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

Latest revision as of 14:18, 19 May 2023

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 or clear oil. Polymorphic (Gaujac et al 2013)
CAS Registry Number: 61-50-7
Composition: C12H16N2
Molecular Weight: 188.26884 g/mol
Melting point: 45-46 and 57-58°C , Polymorphic (Gaujac et al 2013)
Boiling point: Source: Brennendes Wasser

First fumes from 100 °C +

Strong fumes from 160 °C +

No further vaporization from 190 °C

Estimated optimal temp for vaporization 175°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. Following daya from Source: Brennendes Wasser

Naphtha (80 °C, C6-C7, 60-80 °C) "infinite" (the DMT will melt and just create a homogeneous liquid-liquid solution. In the end it may even be a solution of Naphtha in DMT)
Naphtha (20 °C, C6-C7) 2,93 g in 100 ml
Naphtha in the freezer (-20 °C, C6-C7) 109 mg in 100 ml
n-Hexane (20 °C) 770 mg in 100 ml
n-Hexane in the freezer (-20 °C) 83 mg in 100 ml
n-Pentane in the freezer (-20 °C) 50 mg in 100 ml
n-Heptane in the freezer (-20 °C) 92 mg in 100 ml

Almost insoluble in water.

DMT N-Oxide

Appearance: Basic oil (Weak base. Weaker than DMT, NMT or tryptamine.) Fish et al. 1956. Hygroscopic solid Banerjee & Ghosal 1969
XLogP3: 2
Colorimetric reagent results: Here
Solubility:

Soluble in Xylene, Toluene, Limonene (?) Soluble in chloroform Bane1 and Ghosal 1969 Soluble in water. Fish et al. 1955 and Ghosal et al. 1970b and Banerjee & Ghosal 1969

Insoluble in petroleum (naphtha) but appreciably soluble in petroleum which contains fats. Ghosal & Banerjee 1969

Interconversion: It has been claimed that 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)

DMT Citrate

Appearance: Oily forms a gum.
Solubility: Soluble in water, propylene glycol
Insoluble in ethyl acetate

-Nexus sourced.

DMT Benzoate

Appearance: Crystal
Solubility: Soluble in water and ethanol
Mostly soluble in Isopropyl alcohol (at room temperature)
Poorly soluble in room temp propylene glycol

Insoluble: Limonene (but will from in Limonene FB + Benzoic acid)

Appears to not form in ethyl acetate but is mostly insoluble in ethyl acetate? (at room temperature.)
Appears to be mostly insoluble in Acetone and MEK at room temperature.

-Nexus sourced.

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:Source: Brennendes Wasser

108 °C

Boiling point:Source: Brennendes Wasser

First fumes from 160 °C +

Bufotenine turning brown at 170 °C +

strong fumes from 190 °C +

No further vaporization from 230 °C, leaving a black residue

Estimated optimal temp for vaporization 210°C

XLogP: 1.6
XLogP3: 1.2 (PubChem)
pKa: 9.67
Colorimetric reagent results: Here
Solubility:

Source: Brennendes Wasser

1:3 Ethyl Acetate:Naphtha (C6-C7)

Boiling = 7,6 g/l = 760 mg in 100 ml

20 °C = 3,6 g/1 l = 360 mg in 100 ml

- 20 °C = 3,5 g/1 l = 350 mg in 100 ml

Selectively dissolves Bufotenine only, not the more polar Alkaloids. Defat first with Naphtha.

Ethyl Acetate

Boiling = 280 g/1 l = 28 g in 100 ml

20 °C = 72 g/1 l = 7,2 g in 100 ml

- 20 °C = 50 g/1 l = 5 g in 100 ml

For recrystalization (optional, not recommended). Use only minimal amounts of solvent as you can see above! Placement in the freezer did not produce more crystals, just cloudings that cant be collected. Also crystals derived from re-x with Ethyl Acetate start turning grey and otherwise the material keeps its colour, therefore maybe not advised to do a re-x.

boiling D-Limonene

Unconvenient, drops Bufotenine too fast to form crystals. Also high chance to damage Bufotenine at 175 °C. Same goes possibly for Xylene.

1:4 Acetone:Naphtha

Not recommended, check above link for more info

Other solubility data (possibly unreliable, originally from 69ron experiments)

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)

Bufotenine Benzoate

Solubility:

Insoluble in acetone, (almost insoluble in PG/VG)

Bufotenine Citrate

Insoluble in ethyl acetate (will form in EA)-Nexus sourced.

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)

Free base: Stable compound. Colorless crystals. Hofmann 1971 pH 5.2 (in 50% EtOH) Merck 9th More stable than psilocin. Shulgin & Shulgin !997 mp 175-180° Repke & leslie 1977 mp 185-195° (from boiling methanol) Ott 1996 mp 185-195° (from methanol) Picker & Rickards 1970 (Also in Perkal 1981) rnp 185-195° (dec.) (white crystals) Clarke 's 1986 mp 190° Mantle & Waight 1969

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 (estimated 2mg/ml at 25C). 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, PubChem)

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, ethyl acetate, chilled ethyl acetate (O°F)

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 *, ethyl acetate

* 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, ethanol ~10mg/ml (ref: Cayman Chemical) (Merck Index), methanol ~1.0mg/ml (source Sigma Aldrich solution) (Merck Index), dimethyl sulfoxide (DMSO) ~3mg/ml (ref: Cayman Chemical), dimethyl formamide ~0.5mg/ml (ref: Cayman Chemical)

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 acetone (* NOTE: previous sentence is speculation, not yet substantiated by tests as far as we know), 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 * [VERIFIED]

* Possible unreliable web source.

Mescaline Fumarate

Composition: unknown (when prepared by a FASx method it may be a one to one salt (the bifumarate) 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)

no melting, directly sublimating source: Brennendes Wasser

Boiling Pont:

Source: Brennendes Wasser

First fumes from 190 °C, Salvinorin turning brown

No further vaporization from 270 °C, leaving a black residue

Estimated ideal temperature for vaporization: 250 °C

Other data: 760.2 °C (1400 °F) (Wikipedia) likely wrong

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)

Not melting, directly sublimating Source: Brennendes Wasser

Boiling point:

Source: Brennendes Wasser

First fumes from 180 °C +

Sublimation while forming small black clumps at 205 °C +

No further vaporization from 240 °C,

421.4°C at 760mmHg (Lookchem)

XLogP: 2.5
XLogP3: 3.6
pKa: 7.7
Colorimetric reagent results: Here
Solubility: ethanol (~1.5mg/ml), DMSO (~1.5mg/ml), dimethyl formamide and ethyl acetate

(~1.5mg/ml). Reasonably soluble in acetone (at 25°C, acetone can dissolve 4mg/ml mixed harmalas as this test shows) Insoluble in: Basic water, diethyl ether, D Limonene. Low solubility in distilled 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 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

Harmine Citrate

Solubility:

Soluble in water

Insoluble in ethyl acetate (will form in EA)

Nexus sourced

Harmine Tartrate

Solubility:

soluble in water

Insoluble in ethyl acetate (will form in EA)

- Insoluble in acetone (should form in Acetone)

Nexus sourced

Harmaline

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

Freebase Harmaline

Composition: C13H14N2O
Melting point:

232-234 °C (Sigma Aldrich)

Not melting, directly sublimating Source: Brennendes Wasser

Boiling point:

Source: Brennendes Wasser

First fumes from 180 °C +

Sublimation while forming small black clumps at 205 °C +

No further vaporization from 240 °C,

120-140 °C at 0.001 mm/Hg (TIHKAL)

XLogP: 0.8
XLogP3: 1.2
pKa: 9.8
Colorimetric reagent results: Here
Solubility:

Insoluble in D Limonene 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) Soluble in ethyl acetate.

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

Harmaline Citrate

Solubility:

Soluble in water

Insoluble in ethyl acetate

Nexus sourced

Harmaline Tartrate

Solubility:

soluble in water

Insoluble in ethyl acetate (will form in EA)

- Insoluble in acetone (should form in Acetone)

Nexus sourced

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 Vasicinone

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)

@@ Line 1: / Line 1: @@
+For more detailed information on each compound, please visit their individual wikis as linked in the [[:Category:Alkaloids|Alkaloids]] section
 == Psychedelic Compounds Chemical and Physical Properties ==
@@ Line 6: / Line 9: @@
 ==== Freebase DMT ====
 <table><tr><td>[[Image:dmtfreebase.png]]</td><td></table>
-* Appearance: White/Transparent crystals
+* Appearance: White/Transparent crystals or clear oil. Polymorphic (Gaujac et al 2013)
 * 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 [http://isomerdesign.com/PiHKAL/browse.php?domain=tk TIHKAL])
+* Melting point: 45-46 and 57-58°C , Polymorphic (Gaujac et al 2013)
-* Boiling point:
+* Boiling point: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=1065033#post1065033 Source: Brennendes Wasser]
+First fumes from 100 °C +
+Strong fumes from 160 °C +
+No further vaporization from 190 °C
+Estimated optimal temp for vaporization 175°C
 * XLogP: 2.0
 * XLogP3: 2.5 ([http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6089&loc=ec_rcs PubChem])
-* pKa: 8.68 ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+* pKa: 8.68 ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
-* 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 [http://www.anoniem.org/?http://wiki.dmt-nexus.com/DMT_N-Oxide_to_Freebase_DMT in the N-Oxide to Freebase Wiki].
+* Colorimetric reagent results: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 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 [http://www.anoniem.org/?http://wiki.dmt-nexus.me/DMT_N-Oxide_to_Freebase_DMT in the N-Oxide to Freebase Wiki].
 * Solubility:
-Very Soluble in Xylene, Toluene, Limonene, acetone, IPA, methanol, ethanol, DCM, chloroform, ether, MEK, butanol
+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. Following daya from [https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=1090269#post1090269 Source: Brennendes Wasser]
+*Naphtha (80 °C, C6-C7, 60-80 °C) "infinite" (the DMT will melt and just create a homogeneous liquid-liquid solution. In the end it may even be a solution of Naphtha in DMT)
+*Naphtha (20 °C, C6-C7) 2,93 g in 100 ml
+*Naphtha in the freezer (-20 °C, C6-C7) 109 mg in 100 ml
+*n-Hexane (20 °C) 770 mg in 100 ml
+*n-Hexane in the freezer (-20 °C) 83 mg in 100 ml
+*n-Pentane in the freezer (-20 °C) 50 mg in 100 ml
+*n-Heptane in the freezer (-20 °C) 92 mg in 100 ml
-Soluble in naphtha, hexane, heptane but almost insoluble in these solvents at freezing temperatures
 Almost insoluble in water.
@@ Line 25: / Line 46: @@
 ==== DMT N-Oxide ====
 <table><tr><td>[[Image:dmtnoxide.jpg]]</td><td></table>
-* Appearance: Yellow oil
+* Appearance: Basic oil (Weak base. Weaker than DMT, NMT or tryptamine.) Fish et al. 1956.  Hygroscopic solid Banerjee & Ghosal 1969
 * XLogP3: 2
+* Colorimetric reagent results: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 Here]
 * Solubility:
-Soluble in Xylene, Toluene, Limonene
+Soluble in Xylene, Toluene, Limonene (?)
-Slightly soluble in basic water
+Soluble in chloroform Bane1 and Ghosal 1969
-Insoluble in naphtha
+Soluble in water. Fish et al. 1955 and Ghosal et al. 1970b and Banerjee & Ghosal 1969
+Insoluble in petroleum (naphtha) but appreciably soluble in petroleum which contains fats. Ghosal & Banerjee 1969
+* Interconversion: It has been claimed that 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 ([https://www.dmt-nexus.me/forum/resource.ashx?a=7966 Fish et al 1955])
 ==== DMT Fumarate ====
@@ Line 49: / Line 76: @@
 Insoluble in FASA (Fumaric Acid Saturated Acetone)
+==== DMT Citrate ====
+*Appearance: Oily forms a gum.
+* Solubility: Soluble in water, propylene glycol
+*Insoluble in ethyl acetate
+-Nexus sourced.
+==== DMT Benzoate ====
+[[File:DMT-benzoate_3d_model.gif]]
+* Appearance: Crystal
+* Solubility: Soluble in water and ethanol
+* Mostly soluble in Isopropyl alcohol (at room temperature)
+* Poorly soluble in room temp propylene glycol
+* Insoluble: Limonene (but will from in Limonene FB + Benzoic acid)
+*Appears to not form in ethyl acetate but is mostly insoluble in ethyl acetate? (at room temperature.)
+*Appears to be mostly insoluble in Acetone and MEK at room temperature.
+-Nexus sourced.
+===NMT ===
+N-Methyltryptamine, monomethyltryptamine
+==== Freebase NMT ====
+<table><tr><td>[[Image:Nmt.jpg]]</td><td></table>
+* Appearance: Oil, difficult crystallization, eventually forms crystalline stellar aggregates, darkens with exposure to air ([https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=23544&p=2 Source 1], [http://www.erowid.org/library/books_online/tihkal/tihkal50.shtml Source 2])
+* Composition: C11H14N2
+* Molecular Weight: 174.24226 g/mol
+* Melting point: 87-89C (Sigma Aldrich)
+* Boiling point: 336.181 °C at 760 mmHg ([http://www.chemspider.com/Chemical-Structure.11523514.html Chemspider])
+* XLogP3: 2.1 ([http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=6088 PubChem])
+* Colorimetric reagent results: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 Here]
+* Stability/Degradation: Darkens over time, but does not seem to form oxides ([https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=23544&p=2 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. ([https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=23544&p=2 Source] )
+* Pharmacology and activity:
+-Present in trace amounts as part of normal metabolism ([http://www.ncbi.nlm.nih.gov/pubmed/11763413 Source])
+- 1/3 to 1/4 potency of DMT [https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=269093#post269093 Nen (2001)])
+* Further info: [http://www.erowid.org/library/books_online/tihkal/tihkal50.shtml TIHKAL NMT entry]
+[https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=23544 Entheogenic Effects of NMT]
 === 5-MeO-DMT ===
@@ Line 58: / Line 129: @@
 * Composition: C13H18N20
 * Molecular Weight: 218.298 g/mol
-* Melting Point: 69-70°C ([http://isomerdesign.com/PiHKAL/browse.php?domain=tk TIHKAL])
+* Melting Point: 66-67°C, 67-68°C, 69-70°C (Trout's notes and [http://isomerdesign.com/PiHKAL/browse.php?domain=tk TIHKAL])
+* Boiling Point4 : 208-210°C @ 4mm (Hoshino & Shimodaira 1936)
 * XLogP: 1.9
 * XLogP3: 1.5 ([http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1832&loc=ec_rcs PubChem])
+* pKa: 9.3 (Ghosal & Mukherjee 1964)
+* Colorimetric reagent results: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 Here]
 * Stability: Stable under normal temperatures and pressures. Incompatible with strong oxidizing agents, strong acids ([http://ch3v1.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?sort=&query=msds._msdsID%3D11173&target=msds&action=PowerSearch&from=0&format=ccd&searchValue=j%60qQ%40%40IVAdbfRfTJTYrRj%40Bfjb%40%40%40&history=off&realQuery=structure._structureID%3D4638142&onclick=1&selectionInfo=&searchTemplate=uniqueMol.structureString%3D%3F+elsor+uniqueMol.structureID%3D%3F&options=brandqtyoffer Source])
 * Solubility:
+Soluble in: Chloroform, ether, DCM, acetone, methanol, ethanol (Trout's notes on simple tryptamines). Soluble in (at least) 20mg/ml 96% ethanol ([https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=176401#post176401 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 ([http://ch3v1.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?sort=&query=msds._msdsID%3D11173&target=msds&action=PowerSearch&from=0&format=ccd&searchValue=j%60qQ%40%40IVAdbfRfTJTYrRj%40Bfjb%40%40%40&history=off&realQuery=structure._structureID%3D4638142&onclick=1&selectionInfo=&searchTemplate=uniqueMol.structureString%3D%3F+elsor+uniqueMol.structureID%3D%3F&options=brandqtyoffer Source])
@@ Line 78: / Line 156: @@
 * Composition: C12H16N2O
 * Molecular Weight: 204.268 g/mol
-* Melting point:146–147 °C (295–297 °F)
+* Melting point:[https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=1065033#post1065033 Source: Brennendes Wasser]
-* Boiling point: 320 °C (608 °F)
+°C
+* Boiling point:[https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=1065033#post1065033 Source: Brennendes Wasser]
+First fumes from 160 °C +
+Bufotenine turning brown at 170 °C +
+strong fumes from 190 °C +
+No further vaporization from 230 °C, leaving a black residue
+Estimated optimal temp for vaporization 210°C
 * XLogP: 1.6
 * XLogP3: 1.2 ([http://pubchem.ncbi.nlm.nih.gov/ PubChem])
-* pKa:
+* pKa: 9.67
+* Colorimetric reagent results: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 Here]
 * Solubility:
+[https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=93378 Source: Brennendes Wasser]
+'''1:3 Ethyl Acetate:Naphtha (C6-C7)'''
+Boiling = 7,6 g/l = 760 mg in 100 ml
+°C = 3,6 g/1 l = 360 mg in 100 ml
+- 20 °C = 3,5 g/1 l = 350 mg in 100 ml
+Selectively dissolves Bufotenine only, not the more polar Alkaloids. Defat first with Naphtha.
+'''Ethyl Acetate'''
+Boiling = 280 g/1 l = 28 g in 100 ml
+°C = 72 g/1 l = 7,2 g in 100 ml
+- 20 °C = 50 g/1 l = 5 g in 100 ml
+For recrystalization (optional, not recommended).
+Use only minimal amounts of solvent as you can see above! Placement in the freezer did not produce more crystals, just cloudings that cant be collected. Also crystals derived from re-x with Ethyl Acetate start turning grey and otherwise the material keeps its colour, therefore maybe not advised to do a re-x.
+'''boiling D-Limonene'''
+Unconvenient, drops Bufotenine too fast to form crystals. Also high chance to damage Bufotenine at 175 °C.
+Same goes possibly for Xylene.
+'''1:4 Acetone:Naphtha'''
+Not recommended, check above link for more info
+Other solubility data (possibly unreliable, originally from 69ron experiments)
 Acetone @ 20 C: soluble (5 g/100 ml)
@@ Line 96: / Line 227: @@
 D-Limonene (Orange Oil) @ 176 C: soluble (more than 1.7 g/100 ml)
-Dilute Acids and Alkalis: Soluble ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+Dilute Acids and Alkalis: Soluble ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
 Ethanol @ 20 C: soluble
@@ Line 129: / Line 260: @@
 Insoluble in FASA (Fumaric Acid Saturated Acetone)
+==== Bufotenine Benzoate ====
+* Solubility:
+Insoluble in acetone, (almost insoluble in PG/VG)
+=== Bufotenine Citrate ===
+*Insoluble in ethyl acetate (will form in EA)-Nexus sourced.
 === Psilocin ===
@@ Line 140: / Line 279: @@
 * Melting Point: 103-104°C ([http://isomerdesign.com/PiHKAL/read.php?domain=tk&id=18 TIHKAL]) , 173-176°C (Merck Index)
 * XLogP3: 2.1 ([http://pubchem.ncbi.nlm.nih.gov/ PubChem])
+* Colorimetric reagent results: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 Here]
 * Stability/Degradation: Unstable in solution, especially alkaline solution (Merck Index).
 * Solubility:
-Very slightly sol in water ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+Soluble in 70% ethanol. Poorly soluble in dry ethanol, and poorly soluble in ethanol less than 60%. Very slightly soluble in water (sources: [http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index] , [https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=221711#post221711 scientific publications])
 === Psilocybin ===
@@ Line 152: / Line 292: @@
 * Composition: C12H17N2O4P
 * Molecular Weight: 284.248141 g/mol
-* Melting Point: 220-228° from boiling water; 185-195° from boiling methanol ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+* Melting Point: 220-228° from boiling water; 185-195° from boiling methanol ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
+Free base:
+Stable compound. Colorless crystals. Hofmann 1971
+pH 5.2 (in 50% EtOH) Merck 9th
+More stable than psilocin. Shulgin & Shulgin !997
+mp 175-180° Repke & leslie 1977
+mp 185-195° (from boiling methanol) Ott 1996
+mp 185-195° (from methanol) Picker & Rickards 1970
+(Also in Perkal 1981)
+rnp 185-195° (dec.) (white crystals) Clarke 's 1986
+mp 190° Mantle & Waight 1969
 * XLogP3: -1.6 ([http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=10624&loc=ec_rcs PubChem])
+* Colorimetric reagent results: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 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); difficultly soluble in ethanol. Practically insoluble in chloroform, benzene ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+Soluble in water (estimated 2mg/ml at 25C). 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: [http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index] , [https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=221711#post221711 scientific publications], [https://pubchem.ncbi.nlm.nih.gov/compound/Psilocybin#section=Solubility PubChem])
 === Mescaline ===
@@ Line 165: / Line 317: @@
 * CAS Registry Number:  54-04-6
 * Composition: C11H17NO3
-* Melting point: 35-36°C (Kindler and Peschke, 103.  [http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+* Melting point: 35-36°C (Kindler and Peschke, 103.  [http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
 * Boiling point: 180°C (12 mmHg)
 * XLogP: 0.6 ([http://pubchem.ncbi.nlm.nih.gov/ PubChem])
@@ Line 174: / Line 326: @@
 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: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 Here]
 * Solubility
-Soluble in: alcohol, chloroform, benzene, xylene, toluene, acetone, dichloromethane, highly soluble in isopropyl alcohol, soluble in d-limonene
+Soluble in: alcohol, chloroform, benzene, xylene, toluene, acetone, dichloromethane, highly soluble in isopropyl alcohol, soluble in d-limonene, ethyl acetate, chilled ethyl acetate (O°F)
 Moderately soluble in: water
@@ Line 186: / Line 339: @@
 Soluble in water
-Insoluble in: xylene, acetone <nowiki>*</nowiki>
+Insoluble in: xylene, acetone <nowiki>*, ethyl acetate</nowiki>
 <nowiki>*</nowiki> Possible unreliable web source.
@@ Line 196: / Line 349: @@
 * CAS Number: 832-92-8
 * Appearance: colorless crystals, needles
-* Melting point: 184°C ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+* Melting point: 184°C ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
 * Solubility:
-Moderately soluble in: water, alcohol ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index]), methanol (at least 1.0 mg/ml, source Sigma Aldrich solution)
+Moderately soluble in: water, ethanol ~10mg/ml (ref: [https://www.caymanchem.com/pdfs/11950.pdf  Cayman Chemical]) ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index]), methanol ~1.0mg/ml (source Sigma Aldrich solution)
-(Merck Index)
+(Merck Index), dimethyl sulfoxide (DMSO) ~3mg/ml (ref: Cayman Chemical), dimethyl formamide ~0.5mg/ml (ref: [https://www.caymanchem.com/app/template/Product.vm/catalog/11950/promo/emolecules%5B Cayman Chemical])
 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.
+* 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 acetone (* NOTE: previous sentence is speculation, not yet substantiated by tests as far as we know), 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 ====
@@ Line 215: / Line 369: @@
 * Molecular Weight: 309.33606
 * Soluble in: hot water, methanol
-* Almost insoluble in: near freezing water, alcohol, acetone <nowiki>*</nowiki>
+* Almost insoluble in: near freezing water, alcohol, acetone <nowiki>*</nowiki>  [VERIFIED]
 <nowiki>*</nowiki> Possible unreliable web source.
 ==== Mescaline Fumarate ====
-* Composition: unknown (it may be a one to one salt or may not be)
+* Composition: unknown (when prepared by a FASx method it may be a one to one salt (the bifumarate) or may not be)
-* Appearance: unknown
+* Appearance: White powder
 * Melting point: unknown
 * Solubility
-Soluble in: water<nowiki>**</nowiki>, acetone<nowiki>**</nowiki>
+Soluble in: water
-Insoluble in: unknown
+Insoluble in: Limonene, Anydrous IPA, Acetone, MEK (most likely insoluble in all non-polars like xylene and toluene) [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=18705 Source]
-<nowiki>**</nowiki> This information is from various SWIMs on this forum.
 ==== Mescaline Acetate ====
@@ Line 252: / Line 405: @@
 * Melting Point: 152-153 °C ([http://isomerdesign.com/PiHKAL/browse.php?domain=tk TIHKAL])
 * XLogP3: 3.9 ([http://pubchem.ncbi.nlm.nih.gov/ PubChem])
-* pKa: 8.1 in 80% methylcellosolve ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+* pKa: 8.1 in 80% methylcellosolve ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
-* Solubility: Soluble in limonene ([http://www.anoniem.org/?https://www.dmt-nexus.com/forum/default.aspx?g=posts&t=10651 Non-Toxic Iboga Extraction])
+* Colorimetric reagent results: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 Here]
+* Solubility: Soluble in limonene ([http://www.anoniem.org/?https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=10651 Non-Toxic Iboga Extraction]) soluble in acetone (merck)
 ==== Ibogaine Hydrochloride ====
 * Melting Point: 299-300 °C ([http://isomerdesign.com/PiHKAL/browse.php?domain=tk TIHKAL])
-* Solubility: Soluble in water, methanol (Sigma Aldrich)
+* Solubility: Soluble in water, methanol (Sigma Aldrich), slightly soluble in acetone (merck)
 === Voacangine ===
@@ Line 268: / Line 420: @@
 * Composition: C22H28N2O3
 * Molecular Weight: 368.46932 g/mole
-* Melting Point: 136–137 °C ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+* Melting Point: 136–137 °C ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
-* pKa: 7.4 (40% aq methanol); 5.73 (33% DMF)  ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+* pKa: 7.4 (40% aq methanol); 5.73 (33% DMF)  ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
 * XLogP3-AA: 3.5 ([http://pubchem.ncbi.nlm.nih.gov/ PubChem])
@@ Line 280: / Line 432: @@
 * Composition: C16H17N3O
 * Molecular Weight: 267.32568 g/mol
-* XLogP3: 1.6
+* XLogP3: 1.6 ([http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=442072&loc=ec_rcs PubChem])
 === Muscimol ===
@@ Line 294: / Line 444: @@
 * Molecular Weight: 114.10264 g/mol
 * Melting Point: 175°C (Merck Index)
+* Boiling Point: 70°C (Wolfram Alpha)
 * XLogP3-AA: -1.4 ([http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=4266&loc=ec_rcs 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 ([http://www.caymanchem.com/pdfs/13667.pdf Caymanchem.com])
 === Salvinorin A ===
@@ Line 303: / Line 456: @@
 * Composition: C23H28O8
 * Molecular Weight: 432.46362 g/mol
-* Melting Point:242-244 – 238-240 °C (Wikipedia)
+* Melting Point:
-* Boiling Pont: 760.2 °C (1400 °F) (Wikipedia)
-* XLogP3-AA: 2.5 ([http://pubchem.ncbi.nlm.nih.gov/ PubChem])
+-244 – 238-240 °C (Wikipedia)
+no melting, directly sublimating [https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=1065033#post1065033 source: Brennendes Wasser]
+* Boiling Pont:
+[https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=1065033#post1065033 Source: Brennendes Wasser]
+First fumes from 190 °C, Salvinorin turning brown
+No further vaporization from 270 °C, leaving a black residue
+Estimated ideal temperature for vaporization: 250 °C
+Other data:
+.2 °C (1400 °F) (Wikipedia) likely wrong
+* XLogP3-AA: 2.5 ([http://pubchem.ncbi.nlm.nih.gov/ PubChem])
 === Elemicin ===
@@ Line 331: / Line 500: @@
 * Composition: C13H12N2O
 * Molecular Weight: 212.25 (Sigma Aldrich)
-* Melting point: 262-264 °C (Sigma Aldrich)
+* Melting point:
-* Boiling point:
+-264 °C (Sigma Aldrich)
+Not melting, directly sublimating [https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=1065033#post1065033 Source: Brennendes Wasser]
+* Boiling point:
+[https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=1065033#post1065033 Source: Brennendes Wasser]
+First fumes from 180 °C +
+Sublimation while forming small black clumps at 205 °C +
+No further vaporization from 240 °C,
+.4°C at 760mmHg ([http://www.lookchem.com/cas-442/442-51-3.html Lookchem])
 * XLogP: 2.5
 * XLogP3: 3.6
 * pKa: 7.7
-* Solubility:
+* Colorimetric reagent results: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 Here]
-Insoluble in basic water
+* Solubility: ethanol (~1.5mg/ml), DMSO (~1.5mg/ml), dimethyl formamide and ethyl acetate
-* 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 [https://www.dmt-nexus.com/forum/default.aspx?g=posts&t=5725 freebase percentage calculator thread] and the [http://wiki.dmt-nexus.com/Harmalas_Extraction_and_Separation_Guide Harmala Extraction Guide] for more info.
+([https://www.caymanchem.com/app/template/Product.vm/catalog/10010324 ~1.5mg/ml]). Reasonably soluble in acetone (at 25°C, acetone can dissolve 4mg/ml mixed harmalas as [https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=200200#post200200 this test shows])
+Insoluble in: Basic water, diethyl ether, D Limonene. Low solubility in distilled 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 the [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=5725 freebase percentage calculator thread] and the [http://wiki.dmt-nexus.me/Harmalas_Extraction_and_Separation_Guide Harmala Extraction Guide] for more info.
 ==== Harmine Hydrochloride ====
@@ Line 348: / Line 533: @@
 Insoluble in salt-saturated water
+==== Harmine Citrate ====
+*Solubility:
+*Soluble in water
+*Insoluble in ethyl acetate (will form in EA)
+Nexus sourced
+==== Harmine Tartrate ====
+*Solubility:
+*soluble in water
+*Insoluble in ethyl acetate (will form in EA)
+**Insoluble in acetone (should form in Acetone)
+Nexus sourced
 === Harmaline ===
@@ Line 356: / Line 560: @@
 <table><tr><td>[[Image:harmaline.png]]</td><td></table>
 * Composition: C13H14N2O
-* Melting point: 232-234 °C (Sigma Aldrich)
+* Melting point:
-* Boiling point: 120-140 °C at 0.001 mm/Hg ([http://isomerdesign.com/PiHKAL/browse.php?domain=tk TIHKAL])
+-234 °C (Sigma Aldrich)
+Not melting, directly sublimating [https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=1065033#post1065033 Source: Brennendes Wasser]
+* Boiling point:
+[https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=1065033#post1065033 Source: Brennendes Wasser]
+First fumes from 180 °C +
+Sublimation while forming small black clumps at 205 °C +
+No further vaporization from 240 °C,
+-140 °C at 0.001 mm/Hg ([http://isomerdesign.com/PiHKAL/browse.php?domain=tk TIHKAL])
 * XLogP: 0.8
 * XLogP3: 1.2
 * pKa: 9.8
+* Colorimetric reagent results: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 Here]
 * Solubility:
-Slightly soluble in basic water
+Insoluble in D Limonene
-* 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 [https://www.dmt-nexus.com/forum/default.aspx?g=posts&t=5725 freebase percentage calculator thread] and the [http://wiki.dmt-nexus.com/Harmalas_Extraction_and_Separation_Guide Harmala Extraction Guide] for more info.
+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 [https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=200200#post200200 this test shows]) Soluble in ethyl acetate.
+* 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 [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=5725 freebase percentage calculator thread] and the [http://wiki.dmt-nexus.me/Harmalas_Extraction_and_Separation_Guide Harmala Extraction Guide] for more info.
 ==== Harmaline Hydrochloride ====
@@ Line 370: / Line 591: @@
 Insoluble in salt-saturated water
+==== Harmaline Citrate ====
+Solubility:
+Soluble in water
+Insoluble in ethyl acetate
+Nexus sourced
+==== Harmaline Tartrate ====
+*Solubility:
+*soluble in water
+*Insoluble in ethyl acetate (will form in EA)
+**Insoluble in acetone (should form in Acetone)
+Nexus sourced
 === THH ===
@@ Line 381: / Line 623: @@
 * XlogP: 1.9
 * XLogP3: 1.9
+* Colorimetric reagent results: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 Here]
+* Solubility:
+Soluble in chloroform, ethanol & methanol. (Ott 1996.)
+Soluble in ethyl acetate. (Siddiqui et al. 1983)
+Poorly soluble in distilled water
 ==== THH Hydrochloride ====
@@ Line 387: / Line 636: @@
 * Molecular Weight: 252.73988 g/mol
 * Melting Point: 232–234 °C ([http://isomerdesign.com/PiHKAL/browse.php?domain=tk TIHKAL])
+* Boiling point: 399.2 °C at 760 mmHg ([http://www.lookchem.com/TETRAHYDROHARMINE 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 ==
@@ Line 401: / Line 661: @@
 * Boiling point:
 * XLogP3: 1.8
-* pKa:
+* Colorimetric reagent results: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 Here]
+* pKa: 8.52
 * Solubility:
 Sol in alcohol, ether, chloroform; slightly sol in cold acetone. Practically insol in petr ether, water. (Merck Index)
@@ Line 413: / Line 674: @@
 * Composition: C10H15NO
 * Molecular Weight: 165.23 g/mol
-* Melting point: 117-118° ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+* Melting point: 117-118° ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
-* Boiling point: 173° @ 11mmHg ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+* Boiling point: 173° @ 11mmHg ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
-* XlogP3: 2.1 (PubChem)
+* 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. ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+Very sol in alcohol, chloroform, ether. 7 grams dissolve in 1000 ml water. Sparingly sol in benzene, toluene, xylene. Practically insol in petr ether. ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
 ==== Hordenine Hydrochloride ====
@@ Line 424: / Line 685: @@
 * Composition: C10H15NO.HCl
 * Molecular Weight: 201.70 g/mol
-* Melting point: 177° ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+* Melting point: 177° ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
 * Solubility:
-Very sol in water. ([http://wiki.dmt-nexus.com/w/images/8/81/MERCK.pdf Merck Index])
+Very sol in water. ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
+=== Vasicine ===
+(3R)-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-ol;Peganine
+==== Freebase Vasicine ====
+<table><tr><td>[[Image:vasicine.jpg]]</td><td></table>
+* Composition: 	C11H12N2O
+* Molecular Weight: 188.22578 g/mol
+* Melting point: 209-211° C (Decomposes) ([http://www.chemicalland21.com/specialtychem/nd/VASICINE.htm source])
+* XLogP3: 0.4 ([http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=442935&loc=ec_rcs pubchem])
+* Pharmacology: Uterotonic, abortifacient, bronchodilatory activity, expectorant, respiratory stimulant activity, moderate hypotensive activity (sources: [http://www.chemicalland21.com/specialtychem/nd/VASICINE.htm 1], [http://indianmedicine.eldoc.ub.rug.nl/root/A/2091/ 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 [http://wiki.dmt-nexus.me/Harmalas_Extraction_and_Separation_Guide harmala extraction guide for more info])
+=== Vasicinone ===
+(R)-2,3-dihydro-3-hydroxypyrrolo(2,1-b)quinazolin-9(1H)-one
+==== Freebase Vasicinone ====
+<table><tr><td>[[Image:vasicinone.jpg]]</td><td></table>
+* Appearance: White powder
+* Composition: 	C11H10N2O2
+* Molecular Weight: 202.2093 g/mol
+* Melting point: 203°-204° C  ([http://www.chemicalland21.com/specialtychem/nd/VASICINE.htm source])
+* XLogP3: 0.4 ([http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=442935&loc=ec_rcs pubchem])
+* Pharmacology: Uterotonic, abortifacient, bronchodilatory activity, expectorant, respiratory stimulant activity, moderate hypotensive activity (sources: [http://www.chemicalland21.com/specialtychem/nd/VASICINE.htm 1], [http://indianmedicine.eldoc.ub.rug.nl/root/A/2091/ 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 [http://wiki.dmt-nexus.me/Harmalas_Extraction_and_Separation_Guide harmala extraction guide for more info]
+=== Deoxyvasicine ===
+,2,3,9-Tetrahydropyrrolo(2,1-b)quinazoline; Deoxypeganin;
+==== Freebase Deoxyvasicine ====
+<table><tr><td>[[Image:deoxyvasicine.jpg]]</td><td></table>
+* Appearance: White to yellow powder
+* Composition: C11H12N2
+* Molecular Weight: 172.22638 g/mol
+* Melting point: 86-87° C  ([http://www.chemicalland21.com/specialtychem/nd/VASICINE.htm source])
+* XLogP3: 0.4
+* Pharmacology: Uterotonic, abortifacient, bronchodilatory activity, expectorant, respiratory stimulant activity, moderate hypotensive activity (sources: [http://www.chemicalland21.com/specialtychem/nd/VASICINE.htm 1], [http://indianmedicine.eldoc.ub.rug.nl/root/A/2091/ 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 [http://wiki.dmt-nexus.me/Harmalas_Extraction_and_Separation_Guide harmala extraction guide for more info])
 == Solvents and Alkaloids XlogP and XlogP3 ==
@@ Line 466: / Line 769: @@
 * 2.0 - DMT N-oxide
 * 2.1 - Psilocin
+* 2.1 - NMT
 * 2.5 - DMT
 * 2.5 - Salvinorin A

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

Latest revision as of 14:18, 19 May 2023

Contents

Psychedelic Compounds Chemical and Physical Properties

DMT

Freebase DMT

DMT N-Oxide

DMT Fumarate

DMT Citrate

DMT Benzoate

NMT

Freebase NMT

5-MeO-DMT

Freebase 5-MeO-DMT

5-MeO-DMT Hydrochloride

Bufotenine

Freebase Bufotenine

Bufotenine Fumarate

Bufotenine Benzoate

Bufotenine Citrate

Psilocin

Freebase Psilocin

Psilocybin

Psilocybin (Psilocin Phosphate Ester)

Mescaline

Freebase Mescaline

Mescaline Citrate

Mescaline Hydrochloride

Mescaline Picrate

Mescaline Sulfate Dihydrate

Mescaline Fumarate

Mescaline Acetate

Ibogaine

Freebase Ibogaine

Ibogaine Hydrochloride

Voacangine

Voacangine

LSA (ergine)

Freebase LSA

Muscimol

Freebase Muscimol

Salvinorin A

Salvinorin A

Elemicin

Elemicin

Harmine

Freebase Harmine

Harmine Hydrochloride

Harmine Citrate

Harmine Tartrate

Harmaline

Freebase Harmaline

Harmaline Hydrochloride

Harmaline Citrate

Harmaline Tartrate

THH

Freebase THH

THH Hydrochloride

Relevant NOT psychedelic compounds

Gramine

Freebase Gramine

Hordenine

Freebase Hordenine

Hordenine Hydrochloride

Vasicine

Freebase Vasicine

Vasicinone

Freebase Vasicinone

Deoxyvasicine

Freebase Deoxyvasicine

Solvents and Alkaloids XlogP and XlogP3

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