

Ethanol @ 20 C: soluble

Ether @ 20 C: soluble

Ethyl acetate @ 20 C: soluble

Heptane @ 20 C: insoluble

Heptane with 40% MEK @ 20 C: soluble (0.53 g/100 ml)

Heptane with 50% MEK @ 20 C: soluble (1.22 g/100 ml)

IPA @ 20 C: soluble

MEK @ 20 C: soluble

Methanol @ 20 C: soluble

Naphtha @ 20 C: insoluble

Water @ 20 C: nearly insoluble in pure water (no acid or alkali added)

Xylene @ 20 C: nearly insoluble (less than 0.03 g/100 ml)

Xylene @ 144 C: soluble (1.5 g/100 ml)

Bufotenine Fumarate

• Solubility:

Soluble in water Insoluble in FASA (Fumaric Acid Saturated Acetone)

Psilocin

4-HO-DMT - 4-Hydroxy-N,N-dimethyl-tryptamine

Freebase Psilocin

• Composition: C12H16N2O
• Molecular Weight: 204.27 g/mol
• Melting Point: 103-104°C (TIHKAL)
• XLogP3: 2.1 (PubChem)
• Stability/Degradation: Unstable in solution, especially alkaline solution (Merck).
• Solubility:

Very slightly sol in water (Merck)

Psilocybin

4-PO-DMT - O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine

Psilocin Phosphate Ester

• Composition: C12H17N2O4P
• Molecular Weight: 284.248141 g/mol
• XLogP3: -1.6 (PubChem)
• Stability/Degradation: Dephosphorylated into Psilocin under acidic conditions. Also when ingested, by phosphatases enzymes.
• Solubility:

Soluble in water. Soluble in 20 parts boiling water (= 0.79g/ml in boiling water), 120 parts boiling methanol (= 0.0932g/ml in boiling methanol); difficultly soluble in ethanol. Practically insoluble in chloroform, benzene (Merck)

Mescaline

3,4,5-trimethoxyphenethylamine

Freebase Mescaline

• Composition: C11H17NO3
• Melting point: 35-36°C (Kindler and Peschke, 103)
• Boiling point: 180°C (12 mmHg)
• XLogP: 0.6 (PubChem)
• XLogP3: 0.7 (PubChem)
• pKa: 9.56
• Appearance: long needle shaped white crystals
• Molecular weight: 211.26

Notes: forms mescaline carbonate on prolonged exposure to air

• Average dose: 300 to 600 milligrams with a duration of 5 to 12 hours.
• Soluble in: alcohol, chloroform, benzene, xylene, toluene, acetone, dichloromethane, highly soluble in isopropyl alcohol, soluble in d-limonene

Moderately soluble in: water Insoluble in: practically insoluble in ether or petroleum ether

• LD50: i.p. rats 370 mg/kg

Mescaline Citrate

• Soluble in: water

Insoluble in: xylene, acetone * * Possible unreliable web source.

Mescaline Hydrochloride

• Molecular weight: 247.72 (Sigma Aldrich)
• Empirical Formula (Hill Notation): C11H17NO3 • HCl (Sigma Aldrich)
• CAS Number: 832-92-8
• Appearance: colorless crystals, needles
• Melting point: 184°C
• Moderately soluble in: water, alcohol (Merck Index), methanol (at least 1.0 mg/ml, source Sigma Aldrich solution)

Insoluble in: practically insoluble in toluene and acetone, insoluble in isopropyl alcohol, diethyl ether, and d-limonene

• LD50: i.p. rats 132 mg/kg
• Storage temperature: 2-8°C (Sigma Aldrich)
• Isolation: when mescaline hydrochloride is extracted from San Pedro, Achuma, or Peruvian torch, it can be isolated from the other alkaloids by washing it in IPA or acetone (use 10 ml per gram of alkaloids, and wash 2-3 times). The non-mescaline alkaloids dissolve in the IPA or acetate, while the mescaline hydrochloride does not. Note that for the cleanest results use about 2 washes of acetone, and then 2 washes with IPA.

Mescaline Picrate

• Melting point: mp 222°C.

Mescaline Sulfate Dihydrate

• Composition: (C11H17NO3)2 • H2SO4 • 2H2O
• Appearance: prisms
• Melting point: 183–186 °C (361–367 °F)
• Molecular Weight: 309.33606
• Soluble in: hot water, methanol
• Almost insoluble in: near freezing water, alcohol, acetone *

* Possible unreliable web source.

Mescaline Fumarate

• Composition: unknown (it may be a one to one salt or may not be)
• Appearance: unknown
• Melting point: unknown
• Soluble in: water<math>**</math>, acetone**

Insoluble in: unknown ** This information is from various SWIMs on this forum.

Mescaline Acetate

• Composition: unknown
• Appearance: white free flowing powder with a slight waxy texture ***
• Melting point: unknown
• Soluble in: water***, isopropyl alcohol***, acetone***, DMSO*** (more than 5 grams/100 ml), boiling MEK***

Insoluble in: xylene, d-limonene, cold MEK (Methyl Ethyl Ketone) *** *** This information was validated by SWIM and is reliable.

• Isolation: when mescaline acetate is extracted from San Pedro, Achuma, or Peruvian torch, it can be isolated from the other alkaloids by washing it in cold MEK (use 10 ml per gram of alkaloids, and wash 2-3 times). The non-mescaline alkaloids dissolve in the MEK, while the mescaline acetate does not. Mescaline acetate can be recrystallized in MEK by boiling the MEK and then freezing it overnight.

Ibogaine

12-methoxyibogamine

Freebase Ibogaine

• Composition: C20H26N2O
• Molecular Weight: 310.43324 g/mol
• Melting Point: 152-153 °C (TIHKAL)
• XLogP3: 3.9
• Solubility: Soluble in limonene?

Ibogaine Hydrochloride

• Melting Point: 299-300 °C (TIHKAL)
• Solubility: Soluble in water, methanol (Sigma Aldrich)

Voacangine

12-methoxyibogamine-18-carboxylic acid methyl ester

Voacangine

• Composition: C22H28N2O3
• Molecular Weight: 368.46932 g/mole
• Melting Point: 136–137 °C (Wikipedia)
• XLogP3-AA: 3.5

LSA (ergine)

Lysergamide

Freebase LSA

• Composition: C16H17N3O
• Molecular Weight: 267.32568 g/mol
• XLogP3: 1.6

Muscimol

Pantherine, Agarine

Freebase Muscimol

• Appearance: White powder (Sigma Aldrich)
• Composition: C4H6N2O2
• Molecular Weight: 114.10264 g/mol
• Melting Point: 175°C (Merck Index)
• XLogP3-AA: -1.4

Salvinorin A

Note: Technically NOT an alkaloid, as it contains no nitrogen. It is a trans-neoclerodane diterpene.

Salvinorin A

• Composition: C23H28O8
• Molecular Weight: 432.46362 g/mol
• Melting Point:242-244 – 238-240 °C (Wikipedia)
• Boiling Pont: 760.2 °C (1400 °F) (Wikipedia)
• XLogP3-AA: 2.5 (PubChem)

Harmine

7-methoxy-β-carboline

Freebase Harmine

• Composition: C13H12N2O
• Molecular Weight: 212.25 (Sigma Aldrich)
• Melting point: 262-264 °C (Sigma Aldrich)
• Boiling point:
• XLogP: 2.5
• XLogP3: 3.6
• pKa: 7.7

Solubility: Insoluble in basic water Isolation: To separate from harmaline, using pKa properties, raise pH of solution containing both alkaloids to pH 8.75 to precipitate 92% of harmine and only 8% Harmaline. Filter to retrieve precipitated alkaloids, and raise the pH further to retrieve the bulk of harmaline. Check this thread for more info

Harmine Hydrochloride

• Melting Point: 321 °C
• Solubility:

Soluble in water Insoluble in salt-saturated water

Harmaline

3,4-dihydro-7-methoxy-1-methyl-β-carboline

Freebase Harmaline

• Composition: C13H14N2O
• Melting point: 232-234 °C (Sigma Aldrich)
• Boiling point: 120-140 °C at 0.001 mm/Hg (TIHKAL)
• XLogP: 0.8
• XLogP3: 1.2
• pKa: 9.8
• Solubility:

Slightly soluble in basic water Isolation: To separate from harmine, using pKa properties, raise pH of solution containing both alkaloids to pH 8.75 to precipitate 92% of harmine and only 8% Harmaline. Filter to retrieve precipitated alkaloids, and raise the pH further to retrieve the bulk of harmaline.

Harmaline Hydrochloride

• Solubility:

Soluble in water Insoluble in salt-saturated water

THH

Tetrahydroharmine - 7-methoxy-1-methyl-1,2,3,4-tetrahydro-β-carboline

Freebase THH

• Composition: C13H16N2O
• Molecular Weight: 216.27894 g/mol
• Melting Point: 187-190 °C (TIHKAL)
• XlogP: 1.9
• XLogP3: 1.9

THH Hydrochloride

• Composition: C13H17ClN2O
• Molecular Weight: 252.73988 g/mol
• Melting Point: 232–234 °C (TIHKAL)

Relevant NOT psychedelic alkaloids

Gramine

N,N-Dimethyl-1H-indole-3-methanamine

Freebase Gramine

• Composition: C11H14N2
• Molecular Weight: 174.24226 g/mol
• Melting point: 138-139°C (Merck)
• Boiling point:
• XLogP3: 1.8
• pKa:
• Solubility:

Sol in alcohol, ether, chloroform; slightly sol in cold acetone. Practically insol in petr ether (= naphtha?), water. (Merck Index)

Solvents and Alkaloids XlogP and XlogP3

Alkaloid XlogP list

• 0.1 - 6-methoxy-2-methyl-beta-Carboline
• 0.7 - Beta-carboline, 6-methoxy-1,2-dimethyl-1,2-Dimethyl-2H-beta-carbolin-6-yl methyl ether
• 0.7 - Mescaline
• 0.8 - Harmaline
• 1.0 - 5-HO-Tryptamine (serotonin)
• 1.3 - 5-HO-DMT N-oxide (Bufotenine N-oxide)
• 1.6 - 5-HO-DMT (bufotenine)
• 1.7 - N-Methylserotonin
• 1.7 - DMT N-oxide (Dimethyltryptamine N-oxide)
• 1.7 - 5-MeO-NMT (5-Methoxy-N-methyltryptamine)
• 1.7 - 2-Methyl-1,2,3,4-tetrahydro-beta-carboline
• 1.8 - NMT (N-Methyltryptamine)
• 1.9 - 5-MeO-DMT (methoxybufotenin)
• 1.9 - Tetra−Hydro−Harmine (THH)
• 2.0 - DMT (Dimethyltryptamine)
• 2.5 - Harmine

Alkaloid XlogP3 list

• -1.4 - Muscimol
• -1.6 - Psilocybin
• 0.6 - Harmalol
• 0.7 - Mescaline
• 1.2 - Harmaline
• 1.2 - Bufotenine
• 1.5 - 5-MeO-DMT
• 1.6 - LSA (ergine)
• 1.8 - Gramine
• 1.9 - Tetrahydroharmine
• 2.0 - DMT N-oxide
• 2.1 - Psilocin
• 2.5 - DMT
• 2.5 - Salvinorin A
• 2.5 - Elemicin
• 3.5 - Voacangine
• 3.6 - Harmine
• 3.6 - Harman
• 3.9 - Ibogaine

Lower XlogP values are more water soluble, and higher XlogP values are more non-polar soluble.

Solvent XlogP list

• -0.7 - DMSO
• -0.5 - Methanol
• -0.1 - Ethyl Alcohol
• 0.2 - Acetone
• 0.4 - IPA
• 0.4 - MEK (Methyl Ethyl Ketone)
• 0.7 - Ethyl Acetate
• 0.9 - Ethyl Ether
• 1.5 - DCM
• 2.1 - Chloroform
• 2.5 - Toluene
• 2.5 - Xylene
• 3.7 - Limonene
• 4.3 - Heptane (similar to naphtha)