Difference between revisions of "Psychedelic Compounds Chemical and Physical Properties"

Revision as of 21:12, 18 November 2011

For more detailed information on each compound, please visit their individual wikis as linked in the Alkaloids section

Psychedelic Compounds Chemical and Physical Properties

DMT

N,N-Dimethyltryptamine

Freebase DMT

• Appearance: White/Transparent crystals
• CAS Registry Number: 61-50-7
• Composition: C12H16N2
• Molecular Weight: 188.26884 g/mol
• Melting point: 44-68°C (Conflicting reports in literature, as mentioned in TIHKAL)
• Boiling point: Theoretically 360-380°C
• XLogP: 2.0
• XLogP3: 2.5 (PubChem)
• pKa: 8.68 (Merck Index)
• Colorimetric reagent results: Here
• 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 in the N-Oxide to Freebase Wiki.
• Solubility:

Very Soluble in Xylene, Toluene, Limonene, acetone, Isopropyl Alcohol (IPA), methanol, ethanol, Dichloromethane (DCM), chloroform, ether, Butanone (also known as methyl ethyl ketone (MEK)) and 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
• Colorimetric reagent results: Here
• Solubility:

Soluble in Xylene, Toluene, Limonene Soluble in chloroform Bane1 and Ghosal 1969

Slightly soluble in basic water

Insoluble in petroleum (naphtha) but appreciably soluble in petroleum which contains fats. Ghosal & Banerjee 196

• Interconversion: DMT N-Oxide can be reconverted back to DMT by redissolving in dilute acetic acid solution, adding excess zinc dust, mixing for a couple of hours, filtering to remove zinc, adding base and pulling with organic solvent as in a normal extraction. DMT can be oxidized by using hydrogen peroxide (Fish et al 1955)

DMT Fumarate

• Molecular Weight: 492.608 g/mol
• Solubility:

Very soluble in water

Soluble in methanol (~10mg/ml)

Soluble in boiling IPA, Practically insoluble in room temp IPA (~1mg/ml), Insoluble in freeze-cold IPA.

Slightly soluble in ethanol (~5mg/ml)

Insoluble in cold acetone

Insoluble in FASI (Fumaric Acid Saturated IPA)

Insoluble in FASA (Fumaric Acid Saturated Acetone)

NMT

N-Methyltryptamine, monomethyltryptamine

Freebase NMT

• Appearance: Oil, difficult crystallization, eventually forms crystalline stellar aggregates, darkens with exposure to air (Source 1, Source 2)
• Composition: C11H14N2
• Molecular Weight: 174.24226 g/mol
• Melting point: 87-89C (Sigma Aldrich)
• Boiling point: 336.181 °C at 760 mmHg (Chemspider)
• XLogP3: 2.1 (PubChem)
• Colorimetric reagent results: Here
• Stability/Degradation: Darkens over time, but does not seem to form oxides (Source )
• Solubility:

Soluble in methanol, warm ethanol, dichloromethane & choloroform. Soluble to some extent in naphtha (not nearly as much as DMT). It seemed only partially soluble in warm acetic acid. It is likely soluble in xylene. (Source )

• Pharmacology and activity:

-Present in trace amounts as part of normal metabolism (Source)

- 1/3 to 1/4 potency of DMT Nen (2001))

• Further info: TIHKAL NMT entry

Entheogenic Effects of NMT

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: 66-67°C, 67-68°C, 69-70°C (Trout's notes and TIHKAL)
• Boiling Point4 : 208-210°C @ 4mm (Hoshino & Shimodaira 1936)
• XLogP: 1.9
• XLogP3: 1.5 (PubChem)
• pKa: 9.3 (Ghosal & Mukherjee 1964)
• Colorimetric reagent results: Here
• Stability: Stable under normal temperatures and pressures. Incompatible with strong oxidizing agents, strong acids (Source)
• Solubility:

Soluble in: Chloroform, ether, DCM, acetone, methanol, ethanol (Trout's notes on simple tryptamines). Soluble in (at least) 20mg/ml 96% ethanol (Source).

Hexane/Naphtha/Pet ether are commonly used to crystallize it (Ott 1993, Espamer et al 1967, Morimoto & Matsumoto 1966, etc) , so it is probably moderately soluble in these solvents.

Practically Insoluble in water (Source)

5-MeO-DMT Hydrochloride

• Melting Point: 145-146°C (TIHKAL)

Bufotenine

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

Freebase Bufotenine

• CAS Registry Number: 487-93-4
• 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: 9.67
• Colorimetric reagent results: Here
• 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)

Dilute Acids and Alkalis: Soluble (Merck Index)

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

• CAS Registry Number: 520-53-6
• Composition: C12H16N2O
• Molecular Weight: 204.27 g/mol
• Melting Point: 103-104°C (TIHKAL) , 173-176°C (Merck Index)
• XLogP3: 2.1 (PubChem)
• Colorimetric reagent results: Here
• Stability/Degradation: Unstable in solution, especially alkaline solution (Merck Index).
• Solubility:

Soluble in 70% ethanol. Poorly soluble in dry ethanol, and poorly soluble in ethanol less than 60%. Very slightly soluble in water (sources: Merck Index , scientific publications)

Psilocybin

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

Psilocybin (Psilocin Phosphate Ester)

• CAS Registry Number: 520-52-5
• Composition: C12H17N2O4P
• Molecular Weight: 284.248141 g/mol
• Melting Point: 220-228° from boiling water; 185-195° from boiling methanol (Merck Index)
• XLogP3: -1.6 (PubChem)
• Colorimetric reagent results: Here
• 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); very soluble in 70% methanol saturated with KNO3, soluble in dry methanol, difficultly soluble in ethanol, increasingly less soluble in methanol less than 80%. Practically insoluble in chloroform, benzene (sources: Merck Index , scientific publications)

Mescaline

3,4,5-trimethoxyphenethylamine

Freebase Mescaline

• CAS Registry Number: 54-04-6
• Composition: C11H17NO3
• Melting point: 35-36°C (Kindler and Peschke, 103. Merck Index)
• 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.
• Colorimetric reagent results: Here
• Solubility

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

• Solubility

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 (Merck Index)
• Solubility:

Moderately soluble in: water, alcohol (Merck Index), methanol (at least 1.0 mg/ml, source Sigma Aldrich solution) (Merck Index) 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: White powder
• Melting point: unknown
• Solubility

Soluble in: water

Insoluble in: Limonene, Anydrous IPA, Acetone, MEK (most likely insoluble in all non-polars like xylene and toluene) Source

Mescaline Acetate

• Composition: unknown
• Appearance: white free flowing powder with a slight waxy texture ***
• Melting point: unknown
• Solubility:

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

• CAS Registry Number: 83-74-9
• Composition: C20H26N2O
• Molecular Weight: 310.43324 g/mol
• Melting Point: 152-153 °C (TIHKAL)
• XLogP3: 3.9 (PubChem)
• pKa: 8.1 in 80% methylcellosolve (Merck Index)
• Colorimetric reagent results: Here
• Solubility: Soluble in limonene (Non-Toxic Iboga Extraction) soluble in acetone (merck)

Ibogaine Hydrochloride

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

Voacangine

12-methoxyibogamine-18-carboxylic acid methyl ester

Voacangine

• Composition: C22H28N2O3
• Molecular Weight: 368.46932 g/mole
• Melting Point: 136–137 °C (Merck Index)
• pKa: 7.4 (40% aq methanol); 5.73 (33% DMF) (Merck Index)
• XLogP3-AA: 3.5 (PubChem)

LSA (ergine)

Lysergamide

Freebase LSA

CAS Registry Number: 478-94-4

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

Muscimol

Pantherine, Agarine

Freebase Muscimol

• Appearance: White powder (Sigma Aldrich)
• CAS Registry Number: 2763-96-4
• Composition: C4H6N2O2
• Molecular Weight: 114.10264 g/mol
• Melting Point: 175°C (Merck Index)
• Boiling Point: 70°C (Wolfram Alpha)
• XLogP3-AA: -1.4 (PubChem)
• pKa: 4.8 (Indiana University])
• Solubility: Very soluble in water and methanol, slightly soluble in ethanol, DMSO and DMF. ~10mg/ml in phosphate buffered saline @ pH 7.2 (Caymanchem.com)

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)

Elemicin

1,2,3-trimethoxy-5-allylbenzene

Note: Technically NOT an alkaloid, as it contains no nitrogen.

Elemicin

• CAS Number: 487-11-6
• Molecular Formula: C12H16O3
• Molecular Weight: 208.25364 g/mol
• Boiling Point: 152-156 °C @ 17 mmHg, 144-147 °C @ 10 mmHg (Source), 146-147 °C (Source 1 Source 2), 279.8 °C @ 760 mmHg (ChemSpider)
• XlogP3: 2.5 (PubChem)
• Solubility:

Soluble in alcohol, Insoluble in water (Source)

Harmine

7-methoxy-β-carboline

Freebase Harmine

• Composition: C13H12N2O
• Molecular Weight: 212.25 (Sigma Aldrich)
• Melting point: 262-264 °C (Sigma Aldrich)
• Boiling point: 421.4°Cat760mmHg (Lookchem)
• XLogP: 2.5
• XLogP3: 3.6
• pKa: 7.7
• Colorimetric reagent results: Here
• Solubility:

Insoluble in basic water, poorly soluble in distilled water. Reasonably soluble in acetone (at 25°C, acetone can dissolve 4mg/ml mixed harmalas as this test shows)

• 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 the freebase percentage calculator thread and the Harmala Extraction Guide 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
• Colorimetric reagent results: Here
• Solubility:

Slightly soluble in basic water, poorly soluble in distilled water. Reasonably soluble in acetone (at 25°C, acetone can dissolve 4mg/ml mixed harmalas as this test shows)

• 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. Check the freebase percentage calculator thread and the Harmala Extraction Guide for more info.

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
• Colorimetric reagent results: Here
• Solubility:

Soluble in chloroform, ethanol & methanol. (Ott 1996.)

Soluble in ethyl acetate. (Siddiqui et al. 1983)

Poorly soluble in distilled water

THH Hydrochloride

• Composition: C13H17ClN2O
• Molecular Weight: 252.73988 g/mol
• Melting Point: 232–234 °C (TIHKAL)
• Boiling point: 399.2 °C at 760 mmHg (Lookchem)
• Mol File: 40959-16-8.mol
• Flash Point: 195.2 °C
• Enthalpy of Vaporization: 64.99 kJ/mol
• Vapour Pressure: 1.4E-06 mmHg at 25°C
• H-Bond Donor: 3
• H-Bond Acceptor: 2
• Rotatable Bond Count: 1
• Topological Polar Surface Area: 37.1
• Heavy Atom Count: 17
• Complexity: 258

Relevant NOT psychedelic compounds

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
• Colorimetric reagent results: Here
• pKa: 8.52
• Solubility:

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

Hordenine

N,N-dimethyltyramine

Freebase Hordenine

• CAS Registry Number: 539-15-1
• Composition: C10H15NO
• Molecular Weight: 165.23 g/mol
• Melting point: 117-118° (Merck Index)
• Boiling point: 173° @ 11mmHg (Merck Index)
• XlogP3: 2.1 (PubChe[[File:m)
• Solubility:

Very sol in alcohol, chloroform, ether. 7 grams dissolve in 1000 ml water. Sparingly sol in benzene, toluene, xylene. Practically insol in petr ether. (Merck Index)

Hordenine Hydrochloride

• CAS Registry Number: 6027-23-2
• Composition: C10H15NO.HCl
• Molecular Weight: 201.70 g/mol
• Melting point: 177° (Merck Index)
• Solubility:

Very sol in water. (Merck Index)

Vasicine

(3R)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-ol;Peganine

Freebase Vasicine

• Composition: C11H12N2O
• Molecular Weight: 188.22578 g/mol
• Melting point: 209-211° C (Decomposes) (source)
• XLogP3: 0.4 (pubchem)
• Pharmacology: Uterotonic, abortifacient, bronchodilatory activity, expectorant, respiratory stimulant activity, moderate hypotensive activity (sources: 1, 2
• Solubility: Soluble in NaCl-saturated water (harmalas precipitate as HCl salts in NaCl-saturated water, hence vasicine can be separated from harmalas in peganum harmala. Check harmala extraction guide for more info)

Vasicinone

(R)-2,3-dihydro-3-hydroxypyrrolo(2,1-b)quinazolin-9(1H)-one

Freebase Vasicine

• Appearance: White powder
• Composition: C11H10N2O2
• Molecular Weight: 202.2093 g/mol
• Melting point: 203°-204° C (source)
• XLogP3: 0.4 (pubchem)
• Pharmacology: Uterotonic, abortifacient, bronchodilatory activity, expectorant, respiratory stimulant activity, moderate hypotensive activity (sources: 1, 2
• Solubility: Water: 1600 mg/l. Soluble in NaCl-saturated water (harmalas precipitate as HCl salts in NaCl-saturated water, hence vasicinone can be separated from harmalas in peganum harmala. Check harmala extraction guide for more info

Deoxyvasicine

1,2,3,9-Tetrahydropyrrolo(2,1-b)quinazoline; Deoxypeganin;

Freebase Deoxyvasicine

• Appearance: White to yellow powder
• Composition: C11H12N2
• Molecular Weight: 172.22638 g/mol
• Melting point: 86-87° C (source)
• XLogP3: 0.4
• Pharmacology: Uterotonic, abortifacient, bronchodilatory activity, expectorant, respiratory stimulant activity, moderate hypotensive activity (sources: 1, 2
• Solubility: Water: 1600 mg/l. Soluble in NaCl-saturated water (harmalas precipitate as HCl salts in NaCl-saturated water, hence vasicine can be separated from harmalas in peganum harmala. Check harmala extraction guide for more info)

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
• 2.1 - NMT
• 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)