Psychedelic Compounds Chemical and Physical Properties

2020-07-26T16:51:04Z

Elrik: /* Mescaline Fumarate */

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 ==

=== DMT ===
N,N-Dimethyltryptamine

==== Freebase DMT ====
<table><tr><td>[[Image:dmtfreebase.png]]</td><td></table>
* 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: [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.me/w/images/8/81/MERCK.pdf Merck Index])
* 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, 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 ====
<table><tr><td>[[Image:dmtnoxide.jpg]]</td><td></table>
* 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 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 ([https://www.dmt-nexus.me/forum/resource.ashx?a=7966 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 ====

<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 ===
5-methoxy-N,N-dimethyl-tryptamine

==== Freebase 5-MeO-DMT ====
<table><tr><td>[[Image:5meodmtfreebase.png]]</td><td></table>
* 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 [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])

==== 5-MeO-DMT Hydrochloride====
* Melting Point: 145-146°C ([http://isomerdesign.com/PiHKAL/browse.php?domain=tk TIHKAL])

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

==== Freebase Bufotenine ====
<table><tr><td>[[Image:bufoteninefreebase.png]]</td><td></table>
* CAS Registry Number: 487-93-4
* Composition: C12H16N2O
* Molecular Weight: 204.268 g/mol
* Melting point:[https://www.dmt-nexus.me/forum/default.aspx?g=posts&m=1065033#post1065033 Source: Brennendes Wasser]

108 °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: 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

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 ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf 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 ====
<table><tr><td>[[Image:psilocinfreebase.png]]</td><td></table>
* CAS Registry Number: 520-53-6
* Composition: C12H16N2O
* Molecular Weight: 204.27 g/mol
* 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:
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 ===
4-PO-DMT - O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine

==== Psilocybin (Psilocin Phosphate Ester) ====
<table><tr><td>[[Image:psilocybin.png]]</td><td></table>
* 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 ([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 (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 ===
3,4,5-trimethoxyphenethylamine

==== Freebase Mescaline ====
<table><tr><td>[[Image:mescalinefreebase.png]]</td><td></table>
* CAS Registry Number: 54-04-6
* Composition: C11H17NO3
* 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])
* XLogP3: 0.7 ([http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=4076&loc=ec_rcs 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: [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

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 <nowiki>*</nowiki>

<nowiki>*</nowiki> Possible unreliable web source.

==== Mescaline Hydrochloride ====
<table><tr><td>[[Image:mescalinehcl.png]]</td><td></table>
* 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 ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])
* Solubility:
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), 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 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====
<table><tr><td>[[Image:mescalinesulfate.png]]</td><td></table>
* 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 <nowiki>*</nowiki> [VERIFIED]
<nowiki>*</nowiki> 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) [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=18705 Source]

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

Insoluble in: xylene, d-limonene, cold MEK (Methyl Ethyl Ketone) <nowiki>***</nowiki>

<nowiki>***</nowiki> 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 ====
<table><tr><td>[[Image:ibogainefreebase.png]]</td><td></table>
* CAS Registry Number: 83-74-9
* Composition: C20H26N2O
* Molecular Weight: 310.43324 g/mol
* 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.me/w/images/8/81/MERCK.pdf Merck Index])
* 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), slightly soluble in acetone (merck)

=== Voacangine ===
12-methoxyibogamine-18-carboxylic acid methyl ester

==== Voacangine ====
<table><tr><td>[[Image:voacangine.png]]</td><td></table>
* Composition: C22H28N2O3
* Molecular Weight: 368.46932 g/mole
* 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.me/w/images/8/81/MERCK.pdf Merck Index])
* XLogP3-AA: 3.5 ([http://pubchem.ncbi.nlm.nih.gov/ PubChem])

=== LSA (ergine) ===
Lysergamide

==== Freebase LSA ====
<table><tr><td>[[Image:lsafreebase.png]]</td><td></table>
CAS Registry Number: 478-94-4
* Composition: C16H17N3O
* Molecular Weight: 267.32568 g/mol
* XLogP3: 1.6 ([http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=442072&loc=ec_rcs PubChem])

=== Muscimol ===
Pantherine, Agarine

==== Freebase Muscimol ====
<table><tr><td>[[Image:muscimolfreebase.png]]</td><td></table>
* 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 ([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 ===
Note: Technically NOT an alkaloid, as it contains no nitrogen. It is a trans-neoclerodane diterpene.

==== Salvinorin A ====
<table><tr><td>[[Image:salvinorina.png]]</td><td></table>
* Composition: C23H28O8
* Molecular Weight: 432.46362 g/mol
* Melting Point:

242-244 – 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:
760.2 °C (1400 °F) (Wikipedia) likely wrong

* XLogP3-AA: 2.5 ([http://pubchem.ncbi.nlm.nih.gov/ PubChem])

=== Elemicin ===
1,2,3-trimethoxy-5-allylbenzene

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

==== Elemicin ====
<table><tr><td>[[Image:elemicin.png]]</td><td></table>

* 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 ([http://www.thegoodscentscompany.com/data/rw1021681.html Source]), 146-147 °C ([http://www.chemyq.com/En/xz/xz3/20815lmxvj.htm Source 1] [http://www.chunyuan.com.cn/zhanshishow.asp?id=94 Source 2]), 279.8 °C @ 760 mmHg ([http://www.chemspider.com/Chemical-Structure.9830.html ChemSpider])
* XlogP3: 2.5 ([http://pubchem.ncbi.nlm.nih.gov/ PubChem])
* Solubility:
Soluble in alcohol, Insoluble in water ([http://www.thegoodscentscompany.com/data/rw1021681.html Source])

=== Harmine ===
7-methoxy-β-carboline

==== Freebase Harmine ====
<table><tr><td>[[Image:harminefreebase.png]]</td><td></table>
* Composition: C13H12N2O
* Molecular Weight: 212.25 (Sigma Aldrich)
* Melting point:

262-264 °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,

421.4°C at 760mmHg ([http://www.lookchem.com/cas-442/442-51-3.html Lookchem])
* XLogP: 2.5
* XLogP3: 3.6
* pKa: 7.7
* Colorimetric reagent results: [https://www.dmt-nexus.me/forum/default.aspx?g=posts&t=25771 Here]
* Solubility: ethanol (~1.5mg/ml), DMSO (~1.5mg/ml) and dimethyl formamide ([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. 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 ====
<table><tr><td>[[Image:harminehcl.png]]</td><td></table>
* 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 ====
<table><tr><td>[[Image:harmaline.png]]</td><td></table>
* Composition: C13H14N2O
* Melting point:

232-234 °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,

120-140 °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, 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])
* 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 ====
* Solubility:
Soluble in water

Insoluble in salt-saturated water

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

==== Freebase THH ====
<table><tr><td>[[Image:thhfreebase.png]]</td><td></table>
* Composition: C13H16N2O
* Molecular Weight: 216.27894 g/mol
* Melting Point: 187-190 °C ([http://isomerdesign.com/PiHKAL/browse.php?domain=tk TIHKAL])
* 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 ====
<table><tr><td>[[Image:thhhcl.png]]</td><td></table>
* Composition: C13H17ClN2O
* 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 ==

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

==== Freebase Gramine ====
<table><tr><td>[[Image:graminefreebase.png]]</td><td></table>
* Composition: C11H14N2
* Molecular Weight: 174.24226 g/mol
* Melting point: 138-139°C (Merck)
* Boiling point:
* XLogP3: 1.8
* 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)

=== Hordenine ===
N,N-dimethyltyramine

==== Freebase Hordenine ====
<table><tr><td>[[Image:hordeninefreebase.png]]</td><td></table>
* CAS Registry Number: 539-15-1
* Composition: C10H15NO
* Molecular Weight: 165.23 g/mol
* 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.me/w/images/8/81/MERCK.pdf 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. ([http://wiki.dmt-nexus.me/w/images/8/81/MERCK.pdf Merck Index])

==== Hordenine Hydrochloride ====
<table><tr><td>[[Image:hordeninehcl.png]]</td><td></table>
* CAS Registry Number: 6027-23-2
* Composition: C10H15NO.HCl
* Molecular Weight: 201.70 g/mol
* 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.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 ===
1,2,3,9-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 ==

'''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)

DMT-Nexus Wiki - User contributions [en]

Psychedelic Compounds Chemical and Physical Properties